| Branch | Fact | Value | Material · origin | Method | n | Source | Access |
|---|---|---|---|---|---|---|---|
| I. Terpenoid, phenylpropanoid | The MVA pathway is located in the cytosol (partly peroxisomes), MEP in plastids | MVA: cytosol; MEP: plastid | terpenoid | review/experimental | Gutensohn et al. 2021 10.3389/fpls.2021.691754 | full | |
| I. Terpenoid, phenylpropanoid | FPP (C15) serves sesquiterpene synthases in the cytosol; GPP (C10) serves monoterpene synthases in plastids | FPP→C15; GPP→C10 | terpenoid | review | Gutensohn et al. 2021 10.3389/fpls.2021.691754 | full | |
| I. Terpenoid, phenylpropanoid | Nerolidol (cytosol) is emitted at lower levels than linalool (plastid) in transgenic tomato | 60–584-fold | nerolidol vs linalool · transgenic tomato | GC | NR | Gutensohn et al. 2021 10.3389/fpls.2021.691754 | full |
| I. Terpenoid, phenylpropanoid | Overexpression of HMGR (MVA) increases cytosolic nerolidol; DXS (MEP) increases it less | 5.7 (HMGR); 2.5 (DXS)-fold | nerolidol · transgenic tomato | GC | NR | Gutensohn et al. 2021 10.3389/fpls.2021.691754 | full |
| I. Terpenoid, phenylpropanoid | Eugenol (basil) and isoeugenol (petunia) are formed by reduction of coniferyl acetate by an NADPH-dependent reductase | mechanism | eugenol, isoeugenol | enzymology | Koeduka et al. 2006 10.1073/pnas.0603732103 | abstract | |
| I. Terpenoid, phenylpropanoid | Transcripts of phenylpropanoid genes in basil peltate glands as a share of ESTs | ~13 % EST | basil | EST | Gang et al. 2001 10.1104/pp.125.2.539 | abstract | |
| I. Terpenoid, phenylpropanoid | Transcripts of S-adenosyl-methionine synthesis genes in basil peltate glands | ~14 % EST | basil | EST | Gang et al. 2001 10.1104/pp.125.2.539 | abstract | |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in water (alcohol) — literature value cited secondarily | 5.3 µg/L | linalool | literature (Ahmed et al.) | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in deodorised orange juice (alcohol) | 113 µg/L | linalool · Florida, USA | 3-AFC ASTM E-679, best-estimate geometric mean | 39 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in water (hydrocarbon) — literature value cited secondarily | 9.5 µg/L | α-pinene | literature (Ahmed et al.) | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in deodorised orange juice (hydrocarbon) | 1650 µg/L | α-pinene · Florida, USA | 3-AFC ASTM E-679, best-estimate geometric mean | 39 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in water (hydrocarbon) — literature value cited secondarily | 36 µg/L | myrcene | literature (Ahmed et al.) | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in deodorised orange juice (hydrocarbon) | 773 µg/L | myrcene · Florida, USA | 3-AFC ASTM E-679, best-estimate geometric mean | 46 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in water (hydrocarbon) — literature value cited secondarily | 60 µg/L | limonene | literature (Ahmed et al.) | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in deodorised orange juice (hydrocarbon) | 13700 µg/L | limonene · Florida, USA | 3-AFC ASTM E-679, best-estimate geometric mean | 40 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in water (hydrocarbon) — literature value cited secondarily | 140 µg/L | β-pinene | literature (Ahmed et al.) | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in deodorised orange juice (hydrocarbon) | 37200 µg/L | β-pinene · Florida, USA | 3-AFC ASTM E-679, best-estimate geometric mean | 38 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in water (alcohol) — literature value cited secondarily | 280 µg/L | α-terpineol | literature (Ahmed et al.) | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Orthonasal odour threshold in deodorised orange juice (alcohol) | 25900 µg/L | α-terpineol · Florida, USA | 3-AFC ASTM E-679, best-estimate geometric mean | 33 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | γ-Terpinene threshold in orange juice | 3260 µg/L | γ-terpinene · Florida, USA | 3-AFC ASTM E-679 | 51 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | OAV of limonene in freshly squeezed Valencia orange juice (based on the orange-juice threshold) | 1.3–6 | limonene · Florida, USA | headspace & ether extraction; OAV | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | OAV of linalool in Valencia orange juice (orange-juice threshold ≈1; water threshold 15–25) | ≈1 / 15–25 | linalool · Florida, USA | OAV | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of linalool | 3.2 ng/L air | linalool · Germany (Erlangen) | GC-O, internal standard (E)-2-decenal, geometric mean | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of linalyl acetate (esterification weakens it ~35-fold) | 110.9 ng/L air | linalyl acetate · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 8-oxolinalool | 38.1 ng/L air | 8-oxolinalool · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 8-hydroxylinalool | 160.3 ng/L air | 8-hydroxylinalool · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 8-oxolinalyl acetate | 5.9 ng/L air | 8-oxolinalyl acetate · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 8-hydroxylinalyl acetate | 102.8 ng/L air | 8-hydroxylinalyl acetate · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 8-carboxylinalyl acetate | 6.1 ng/L air | 8-carboxylinalyl acetate · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | 8-Carboxylinalool is odourless | odourless | 8-carboxylinalool · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Range of individual thresholds in the linalool-derivative study | 0.6–989 ng/L air | linalool derivatives · Germany | GC-O | 8 | Elsharif et al. 2015 10.3389/fchem.2015.00057 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of geraniol (E) | 14 ng/L air | geraniol · Germany | GC-O | NR | Elsharif & Buettner 2018 10.1021/acs.jafc.6b04534 | abstract |
| I. Terpenoid, phenylpropanoid | Air threshold of nerol (Z) | 60 ng/L air | nerol · Germany | GC-O | NR | Elsharif & Buettner 2018 10.1021/acs.jafc.6b04534 | abstract |
| I. Terpenoid, phenylpropanoid | Conclusion: E/Z configuration at C-1 mainly affects potency; C-8 oxidation mainly affects odour quality | qualitative | geraniol/nerol · Germany | GC-O | NR | Elsharif & Buettner 2018 10.1021/acs.jafc.6b04534 | abstract |
| I. Terpenoid, phenylpropanoid | Air threshold of 8-oxoneryl acetate (most potent) and 8-oxonerol (least potent) | 8.8 / 493 ng/L air | 8-oxoneryl acetate / 8-oxonerol · Germany | GC-O | NR | Elsharif & Buettner 2018 10.1021/acs.jafc.6b04534 | abstract |
| I. Terpenoid, phenylpropanoid | Odour description: geraniol citrusy-floral; nerol resinous-citrusy-floral | qualitative | geraniol, nerol · Germany | sensory evaluation | 15 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 2-methyllinalool (floral odour) | 1.8 ng/L air | 2-methyllinalool · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 2-methyl-α-fenchol (musty odour) | 3.6 ng/L air | 2-methyl-α-fenchol · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 2-methylgeraniol (floral odour) | 5.4 ng/L air | 2-methylgeraniol · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 2-methylcitronellol (citrus odour) | 7.2 ng/L air | 2-methylcitronellol · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Air threshold of 4-methylgeraniol (citrus odour) | 16 ng/L air | 4-methylgeraniol · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Methylation of geraniol: C-8 → resinous; C-4 → lemony; C-2 → unchanged | qualitative | geraniol derivatives · Germany | sensory | 15 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Oxygenated terpenoids have thresholds only slightly lower than acyclic terpenes (authors’ remark) | qualitative | non-classical terpenes · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Threshold of (+)-nootkatone in water (secondary citation) | 0.6–1.0 µg/L | (+)-nootkatone | literature | NR | Sommer et al. 2022 (secondary) 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Threshold of (−)-nootkatone in water (secondary citation) | 400–800 µg/L | (−)-nootkatone | literature | NR | Sommer et al. 2022 (secondary) 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Thresholds of the two citronellol enantiomers measured ~20-fold higher than Schoenauer & Schieberle but comparable to Elsharif & Buettner | ~20-fold | citronellol · Germany | GC-O | 3 | Sommer et al. 2022 10.3390/molecules27123827 | full |
| I. Terpenoid, phenylpropanoid | Carvone: (R)-(−) spearmint, (S)-(+) caraway — chemical and sensory data | qualitative | carvone · USA | GC + sensory | NR | Leitereg et al. 1971 10.1021/jf60176a035 | abstract |
| I. Terpenoid, phenylpropanoid | Threshold ratio β-pinene/α-pinene (exocyclic vs endocyclic double bond) | ~15 (water); ~23 (orange juice)-fold | α-/β-pinene · Florida, USA | 3-AFC | 38–39 | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Threshold ratio α-terpineol (cyclic) / linalool (acyclic) in water | ~53-fold | linalool vs α-terpineol | literature | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Threshold ratio limonene (cyclic) / myrcene (acyclic) in water | ~1.7-fold | myrcene vs limonene | literature | NR | Plotto et al. 2004 10.1002/ffj.1470 | full |
| I. Terpenoid, phenylpropanoid | Monoterpene hydrocarbons in cold-pressed Ponkan peel oil | >89.6 % w/w | Ponkan mandarin peel oil · Japan (exact location NR) | cold-pressed; GC, GC-MS | NR | Sawamura et al. 2004 10.1271/bbb.68.1690 | abstract |
| I. Terpenoid, phenylpropanoid | Limonene in cold-pressed Ponkan peel oil — acts only as background | ~80.3 % | Ponkan mandarin peel oil | cold-pressed; GC-MS; sniffing + reconstitution | NR | Sawamura et al. 2004 10.1271/bbb.68.1690 | abstract |
| I. Terpenoid, phenylpropanoid | OAV of 1,8-cineole in fresh ginger | ~65,000 | fresh ginger · China | SIDA | NR | Schaller & Schieberle 2020 10.1021/acs.jafc.0c06733 | abstract |
| I. Terpenoid, phenylpropanoid | OAV of myrcene (hydrocarbon) in fresh ginger — counter-example | ~19,000 | fresh ginger · China | SIDA | NR | Schaller & Schieberle 2020 10.1021/acs.jafc.0c06733 | abstract |
| I. Terpenoid, phenylpropanoid | ISO 3518:2002 range for α-santalol (S. album oil), per the introduction | 41–54 % | sandalwood oil | ISO 3518:2002 (cited secondarily) | Kucharska et al. 2021 10.3390/molecules26082249 | full | |
| I. Terpenoid, phenylpropanoid | ISO 3518:2002 range for β-santalol, per the introduction | 16–24 % | sandalwood oil | ISO 3518:2002 (cited secondarily) | Kucharska et al. 2021 10.3390/molecules26082249 | full | |
| I. Terpenoid, phenylpropanoid | Number of commercial ‘sandalwood’ oils meeting ISO 3518 (α-santalol) | 0/6 samples | commercial sandalwood oils · EU (Poland) | GC-MS HP-INNOWax, % area | 6 | Kucharska et al. 2021 10.3390/molecules26082249 | full |
| I. Terpenoid, phenylpropanoid | α-Santalol in the only Indian S. album sample (below the 41% minimum) | 37.12 % area | S. album oil · India | GC-MS | 1 | Kucharska et al. 2021 10.3390/molecules26082249 | full |
| I. Terpenoid, phenylpropanoid | β-Santalol in the Indian S. album sample | 21.95 % area | S. album oil · India | GC-MS | 1 | Kucharska et al. 2021 10.3390/molecules26082249 | full |
| I. Terpenoid, phenylpropanoid | Valerianol in ‘West Indian sandalwood’ (Amyris balsamifera) | 14.38–14.53 % area | Amyris oil | GC-MS | 2 | Kucharska et al. 2021 10.3390/molecules26082249 | full |
| I. Terpenoid, phenylpropanoid | (−)-(Z)-β-Santalol is the main sandalwood odorant; GC-O dilution factor | 1024 FD | sandalwood oil | GC-O (Brunke 1995, cited secondarily) | NR | Birkbeck 2017 10.2533/chimia.2017.823 | full |
| I. Terpenoid, phenylpropanoid | (+)-(Z)-β-Santalol is odourless | odourless | β-santalol | asymmetric synthesis (Helmchen, cited secondarily) | Birkbeck 2017 10.2533/chimia.2017.823 | full | |
| I. Terpenoid, phenylpropanoid | Nor-bergamotenone GC-O dilution factor (nutty, sandalwood odour) | 256 FD | sandalwood oil | GC-O | NR | Birkbeck 2017 10.2533/chimia.2017.823 | full |
| I. Terpenoid, phenylpropanoid | Sesquiterpene alcohols in East Indian sandalwood oil | >90 % | S. album oil · India | review | Birkbeck 2017 10.2533/chimia.2017.823 | full | |
| I. Terpenoid, phenylpropanoid | Steam-distillation yield of sandalwood from heartwood | 5–7 % | S. album wood | steam distillation | Birkbeck 2017 10.2533/chimia.2017.823 | full | |
| I. Terpenoid, phenylpropanoid | S. spicatum contains about half the (Z)-α/β-santalol of S. album | ~0.5× | S. spicatum · Australia | review | Birkbeck 2017 10.2533/chimia.2017.823 | full | |
| I. Terpenoid, phenylpropanoid | Key odorant of vetiver: (+)-2-epi-ziza-6(13)en-3-one, threshold | 29 pg/L air | vetiver oil | synthesis + GC-O | NR | List et al. 2020 10.1002/anie.202014609 | partial |
| I. Terpenoid, phenylpropanoid | Khusimol in commercial vetiver from 9 origins | 3.4–13.7 % | vetiver oil · Brazil, China, Haiti, India, Java, Madagascar, Mexico, Réunion, El Salvador | GC/MS | 9 origins (n per origin NR) | Champagnat et al. 2006 10.1080/10412905.2006.9699129 | abstract |
| I. Terpenoid, phenylpropanoid | α-Vetivone in commercial vetiver | 2.5–6.3 % | vetiver oil · 9 countries | GC/MS | 9 origins | Champagnat et al. 2006 10.1080/10412905.2006.9699129 | abstract |
| I. Terpenoid, phenylpropanoid | β-Vetispirene in vetiver | 1.6–4.5 % | vetiver oil · 9 countries | GC/MS | 9 origins | Champagnat et al. 2006 10.1080/10412905.2006.9699129 | abstract |
| I. Terpenoid, phenylpropanoid | Vetiselinenol in vetiver | 1.3–7.8 % | vetiver oil · 9 countries | GC/MS | 9 origins | Champagnat et al. 2006 10.1080/10412905.2006.9699129 | abstract |
| I. Terpenoid, phenylpropanoid | No significant compositional difference between the 9 vetiver origins | qualitative | vetiver oil · 9 countries | HCA/PCA | 9 origins | Champagnat et al. 2006 10.1080/10412905.2006.9699129 | abstract |
| I. Terpenoid, phenylpropanoid | β-Vetivone in vetiver (summary table) | 2.0–4.9 % | vetiver oil | NR | NR | Suyono & Susanti 2020 10.5220/0009954400090012 | full |
| I. Terpenoid, phenylpropanoid | Patchoulol (Ling et al. 1992, cited secondarily) | 31.86 % | patchouli oil | NR | NR | Khairan et al. 2020 (secondary) 10.5220/0009956600670073 | full |
| I. Terpenoid, phenylpropanoid | Patchoulol across 4 harvest seasons (Blank et al. 2011, cited secondarily) | 55.25–68.41 % | patchouli oil · NR (Brazil?) | GC-FID | 4 seasons | Khairan et al. 2020 (secondary) 10.5220/0009956600670073 | full |
| I. Terpenoid, phenylpropanoid | Patchoulol by Chinese province: Guangxi/Guangdong/Hunan (cited secondarily) | 40.81 / 43.51 / 51.70 % | patchouli oil · China | GC-FID + chemometrics | 36 | Khairan et al. 2020 (secondary) 10.5220/0009956600670073 | full |
| I. Terpenoid, phenylpropanoid | α-Bulnesene in patchouli (Blank 2011, cited secondarily) | 5.82–10.32 % | patchouli oil | GC-FID | 4 seasons | Khairan et al. 2020 (secondary) 10.5220/0009956600670073 | full |
| I. Terpenoid, phenylpropanoid | α-Guaiene in patchouli (Blank 2011) | 3.73–7.43 % | patchouli oil | GC-FID | 4 seasons | Khairan et al. 2020 (secondary) 10.5220/0009956600670073 | full |
| I. Terpenoid, phenylpropanoid | Pogostone in Chinese patchouli | 2.11–9.65 % | patchouli oil · China | GC-FID | 36 | Khairan et al. 2020 (secondary) 10.5220/0009956600670073 | full |
| I. Terpenoid, phenylpropanoid | Heartwood oil composition of J. virginiana: α-cedrene/β-cedrene/thujopsene/cedrol/widdrol | 27.2/7.7/27.6/15.8/1.0 % | J. virginiana cedarwood oil · Bastrop Co., Texas | steam distillation 20 h; GLC + GC-MS | 9 | Adams 1987 10.1007/bf02859346 | full |
| I. Terpenoid, phenylpropanoid | Heartwood oil composition of J. ashei: α-cedrene/β-cedrene/thujopsene/cedrol/widdrol | 1.8/1.6/60.4/19.0/1.1 % | J. ashei cedarwood oil · Junction/Ozona, Texas | steam distillation 20 h; GLC + GC-MS | 10 | Adams 1987 10.1007/bf02859346 | full |
| I. Terpenoid, phenylpropanoid | Heartwood oil composition of J. occidentalis var. occidentalis: α-cedrene/β-cedrene/thujopsene/cedrol/widdrol | 8.8/2.6/18.9/38.9/1.6 % | J. occidentalis var. occidentalis cedarwood oil · Malheur Co., Oregon | steam distillation 20 h; GLC + GC-MS | 10 | Adams 1987 10.1007/bf02859346 | full |
| I. Terpenoid, phenylpropanoid | Heartwood oil composition of J. deppeana: α-cedrene/β-cedrene/thujopsene/cedrol/widdrol | 16.9/3.9/14.9/26.4/1.0 % | J. deppeana cedarwood oil · Jeff Davis Co., Texas | steam distillation 20 h; GLC + GC-MS | 10 | Adams 1987 10.1007/bf02859346 | full |
| I. Terpenoid, phenylpropanoid | Number of volatile/semi-volatile compounds identified in agarwood | >150 compounds | agarwood (Aquilaria) | review | Naef 2011 10.1002/ffj.2034 | abstract | |
| I. Terpenoid, phenylpropanoid | Total sesquiterpenes + chromones in agarwood from 4 Aquilaria species; sesquiterpene/chromone ratio | 367 (55.86% / 44.14%) compounds | agarwood · A. sinensis, A. malaccensis, A. crassna, A. subintegra | review | Gao et al. 2019 10.1039/C8RA09409H | full | |
| I. Terpenoid, phenylpropanoid | Resin content (ethanol extract) of wild Kynam | 49.85 ± 9.94 % | wild Kynam agarwood · Vietnam (3), Hainan (2), Hong Kong (2) | ethanol reflux extraction | 7 | Yang et al. 2021 10.3390/molecules26020436 | full |
| I. Terpenoid, phenylpropanoid | Resin content of cultivated Kynam | 46.52 ± 11.25 % | cultivated Kynam agarwood (grafted A. sinensis) · Dianbai, Guangdong | ethanol reflux extraction | 22 | Yang et al. 2021 10.3390/molecules26020436 | full |
| I. Terpenoid, phenylpropanoid | 2-(2-Phenylethyl)chromones 59+60 in wild Kynam | 43.89–73.04 % (area-normalised) | wild Kynam agarwood · Vietnam/Hainan/Hong Kong | ultrasonic Et2O extraction; GC-MS HP-5MS | 7 | Yang et al. 2021 10.3390/molecules26020436 | full |
| I. Terpenoid, phenylpropanoid | 2-(2-Phenylethyl)chromones 59+60 in cultivated Kynam | 72.43–95.61 % | cultivated Kynam agarwood · Guangdong | GC-MS | 22 | Yang et al. 2021 10.3390/molecules26020436 | full |
| I. Terpenoid, phenylpropanoid | Number of guaianes / agarofurans: wild vs cultivated Kynam | 10/3 vs 3/1 compounds | Kynam agarwood | GC-MS | 7 vs 22 | Yang et al. 2021 10.3390/molecules26020436 | full |
| I. Terpenoid, phenylpropanoid | LD50 trans- vs cis-anethole (mouse i.p.; Caujolle & Meynier 1958) | 1410 vs 95 mg/kg bw | anethole | acute toxicity | NR | JECFA 1967 (FAO NMRS 44A) NR (JECFA WHO/Food Add./68.33) | full |
| I. Terpenoid, phenylpropanoid | LD50 trans- vs cis-anethole (mouse i.p.; Boissier et al. 1967) | 650 vs 135 mg/kg bw | anethole | acute toxicity | NR | JECFA 1967 (FAO NMRS 44A) NR (JECFA WHO/Food Add./68.33) | full |
| I. Terpenoid, phenylpropanoid | LD50 trans- vs cis-anethole (rat i.p.; Boissier et al. 1967) | 900 vs 93 mg/kg bw | anethole | acute toxicity | NR | JECFA 1967 (FAO NMRS 44A) NR (JECFA WHO/Food Add./68.33) | full |
| I. Terpenoid, phenylpropanoid | LD50 trans- vs cis-anethole (rat oral; Shelansky & Gabriel 1958) | 2940 vs 150 mg/kg bw | anethole | acute toxicity | NR | JECFA 1967 (FAO NMRS 44A) NR (JECFA WHO/Food Add./68.33) | full |
| I. Terpenoid, phenylpropanoid | Specification for maximum cis-anethole in anethole | ≤1 % | trans-anethole | GLC | JECFA 1967 NR (WHO/Food Add./68.33) | full | |
| I. Terpenoid, phenylpropanoid | Conditional ADI for trans-anethole (1967) | 0–1.25 mg/kg bw | trans-anethole | NOEL rat 2500 ppm | JECFA 1967 NR (WHO/Food Add./68.33) | full | |
| I. Terpenoid, phenylpropanoid | Estragole: SCF concluded it is a genotoxic carcinogen; no safe threshold set | qualitative | estragole · EU | risk assessment | SCF 2001 (out104) NR (SCF/CS/FLAV/FLAVOUR/6 ADD2 final) | full | |
| I. Terpenoid, phenylpropanoid | Mean / P97.5 estragole exposure (consumers) | 4.3 / 8.7 mg/day | estragole · EU | exposure estimate | SCF 2001 (out104) NR | full | |
| I. Terpenoid, phenylpropanoid | Estragole in tarragon oil (SCF) | 60–75 % of oil | tarragon oil | literature compilation | NR | SCF 2001 (out104) NR | full |
| I. Terpenoid, phenylpropanoid | Estragole in sweet basil oil (SCF) | 20–43 % of oil | sweet basil oil | literature compilation | NR | SCF 2001 (out104) NR | full |
| I. Terpenoid, phenylpropanoid | Estragole in sweet fennel oil (SCF) | 5–20 % of oil | sweet fennel oil | literature compilation | NR | SCF 2001 (out104) NR | full |
| I. Terpenoid, phenylpropanoid | Estragole in anise oil (anis vert) (SCF) | ~1 % of oil | anise oil (anis vert) | literature compilation | NR | SCF 2001 (out104) NR | full |
| I. Terpenoid, phenylpropanoid | Estragole in star anise oil (SCF) | 5–6 % of oil | star anise oil | literature compilation | NR | SCF 2001 (out104) NR | full |
| I. Terpenoid, phenylpropanoid | Estragole in sweet fennel oil (EMA Table 1) | 1.5–5.0 % of oil | sweet fennel oil | compilation (EFSA 2009, CoE) | NR | EMA/HMPC/137212/2005 Rev 1 (2014 draft) NR (EMA doc ID) | full |
| I. Terpenoid, phenylpropanoid | Estragole in bitter fennel oil (EMA Table 1) | 3.5–12.0 % of oil | bitter fennel oil | compilation (EFSA 2009, CoE) | NR | EMA/HMPC/137212/2005 Rev 1 (2014 draft) NR (EMA doc ID) | full |
| I. Terpenoid, phenylpropanoid | Estragole in anise oil (EMA Table 1) | 1–5 % of oil | anise oil | compilation (EFSA 2009, CoE) | NR | EMA/HMPC/137212/2005 Rev 1 (2014 draft) NR (EMA doc ID) | full |
| I. Terpenoid, phenylpropanoid | Estragole in star anise oil (EMA Table 1) | 5–6 % of oil | star anise oil | compilation (EFSA 2009, CoE) | NR | EMA/HMPC/137212/2005 Rev 1 (2014 draft) NR (EMA doc ID) | full |
| I. Terpenoid, phenylpropanoid | Estragole in tarragon oil (EMA Table 1) | 60–75 % of oil | tarragon oil | compilation (EFSA 2009, CoE) | NR | EMA/HMPC/137212/2005 Rev 1 (2014 draft) NR (EMA doc ID) | full |
| I. Terpenoid, phenylpropanoid | Estragole in basil oil (EMA Table 1) | 20–89 % of oil | basil oil | compilation (EFSA 2009, CoE) | NR | EMA/HMPC/137212/2005 Rev 1 (2014 draft) NR (EMA doc ID) | full |
| I. Terpenoid, phenylpropanoid | Acceptable intake of estragole in herbal medicinal products | 10 µg/kg bw/day | estragole · EU | BMDL10 10 mg/kg ÷ 1,000 | EMA/HMPC/137212/2005 Rev 1 NR | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of estragole in dairy products | 50 mg/kg | estragole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of estragole in processed fruit, vegetables, nuts and seeds | 50 mg/kg | estragole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of estragole in fish products | 50 mg/kg | estragole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of estragole in non-alcoholic beverages | 10 mg/kg | estragole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of methyleugenol in dairy products | 20 mg/kg | methyleugenol · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of methyleugenol in meat | 15 mg/kg | methyleugenol · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of methyleugenol in fish | 10 mg/kg | methyleugenol · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of methyleugenol in soups and sauces | 60 mg/kg | methyleugenol · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of methyleugenol in savoury snacks | 20 mg/kg | methyleugenol · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of methyleugenol in non-alcoholic beverages | 1 mg/kg | methyleugenol · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of safrole in meat | 15 mg/kg | safrole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of safrole in fish | 15 mg/kg | safrole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of safrole in soups and sauces | 25 mg/kg | safrole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Maximum level of safrole in non-alcoholic beverages | 1 mg/kg | safrole · EU | Reg. (EC) 1334/2008 Annex III Part B | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Estragole, methyleugenol, safrole, β-asarone, coumarin, pulegone, thujone... may not be added as such to food | Annex III Part A | multiple substances · EU | Reg. (EC) 1334/2008 | EU 1334/2008 NR (CELEX 32008R1334) | full | |
| I. Terpenoid, phenylpropanoid | Methyleugenol: SCF concluded it is a genotoxic carcinogen | qualitative | methyleugenol · EU | risk assessment | SCF 2001 (out102) NR | full | |
| I. Terpenoid, phenylpropanoid | Mean / P97.5 methyleugenol exposure | 13 / 36 mg/person/day | methyleugenol · UK (calculated) | estimate | SCF 2001 (out102) NR | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 4 (fine fragrance) | 0.011 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 5A (body lotion) | 0.0015 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 1 & 3 | 0.00042 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 2 | 0.0015 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 6 | 0.0010 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 8 | 0.000069 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for methyleugenol in the finished product, Cat 12 | 0.066 % | methyleugenol · international | IFRA Standard Amendment 51 (2023), Restriction | IFRA STD 100 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | IFRA limit for total safrole+isosafrole+dihydrosafrole in the finished product (all categories) | 0.01 % | safrole, isosafrole, dihydrosafrole · international | IFRA Amendment 17 (1987) | IFRA STD 179 NR (IFRA Standard) | full | |
| I. Terpenoid, phenylpropanoid | Safrole: ‘reasonably anticipated to be a human carcinogen’, first listed | 1981 | safrole · USA | NTP RoC 15th ed. | NTP RoC 15 NR (NTP RoC profile) | full | |
| I. Terpenoid, phenylpropanoid | FDA bans the addition of safrole/sassafras oil to food | 1960 | safrole · USA | regulation | NTP RoC 15 NR | full | |
| I. Terpenoid, phenylpropanoid | Output of safrole-rich oil in East/South-East Asia (UNODC 2006, cited secondarily) | ~1,500 tonnes/year | safrole-rich oil · China ~800; Myanmar 230–490; Cambodia 250; Laos 45; Indonesia 35 | survey | TNI (Blickman) 2009 NR (press/NGO) | full | |
| I. Terpenoid, phenylpropanoid | Number of safrole-rich plant species in East and South-East Asia (UNODC 2006) | 361 species | safrole-rich plants · East/South-East Asia | survey | TNI (Blickman) 2009 NR | full | |
| I. Terpenoid, phenylpropanoid | Vietnam bans sassafras oil production (per TNI; legal text not verified) | 1999 | safrole-rich oil · Vietnam | press | TNI (Blickman) 2009 NR | full | |
| I. Terpenoid, phenylpropanoid | Cinnamaldehyde in Yen Bai cassia bark oil | ~93.3 % | Cinnamomum cassia bark oil · Yen Bai, Vietnam | steam distillation 180 min; GC-MS | NR | Study on the production and composition of essential oil from Cinnamomum cassia bark in Yen Bai province of Vietnam · Tropical Journal of Natural Product Research 8(4):6807-6813, 2024 NR (Trop J Nat Prod Res 8:6807) | abstract |
| I. Terpenoid, phenylpropanoid | Yield of Yen Bai cassia bark oil | 3.38 % | Cinnamomum cassia bark · Yen Bai, Vietnam | steam distillation | NR | Study on the production and composition of essential oil from Cinnamomum cassia bark in Yen Bai province of Vietnam · Tropical Journal of Natural Product Research 8(4):6807-6813, 2024 NR | abstract |
| I. Terpenoid, phenylpropanoid | Oxidation products of d-limonene on air exposure: (R)-carvone, limonene oxide (strong sensitiser), carveol (negligible) | 5 main products | d-limonene · Sweden | GC; FCAT, GPMT | NR | Karlberg et al. 1992 10.1111/j.1600-0536.1992.tb00129.x | abstract |
| I. Terpenoid, phenylpropanoid | Linalool is unstable after 45 weeks of air exposure: ~30% remains, hydroperoxides ~15% | 30 / 15 % | linalool · Sweden (dossier) | experimental oxidation | NR | ECHA RAC 2015 NR (ECHA RAC opinion CLH linalool) | full |
| I. Terpenoid, phenylpropanoid | Linalool in commercial products aged ≥2 years: oxides ≤1.8%, hydroperoxides ~0.6% | 1.8 / 0.6 % | commercial linalool · EU | industry data | NR | ECHA RAC 2015 NR | full |
| I. Terpenoid, phenylpropanoid | Tocopherol 200–300 ppm reduces linalool hydroperoxide formation after 23 days at room temperature | >30-fold | linalool · EU | industry semi-quantitative colorimetric test | NR | ECHA RAC 2015 NR | full |
| I. Terpenoid, phenylpropanoid | RAC classification of linalool | Skin Sens. 1B (H317) | linalool · EU | CLP | ECHA RAC 2015 NR | full | |
| I. Terpenoid, phenylpropanoid | EC3 (LLNA) of linalool hydroperoxides in Sköld 2004 (RAC regards it as borderline) | 1.6 % | linalool hydroperoxide · Sweden | LLNA | NR | ECHA RAC 2015 citing Sköld et al. 2004 10.1021/tx049831z | partial |
| I. Terpenoid, phenylpropanoid | Proposed patch-test concentration for oxidised linalool | 6.0 % in petrolatum | oxidised linalool · Sweden and other countries | patch test | 3418 | Christensson et al. 2010 10.1111/j.1600-0536.2009.01657.x | abstract |
| I. Terpenoid, phenylpropanoid | EC3 of pure linalyl acetate vs after 10 weeks of oxidation | 25 → 3.6 % | linalyl acetate · Sweden | LLNA | NR | Sköld et al. 2008 10.1111/j.1600-0536.2007.01262.x | abstract |
| I. Terpenoid, phenylpropanoid | Main linalool hydroperoxide (DFT + experiment): 7-hydroperoxy-3,7-dimethylocta-1,5-dien-3-ol | qualitative | linalool | DFT | Bäcktorp et al. 2006 10.1021/jp0603278 | abstract | |
| I. Terpenoid, phenylpropanoid | Conditions for acid-catalysed citral degradation in the model | pH 1.8; 40 °C; 4 days | citral (citric acid emulsion) · Germany | HRGC + sniffing | NR | Schieberle et al. 1988 10.1007/BF01454320 | abstract |
| I. Terpenoid, phenylpropanoid | Air threshold of a citral degradation product: p-cresol | 0.3–1.0 ng/L air | p-cresol · Germany | GC-O | NR | Schieberle et al. 1988 10.1007/BF01454320 | abstract |
| I. Terpenoid, phenylpropanoid | Air threshold of a citral degradation product: o-cresol | 0.7–2.7 ng/L air | o-cresol · Germany | GC-O | NR | Schieberle et al. 1988 10.1007/BF01454320 | abstract |
| I. Terpenoid, phenylpropanoid | Air threshold of a citral degradation product: p-methylacetophenone | 2.7–10.8 ng/L air | p-methylacetophenone · Germany | GC-O | NR | Schieberle et al. 1988 10.1007/BF01454320 | abstract |
| I. Terpenoid, phenylpropanoid | Air threshold of a citral degradation product: α,p-dimethylstyrene | 665–2660 ng/L air | α,p-dimethylstyrene · Germany | GC-O | NR | Schieberle et al. 1988 10.1007/BF01454320 | abstract |
| I. Terpenoid, phenylpropanoid | Isomerisation geranial→neral / neral→geranial with soy protein at pH 7.0 over 100 minutes | ~37 / ~60 % | citral · China | GC | NR | Guo et al. 2022 10.3389/fnut.2022.929023 | full |
| I. Terpenoid, phenylpropanoid | p-Cymene in fresh tea tree oil vs signs of oxidation | 2–4 vs ≥6 % | tea tree oil | industry experience | Tisserand Institute (web) NR (web) | full | |
| I. Terpenoid, phenylpropanoid | Temperature, light and oxygen are the main factors causing oxidation and polymerisation of essential oils | qualitative | essential oils | review | Turek & Stintzing 2013 10.1111/1541-4337.12006 | abstract | |
| II. Non-terpenoid families | Odour detection threshold (ODT, P=0.5 between chance and perfect) of propanal in air | 2.0 ppb (by volume) | propanal · USA (laboratory) | VDD8 vapour-delivery device, ascending 3-AFC, concentrations checked by GC-FID; logistic function | 16 | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Odour detection threshold (ODT, P=0.5 between chance and perfect) of butanal in air | 0.46 ppb (by volume) | butanal · USA (laboratory) | VDD8 vapour-delivery device, ascending 3-AFC, concentrations checked by GC-FID; logistic function | 18 | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Odour detection threshold (ODT, P=0.5 between chance and perfect) of hexanal in air | 0.33 ppb (by volume) | hexanal · USA (laboratory) | VDD8 vapour-delivery device, ascending 3-AFC, concentrations checked by GC-FID; logistic function | 16 | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Odour detection threshold (ODT, P=0.5 between chance and perfect) of octanal in air | 0.17 ppb (by volume) | octanal · USA (laboratory) | VDD8 vapour-delivery device, ascending 3-AFC, concentrations checked by GC-FID; logistic function | 16 | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Odour detection threshold (ODT, P=0.5 between chance and perfect) of nonanal in air | 0.53 ppb (by volume) | nonanal · USA (laboratory) | VDD8 vapour-delivery device, ascending 3-AFC, concentrations checked by GC-FID; logistic function | 17 | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Odour detection threshold (ODT, P=0.5 between chance and perfect) of helional in air | 0.14 ppb (by volume) | helional · USA (laboratory) | VDD8 vapour-delivery device, ascending 3-AFC, concentrations checked by GC-FID; logistic function | 17 | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Threshold trend with chain length: falls from propanal to octanal (lowest in the series), reverses and rises at nonanal | C8 = minimum | straight-chain aldehydes C3–C9 | as above | 43 people in total | Cometto-Muñiz & Abraham 2010 10.1093/chemse/bjq018 | full |
| II. Non-terpenoid families | Odour threshold of hexanal in the Leffingwell compilation table | 4.5–5 ppb | hexanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of heptanal in the Leffingwell compilation table | 3 ppb | heptanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of octanal in the Leffingwell compilation table | 0.7 ppb | octanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of nonanal in the Leffingwell compilation table | 1 ppb | nonanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of decanal in the Leffingwell compilation table | 0.1–2 ppb | decanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of undecanal in the Leffingwell compilation table | 5 ppb | undecanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of dodecanal in the Leffingwell compilation table | 2 ppb | dodecanal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of (E)-2-decenal (recorded as ‘2-decenal’) in the Leffingwell compilation table | 0.3–0.4 ppb | (E)-2-decenal (recorded as ‘2-decenal’) | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of (E)-2-nonenal in the Leffingwell compilation table | 0.08–0.1 ppb | (E)-2-nonenal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of (E,E)-2,4-decadienal in the Leffingwell compilation table | 0.07 ppb | (E,E)-2,4-decadienal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of (Z)-3-hexenal in the Leffingwell compilation table | 0.25 ppb | (Z)-3-hexenal | Literature compilation (ASTM DS 48A, Buttery et al.) | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour descriptions of straight-chain aldehydes by chain length: short chains pungent and unpleasant; C8–C12 waxy–floral; nonanal fatty-waxy-floral; decanal fatty-orange; undecanal green-fatty-orange-blossom; dodecanal fatty-orange-blossom; C14 weak, fatty, citrus-ambergris | qualitative | aldehyde C9–C14 | Sensory description (compiled from Arctander; Gibka & Glinski) | NR | Cotton 2008, Molecule of the Month (Univ. Bristol) – Chanel No 5 & 2-methylundecanal NR | full |
| II. Non-terpenoid families | Adding a methyl group at C2 makes the odour stronger and more pleasant and reduces the fatty note (e.g. 2-methylundecanal: herbal–orange–ambergris) | qualitative | 2-methylalkanal C8–C13 | Sensory description | NR | Cotton 2008, Molecule of the Month (Bristol) NR | full |
| II. Non-terpenoid families | History: 2-methylundecanal was used by Robert Bienaimé in Quelques Fleurs (1912); Ernest Beaux used undecanal, dodecanal and undec-10-enal in Rallet No. 1 (1914) and then added 2-methylalkanals; the top note of today’s Chanel No 5 contains C10–C12 aldehydes | 1912; 1914 | C10–C12 aldehydes, 2-methylundecanal · France | History (citing Kraft, Leard & Goutell 2007, Perfumer & Flavorist) | NR | Cotton 2008, Molecule of the Month (Bristol) NR | full |
| II. Non-terpenoid families | Odour threshold of ethyl butyrate in the Leffingwell table | 1 ppb | ethyl butyrate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of ethyl isobutyrate in the Leffingwell table | 0.1 ppb | ethyl isobutyrate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of ethyl 2-methylbutyrate in the Leffingwell table | 0.1–0.3 ppb | ethyl 2-methylbutyrate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of ethyl hexanoate in the Leffingwell table | 1 ppb | ethyl hexanoate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of isoamyl acetate in the Leffingwell table | 2 ppb | isoamyl acetate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of hexyl acetate in the Leffingwell table | 2 ppb | hexyl acetate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of ethyl acetate in the Leffingwell table | 5–5000 ppb | ethyl acetate | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Inference from the same table: esters branched in the acid part (isobutyrate, 2-methylbutyrate) have thresholds about 3–10 times lower than the straight-chain ester with the same carbon number (ethyl butyrate) | ~3–10× ratio | ethyl butyrate vs ethyl isobutyrate / ethyl 2-methylbutyrate | Inference from the table data | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Fruit volatile esters are formed in the final step by alcohol acyltransferase (AAT), which joins an alcohol to an acyl-CoA; the enzyme’s substrate preference does not fully match the fruit’s ester profile → precursor (alcohol) supply is the limiting factor; feeding SAAT-transgenic petunia with isoamyl alcohol produced the corresponding acetate | qualitative | fruit esters (strawberry, banana) · Fragaria vesca, F. × ananassa, Musa sapientum | Recombinant expression in E. coli; transgenic plants | NR | Beekwilder et al. 2004 Plant Physiol 135:1865 10.1104/pp.104.042580 | abstract |
| II. Non-terpenoid families | OAV of ethyl octanoate in Chinese Syrah wines (Ningxia / Yunnan) | 54.9 / 11.7 dimensionless | ethyl octanoate · China: Ningxia (NS), Yunnan (YS) | GC-O-MS, quantification, aroma reconstitution | NR | Zhao et al. 2017 Molecules 22:1045 10.3390/molecules22071045 | partial |
| II. Non-terpenoid families | OAV of ethyl hexanoate in Chinese Syrah wines (Ningxia / Yunnan) | 38.1 / 10.8 dimensionless | ethyl hexanoate · China: Ningxia (NS), Yunnan (YS) | GC-O-MS, quantification, aroma reconstitution | NR | Zhao et al. 2017 Molecules 22:1045 10.3390/molecules22071045 | partial |
| II. Non-terpenoid families | OAV of ethyl isovalerate in Chinese Syrah wines (Ningxia / Yunnan) | 43.8 / 27.3 dimensionless | ethyl isovalerate · China: Ningxia (NS), Yunnan (YS) | GC-O-MS, quantification, aroma reconstitution | NR | Zhao et al. 2017 Molecules 22:1045 10.3390/molecules22071045 | partial |
| II. Non-terpenoid families | OAV of ethyl isobutyrate in Chinese Syrah wines (Ningxia / Yunnan) | 17.6 / 10.9 dimensionless | ethyl isobutyrate · China: Ningxia (NS), Yunnan (YS) | GC-O-MS, quantification, aroma reconstitution | NR | Zhao et al. 2017 Molecules 22:1045 10.3390/molecules22071045 | partial |
| II. Non-terpenoid families | OAV of isoamyl acetate in Chinese Syrah wines (Ningxia / Yunnan) | 13.6 / 8.1 dimensionless | isoamyl acetate · China: Ningxia (NS), Yunnan (YS) | GC-O-MS, quantification, aroma reconstitution | NR | Zhao et al. 2017 Molecules 22:1045 10.3390/molecules22071045 | partial |
| II. Non-terpenoid families | Benzyl acetate in Egyptian J. sambac: 23.7 % (headspace of concrete) / 14.2 % (absolute) | 23.7 / 14.2 % GC area | Jasminum sambac – concrete HS & absolute · Egypt (flowers picked in July) | HS-SPME (PDMS fibre) and absolute; GC-MS | NR | Edris, Chizzola & Franz 2008 Eur Food Res Technol 226:621 10.1007/s00217-007-0623-y | partial |
| II. Non-terpenoid families | Linalool / benzyl alcohol / (Z)-3-hexenyl benzoate / (E,E)-α-farnesene in Egyptian J. sambac (HS / absolute) | 10.6/6.3; 7.7/8.4; 4.9/9.4; 15.9/13.1 % GC area | Jasminum sambac · Egypt | HS-SPME and absolute; GC-MS | NR | Edris et al. 2008 10.1007/s00217-007-0623-y | partial |
| II. Non-terpenoid families | Odour threshold of γ-hexalactone in the Leffingwell table | 1600 ppb | γ-hexalactone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of γ-heptalactone in the Leffingwell table | 400 ppb | γ-heptalactone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of γ-octalactone in the Leffingwell table | 7 ppb | γ-octalactone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of γ-decalactone in the Leffingwell table | 11 ppb | γ-decalactone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of γ-dodecalactone in the Leffingwell table | 7 ppb | γ-dodecalactone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Odour threshold of δ-decalactone in the Leffingwell table | 100 ppb | δ-decalactone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Inference from the same table: γ-lactone thresholds fall by ~2 orders of magnitude as the chain grows from C6–C7 to C8–C12; δ-decalactone (6-membered ring) has a threshold ~9 times higher than γ-decalactone (5-membered ring) | ~200× ; ~9× ratio | γ-/δ-lactones | Inference from the table data | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Detection thresholds in Australian red wine: lowest 8 µg/L ((R)-γ-dodecalactone), highest 285 µg/L ((R)-γ-nonalactone); the two enantiomers differ significantly (p<0.05) for every lactone except γ-decalactone | 8 – 285 µg/L | (R)/(S)-γ-octa/nona/deca/undeca/dodecalactone · Australia (red wine) | Sensory threshold in a wine matrix; enantioselective GC-MS | 34 red wines + 7 botrytis white wines (analysed) | Cooke et al. 2009 J Agric Food Chem 57:2462 10.1021/jf802866f | abstract |
| II. Non-terpenoid families | (R)-γ-nonalactone predominates over (S) in most dry red and botrytis wines; (R)-γ-octalactone predominates in botrytis wines | qualitative | γ-nonalactone, γ-octalactone · Australia | enantioselective GC-MS | 41 wines | Cooke et al. 2009 10.1021/jf802866f | abstract |
| II. Non-terpenoid families | Cryptocarya massoy oil (bark): C-10 massoia lactone / C-12 massoia lactone / benzyl benzoate; yield | 64.8 / 17.4 / 13.4; yield 0.70 % (% GC area) | massoia oil – bark · Papua New Guinea (Central Province, near Epa village; 2003) | Hydrodistillation 8 h; GC-MS (BPX-5), RI + mass spectra | NR | Rali, Wossa & Leach 2007 Molecules 12:149 10.3390/12020149 | full |
| II. Non-terpenoid families | Cryptocarya massoy oil (heartwood): C-10 massoia lactone / C-12 massoia lactone / benzyl benzoate; yield | 68.4 / 27.7 / not detected; yield 1.20 % (% GC area) | massoia oil – heartwood · Papua New Guinea (Central Province, near Epa village; 2003) | Hydrodistillation 8 h; GC-MS (BPX-5), RI + mass spectra | NR | Rali, Wossa & Leach 2007 Molecules 12:149 10.3390/12020149 | full |
| II. Non-terpenoid families | Cryptocarya massoy oil (fruit): C-10 massoia lactone / C-12 massoia lactone / benzyl benzoate; yield | 1.4 / 0.2 / 68.3; yield 1.03 % (% GC area) | massoia oil – fruit · Papua New Guinea (Central Province, near Epa village; 2003) | Hydrodistillation 8 h; GC-MS (BPX-5), RI + mass spectra | NR | Rali, Wossa & Leach 2007 Molecules 12:149 10.3390/12020149 | full |
| II. Non-terpenoid families | Massoia heartwood also contains C-14 massoia lactone 1.4 % and δ-decalactone 2.5 % | 1.4 ; 2.5 % GC area | massoia oil – heartwood · Papua New Guinea | GC-MS | NR | Rali et al. 2007 10.3390/12020149 | full |
| II. Non-terpenoid families | Coumarin content of tonka beans (Dipteryx odorata) | 20.4–43.4 mg/g | coumarin – tonka beans · commercial (origin unknown) | HPLC-DAD 280 nm, MeOH:H2O 80:20 extraction, internal standard 3,4-dimethoxybenzaldehyde | 6 samples × 3 replicates | Toma, Stegmüller & Richling 2025 Eur Food Res Technol 251:513 10.1007/s00217-024-04648-z | partial |
| II. Non-terpenoid families | Cassia bark contains up to 76.1 g/kg coumarin (especially C. loureiroi, C. burmannii); Ceylon cinnamon (C. verum) only traces | ≤ 76.1 g/kg | coumarin – cassia cinnamon | Citation of other studies | NR | Toma et al. 2025 (secondary citation) 10.1007/s00217-024-04648-z | partial |
| II. Non-terpenoid families | Coumarin TDI 0.1 mg/kg body weight/day (based on the hepatotoxicity NOAEL in animals) | 0.1 mg/kg bw/day | coumarin · EU | Toxicological evaluation (EFSA/AFC) | NR | Toma et al. 2025 (citing EFSA) 10.1007/s00217-024-04648-z | partial |
| II. Non-terpenoid families | Coumarin may not be added as such to food (EU Reg. 1334/2008); limit in alcoholic beverages 10 mg/L | 10 mg/L | coumarin · EU | Regulation | — | Toma et al. 2025 (citing Reg. (EC) 1334/2008) 10.1007/s00217-024-04648-z | partial |
| II. Non-terpenoid families | Coumarin is in Annex III (entry 77) of Reg. (EC) 1223/2009; fragrance allergens must be labelled above 0.001 % (leave-on products) or 0.01 % (rinse-off products) | 0.001 ; 0.01 % in the finished product | coumarin (and fragrance allergens in general) · EU | Cosmetics regulation | — | Measurlabs – summary of Reg. (EC) 1223/2009 & (EU) 2023/1545 NR | partial |
| II. Non-terpenoid families | Nitro musks: threshold of musk ketone | 0.1 ng/L air | musk ketone | GC-olfactometry/olfactory threshold (Givaudan) | NR | Hauser, Kraft & Carreira 2020 CHIMIA 74:247 10.2533/chimia.2020.247 | full |
| II. Non-terpenoid families | Thresholds of Moxalone (musky-fruity) and Klausenone | 1.0 ; 1.0 ng/L air | Moxalone, Klausenone | Olfactory evaluation | NR | Hauser et al. 2020 CHIMIA 10.2533/chimia.2020.247 | full |
| II. Non-terpenoid families | Musk Baur – the first nitro musk – discovered by chance by Albert Baur while researching explosives | 1888 (Wikipedia) / 1891 (published in Ber. Dtsch. Chem. Ges., per Moore 2005) | Musk Baur · Germany | History | — | Hauser et al. 2020; Moore 2005 (seminar UIUC); Wikipedia 'Synthetic musk' 10.2533/chimia.2020.247 | full |
| II. Non-terpenoid families | Stoll’s rule (1936): macrocyclic musks need a 14–19-membered ring and at least one C=O or NH group; lactones and keto-ethers are the strongest; >1 oxygen in the ring weakens the odour | 14–19 ring atoms | musk macrocyclic | Structure–odour rules (review) | — | Moore 2005, seminar abstract UIUC (citing Stoll 1936) NR | full |
| II. Non-terpenoid families | Observed upper molecular-weight limit of macrocyclic musks | ~300 g/mol | musk macrocyclic | Structure–odour observation | — | Moore 2005 (citing Kraft & Cadalbert, Chem Eur J 2001) NR | full |
| II. Non-terpenoid families | Beets (1957): MW 200–300, compact structure, a polar group; Theimer & Davies (1967): cross-section 40–57 Ų, length/width ratio 2.8–3.3 | 200–300 ; 40–57 ; 2.8–3.3 g/mol ; Ų ; — | musk | Historical structure–odour models | — | Moore 2005 (citing) NR | full |
| II. Non-terpenoid families | Ružička 1926 established the structures of muscone (15-membered ring) and civetone (17-membered ring); oxidation of both gives the same diacid HO2C-(CH2)15-CO2H; refuted Baeyer’s hypothesis (rings > 8 unstable); Nobel Prize in Chemistry 1939 | 15 ; 17 ring atoms | muscone, civetone · Switzerland | Structural history | — | Moore 2005 (citing Ružička, Stoll & Schinz, Helv Chim Acta 1926) NR | full |
| II. Non-terpenoid families | Macrocyclic musks < 25 % of world musk output in 1998, projected 60–65 % in 2008 | <25 → 60–65 % | macrocyclic musks · global | Market estimate | — | Moore 2005 (citing Gautschi et al., Chimia 2001) NR | full |
| II. Non-terpenoid families | Helvetolide (Firmenich, 1990) was the first commercial alicyclic musk; Cyclomusk (1975) was the first member of the class; Romandolide about 10 years later | 1990 ; 1975 | Helvetolide, Romandolide · Switzerland | History | — | Wikipedia 'Synthetic musk' (citing Eh 2004 Chem Biodivers 1:1975; Kraft 2004) NR | partial |
| II. Non-terpenoid families | Helvetolide = 4-(3,3-dimethyl-1-cyclohexyl)-2,2-dimethyl-3-oxapentyl propionate (Firmenich trade name); use of traditional musks is being progressively restricted because of environmental concerns | qualitative | Helvetolide | Patent | — | US 7,384,906 B2 (Givaudan; inventor P. Kraft; granted 2008) NR | partial |
| II. Non-terpenoid families | Musk ambrette (CAS 83-66-9) – Annex II entry 414; Moskene (116-66-5) – entry 421; Musk tibetene (145-39-1) – entry 422: banned in EU cosmetics | banned | musk ambrette, moskene, tibetene · EU | Reg. (EC) 1223/2009 Annex II | — | CosIng (via cosingchecker.com) NR | partial |
| II. Non-terpenoid families | Limits for musk xylene (CAS 81-15-2, Annex III entry 96): fine fragrance 1.0 %; eau de toilette 0.4 %; other products 0.03 %; excluding oral-care products | 1.0 / 0.4 / 0.03 % of finished product | musk xylene · EU | Directive 2004/88/EC amending Annex III of 76/768/EEC | — | Directive 2004/88/EC (legislation.gov.uk) NR | full |
| II. Non-terpenoid families | Limits for musk ketone (CAS 81-14-1, Annex III entry 97): fine fragrance 1.4 %; eau de toilette 0.56 %; other products 0.042 % | 1.4 / 0.56 / 0.042 % of finished product | musk ketone · EU | Directive 2004/88/EC | — | Directive 2004/88/EC NR | full |
| II. Non-terpenoid families | Musk xylene in REACH Annex XIV entry 1: vPvB properties; application deadline 21/02/2013; sunset date 21/08/2014; no exemptions | 21/08/2014 date | musk xylene · EU | REACH Annex XIV | — | REACH Annex XIV (reachonline.eu) NR | full |
| II. Non-terpenoid families | California (passed 7/10/2025): bans musk ambrette, tibetene, moskene and musk xylene in cosmetics from 01/01/2027; musk ketone limited to 1.4 % / 0.56 % / 0 % (oral care) / 0.042 % | 01/01/2027 effective date | nitro musks · California, USA | State law (H&S Code §108980 extended) | — | SGS SafeGuardS 172/25 (26/11/2025) NR | full |
| II. Non-terpenoid families | Polycyclic musks: US production/import of HHCB (Galaxolide) 1–10 million lb/year (1994–2006); 3.1 million lb (2012) | 1–10 M ; 3.1 M lb/year | HHCB · USA | US EPA CDR/IUR | — | Krowech, Plummer & Hoover 2013 (OEHHA, Biomonitoring California) NR | full |
| II. Non-terpenoid families | HHCB and AHTN in Massachusetts breast milk: HHCB detected in 97 %, mean 220 ng/g lipid (<5–917); AHTN 56 %, mean 46.8 ng/g lipid (<5–144) | 220 ; 46.8 ng/g lipid | HHCB, AHTN · Massachusetts, USA | GC-MS (Reiner et al. 2007) | 39 | OEHHA 2013 (citing Reiner et al. 2007) NR | full |
| II. Non-terpenoid families | log Kow HHCB 5.9; AHTN 5.7 | 5.9 ; 5.7 log Kow | HHCB, AHTN | SRC 2013 | — | OEHHA 2013 NR | full |
| II. Non-terpenoid families | HHCB: EU 1,000–10,000 t/year; the 2008 Dutch risk assessment report concluded it does NOT meet the PBT criteria; ANSES 2019 reached no conclusion and recommended further study of reproductive–developmental toxicity and endocrine mechanisms | 1,000–10,000 t/year | HHCB · EU / France | RMOA (ANSES) | — | ANSES 2019 RMOA HHCB (EC 214-946-9) NR | full |
| II. Non-terpenoid families | Specific anosmia to musk: ~7 % of white people, 0 % of people of African descent (Whissell-Buechy & Amoore); Le Magnen: ~50 % of adult men cannot smell cyclopentadecanolide | ~7 ; ~50 % of subjects | musk (pentadecanolide/cyclopentadecanolide) | Threshold measurement/anosmia classification | NR | Koelega 1976 J Soc Cosmet Chem 27(7) (cited secondarily); original: Whissell-Buechy & Amoore 1973 Nature 242:271 10.1038/242271a0 | partial |
| II. Non-terpenoid families | (−)-Ambrox: odour threshold 0.2 ng/L; isomer (II) almost odourless (>500 ng/L); epi-Ambrox (III) ~10 times weaker | 0.2 ; >500 ; ~10× weaker ng/L | (−)-Ambrox and stereoisomers | Sensory example in a patent | NR | US 10,294,211 (priority GB 2015; Ambrofix™ – Givaudan) NR | partial |
| II. Non-terpenoid families | 9-epi-Ambrox: threshold 0.15 ppb, ‘the lowest ever recorded’ (per Ohloff et al.) | 0.15 ppb | 9-epi-Ambrox | Citing Ohloff et al. | NR | Maleczka & Paquette 1991 J Org Chem 56:6538 NR | partial |
| II. Non-terpenoid families | Ambrox was identified in ambergris tincture in 1977; it arose from research on the oxidation of sclareol (a labdane diterpenoid); the ambergris odour is due to oxidative degradation products of (−)-ambrein | 1977 | Ambrox, ambrein, sclareol | Review | — | Winter 1990 Pure Appl Chem 62:1377 NR | full |
| II. Non-terpenoid families | The ‘spatial accessibility’ of the oxygen atom is essential for ambergris odour; a threshold of accessible polar surface area (1.4 Å probe) is required for activity; e.g. ether 22: 8.0 Ų (active), spiroether 31: 0.7 Ų (almost odourless) | 8.0 ; 0.7 Ų | ambergris-type ethers · Firmenich | MM2 calculation + odour evaluation | — | Winter 1990 Pure Appl Chem 62:1377 NR | full |
| II. Non-terpenoid families | Ohloff & Giersch 1985: intensity rises when an equatorial alkyl group is introduced at C(9) of drimane derivatives; γ-bicyclohomofarnesal: complete stereochemical control over odour perception | qualitative | drimane derivatives | Structure–odour | — | Ohloff & Giersch 1985 Croat Chem Acta 58:491 NR | abstract |
| II. Non-terpenoid families | Iso E Super: an impurity of ~5 % determines the woody odour, with a threshold ~100,000 times lower than the main component; Fahrenheit (1988) 25 %; Perles de Lalique (2007) 80 % | ~5 ; ~10^5 ; 25 ; 80 % ; fold ; % | Iso E Super (OTNE) | Science journalism (Chemistry World) | — | Davies, Chemistry World 'The sweet scent of success' NR | full |
| II. Non-terpenoid families | OTNE (Iso E Super) is a multi-constituent mixture of 3 isomers (CAS 54464-57-2, 68155-66-8, 68155-67-9); IFF patent US 3,929,677 (1975); Eternity (1988) contains 11.7 % OTNE in its fragrance portion | 11.7 % | OTNE | ECHA dossier; patent | — | Wikipedia 'Iso E Super' (citing ECHA, US 3,929,677) NR | partial |
| II. Non-terpenoid families | β-Damascenone in Bulgarian rose oil: 0.14 % by mass but 70.0 % of relative ‘odour units’ | 0.14 ; 70.0 % ; % odour units | β-damascenone – rose oil (Rosa damascena) · Bulgaria | Kováts analysis; odour-unit calculation | NR | Cotton 2015, Molecule of the Month (Bristol), citing Demole et al. 1970 Helv Chim Acta 53:541 10.6084/m9.figshare.5259814 | full |
| II. Non-terpenoid families | β-Damascenone threshold | 0.009 ppb | β-damascenone | Odour-unit table | NR | Cotton 2015 MOTM (Bristol) 10.6084/m9.figshare.5259814 | full |
| II. Non-terpenoid families | β-Damascenone / β-ionone thresholds in the Leffingwell table | 0.002 / 0.007 ppb | β-damascenone, β-ionone | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | β-Damascenone can form from carotenoid (neoxanthin) cleavage with oxidation; present in wine, beer, tea, tomato, baked apple, passion fruit | qualitative | β-damascenone | Review | — | Cotton 2015 MOTM (citing Ohloff et al. 1973 Helv Chim Acta 56:1503) NR | full |
| II. Non-terpenoid families | 1-p-Menthene-8-thiol: threshold 0.000034 ng/L air | 0.000034 ng/L air | 1-p-menthene-8-thiol (grapefruit mercaptan) · Germany | GC-O, air threshold | NR | Schoenauer & Schieberle 2016 J Agric Food Chem 64:3849 10.1021/acs.jafc.6b01645 | abstract |
| II. Non-terpenoid families | Hydrogenating the double bond clearly raises the threshold; an SH group on the ring gives a higher threshold (compared with SH at the tertiary C8) | qualitative | monoterpenoid thiol derivatives | Structure–odour | — | Schoenauer & Schieberle 2016 10.1021/acs.jafc.6b01645 | abstract |
| II. Non-terpenoid families | Thiol thresholds in the Leffingwell table: methanethiol 0.02; propanethiol 3.1; butanethiol 6; benzenethiol 13,500; furfuryl mercaptan 0.005; 1-p-menthene-8-thiol 0.0001 | see ppb fact | thiol | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Sensory thresholds of wine thiols: 4MMP 0.8 ng/L (box tree); 3MH 60 ng/L (grapefruit); 3MHA 4.2 ng/L (passion fruit) | 0.8 ; 60 ; 4.2 ng/L | 4MMP, 3MH, 3MHA · France (Bordeaux) | Threshold in model solution | NR | Musumeci et al. 2015 Molecules 20:12280 (citing Tominaga et al. 1998 JAFC; 2000 AJEV) 10.3390/molecules200712280 | full |
| II. Non-terpenoid families | 4MMP threshold: 0.8 ng/L in model solution but 3 ng/L in white and red wine | 0.8 ; 3 ng/L | 4MMP | Citing Capone et al. 2010 | NR | Ferreira D. et al. (repositorio.ucp.pt, year/journal unclear) NR | partial |
| II. Non-terpenoid families | 4MMP concentrations in wine: Sauvignon blanc NY 27 ± 8; Sauvignon blanc CA 43–50 (regional means); Riesling NY 2.3 ± 2.5; Cabernet Sauvignon < LOD | 27 ; 43–50 ; 2.3 ng/L | 4MMP – wine · New York & California, USA | HS-SPME-GC-MS after extractive alkylation | ~30 NY wines + CA wines | Musumeci et al. 2015 10.3390/molecules200712280 | full |
| II. Non-terpenoid families | 3MH concentrations: Sauvignon blanc NY 446 ± 154; Riesling NY 569 ± 334; Sauvignon blanc CA 438–835; Cabernet Sauvignon CA 405–765 | 446 ; 569 ; 438–835 ; 405–765 ng/L | 3MH – wine · New York & California | HS-SPME-GC-MS | ~30 NY wines + CA wines | Musumeci et al. 2015 10.3390/molecules200712280 | full |
| II. Non-terpenoid families | Polyfunctional thiols in wine arise mainly during fermentation from non-volatile precursors (S-glutathione and S-cysteine conjugates); 3MHA is formed by partial enzymatic acetylation of 3MH | qualitative | 3MH, 3MHA, 4MMP | Review (citing Roland et al. 2011 Chem Rev) | — | Musumeci et al. 2015 10.3390/molecules200712280 | full |
| II. Non-terpenoid families | Hand-squeezed grapefruit juice: 25 odour-active compounds quantified; 4MMP and 1-p-menthene-8-thiol are the key sulphur compounds | 25 compounds | grapefruit juice (Citrus paradisi) · Germany (laboratory) | SIDA quantification + aroma reconstitution | NR | Buettner & Schieberle 2001 J Agric Food Chem 49:1358 10.1021/jf001235x | abstract |
| II. Non-terpenoid families | OAV calculated from the data above: 4MMP in NY Sauvignon blanc = 27/0.8 ≈ 34 (model threshold) or 27/3 ≈ 9 (wine threshold); 3MH = 446/60 ≈ 7.4 | ≈34 or ≈9 ; ≈7.4 dimensionless | 4MMP, 3MH · New York | Calculation | — | Inference from Musumeci et al. 2015 + Ferreira/Capone 2010 10.3390/molecules200712280 | full |
| II. Non-terpenoid families | 2-Methoxy-3-isobutylpyrazine (IBMP): threshold 2 parts per trillion (ppt) | 2 ppt (ng/L) | IBMP | Citing Buttery et al. 1969 (bell pepper) | NR | Harris et al. 1987 Vitis 26:201 (citing Buttery et al. 1969 J Agric Food Chem) NR | full |
| II. Non-terpenoid families | IBMP in 1985 New Zealand Sauvignon blanc: 35 ± 2 ppt (33–38); IPMP at most 6 ppt; SBMP at most ~0.5 ppt | 35 ; ≤6 ; ≤0.5 ppt | methoxypyrazine – wine · New Zealand | GC-MS (isotope dilution) | several bottles from the same lot | Harris et al. 1987 Vitis 26:201 NR | full |
| II. Non-terpenoid families | Pyrazine thresholds (Leffingwell table): 2-methylpyrazine 60–105,000; 2,5-dimethyl 800–1,800; tetramethyl 1,000–10,000; 2-methoxypyrazine 400–700; 2-methoxy-3-methyl 3–7; 2-ethyl-3-methoxy 0.4–0.425; 2-ethyl-3,6-dimethyl 0.4–5; IBMP 0.002–0.016; IPMP 0.002–10; SBMP 0.001 | see ppb fact | pyrazine | Literature compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Inference: adding a methoxy group + a branched alkyl at position 3 lowers the pyrazine threshold from the ppm range (methylpyrazine) to the ppt range (IBMP, SBMP) — a difference of ~5–7 orders of magnitude | ~10^5–10^7-fold | pyrazine | Inference from the table | — | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Indole: threshold 140 ppb (Leffingwell table) | 140 ppb | indole | Compilation | NR | Leffingwell threshold table (archived copy at SZU, Czech Republic); origin recorded by reference number in the table NR | partial |
| II. Non-terpenoid families | Indole in Egyptian J. sambac: 13.1 % (HS of concrete) / 13.4 % (absolute); methyl anthranilate 5.0 % / 4.7 % | 13.1/13.4 ; 5.0/4.7 % GC area | Jasminum sambac · Egypt | HS-SPME; GC-MS | NR | Edris et al. 2008 10.1007/s00217-007-0623-y | partial |
| II. Non-terpenoid families | The ‘foxy’ odour of Concord grapes is mainly due to methyl anthranilate accumulation; AMAT gene (anthraniloyl-CoA:methanol acyltransferase); 426 bp and/or 42 bp deletions in the promoter are associated with high AMAT expression; confirmed in > 1,300 Vitis samples | 426 ; 42 ; >1300 bp ; bp ; samples | methyl anthranilate – V. labrusca grapes · USA | Genetics / gene expression | > 1,300 cultivar samples | Yang et al. 2020 Hortic Res 7:67 10.1038/s41438-020-0304-6 | partial |
| II. Non-terpenoid families | Definition OAV = concentration / odour threshold; compounds with high OAV are usually essential, but there are exceptions (masking, or low-OAV compounds that matter); synthetic aroma models + omission experiments are used for confirmation | definition | — | Methodological review | — | Grosch 2001 Chem Senses 26:533 10.1093/chemse/26.5.533 | abstract |
| II. Non-terpenoid families | Grenache rosé wine (Calatayud): AEDA detected 38 compounds and identified 35; a model of 24 compounds with OAV > 0.5 closely reproduced the aroma; 3MH most important; omitting β-damascenone (second-highest OAV) changed it only slightly | 38 ; 35 ; 24 ; >0.5 compounds ; OAV threshold | Grenache rosé wine · Calatayud, Spain | AEDA, quantification, reconstitution + omission | NR | J Agric Food Chem 2002 50:4048 (Ferreira group, Zaragoza — authors not verified) 10.1021/jf0115645 | abstract |
| II. Non-terpenoid families | The ‘character-impact compound’ concept – review chapter by McGorrin | — | — | Book chapter | — | McGorrin 2007 'Character-impact flavor compounds', Sensory-Directed Flavor Analysis (CRC) 10.1201/9781420017045.ch9 | abstract |
| II. Non-terpenoid families | Rossiter 1996 ‘Structure−Odor Relationships’ Chem Rev 96(8):3201–3240 – metadata verified, full text not accessed | — | — | Review | — | Rossiter 1996 10.1021/cr950068a | abstract |
| II. Non-terpenoid families | Kraft, Bajgrowicz, Denis & Fráter 2000 ‘Odds and Trends: Recent Developments in the Chemistry of Odorants’ Angew Chem Int Ed 39(17):2980–3010 – metadata verified, full text not accessed | — | — | Review | — | Kraft et al. 2000 10.1002/1521-3773(20000901)39:17<2980::AID-ANIE2980>3.0.CO;2-# | abstract |
A monograph compiled from 718 sourced facts collected under a common protocol and cross-checked independently. Items labelled Inference are the compilers’ own judgements. Diagrams are newly drawn from published data. Scientific reference material — not legal or medical advice, and no substitute for the text of the standards.