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Compound library · Biosynthetic pathways

Terpenoid pathway

Plants build them from identical five-carbon blocks

58 compounds in the library

Volatility band
150 °CTop Middle > 290 °CBase

58 compounds follow this pathway Right of it are compounds heavier than the essential-oil range — they remain after the main axis has run out.

This is the largest pathway in aromatics. The plant starts from a five-carbon block called isoprene and joins blocks together: two blocks make a ten-carbon monoterpene, three make a fifteen-carbon sesquiterpene.

That way of assembling explains why every monoterpene has ten carbons and every sesquiterpene fifteen. Look at the formula column in the library and you will see it at once: C10 and C15 again and again.

Once the skeleton is assembled, the plant adds functional groups — hydroxyl to make an alcohol, carbonyl to make an aldehyde or ketone. That is why linalool, citral, camphor and menthol are all terpenoids even though they belong to four different chemical families. Chemical family is about the functional group; pathway is about the skeleton.

Compounds that follow this pathway

CompoundChemical familyBoiling pointThreshold
α-Thujene Monoterpenes 152 °C —
α-Pinene Monoterpenes 155 °C 100 ppb
Camphene Monoterpenes 159 °C —
Sabinene Monoterpenes 163 °C —
β-Pinene Monoterpenes 166 °C 140 ppb
Myrcene Monoterpenes 167 °C 15 ppb
δ-3-Carene Monoterpenes 170 °C —
β-Phellandrene Monoterpenes 172 °C —
α-Terpinene Monoterpenes 175 °C —
α-Phellandrene Monoterpenes 175 °C —
Limonene Monoterpenes 176 °C 200 ppb
1,8-Cineole Oxides 176 °C 1 ppb
cis-β-Ocimene Monoterpenes 177 °C —
p-Cymene Monoterpenes 177 °C 11 ppb
(E)-β-Ocimene Monoterpenes 177 °C —
p-Menth-1-ene Monoterpenes 177 °C —
γ-Terpinene Monoterpenes 183 °C —
Terpinolene Monoterpenes 186 °C 200 ppb
Fenchone Ketones 193 °C —
Linalool Alcohols 198 °C 6 ppb
Camphor Ketones 204 °C 500 ppb
Citronellal Aldehydes 207 °C 10 ppb
Terpinen-4-ol Alcohols 209 °C —
Menthol Alcohols 212 °C 300 ppb
Borneol Alcohols 213 °C —
α-Terpineol Alcohols 219 °C 330 ppb
Linalyl acetate Esters 220 °C —
Citronellol Alcohols 225 °C 40 ppb
Neral Aldehydes 227 °C 30 ppb
Citral Aldehydes 229 °C 30 ppb
Geranial Aldehydes 229 °C 32 ppb
Geraniol Alcohols 230 °C 40 ppb
Lavandulyl acetate Esters 230 °C —
Carvone Ketones 231 °C 10 ppb
Perillaldehyde Aldehydes 237 °C —
β-Elemene Sesquiterpenes 252 °C —
Longifolene Sesquiterpenes 254 °C —
α-Copaene Sesquiterpenes 262 °C —
α-Cedrene Sesquiterpenes 262 °C —
β-Caryophyllene Sesquiterpenes 264 °C 64 ppb
Zingiberene Sesquiterpenes 269 °C —
α-Farnesene Sesquiterpenes 270 °C —
β-Selinene Sesquiterpenes 270 °C —
Bicyclogermacrene Sesquiterpenes 272 °C —
Cedrol Alcohols 273 °C —
Valencene Sesquiterpenes 274 °C —
β-Bisabolene Sesquiterpenes 274 °C —
α-Humulene Sesquiterpenes 275 °C 120 ppb
Germacrene D Sesquiterpenes 275 °C —
δ-Cadinene Sesquiterpenes 275 °C —
Nerolidol Alcohols 276 °C —
Caryophyllene oxide Oxides 280 °C —
Patchoulol Alcohols 287 °C —
Guaiol Alcohols 288 °C —
Nootkatone Ketones 290 °C 1 ppb
α-Vetivone Ketones 300 °C —
α-Santalol Alcohols 301 °C —
α-Bisabolol Alcohols 314 °C —

Three axes, three questions

This library classifies compounds along three axes, and each answers a different question.

Boiling point tells you when you smell a compound — early or late on the smelling strip. Chemical family tells you how it behaves — stable or fragile, and how to recognise it on an analysis. Biosynthetic pathway tells you where it comes from.

The third axis is the explanatory one. The other two describe how compounds cluster into groups; this one says why they cluster that way.