Chirality & Odour Perception

Bicyclic Terpenoid Odorants

by John C. Leffingwell, Ph.D.

Photo by permission of M. Roudintska - Art & Parfum

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones & Furanones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

Bicyclic Terpenoid Odorants

 

(1R,5R)-(+)-alpha-pinene - harsh, terpene-like, minty

NA

(1S,5S)-(-)-alpha-pinene - harsh, terpene-like, coniferous

NA

(R)-(+)-isoborneol - camphoraceous, celluloid-like

NA

(S)-(-)-isoborneol - camphoraceous, sweet & musty

NA

(S)-(+)-2-methylisoborneol - camphoraceous, rubbery (Tyler)

NA

(R)-(-)-2-methylisoborneol - camphoraceous, rubbery (Tyler); also described as musty, mold-like, earthy by Blank & Grosch

0.006-0.012 ng/liter (air)

(R)-(+)-2-methylborneol - camphoraceous, rubbery

NA

(S)-(-)-2-methylborneol - camphoraceous, rubbery

NA

(1R,4S)-(+)-fenchone - camphoraceous, strong, diffusive, sweet odor

240-510

(1S,4R)-(-)-fenchone - camphoraceous, strong, diffusive, sweet odor

350-440

(1R,4R)-(+)-camphor - camphoraceous

1000-1290

(1S,4S)-(-)-camphor - camphoraceous

520

(1S,4R,6S)-6-Acetoxy-1,8-cineole - woody (weak)

NA

(1R,4S,6R)-6-Acetoxy-1,8-cineole - woody, Alpinia galanga like and stronger than the (1S,4R,6S)- isomer

NA

(1S,4R,6R)-6-Acetoxy-1,8-cineole - weak

NA

(1R,4S,6S)-6-Acetoxy-1,8-cineole - fruity, sweet

NA

(1S,4R,5R)-5-Acetoxy-1,8-cineole - sweet floral, weak (virtually to weak to evaluate)

NA

(1R,4S,5S)-5-Acetoxy-1,8-cineole - sweet floral, weak (virtually to weak to evaluate)

NA

(1S,4R,5S)-5-Acetoxy-1,8-cineole - camphoraceous

NA

(1R,4S,5R)-5-Acetoxy-1,8-cineole - mild woody

NA

(1S,2R,4S)-(-)-borneol - camphoraceous, India ink like, slight fatty-putrid ( odor evaluation by GC-olfactometry) (Nishimura); (-)-Borneol has a camphoraceous and evident woody odor (Tabanca et. al & Jogdeo)

80 ppb

(1R,2S,4R)-(+)-borneol - camphoraceous, India ink like ( odor evaluation by GC-olfactometry) (Nishimura); The (+) form has a camphoraceous odor and a slightly sharp, earthy-peppery note different from that of the (-) form (Tabanca et. al).

180 ppb

(1S,2S,5R)-(-)-Isopinocamphone - Sweet camphoraceous, cheap spruce needle oil, also musty-woody

NA

(1R,2R,5S)-(+)-Isopinocamphone - Camphoraceaous, borneol-like, spruce needle note, later also terpineol-like

NA

(1S,2S,4E,5S)-(-)-4-propylidene-isopinocamphone - Woody, musty, terpineol-like, stale

NA

(1R,2R,4E,5R)-(+)-4-propylidene-isopinocamphone - Damascone-like, fine rose odour, ethylrosat®-like, camphoraceous and herbaceous side note

NA

(1S,2S,4E,5S)-(-)-4-heptylidene-isopinocamphone - Mushroom flavour, champignon-like

NA

(1R,2R,4E,5R)-(+)-4-heptylidene-isopinocamphone - Anethol-like, menthol note with a cooling effect, camphoraceous

NA

(1S,2S,4E,5S)-(-)-4-dodecylidene-isopinocamphone - Difficult to describe, eventually a bit spicy, methylnonene-acetaldehyde-like

NA

(1R,2R,4E,5R)-(+)-4-dodecylidene-isopinocamphone - Weak, sweet, cocoa note

NA

(1S,2S,4E,5S)-(-)-4-benzylidene-isopinocamphone - Weak odour reminiscent of cresol, sweet, biscuit-like

NA

(1R,2R,4E,5R)-(+)-4-benzylidene-isopinocamphone - Difficult to describe, eventually vanilla note

NA

(1S,2S,4E,5S)-(-)-4-cinnamylidene-isopinocamphone - Strong cinnamic flavour, styrax note, balsamic

NA

(1R,2R,4E,5R)-(+)-4-cinnamylidene-isopinocamphone - Very weak, indefinable

NA

(1S,2S,4E,5S)-(-)-4-[2-pyridinylmethylene]-isopinocamphone - Weak, sweet, aniseed note

NA

(1R,2R,4E,5R)-(+)-4-[2-pyridinylmethylene]-isopinocamphone - Fatty, green, toluyl-acetaldehyde-like, later woody, sweetish

NA

(1S,2S,4E,5S)-(-)-4-furfurylidene-isopinocamphone - Phenolic, benzaldehyde, chemical, reminiscent of Peruvian balm

NA

(1R,2R,4E,5R)-(+)-furfurylidene-isopinocamphone - Phenolic, later benzaldehyde, marzipan note

NA

(1S,2S,4E,5S)-(-)-4-(4'-methoxybenzylidene)-isopinocamphone - Very weak woody, soft, eventually sweetish

NA

(1R,2R,4E,5R)-(+)-4-(4'-methoxybenzylidene)-isopinocamphone - Very weak woody

NA

(1S,2S,4E,5S)-(-)-4-(3'-methoxybenzylidene)-isopinocamphone - Very weak, aromatic, sweetish

NA

(1R,2R,4E,5R)-(+)-4-(3'-methoxybenzylidene)-isopinocamphone - Very weak, aromatic, ionone-like

NA

(1S,2S,4E,5S)-(-)-4-cyclohexylmethylene-isopinocamphone - Fatty, oily, marzipan-like, peanut note

NA

(1R,2R,4E,5R)-(+)-4-cyclohexylmethylene-isopinocamphone - Woody, cedarwood, later note of camomile tea

NA

(3R,3aR,7aS)-Dill ether - faintly herbal, unspecific

NA

(3S,3aS,7aR)-Dill ether - Dill; The naturally occurring dill ether - showed the typical odour of dill oil.

25 ppb in water

(3S,3aR,7aS)-Dill ether - herbal, sweet

NA

(3R,3aS,7aR)-Dill ether - fruity-sweet

NA

(1R)-(+)-menthofuran - Mint-like, leafy, herbal, camphor-like

0.1-0.2 ppb in air

(1S)-(-)-menthofuran - Herbal, fatty, thyme-like, turpentine

NA

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