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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