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

(S)-(+)-isoborneol - camphoraceous, celluloid-like (Boelens et al.); Camphoraceous, India ink-like (Nishimura)

NA

(R)-(-)-isoborneol - camphoraceous, sweet & musty (Boelens et al.); Camphoraceous, India ink-like (Nishimura)

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,2R,4S)-2-methylfenchol (94:6 endo/exo) - main odor character - earthy, secondary odor character - woody

NA

(1S,2S,4R) -2-methylfenchol (95:5 endo/exo) - main odor character - earthy, secondary odor character - musk

NA

(1R,2R,4S)-2-ethylfenchol (93:7 endo/exo) - main odor character - earthy, secondary odor character - camphor

NA

(1S,2S,4R)-2-ethylfenchol (93:7 endo/exo) - main odor character - earthy, secondary odor character - moldy

NA

(1R,2R,4S)-2-butylfenchol (99:1 endo/exo) - main odor character - earthy, secondary odor character - camphor

NA

(1S,2S,4R)-2-butylfenchol (99:1 endo/exo) - main odor character - earthy, secondary odor character - camphor

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,2S,4R)-(+)-2-Acetoxy-1,8-cineole - woody (weak) - Kubota et al.; Sharp, fruity, sweet odor - Miyazawa and Hashimoto

NA

(1R,2R,4S)-(-)-2-Acetoxy-1,8-cineole - woody, Alpinia galanga like and stronger than the (1S,2S,4R)- isomer - Kubota et al; Camphorous, dry odor - Miyazawa and Hashimoto

NA

(1S,2R,4R)-2-Acetoxy-1,8-cineole - weak

NA

(1R,2S,2S)-2-Acetoxy-1,8-cineole - fruity, sweet

NA

(1S,3R,4R)-3-acetoxy-1,8-cineole - sweet floral, weak

NA

(1R,3S,4S)-3-Acetoxy-1,8-cineole - sweet floral, weak

NA

(1S,3S,4R)-3-Acetoxy-1,8-cineole - camphoraceous (Kubota, et al.); camphor-like, smooth (Loandos et al.)

NA

(1R,3R,4S)-3-Acetoxy-1,8-cineole - mild woody (Kubota, et al.); woody (Loandos et al.)

NA

(1S,2S,4R)-(-)-2-Hydroxy-1,8-cineole - Cineole-like, sweet odor (Miyazawa and Hashimoto); Also described as Citrus (2), sweet (1), grape juice (1), eucalyptus (1) as evaluated by 6 panelists by GC-O (Kirsch and Buettner)

NA

(1R,2R,4S)-(+)-2-Hydroxy-1,8-cineole - Camphorous odor (Miyazawa and Hashimoto); Also described as Eucalyptus (5), pine needle (4), fresh/pungent (3), citrus (2), cleanser (2), soapy (1), flowery (1), sweet (1) as evaluated by 6 panelists by GC-O (Kirsch and Buettner)

NA

(1S,2R,4R)-(-)-2-Hydroxy-1,8-cineole - Eucalyptus (4), pine needle (3), faecal (2), earthy (1), plastic (1) as evaluated by 5 panelists by GC-O (Kirsch and Buettner)

NA

(1R,2S,4S)-(+)-2-Hydroxy-1,8-cineole - Eucalyptus (6), fresh/pungent (1), earthy (1), musty (1), soapy (1), sweet (1) as evaluated by 6 panelists by GC-O (Kirsch and Buettner)

NA

(8S)-(+)-9-Hydroxy-1,8-cineole - Eucalyptus (5), pine needle (1), fatty (1) as evaluated by 5-6 panelists by GC-O (Kirsch and Buettner)

NA

(8R)-(-)-9-Hydroxy-1,8-cineole - Eucalyptus (4), plastic (4), musty (2), rotten (1), sweet (1), dusty (1) as evaluated by 5-6 panelists by GC-O (Kirsch and Buettner)

NA

(1S,3S,4R)-(+)-3-Hydroxy-1,8-cineole - spicy (weak)

NA

(1R,3R,4S)-(-)-3-Hydroxy-1,8-cineole - camphoraceous, sweet

NA

(1S,4S)-(-)-3-Oxo-cineole - spicy

NA

(1R,4R)-(+)-3-Oxo-cineole - sweet, cineole-like (weak)

NA

(1S,2R,4S)-(-)-borneol - camphoraceous, India ink like ( 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, slight fatty-putrid ( 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

(1S,5R)-(+)-Myrtenal - Probability levels of significant differentiation between the enantiomer pairs - >99.0% with 96 untrained panelists; >99.0% with 28 expert panelists; overall >99.9% (all 124 panelists). Theimer's personal comments indicates that he had no problem in differentiating the enantiomers - the d- and l-myrtenals suggested cuminic aldehyde and cyclohexyl acetaldehyde respectively.

NA

(1R,5S)-(-)-Myrtenal - Probability levels of significant differentiation between the enantiomer pairs - >99.0% with 96 untrained panelists; >99.0% with 28 expert panelists; overall >99.9% (all 124 panelists). Theimer's personal comments indicates that he had no problem in differentiating the enantiomers - the d- and l-myrtenals suggested cuminic aldehyde and cyclohexyl acetaldehyde respectively.

NA

(1S,5R)-(+)-Myrtenal diethyl acetal - Probability levels of significant differentiation between the enantiomer pairs - >25.0% with 37 untrained panelists; >90.0% with 29 expert panelists; overall >98.0% (all 66 panelists). No comments on the odor of the enantiomers was provided in Theimer's paper.

NA

(1R,5S)-(-)-Myrtenal diethyl acetal - Probability levels of significant differentiation between the enantiomer pairs - >25.0% with 37 untrained panelists; >90.0% with 29 expert panelists; overall >98.0% (all 66 panelists). No comments on the odor of the enantiomers was provided in Theimer's paper.

NA

(1S,5R)-(+)-Pinoacetaldehyde - Probability levels of significant differentiation between the enantiomer pairs - >95.0% with 42 untrained panelists; >95.0% with 20 expert panelists; overall >98.0% (all 62 panelists). Theimer's personal comments indicates that he had no problem in differentiating the enantiomers of the pinoacetaldehydes since the laevo had a "hydroxycitronellal" character and the dextro reminded of cyclohexyl acetaldehyde.

NA

(1R,5S)-(-)-Pinoacetaldehyde - Probability levels of significant differentiation between the enantiomer pairs - >95.0% with 42 untrained panelists; >95.0% with 20 expert panelists; overall >98.0% (all 62 panelists). Theimer's personal comments indicates that he had no problem in differentiating the enantiomers of the pinoacetaldehydes since the laevo had a "hydroxycitronellal" character and the dextro reminded of cyclohexyl acetaldehyde.

NA

(1S,3R,5S)-(+)-trans-Pinocarvyl propionate - Probability levels of significant differentiation between the enantiomer pairs - >99.9% with 32 untrained panelists; >99.9% with 19 expert panelists; overall >99.9% (all 51 panelists). No comments on the odor of the enantiomers was provided in Theimer's paper.

NA

(1R,3S,5R)-(-)-trans-Pinocarvyl propionate - Probability levels of significant differentiation between the enantiomer pairs - >99.9% with 32 untrained panelists; >99.9% with 19 expert panelists; overall >99.9% (all 51 panelists). No comments on the odor of the enantiomers was provided in Theimer's paper.

NA

(1S,3R,5S)-(+)-trans-Pinocarveol - Probability levels of significant differentiation between the enantiomer pairs - >90.0% with 99 untrained panelists; >99.9% with 29 expert panelists; overall >99.9% (all 128 panelists). Theimer's personal comments indicates that he had no problem in differentiating the enantiomers - the (-)- and (+)-pinocarveols "were easily separated by reminding of geraniol palmarosa and camphor respectively".

NA

(1R,3S,5R)-(-)-trans-Pinocarveol - Probability levels of significant differentiation between the enantiomer pairs - >90.0% with 99 untrained panelists; >99.9% with 29 expert panelists; overall >99.9% (all 128 panelists). Theimer's personal comments indicates that he had no problem in differentiating the enantiomers - the (-)- and (+)-pinocarveols "were easily separated by reminding of geraniol palmarosa and camphor respectively".

NA

(+)-(1S,4R)-Fenchone oxime - roasted onion fragrance

NA

(-)-(1R,4S)-Fenchone oxime - weak, turnip fragrance

NA

(+)-(1S,4R)-Fenchone oxime O-methyl ether - borneol–turpentine fragrance

NA

(-)-(1R,4S)-Fenchone oxime O-methyl ether - turpentine fragrance

NA

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