Chirality & Odour Perception

Steroid Urine Type Odorants & Sandalwood Type 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

Enantiomer & Odor Description

 Odour Threshold (PPB)

Steroid Urine Type Odorants

.

(+)-androstenone - strong urine odor

0.18

(-)-androstenone - odorless

Odorless

(-)-androsta-4,16-dien-3-one - odorless

Odorless

(+)-androsta-4,16-dien-3-one - very persistent odor of urine & sweat

0.98

(+)-5-alpha-androst-16-en-3-alpha-ol - Animalic, musk-like odor with a strong (fine) sandalwood tonality

0.02

ent-(-)-5-alpha-androst-16-en-3-alpha-ol - Weaker with a detection threshold level about six orders of magnitude higher than 5-alpha-androst-16-en-3-alpha-ol

NA

Non-Steroid Urine Type Odorants

NA

(+)-2-Methyl-4-(5,5,6-exo-trimethyl-2-exo-norbornyl)cyclohexanone - urinous - about 1% that of (+)-Androstenone.

NA

(-)-2-Methyl-4-(5,5,6-exo-trimethyl-2-exo-norborny)cyclohexanone - strongly urinous - about 20% that of (+)-Androstenone

0.28 ppb in water

(+)-2-Methyl-4-(5,5,6-exo-trimethyl-2-endo-norborny)cyclohexanone (liquid [axial? methyl] isomer - weakly urinous - about 0.4% that of (+)-Androstenone.

NA

(-)-2-Methyl-4-(5,5,6-exo-trimethyl-2-endo-norborny)cyclohexanone (liquid [axial? methyl] isomer) - moderately strong urinous about 4% that of (+)-Androstenone

NA

(+)-2-Methyl-4-(5,5,6-exo-trimethyl-2-endo-norborny)cyclohexanone (solid [equitorial methyl?] isomer) - weakly urinous about 0.2% that of (+)-Androstenone.

NA

(-)-2-Methyl-4-(5,5,6-exo-trimethyl-2-endo-norborny)cyclohexanone (solid [equitorial? methyl] isomer) - urinous - about 1% that of (+)-Androstenone.

NA

(+)-4-(2-endo-Bornyl)-2-methylcyclohexanone - very weakly urinous (near perception threshold) - about 0.1% that of (+)-Androstenone

NA

(-)-4-(2-endo-Bornyl)-2-methylcyclohexanone - Not urinous, odorless (near perception threshold); woody-camphoraceous at high concentrations

NA

(-)-4-(2-exo-Bornyl)-2-methylcyclohexanone - Not urinous, odorless (near perception threshold); woody-camphoraceous at high concentrations

NA

(+)-4-(2-exo-Bornyl)-2-methylcyclohexanone - Not urinous, odorless (near perception threshold); woody-camphoraceous at high concentrations

NA

Nature Identical Sandalwood Odorants

(-)-(1'S,2'R,4'R)-(Z)-beta-santalol - Typical sandalwood scent, identical to the natural product (Krotz & Helmchen); very strong, woody to animal, typical sandalwood (Brunke); sandalwood, natural, woody, milky (Chapuis)

NA

(+)-(1'R,2'S,4'S)-(Z)-beta-santalol - No scent (odorless).

Odorless

(-)-(1'S,2'R,4'R)- (E)-beta-santalol - Scent similar to (-)-(1'S,2'R,4'R) -(Z)-beta-santalol but less intense (Krotz & Helmchen); woody, medicinal, phenolic, very weakly sandalwood (Brunke).

NA

(+)-(1'R,2'S,4'S)- (E)-beta-santalol - No scent (odorless).

Odorless

(-)-(1'S,2'S,4'R)-(Z)-epi-beta-santalol - not (like) sandalwood (Chapuis)

NA

(+)-(1'R,2'R,4'S)-(Z)-epi-beta-santalol - weak woody (Brunke); woody, sandalwood, sweet, weak (Chapuis)

NA

(1S,2R,4R)-(-)-beta-Santalene - Essentially no scent when freshly purified.

NA

(1R,2S,4S)-(+)-beta-Santalene - Essentially no scent when freshly purified.

NA

(+)-(1'R,2'R,3'R,4'S,5'R)-(E)-alpha-Photosantalol - Sandalwood, natural, pleasant, strong

NA

(-)-(1'S,2'S,3'S,4'R,5'S)-(E)-alpha-Photosantalol - Woody, sandalwood, weak

NA

(-)-(1'S,2'R,4'R)-(E)-beta-Photosantalol - Sandalwood, similar to (-)-(Z)-beta-Santalol

NA

(+)-(1'R,2'S,4'S)-(E)-beta-Photosantalol - Odor not known

NA

Sandalwood Type Odorants from Campholenic aldehyde

 

(-)-(1'R)-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-1-al - fragrance further possessing an aldehydic note, reminiscent of citronellal, citrusy, spicy, recalling the odor of the citronella leaves. As to its bottom note, it has a character which is reminiscent of the odor of 3-(4-tert-butyl-1-phenyl)-2-methylpropanal, but with an even greener connotation and a slightly orangy aspect

NA

(+)-(1'S)-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-1-al - a more metallic and aldehydic odor, recalling that of trans-4-decenal, and the bottom note of which is more floral and even stronger in the aqueous character. The use of this latter compound to enhance the latter odor character in perfumed compositions and articles is in fact preferred to that of its (-)-(1'R)-enantiomer

NA

(-)-(1'R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile - a woody-citrus, fruity and slightly fatty odor prefered to the (+)-(1'S)-isomer

NA

(+)-(1'S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-pentenenitrile - not as prefered an odor as the (-)-(1'R)-isomer

NA

(-)-(1'R,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - citrus, fruity and fresh character accompanied by a sandalwood bottom character

NA

(+)-(1'S,2s)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - odor not described other than to say the (1'R)-isomers are preferred

(-)-(1'R,2S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - a sandalwood odor wherein the desired fruity-citrus character of the (-)-(1'R,2R)-isomer is no longer present

NA

(+)-(1'S,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-pentenenitrile - odor not described other than to say the (1'R)-isomers are preferred

(-)-(1'R,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - elegant and powerful sandalwood note (prefered of the four isomers)

NA

(+)-(1'S,2S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - odor is less rich in the precious "lait de santal" type odor character present in the (-)-(1'R,2R)- and (-)-(1'R,2S)- isomers

NA

(-)-(1'R,2S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - sandalwood note is not as powerful as the (-)-(1'R,2R)-isomer but is accompanied of a more marked woody-cedar character

NA

(+)-(1'S,2R)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-ol - odor is less rich in the precious "lait de santal" type odor character present in the (-)-(1'R,2R)- and (-)-(1'R,2S)- isomers

NA

(-)-(1'R,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol - develops a sandalwood note, the character of which is strongly reminiscent of the typical milky odor of sandalwood

NA

(+)-(1'S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4-penten-2-ol - drier, more woody-cedar and less milky than that of its (-)-(1'R,E)- isomer

NA

(+)-(1'S,2S,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - develops a sandalwood note of remarkable strength, wherein the typical milky character is represented at its best and accompanied by a slightly animal note; prefered of four possible isomers

NA

(-)-(1'R,2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weakest and less characteristic sandalwood note than any of the other isomers

NA

(+)-(1'S,2R,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - ranked in 3d place of 4 isomers for its sandalwood odor

NA

(-)-(1'R,2S,E)-3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol - weaker and less characteristic sandalwood note than the (+)-(1'S,2S,E)-isomer but superior to the (+)-(1'S,2R,E)- or (-)-(1'R,2R,E)- isomers

NA

(1'R,E)-(+)-2-Methyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - fresh and strong sandalwood oil odor associated with green trees

51

(1'S,E)-(-)-2-Methyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - dry and weak sandalwood oil odor with a milky and floral note

424

(1'R,Z)-(+)-2-Methyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - Green, tomato, weak

NA

(1'S,Z)-(+)-2-Methyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - Woody, sandalwood, milk, very weak

NA

(1'R,E)-(-)-2-Ethyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - clean, bright and strong sandalwood oil odor with richness and a woody note

0.85

(1'S,E)-(-)-2-Ethyl-4-(2,2,3-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - milky sandalwood oil odor with a cedar character

44

(1'R,E)-(+)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - soft and warm sandalwood oil odor

NA

1'S,E)-(-)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - slightly sandalwood, weak

NA

(1'R,Z)-(-)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - green, vaguely fruity, woody

NA

(1'S,Z)-(+)-2-Propyl-4-(2',2',3'-trimethyl-cyclopent-3-enyl)-but-2-en-1-ol - woody, very weak

NA

(1'R,E)-(-)-2,2-dimethyl-4-(2',2',3'-trimethylcyclopent-3-enyl)-but-3-en-1-ol - Vaguely fruity, woody

NA

(1'S,E)-(+)-2,2-dimethyl-4-(2',2',3'-trimethylcyclopent-3-enyl)-but-3-en-1-ol - sandalwood, fruity, dorisyl

NA

(-)-(1'R)-2-methyl-4-(2',2',3'- trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-al - possesses an unexpected odor in view of the prior knowledge regarding the odor properties of campholenic aldehyde derivatives. It develops a woody-sandalwood type odor note, slightly aldehydic, which is more reminiscent of the cedar-pine odor connotation than of the sandalwood type one, which note is combined with a distinct marine, ozone character. The latter is reinforced in the bottom note, which is strongly ozone-marine-like, recalling the odor of seaweeds. In addition, the odor of this compound has a good strength and tenacity.

NA

(+)-(1'S)-2-methyl-4-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl) -4-penten-1-al - woody, sandalwood, aldehydic, faintly aqueous

NA

 (1'S,1''S,2'S,3''R,5''R)-Javanol - sandalwood, creamy, warm, strong

NA

(1'R,1''R,2'R,3''S,5''S)-Javanol - lactonic, lily of the valley

NA

(1'R,1''S,2'R,3''R,5''R)-Javanol - lactonic, with a sandalwood aspect

NA

(1'S,1''R,2'S,3''S,5''S)-Javanol - floral, rosy, milky, sandalwood

NA

(-)-axial-4-((1'R)-2,2,3-trimethylcyclopent-3-enyl)cyclohexanol - not specific, vaguely sandalwood

NA

(+)-axial-4-((1'S)-2,2,3-trimethylcyclopent-3-enyl)cyclohexanol - vaguely woody, slightly sandalwood

NA

(-)-equatorial-4-((1'R)-2,2,3-trimethylcyclopent-3-enyl)cyclohexanol - woody, metallic

NA

(+)-equatorial-4-((1'S)-2,2,3-trimethylcyclopent-3-enyl)cyclohexanol - without character

NA

(-)-axial-1-Methyl-4-[(1'R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexanol - Weak, floral

NA

(+)-axial-1-Methyl-4-[(1'S)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexanol - Slightly sandalwood, weak

NA

(-)-equatorial-1-Methyl-4-[(1'R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexanol - Weak

NA

(+)-equatorial-1-Methyl-4-[(1'S)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexanol - Slightly sandalwood

NA

(-)-(1:1 2E/Z)-2-{(4S)-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexylidene}ethanol (1:1 mixture of E/Z isomers) - Without character

NA

(+)-(1:1 2E/Z)-2-{(4R)-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexylidene}ethanol (1:1 mixture of E/Z isomers) - Green, cucumber, fatty, mastic

NA

(-)-(2E/Z)-2-{(4S)-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexylidene}propan-1-ol (1:1 mixture of E/Z isomers) - Woody, sandalwood, urine, transpiration

NA

(+)-(2E/Z)-2-{(4R)-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexylidene}propan-1-ol (1:1 mixture of E/Z isomers) - Woody, vaguely sandalwood, weak

NA

(-)-{trans-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexyl}methanol - Woody, cedar

NA

(+)-{trans-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexyl}methanol - Woody

NA

(-)-(1RS)-1-{trans-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexyl}ethanol - Sandalwood, vague, weak

NA

(+)-(1RS)-1-{trans-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexyl}ethanol - Vague

NA

(-)-2-{trans-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexyl}propan-2-ol - Without olfactive character

NA

(+)-2-{trans-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]cyclohexyl}propan-2-ol - Without character

NA

(1R,2'R,3'S)-Ebanol - weak, no sandalwood odor relevance

>100 (relative in series)

(1S,2'S,3'R)-Ebanol - Powerful sandalwood, more than 100X more powerful than its enantiomer (based on relative GC sniff threshold) and more than 3X stronger than (1R,2'S,3'R)-Ebanol

1 (relative in series)

(1R,2'S,3'S)-Ebanol - Slight sandalwood relevance, both enantiomers weak

>100 (relative in series)

(1S,2'R,3'R)-Ebanol - No sandalwood relevance, both enantiomers weak

>100 (relative in series)

(1R,2'S,3'R)-Ebanol - Powerful sandalwood, more than 33X more powerful than its enantiomer and more than 3X weaker than (1S,2'S,3'R)-Ebanol

3 (relative in series)

(1S,2'R,3'S)-Ebanol - no sandalwood relevance

>100 (relative in series)

(1R,2'R,3'R)-Ebanol - no sandalwood relevance

>100 (relative in series)

(1S,2'S,3'S)-Ebanol - no sandalwood relevance

>100 (relative in series)

(-)-(2R)-2-methyl-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]butan-1-ol - peculiar sandalwood's strongly excellent smell

18.7

(+)-(2S)-2-methyl-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]butan-1-ol - weak and less preferred enantiomer

166.0

(+)-(2R)-2-methyl-4-[(1S)-2,2,3-trimethylcyclopent-3-en-1-yl]butan-1-ol - peculiar sandalwood's strongly excellent smell

14.5

(-)-(2S)-2-methyl-4-[(1R)-2,2,3-trimethylcyclopent-3-en-1-yl]butan-1-ol - weak and less preferred enantiomer

176.8

(+)-(3R,1'S)-HomoPolysantol - Very clean but less intense sandalwood scent than the (+)-(3S,1'S)-enantiomer, with woody, borneol and cashmeran notes at the end (by GC-sniffing); On blotting paper strips Lucta perfumers described it as: Top notes: smoky, tarry, phenolic, guaiacol, woody on cedar, sandal and benjui notes. Heart notes: sandalwood and burnt scents. Base note: weak sandalwood odour.

NA

(-)-(3S,1'R)-HomoPolysantol - Very clean sandalwood odour, with waxy note at end (by GC-sniffing); On blotting paper strips Lucta perfumers described it as: - Top notes: sandalwood, polysantol-type, woody and dry. Heart notes: sandalwood and sandela very intense. Base note: mild but clear sandalwood note. (Best of the four diastereoisomers)

NA

(-)-(3R,1'R)-HomoPolysantol - Sandalwood pure note, with a waxy note at the end (by GC-sniffing); On blotting paper strips Lucta perfumers described it as: Top notes: weak spicy, sandalwood, woody and dry. Heart notes: weak spicy and sandalwood. Base note: almost odourless.

NA

(+)-(3S,1'S)-HomoPolysantol - Sandalwood pure note (by GC-sniffing); On blotting paper strips Lucta perfumers described it as: Top notes: phenolic, leather, styrax, sandalwood and woody. Heart notes: very clean sandalwood and sandela scents. Base note: almost odourless.

NA

Other Sandalwood Odorants

(1R,3R,1'S,2'R,4'S,6'S)-(+)-threo-trans-3-isocamphylcyclohexanol - Strong, diffusive, and sandalwood-like odor; natural sandalwood odor, but very strong and keen

0.2

(1S,3S,1'R,2'S,4'R,6'R)-(-)-threo-trans-3-isocamphylcyclohexanol - weak, moldy and woody odor

200

(1S,3S,1'S,2'R,4'S,6'S) (+)-erythro-trans-3-isocamphylcyclohexanol - sandalwood like odor without moldy feeling, and it is sufficiently diffusive

7

(1R,3R,1'R,2'S,4'R,6'R)-(-)-erythro-trans-3-isocamphylcyclohexanol - strong, warm sandalwood odor

3

(-)-(1S,E)-5-(2',2-dimethyl-3'-methylene-1'-cyclohexyl)-3,3-dimethyl-4-penten-2-ol - Woody, sandal, sweet note, reminiscent of the odor of the bark and milk of the sandalwood tree.

NA

(+)-(1'R,E)-5-(2',2-dimethyl-3'-methylene-1'-cyclohexyl)-3,3-dimethyl-4-penten-2-ol - Sandalwood odor, but distinctly different than the (-)-(1S,E)-isomers

NA

(+)-(1S,3R,6R,8R)-8-tertbutylbicyclo[4.4.0]decan-3-ol - strong, sandalwood like, warm, sweet and fatty, long persisting,

NA

(-)-(1R,3S,6S,8S)-8-tertbutylbicyclo[4.4.0]decan-3-ol - very weak, fatty, hardly perceptible, remote reminiscent to animal notes.

NA

(2S,3R,4E)-3-methyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - very strong, sandal(wood), animalic

5

(2R,3S,4E)-3-methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - weak, woody

168

(2R,3S,4E)-3-methyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - sandal(wood), animalic

70

(2S,3R,4E)-3-methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - woody

72

(2R,3R,4E)-3-methyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - sandal(wood), floral

137

(2S,3S,4E)-3-methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - very weak floral

159

(2S,3S,4E)-3-methyl-4-[(1R,2R,6R,7R)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - strong sandal(wood), floral

46

(2R,3R,4E)-3-methyl-4-[(1S,2S,6S,7S)-tricyclo[5.2.1.02,6]dec-4-en-8-ylidene]butan-2-ol - weak floral

204

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