Chirality & Odour Perception
John C. Leffingwell, Ph.D.

The trans-3-Isocamphylcyclohexanols

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Photo by permission of M. Roudintska - Art & Parfum

(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; also described by Emura (Koryo) as "Strong Typical Sandalwood Odor."

Threshold = 0.2 ppb

= (1R,3R,1'S,2'R,4'S,6'S)-(+)-threo-trans-3-(5,5,6-Trimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohexanol

Ref: Makato Emura, Takaaki Toyoda, Itsuo Nishino; PERFUME HAVING OPTICALLY ACTIVE TRANS-3-ISOCAMPHYLCYCLOHEXANOL AS EFFECTIVE COMPONENT, Japanese Patent No. 11-35968 (Sept. 2, 1999); Makato Emura. Recent approaches toward the aroma of incense wood, Koryo, Vol. 218, 113-124 (2003)

The author thanks Mr. Kiyoshi Okumura for assistance in translating portions of the above mentioned Japanese patent.

Various complex mixtures containing between 5-20% of the active stereoisomers have been sold under the tradenames of Sandela® (Givaudan), Sandel (H&R), Indisan, Isobornylcyclohexanol, Mysorol (Naarden), Rhodanthial, Sandarome, Sandenol, Sandiff® (IFF), Santal A, Santalex® T (Takasago), Santalydol, etc.

(1S,3S,1'R,2'S,4'R,6'R)-(-)-threo-trans-3-isocamphylcyclohexanol - weak, moldy and woody odor; also described by Emura (Koryo) as "Weak Musty Woody Odor."

Threshold = 200 ppb

= (1S,3S,1'R,2'S,4'R,6'R)-(-)-erythro-trans-3-(5,5,6-Trimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohexanol

Ref: Makato Emura, Takaaki Toyoda, Itsuo Nishino; PERFUME HAVING OPTICALLY ACTIVE TRANS-3-ISOCAMPHYLCYCLOHEXANOL AS EFFECTIVE COMPONENT, Japanese Patent No. 11-35968 (Sept. 2, 1999); Makato Emura. Recent approaches toward the aroma of incense wood, Koryo, Vol. 218, 113-124 (2003)

The author thanks Mr. Kiyoshi Okumura for assistance in translating portions of the above mentioned Japanese patent.

Various complex mixtures containing between 5-20% of the active stereoisomers have been sold under the tradenames of Sandela® (Givaudan), Indisan, Isobornylcyclohexanol, Mysorol (Naarden), Rhodanthial, Sandarome, Sandenol, Sandiff® (IFF), Santal A, Santalex® T (Takasago), Santalydol, etc.

(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; also described by Emura (Koryo) as "Sandalwood Odor."

Threshold = 7 ppb

= (1S,3S,1'S,2'R,4'S,6'S)-(+)-erythro-trans-3-(5,5,6-Trimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohexanol

Ref: Makato Emura, Takaaki Toyoda, Itsuo Nishino; PERFUME HAVING OPTICALLY ACTIVE TRANS-3-ISOCAMPHYLCYCLOHEXANOL AS EFFECTIVE COMPONENT, Japanese Patent No. 11-35968 (Sept. 2, 1999); Makato Emura. Recent approaches toward the aroma of incense wood, Koryo, Vol. 218, 113-124 (2003)

The author thanks Mr. Kiyoshi Okumura for assistance in translating portions of the above mentioned Japanese patent.

Various complex mixtures containing between 5-20% of the active stereoisomers have been sold under the tradenames of Sandela® (Givaudan), Indisan, Isobornylcyclohexanol, Mysorol (Naarden), Rhodanthial, Sandarome, Sandenol, Sandiff® (IFF), Santal A, Santalex® T (Takasago), Santalydol, etc.

(1R,3R,1'R,2'S,4'R,6'R)-(-)-erythro-trans-3-isocamphylcyclohexanol - strong, warm sandalwood odor; also described by Emura (Koryo) as :Sandalwood Odor."

Threshold = 3 ppb

= (1R,3R,1'R,2'S,4'R,6'R)-(+)-erythro-trans-3-(5,5,6-Trimethyl-bicyclo[2.2.1]hept-2-yl)-cyclohexanol

Ref: Makato Emura, Takaaki Toyoda, Itsuo Nishino; PERFUME HAVING OPTICALLY ACTIVE TRANS-3-ISOCAMPHYLCYCLOHEXANOL AS EFFECTIVE COMPONENT, Japanese Patent No. 11-35968 (Sept. 2, 1999); Makato Emura. Recent approaches toward the aroma of incense wood, Koryo, Vol. 218, 113-124 (2003)

The author thanks Mr. Kiyoshi Okumura for assistance in translating portions of the above mentioned Japanese patent.

Various complex mixtures containing between 5-20% of the active stereoisomers have been sold under the tradenames of Sandela® (Givaudan), Indisan, Isobornylcyclohexanol, Mysorol (Naarden), Rhodanthial, Sandarome, Sandenol, Sandiff® (IFF), Santal A, Santalex® T (Takasago), Santalydol, etc.

Cyclic Terpenoid Odorants

Bicyclic Terpenoid Odorants

Acyclic Terpenoid Odorants

Ionones, Irones, Damascones & Structurally Related Odorants

Acyclics (Alcohols, Esters, Acids, Aldehydes)

Lactones

Sesquiterpenoid Related Odorants

Steroid Urine Type Odorants

Sandalwood Type Odorants

Musk Odorants

Miscellaneous

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