Androstenol

Androstenol

Systematic (IUPAC) name
(2R,5R,7S,15R)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-13-en-5-ol
Clinical data
Identifiers
CAS Registry Number	none N
ATC code	None
PubChem	CID 101989
IUPHAR ligand	2761
DrugBank	DB01889 Y
ChemSpider	92136 Y
ChEBI	CHEBI:40933 Y
ChEMBL	CHEMBL142348 Y
Chemical data
Formula	C19H30O
Molecular mass	274.440 g/mol
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC=C2)CC[C@@H]4[C@@]3(CC[C@H](C4)O)C
InChI InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1  Y Key:KRVXMNNRSSQZJP-PHFHYRSDSA-N  Y
N (what is this?)  (verify)

Androstenol is a sex pheromone in pigs, possessing a musk-like odor.

It is found in large quantities in boar saliva, but also in smaller quantities in human sweat glands. It is analogous to sex hormones yet has minimal or no androgenic activity. Androstenol is secreted by the adrenal gland into systemic circulation in humans: Systemic effects have not been well studied.

Androstenol, or a chemical derivative, is found in truffles, and is offered as an explanation for how pigs locate them deep in the ground.

Both isomers have a weak, characteristic odor; however alpha-androstenol is often associated with a sandalwood-like aroma due to residual solvents (alkyl acetates).

See also

• Androstadienone
• Androstatrione
• Androstenone
• Androsterone
• Dehydroepiandrosterone
• Estratetraenol
• Diestratetraenol

External links

• The Pheromone Androstenol (5{alpha}-Androst-16-en-3{alpha}-ol) Is a Neurosteroid Positive Modulator of GABAA Receptors -- Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA 317 (2): 694 -- Journal of Pharmacology and Experimental Therapeutics

• The pheromone androstenol (5?-androst-16-en-3?-ol) is a neurosteroid positive modulator of GABAA receptors

• ScienceDirect - The Journal of Steroid Biochemistry and Molecular Biology : Metabolism of the 16-androstene steroids in primary cultured porcine hepatocytes

• SpringerLink - Book Chapter

• Androstanols :: metabolism

Further reading

• Kirk-Smith, M.D., Booth, D.A., Carroll, D., and Davies, P. (1978) "Human social attitudes affected by androstenol". Research Communications in Psychology, Psychiatry and Behaviour, 3, 379–384.