Androstenol

Androstenol
Clinical data
ATC code
  • none
Identifiers
  • (2R,5R,7S,15R)-2,15-Dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-13-en-5-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.013.248 Edit this at Wikidata
Chemical and physical data
FormulaC19H30O
Molar mass274.448 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:KRVXMNNRSSQZJP-PHFHYRSDSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Androstenol, also known as 5α-androst-16-en-3α-ol (shortened to 3α,5α-androstenol or 3α-androstenol), is a 16-androstene class steroidal pheromone and neurosteroid in humans and other mammals, notably pigs.[1] It possesses a characteristic musk-like odor.[2]

Androstenol, or a derivative, is found in black truffles. This was offered as an explanation for how pigs locate them deep in the ground: Androstenol is produced in the saliva of male pigs. However, experiments in France using pigs to scent truffles, truffle scent extract, and purified androstenol showed that pigs responded to the first two (actually trying to eat dirt containing the truffle extract), but ignored the androstenol.[3]

A stereoisomer of androstenol, 3β-androstenol (5α-androst-16-en-3β-ol), is also endogenous to humans (as well as to pigs), behaving as a pheromone and contributing to axillary odor.[4]

  1. ^ Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA (May 2006). "The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors". The Journal of Pharmacology and Experimental Therapeutics. 317 (2): 694–703. doi:10.1124/jpet.105.098319. PMID 16415088. S2CID 95393004.
  2. ^ Semwal A, Kumar R, Teotia UV, Singh R (2013). "Pheromones and their role as aphrodisiacs: A review". Journal of Acute Disease. 2 (4): 253–261. doi:10.1016/S2221-6189(13)60140-7.
  3. ^ Kunzig R (November 2000). "The Biology of Truffles". Discover Magazine.
  4. ^ Pause BM (October 2004). "Are androgen steroids acting as pheromones in humans?". Physiology & Behavior. 83 (1): 21–9. doi:10.1016/S0031-9384(04)00345-2. PMID 15501487.