Androstenol

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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
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

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]

Biosynthesis

In humans and boars, androstenol is

nasal mucosa from androstenone, and likely also from androstadienol and androstadienone in this area.[1]

Distribution

Considerable amounts of androstenol are present in human urine, and it is also present in the blood plasma and saliva of humans and pigs as well as in the

sweat of humans.[1] Due to its ability to cross the blood–brain barrier, androstenol is likely present in the central nervous system as well.[1]

Biological activity

Androstenol, similarly to the related endogenous steroids

positive allosteric modulator of the GABAA.[1] It has been proposed that this action may mediate the pheromone effects of androstenol.[1] Moreover, as androstadienol, androstadienone, and androstenone are all converted into androstenol, it could mediate their pheromone effects as well.[1] In animals, androstenol has been found to produce anxiolytic-like, antidepressant-like, and anticonvulsant effects.[1] Androstenol has also been found to modify the behavioral and social responses of humans.[1] In addition, androstenol has been found to decrease luteinizing hormone (LH) pulse frequency during the follicular phase of the human menstrual cycle.[6] In accordance, it has been proposed that androstenol may be involved in the menstrual synchrony of women.[2][6]

In contrast to androstenol (3α-androstenol), its 3β-epimer, 3β-androstenol, does not potentiate the GABAA receptor, even at high concentrations.

3β-androstanediol, which similarly do not act as such, in contrast to their 3α-hydroxy variants.[1]

Androstenol, along with several isomers of androstanol, is an antagonist of the constitutive androstane receptor (CAR).[7] Androstenol has minimal or no androgenic activity.[2]

See also

References

  1. ^
    S2CID 95393004
    .
  2. ^
    doi:10.1016/S2221-6189(13)60140-7
    .
  3. ^ Kunzig R (November 2000). "The Biology of Truffles". Discover Magazine.
  4. PMID 15501487
    .
  5. ^ Johannes J, Weusten AM (1989). Biochemical pathways in human testicular steroidogenesis (PDF). Pressa Trajectina.
  6. ^
    PMID 17433821
    .
  7. ISBN 978-3-642-55041-6
    .
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