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| ECHA InfoCard | 100.013.248 |
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| Formula | C19H30O |
| Molar mass | 274.448 g·mol−1 |
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Androstenol, also known as5α-androst-16-en-3α-ol (shortened to3α,5α-androstenol or3α-androstenol), is a 16-androstene classsteroidalpheromone andneurosteroid in humans and other mammals, notably pigs.[1] It possesses a characteristicmusk-like odor.[2]
Androstenol, or a derivative, is found inblack 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]
Astereoisomer 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]
In humans and boars, androstenol isbiosynthesized in thetestes.[1]Pregnenolone is metabolized intoandrostadienol by the 16-ene-synthetase activity ofCYP17A1.[1] Androstadienol is then sequentially converted into androstenol by3β-hydroxysteroid dehydrogenase (androstadienol toandrostadienone),5α-reductase (androstadienone toandrostenone), and3α-hydroxysteroid dehydrogenase (androstenone to androstenol), in a manner analogous to the biosynthesis of3α-androstanediol fromdehydroepiandrosterone (DHEA).[1][5] Androstenol may also be synthesized in theadrenal glands and theovaries in humans.[1] In addition, androstenol may be synthesized in the humannasal mucosa from androstenone, and likely also from androstadienol and androstadienone in this area.[1]
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 theaxillarysweat of humans.[1] Due to its ability to cross theblood–brain barrier, androstenol is likely present in thecentral nervous system as well.[1]
Androstenol, similarly to the related endogenous steroids3α-androstanediol andandrosterone, has been found to act as a potentpositive allosteric modulator of theGABAA.[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 produceanxiolytic-like,antidepressant-like, andanticonvulsant effects.[1] Androstenol has also been found to modify the behavioral and social responses of humans.[1] In addition, androstenol has been found to decreaseluteinizing hormone (LH) pulse frequency during thefollicular phase of the humanmenstrual cycle.[6] In accordance, it has been proposed that androstenol may be involved in themenstrual 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.[1] This is in accordance with other 3β-hydroxy steroids, includingisopregnanolone,epipregnanolone,3β-dihydroprogesterone, and3β-androstanediol, which similarly do not act as such, in contrast to their 3α-hydroxy variants.[1]
Androstenol, along with several isomers ofandrostanol, is anantagonist of theconstitutive androstane receptor (CAR).[7] Androstenol has minimal or noandrogenic activity.[2]