3β-Androstenol

{{short description|Chemical compound}}

{{Chembox

| ImageFile = 3β-Androstenol.svg

| ImageSize = 200px

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| IUPACName = 5α-Androst-16-en-3β-ol

| SystematicName = (3aS,3bR,5aS,7S,9aS,9bS,11aR)-9a,11a-Dimethyl-3a,3b,4,5,5a,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-3H-cyclopenta[a]phenanthren-7-ol

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| Section1 = {{Chembox Identifiers

| CASNo = 7148-51-8

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = EPQ9QH9KXZ

| ChemSpiderID = 133479

| StdInChI = 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

| StdInChIKey = KRVXMNNRSSQZJP-LOVVWNRFSA-N

| PubChem = 151449

| 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

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| Section2 = {{Chembox Properties

| C=19 | H=30 | O=1

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| Section3 = {{Chembox Hazards

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{{Distinguish|3α-Androstenol}}

3β-Androstenol, also known as 5α-androst-16-en-3β-ol, is a naturally occurring mammalian pheromone known to be present in humans and pigs.{{cite journal | vauthors = Kanlayavattanakul M, Lourith N | title = Body malodours and their topical treatment agents | journal = International Journal of Cosmetic Science | volume = 33 | issue = 4 | pages = 298–311 | year = 2011 | pmid = 21401651 | doi = 10.1111/j.1468-2494.2011.00649.x | s2cid = 11235250 | doi-access = free }}{{cite book|author=Richard L. Doty|title=The Great Pheromone Myth|url=https://books.google.com/books?id=oZmk-XWeAn8C&pg=PA139|date=27 January 2010|publisher=JHU Press|isbn=978-0-8018-9347-6|pages=139–}}{{cite journal | vauthors = Fischer J, Elsinghorst PW, Bücking M, Tholen E, Petersen B, Wüst M | title = Development of a candidate reference method for the simultaneous quantitation of the boar taint compounds androstenone, 3α-androstenol, 3β-androstenol, skatole, and indole in pig fat by means of stable isotope dilution analysis-headspace solid-phase microextraction-gas chromatography/mass spectrometry | journal = Anal. Chem. | volume = 83 | issue = 17 | pages = 6785–91 | year = 2011 | pmid = 21800819 | doi = 10.1021/ac201465q }} It is thought to play a role in axillary odor. It is produced from androstenone via the enzyme 3β-hydroxysteroid dehydrogenase. Unlike its C3α epimer 3α-androstenol, 3β-androstenol shows no potentiation of the GABA_A receptor or anticonvulsant activity.{{cite journal | vauthors = Sinclair PA, Hancock S, Gilmore WJ, Squires EJ | title = Metabolism of the 16-androstene steroids in primary cultured porcine hepatocytes | journal = J. Steroid Biochem. Mol. Biol. | volume = 96 | issue = 1 | pages = 79–87 | year = 2005 | pmid = 15896952 | doi = 10.1016/j.jsbmb.2005.01.030 | s2cid = 9435153 }}