Androstadienol

[1][2] Androstadienol and androstadienone are odorless compounds secreted by the apocrine glands, and via conversion into the more powerfully-odorous androstenone and androstenol (catalyzed by aerobic corynebacteria, particularly Corynebacterium xerosis, in men, and Micrococcaceae spp.in women), are considered to be mainly responsible for the "musky" component of axillary (underarm) odor.[1][2] Androstadienone, which is produced from androstadienol, has been found to affect brain activity.[6] Specifically, it has been found to activate the hypothalamus, most maximally the medial preoptic and anterior hypothalamic areas, in heterosexual women and homosexual men, but not in heterosexual men (who instead experienced hypothalamic activation in response to smelling estratetraenol, an estrogen-related pheromone, while heterosexual women and homosexual men did not).[6] The affected brain areas are thought to be involved in sexual behavior, attention, visual perception/recognition, and social cognition.
androstanedioneandrostanediolandrostenedioneandrostenediolATC codeIUPAC nameCAS NumberChemSpiderCompTox DashboardFormulaMolar massSMILES16-androsteneendogenoussteroidpheromonechemical intermediateandrostadienoneapocrine glandsandrostenoneandrostenolaerobiccorynebacteriaCorynebacterium xerosisMicrococcaceae spp.axillarysynthesizedpregnenoloneCYP17A13β-hydroxysteroid dehydrogenasesex differenceshypothalamusheterosexualhomosexual menestratetraenolestrogenprefrontal cortexsuperior temporal cortexolfactory areassexual behaviorattentionvisual perception/recognitionsocial cognitionpheromonesvomeropherinesSteroids3α-Androstenol3β-AndrostenolAndrosteroneVolatileaminesTrimethylaminePherinesFasedienolItruvonePrecursorsCholesterol22R-Hydroxycholesterol20α,22R-Dihydroxycholesterol17α-Hydroxypregnenolone21-HydroxypregnenoloneCorticosteroidsGlucocorticoids3α,5α-Tetrahydrocorticosterone5α-Dihydrocorticosterone11-Deoxycorticosterone11-Deoxycortisol11-Ketoprogesterone21-Deoxycortisol21-DeoxycortisoneCorticosteroneCortisolCortisone17α-HydroxyprogesteroneProgesterone5α-DihydrocortisolMineralocorticoids5α-Dihydroaldosterone11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)11β-Hydroxyprogesterone (21-deoxycorticosterone)18-Hydroxy-11-deoxycorticosterone18-HydroxycorticosteroneAldosteroneSex steroidsAndrogens11-Ketodihydrotestosterone11-Ketotestosterone7β-Hydroxyepiandrosterone11β-HydroxyandrostenedioneAdrenosterone (11-ketoandrostenedione)DehydroandrosteroneDHEA sulfateDihydrotestosteroneEpiandrosteroneEpitestosterone16α-Hydroxyandrostenedione16α-Hydroxy-DHEA16α-Hydroxy-DHEA sulfateTestosterone3α-Androstanediol3α-Androstanediol glucuronide3β-Androstanediol5β-Dihydrotestosterone3α-Etiocholanediol3β-EtiocholanediolAndrostenediol sulfateAndrostenetriolAndrosterone glucuronideAndrosterone sulfateEtiocholanedioneEtiocholanoloneEtiocholanolone glucuronideEpietiocholanoloneTestosterone glucuronideTestosterone sulfateEstrogensEstetrolEstradiolEstroneEstriol17α-Estradiol16β-Epiestriol (16β-hydroxyestradiol)17α-Epiestriol (16α-hydroxy-17α-estradiol)16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)2-Hydroxyestradiol2-Hydroxyestriol2-Hydroxyestrone4-Hydroxyestradiol4-Hydroxyestriol4-Hydroxyestrone4-Methoxyestradiol4-Methoxyestrone16α-Hydroxyestrone16β-Hydroxyestrone16-Ketoestradiol16-Ketoestrone27-Hydroxycholesterol4-Androstenedione5-Androstenediol7-Keto-DHEA7α-Hydroxy-DHEA2-Methoxyestradiol2-Methoxyestrone2-Methoxyestriol4-MethoxyestriolEstradiol disulfateEstradiol glucuronideEstradiol 3-glucuronideEstradiol 3-glucuronide 17β-sulfateEstradiol sulfateEstradiol 17β-sulfateEstrone glucuronideEstrone sulfateEstriol glucuronideEstriol sulfateLipoidal estradiolestradiol stearateestradiol palmitateProgestogens16α-Hydroxyprogesterone20α-Dihydroprogesterone20β-Dihydroprogesterone5α-Dihydroprogesterone5α-DHDOCAllopregnanediolPregnanediolPregnanediol glucuronidePregnanetriolNeurosteroids24S-Hydroxycholesterol3α-Dihydroprogesterone3β-Dihydroprogesterone5β-DihydroprogesteroneAllopregnanoloneEpipregnanoloneIsopregnanolonePregnanolonePregnenolone sulfate7β-Hydroxy-DHEA7α-HydroxyepiandrosteroneVitamin D7-DehydrocholesterolCalcidiol/CalcifediolCalcitriolCholecalciferol7α-Hydroxycholesterol11α-Hydroxyprogesterone11β-HydroxyprogesteroneCholesterol sulfate