3β-androstanediol

3β-Androstanediol
Names

IUPAC name (3β,5α,17β)-Androstane-3,17-diol
Systematic IUPAC name (1S,2S,5S,7S,10R,11S,14S,15S)-2,15-Dimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadecane-5,14-diol
Other names 3β-Androstanediol; 3β-Diol; Maxterone
Identifiers
CAS Number	571-20-0
3D model (JSmol)	Interactive image
ChemSpider	211834
ECHA InfoCard	100.008.487
PubChem CID	242332
InChI InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1 Key: CBMYJHIOYJEBSB-YSZCXEEOSA-N InChI=1/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1 Key: CBMYJHIOYJEBSB-YSZCXEEOBK
SMILES O[C@H]4CC[C@]3([C@@H](CC[C@H]2[C@@H]1CC[C@H](O)[C@@]1(C)CC[C@@H]23)C4)C
Properties
Chemical formula	C₁₉H₃₂O₂
Molar mass	292.46 g·mol⁻¹
Melting point	168–170 °C (334–338 °F; 441–443 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3β-Androstanediol, also known as 5α-androstane-3β,17β-diol, and often shortened to 3β-diol, is an endogenous steroid hormone. It is a 5α-reduced and 17β-hydroxylated metabolite of dehydroepiandrosterone (DHEA) as well as a 3β-hydroxylated metabolite of dihydrotestosterone (DHT). 3β-Diol is a selective, potent, high-affinity full agonist of the ERβ, and hence, an estrogen. It has higher affinity for this receptor than estradiol. In contrast to ERβ, 3β-diol does not bind to the androgen receptor (AR). 3β-Diol has been reported to also bind to ERα with low nanomolar affinity, with several-fold lower affinity relative to ERβ. It has approximately 3% and 7% of the affinity of estradiol at the ERα and ERβ, respectively. Unlike its 3α-isomer, 3α-androstanediol (3α-diol), 3β-diol does not bind to the GABA_A receptor.

3β-Diol appears to be the endogenous ligand of ERβ in the prostate gland, and as a result of activation of the ERβ, 3β-diol has antiproliferative effects against prostate cancer cells. Through the ERβ, 3β-diol positively regulates neurons and signaling in the paraventricular nucleus of hypothalamus (PVN), and has been found to have antidepressant,anxiolytic,cognitive-enhancing, and stress-relieving effects via this action. Androgens, including testosterone and dihydrotestosterone (DHT), are known to downregulate the hypothalamic-pituitary-adrenal axis, and this has been found to be due in part or full to their conversion into 3β-diol rather than to activation of the AR.