16α-Hydroxy-DHEA

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477209093

| ImageFile=16-hydroxydehydroepiandrosterone.png

| ImageSize=250

| ImageFile2=16-Hidroxidehidroepiandrosterona3D.png

| ImageSize2=250

| IUPACName=3β,16α-Dihydroxyandrost-5-en-17-one

| SystematicName=(2R,3aS,3bR,7S,9aR,9bS,11aS)-3,7-Dihydroxy-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one

|Section1={{Chembox Identifiers

| InChI = 1/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1

| InChIKey = QQIVKFZWLZJXJT-DNKQKWOHBQ

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = QQIVKFZWLZJXJT-DNKQKWOHSA-N

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

| CASNo=1232-73-1

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

| UNII = WU2DU6GA72

| PubChem=102030

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 27771

| ChemSpiderID=92168

| SMILES = O=C3[C@]2(CC[C@@H]1[C@@]4(C(=C/C[C@H]1[C@@H]2C[C@H]3O)\C[C@@H](O)CC4)C)C

}}

|Section2={{Chembox Properties

| Formula=C₁₉H₂₈O₃

| MolarMass=304.42 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

16α-Hydroxydehydroepiandrosterone (16α-hydroxy-DHEA or 16α-OH-DHEA) is an endogenous metabolite of dehydroepiandrosterone (DHEA). Both 16α-OH-DHEA and its 3β-sulfate ester, 16α-OH-DHEA-S, are intermediates in the biosynthesis of estriol from dehydroepiandrosterone (DHEA).{{cite journal |vauthors=Raju U, Bradlow HL, Levitz M |title=Estriol-3-sulfate in human breast cyst fluid. Concentrations, possible origin, and physiologic implications |journal=Ann. N. Y. Acad. Sci. |volume=586 |pages=83–7 |year=1990 |pmid=2141460 |doi= 10.1111/j.1749-6632.1990.tb17793.x }} 16α-OH-DHEA has estrogenic activity.{{cite journal | vauthors = Miller KK, Al-Rayyan N, Ivanova MM, Mattingly KA, Ripp SL, Klinge CM, Prough RA | title = DHEA metabolites activate estrogen receptors alpha and beta | journal = Steroids | volume = 78 | issue = 1 | pages = 15–25 | year = 2013 | pmid = 23123738 | pmc = 3529809 | doi = 10.1016/j.steroids.2012.10.002 }}