8,9-Dehydroestrone

{{Short description|Chemical compound}}

{{Infobox drug

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| IUPAC_name = (13S,14S)-3-Hydroxy-13-methyl-7,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one

| image = 8,9-Dehydroestrone.svg

| width = 225px

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| routes_of_administration = By mouth

| class = Estrogen

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| CAS_number = 474-87-3

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| PubChem = 6451472

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| ChemSpiderID = 4953937

| UNII = 7C1N8RKG9F

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| synonyms = Δ⁸-Estrone; Estra-1,3,5(10),8-tetraen-3-ol-17-one

| C=18 | H=20 | O=2

| SMILES = C[C@]12CCC3=C([C@@H]1CCC2=O)CCC4=C3C=CC(=C4)O

| StdInChI_Ref =

| StdInChI = 1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,16,19H,2,4,6-9H2,1H3/t16-,18-/m0/s1

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| StdInChIKey = OUGSRCWSHMWPQE-WMZOPIPTSA-N

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8,9-Dehydroestrone, or Δ⁸-estrone, also known as estra-1,3,5(10),8-tetraen-3-ol-17-one, is a naturally occurring estrogen found in horses which is closely related to equilin, equilenin, and estrone, and, as the 3-sulfate ester sodium salt, is a minor constituent (3.5%) of conjugated estrogens (Premarin).{{cite book| vauthors = Fritz MA, Speroff L | chapter = Postmenopausal Hormone Therapy |title=Clinical Gynecologic Endocrinology and Infertility| chapter-url = https://books.google.com/books?id=KZLubBxJEwEC&pg=PA751 |date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=751–}}{{cite journal | vauthors = Bhavnani BR | title = Pharmacokinetics and pharmacodynamics of conjugated equine estrogens: chemistry and metabolism | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 217 | issue = 1 | pages = 6–16 | date = January 1998 | pmid = 9421201 | doi = 10.3181/00379727-217-44199 | s2cid = 45177839 }}{{cite journal | vauthors = Bhavnani BR, Cecutti A, Gerulath A | title = Pharmacokinetics and pharmacodynamics of a novel estrogen delta8-estrone in postmenopausal women and men | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 67 | issue = 2 | pages = 119–131 | date = October 1998 | pmid = 9877212 | doi = 10.1016/s0960-0760(98)00082-x | s2cid = 54352249 }}{{cite journal | vauthors = Baracat E, Haidar M, Lopez FJ, Pickar J, Dey M, Negro-Vilar A | title = Estrogen activity and novel tissue selectivity of delta8,9-dehydroestrone sulfate in postmenopausal women | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 84 | issue = 6 | pages = 2020–2027 | date = June 1999 | pmid = 10372704 | doi = 10.1210/jcem.84.6.5800 | doi-access = free }} It produces 8,9-dehydro-17β-estradiol as an important active metabolite, analogously to conversion of estrone or estrone sulfate into estradiol.{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | date = August 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }} The compound was first described in 1997.{{cite journal | vauthors = Bhavnani BR, Cecutti A, Dey MS | title = Effects in postmenopausal women of delta-8-estrone sulfate: A novel estrogen component of Premarin. | journal = Journal Society Gynecologic Investigation | date = 1997 | volume = 4 | issue = 1 (Suppl | pages = 392 }} In addition to 8,9-dehydroestrone and 8,9-dehydro-17β-estradiol, 8,9-dehydro-17α-estradiol is likely also to be present in conjugated estrogens, but has not been identified at this time.