Equilenin

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Chemical compound

title: "Equilenin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["sterols", "hydroxyarenes", "estranes", "estrogens", "ketones"] description: "Chemical compound" topic_path: "general/sterols" source: "https://en.wikipedia.org/wiki/Equilenin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 461094560 | IUPAC_name = (13S,14S)-3-hydroxy-13-methyl-12,14,15,16-tetrahydro-11H-cyclopenta[a]phenanthren-17-one | image = Equilenin.svg | image_class = skin-invert-image | width = 225px

| tradename = | pregnancy_category = | legal_status = | routes_of_administration = By mouth | class = Estrogen

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 517-09-9 | UNII_Ref = | UNII = W8FTJ17C4J | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 444865 | DrugBank_Ref = | DrugBank = DB03515 | ChemSpiderID_Ref = | ChemSpiderID = 392668 | KEGG_Ref = | KEGG = C14303 | ChEBI = 34739 | ChEMBL_Ref = | ChEMBL = 225546 | synonyms = 6,8-Didehydroestrone; Estra-1,3,5(10),6,8-pentaen-3-ol-17-one

| C=18 | H=18 | O=2 | SMILES = O=C4[C@]3(CCc1c(ccc2c1ccc(O)c2)[C@@H]3CC4)C | StdInChI_Ref = | StdInChI = 1S/C18H18O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2-5,10,16,19H,6-9H2,1H3/t16-,18-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = PDRGHUMCVRDZLQ-WMZOPIPTSA-N

Equilenin, also known as 6,8-didehydroestrone, as well as estra-1,3,5(10),6,8-pentaen-3-ol-17-one, is a naturally occurring steroidal estrogen obtained from the urine of pregnant mares. It is used as one of the components in conjugated estrogens (brand name Premarin). It was the first complex natural product to be fully synthesized, in work reported by 1940 by Bachmann and Wilds.

Chemistry

Synthesis

Total synthesis

The synthesis developed by the Bachmann group started from Butenand's ketone – and which can be readily prepared from 1,6-Cleve's acid. The approach was based on well-established transformations like the Claisen condensation, the Reformatsky reaction, the Arndt–Eistert reaction, and the Dieckmann condensation. in this synthesis, a mixture of stereoisomers were prepared and then resolved, and the choice of target was partly because of the existence of only two chiral carbons and hence only four stereoisomers.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/0/00/Bachmann's_total_synthesis_of_equilenin.jpg"] ::

The overall yield of the synthesis was 2.7% based on a twenty-step process starting from Cleve's acid.

References

References

  1. (14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
  2. (28 March 2012). "Clinical Gynecologic Endocrinology and Infertility". Lippincott Williams & Wilkins.
  3. (1940). "The Total Synthesis of the Sex Hormone Equilenin and Its Stereoisomers". [[J. Am. Chem. Soc.]].
  4. (1939). "The Total Synthesis of the Sex Hormone Equilenin". [[J. Am. Chem. Soc.]].
  5. (1974). "Natural Products Chemistry". [[Academic Press]].
  6. (January 2000). "The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century". Angewandte Chemie.

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sterolshydroxyarenesestranesestrogensketones