517-09-9

Usage

Uses

Used in Pharmaceutical Industry:
EQUILENIN is used as a pharmaceutical compound for its estrogenic properties. It is a component of conjugated estrogenic hormones, which are used in hormone replacement therapy and other medical treatments related to estrogen deficiency.
Used in Environmental Protection:
EQUILENIN is recognized as a contaminant of emerging concern by the United States Environmental Protection Agency (EPA). It is included in the Drinking Water Contaminant Candidate List 3 (CCL 3), indicating its potential impact on environmental and food contaminants. Efforts are made to monitor and control the presence of EQUILENIN in water sources to ensure public health and safety.

Purification Methods

Crystallise (+)-equilenin from EtOH (solubility is 0.63% at 18o, 2.5% at 78o), aqueous EtOH or *C6H6 (Norite) and dry it in a vacuum. It sublimes on melting and at 170-180o/0.01mm. The acetate crystallises from MeOH with m 165-167o and [ ] D +71o (c 1, CHCl3). [Bachmann et al. J Am Chem Soc 62 824 1940, Beilstein 8 III 1522, 1523, 1525, 8 IV 1420.]

InChI:InChI=1/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

Upstream product

• 6030-91-7 equilenin acetate 
• 1423-97-8 17β-dihydroequilenin 
• 1758-24-3 3-acetoxy-estra-1,3,5⁽¹⁰⁾,6-tetraen-17-one 
• 412305-64-7 7-methoxy-10,11-dihydro-phenanthro[2,1-d]isoxazole 
• 56588-56-8 3-methoxy-13-methyl-17-oxo-12,13,16,17-tetrahydro-11H-cyclopenta[a]phenanthrene-15-carboxylic acid methyl ester 
• 94040-39-8 rac-3-methoxy-16.17-seco-estrapentaene-(1.3.5.7.9)-dioic acid-(16.18)-18-methyl ester 
• 6636-49-3 methyl 1,2,3,4-tetrahydro-7-methoxy-1α-methoxycarbonylmethyl-2β-methylphenanthrene-2α-carboxylate 
• 82182-42-1 rac-3-methoxy-17.17a-seco-D-homo-estrapentaene-(1.3.5.7.9)-dioic acid-(17.18)-dimethyl ester 
• 6636-51-7 methyl 1,2,3,4-tetrahydro-1-hydroxy-7-methoxy-1-methoxycarbonylmethyl-2-methylphenanthrene-2-carboxylate 
• 62017-80-5 methyl 1,2,3,4-tetrahydro-7-methoxy-2-methyl-1-oxophenanthrene-2-carboxylate 
• 82182-41-0 (+/-)-(2c-carboxy-7-methoxy-2t-methyl-1,2,3,4-tetrahydro-[1r]phenanthryl)-acetic acid 
• 82182-40-9 (+/-)-(7-methoxy-2-methyl-2-carboxy-3.4-dihydro-2H-phenanthrylidene-(1seqtrans))-acetic acid 
• 412282-70-3 7-methoxy-2-methyl-1-oxo-1,2,3,4-tetrahydro-phenanthrene-2-carbonitrile 
• 21513-03-1 3-methoxy-1,3,5⁽¹⁰⁾,6,8,14-estrahexaen-17-one 

Downstream Products

• 41761-49-3 (13S)-3-amino-13-methyl-(13r,14t)-11,12,13,14,15,16-hexahydro-cyclopenta[a]phenanthren-17-one 
• 17659-99-3 (+/-)-Z-Bisdehydrodoisynolic acid 
• 5684-12-8 3-hydroxy-16.17-seco-estrapentaen-(A.B)-oic acid-(17) 
• 16680-48-1 sodium sulfate equilenin 
• 6030-91-7 equilenin acetate 
• 1423-97-8 17β-dihydroequilenin 
• 6639-99-2 17α-dihydroequilenin 
• 3907-67-3 3-O-methylequilinine 
• 53-16-7 Estrone 
• 105795-59-3 8a-methyl-2-phenethyl-(8ar,11at)-2,3,7,8,8a,10,11,11a-octahydro-1H-cyclopenta[7,8]phenanthro[1,2-e][1,3]oxazin-9-one 
• 102263-47-8 2-benzyl-8a-methyl-(8ar,11at)-2,3,7,8,8a,10,11,11a-octahydro-1H-cyclopenta[7,8]phenanthro[1,2-e][1,3]oxazin-9-one 
• 517-07-7 estra-5,7,9-triene-3β,17β-diol 
• 15342-12-8 estra-5,7,9-trien-17β-ol 
• 131944-03-1 16α-hydroxyequilenin 

Relevant academic research and scientific papers

Practical semisynthesis of equilenin and its derivatives

Equilenin 2 and its derivatives are important intermediates in the synthesis of steroidal drugs. Until now, these estrogens were produced by extraction from pregnant mare's urine due to the lack of efficient synthetic methods. Most reported semisyntheses of equilenin involve expensive raw materials or toxic reagents to suppress undesired epimerization at C/D ring juncture. Herein, we reported a practical synthesis of highly pure equilenin and its derivatives from an easily available raw material 6 with conventional reagents.

6-Hydroxyequilenins as estrogenic agents

This invention provides estrogen receptor modulators of formula 1, having the structure wherein, R1 is hydrogen, alkyl of 1-6 carbon atoms, benzyl, alkylcarbonyl of 2-7 carbon atoms, or benzoyl; X is R2 is hydrogen, alkyl of 1-6 carbon atoms, benzyl, alkylcarbonyl of 2-7 carbon atoms, or benzoyl; R3 is hydrogen, alkyl of 1-6 carbon atoms, hydroxy, or alkoxy of 1-6 carbon atoms; a pharmaceutically acceptable salt thereof, a pharmaceutically acceptable salt of a sulfate ester of the hydrdoxyl group at the 3- or 17-position when R1 or R2 is hydrogen, or a glucuronide of the hydrdoxyl group at the 3- or 17-position when R1 or R2 is hydrogen.

An effective approach to B-ring aromatization of equilin

Epoxidation of equilin followed by rearrangement-elimination catalyzed by either proton acids or Lewis acids generates an estrogen with an aromatic B-ring. This procedure represents an effective method for the conversion of an equilin nucleus to an equilenin nucleus.

Treating cardiac disorders with Δ9(11)-dehydro-8-isoestrone

This invention relates to 8α-3-hydroxyestra- 1,3,5( 10),9( 11 )tetraen-17-one (Δ9( 11 )-dehydro-8-isoestrone) (VI), STR1 to the process for its preparation, to pharmaceutical compositions containing said 8α-3-hydroxyestra- 1,3,5(10), 9(11)tetraen-17-one (Δ9(11)-dehydro-8-isoestrone) (VI) and to the use of said 8α-3-hydroxyestra-1,3,5(10),9(11 )tetraen-17-one (A9( 11 )-dehydro-8-isoestrone) (VI) for modifying the balance between bone production and bone resorption, and as an antioxidant in a host animal, including man.