3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one

Base Information

• Chemical Name: 3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one
• CAS No.: 474-86-2
• Molecular Formula: C18H20 O2
• Molecular Weight: 268.356
• Hs Code.: 2937230000
• NSC Number: 756756
• DSSTox Substance ID: DTXSID90859387
• Wikidata: Q27163738
• ChEMBL ID: CHEMBL1474552
• Mol file: 474-86-2.mol

Synonyms:SR-05000001615;Spectrum_000285;Spectrum2_000746;Spectrum3_000416;Spectrum4_001635;Spectrum5_000449;BSPBio_001972;KBioGR_002069;KBioSS_000765;DivK1c_000812;SPECTRUM1500275;SPBio_000732;CHEMBL1474552;SCHEMBL14136188;CHEBI:91940;HMS502I14;KBio1_000812;KBio2_000765;KBio2_003333;KBio2_005901;KBio3_001192;DTXSID90859387;NINDS_000812;WKRLQDKEXYKHJB-UHFFFAOYSA-N;HMS1920K18;HMS2094I15;Pharmakon1600-01500275;CCG-40143;NSC756756;NSC-756756;3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one;IDI1_000812;NCGC00094667-01;NCGC00094667-02;NCGC00094667-03;NCGC00178887-01;LS-64748;SBI-0051364.P003;FT-0667944;AB00051978_02;SR-05000001615-1;SR-05000001615-2;BRD-A88080608-001-01-8;BRD-A88080608-001-03-4;Q27163738

Chemical Property of 3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one

Chemical Property:

• Appearance/Colour: plate powder, soluble in alcohol, acetone, sparingly soluble in water.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 238-240 °C(lit.)
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 459.1 °C at 760 mmHg
• PKA: pKa 10.26±0.04(H2O t=23±2) (Uncertain)
• Flash Point: 195.4 °C
• PSA: 37.30000
• Density: 1.22 g/cm³
• LogP: 3.73750
• Storage Temp.: Refrigerator
• Water Solubility.: 1.4mg/L(25 oC)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 268.146329876
• Heavy Atom Count: 20
• Complexity: 466

Purity/Quality:

Equilin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 40-62-63-39/23/24/25-23/24/25-11
• Safety Statements: 36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC3C(=CCC4=C3C=CC(=C4)O)C1CCC2=O
• Uses: Equilin is an estrogen found in Premarin, which is a mixture of conjugated estrogens widely used in hormone replacement therapy.

Technology Process of 3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one

There total 33 articles about 3-hydroxy-13-methyl-9,11,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

C22H26O4 → equilin (474-86-2)

Guidance literature:

C₂₂H₂₆O₄; With hydrogenchloride; In methanol; water; at 20 ℃; for 1h;

With potassium carbonate; In methanol; water; at 20 ℃; for 0.5h;

Reference yield:

3-methoxyestra-1,3,5(10),8(9)-tetraen-17β-ol (6733-79-5) → equilin (474-86-2)

Guidance literature:

Multi-step reaction with 6 steps

1: MCPBA, K₂CO₃ / benzene; hexane

2: H₂ / Pd-C / ethanol

3: POCl₃

4: NaOH / methanol

5: MeMgI / diethyl ether / (heating)

6: Al(OiPr)3, MeCOEt / benzene

With sodium hydroxide; methyl magnesium iodide; hydrogen; aluminum isopropoxide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; butanone; trichlorophosphate; palladium on activated charcoal; In methanol; diethyl ether; ethanol; hexane; benzene;

DOI:10.1016/S0040-4020(01)92768-1

Reference yield:

8α, 17β-dihydroxy-3-methoxy-oestra-1,3,5(10),9(11)-tetraen (13944-54-2) → equilin (474-86-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd-C / ethanol

2: POCl₃

3: NaOH / methanol

4: MeMgI / diethyl ether / (heating)

5: Al(OiPr)3, MeCOEt / benzene

With sodium hydroxide; methyl magnesium iodide; hydrogen; aluminum isopropoxide; butanone; trichlorophosphate; palladium on activated charcoal; In methanol; diethyl ether; ethanol; benzene;

DOI:10.1016/S0040-4020(01)92768-1

upstream raw materials:

Equilenin-ethylenketal

(9S,13S,14S,17S)-13-Methyl-9,11,12,13,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

4,7-estradiene-3,17-dione

19-nortestosterone acetate

Downstream raw materials:

estra-1,3,5⁽¹⁰⁾,7-tetraene-17-one-3-acetate

17alpha-Dihydroequilin

equilenin

equilenin acetate

Refernces

• 1、 -. "Method for synthesizing equilin". . . Retrieved 2021/05/26.