Etienic acid

Base Information

• Chemical Name: Etienic acid
• CAS No.: 302-97-6
• Molecular Formula: C20H28O3
• Molecular Weight: 316.441
• European Community (EC) Number: 414-990-0,629-724-0
• UNII: 6E3DV757KY
• DSSTox Substance ID: DTXSID0057706
• Nikkaji Number: J38.855F
• Wikidata: Q27264655
• ChEMBL ID: CHEMBL3185181
• Mol file: 302-97-6.mol

Synonyms:(17beta)-3-oxoandrost-4-ene-17-carboxylic acid;4-androsten-3-one-17 beta-carboxylic acid;AOBCA;etienic acid

Chemical Property of Etienic acid

Chemical Property:

• Vapor Pressure: 1.08E-10mmHg at 25°C
• Melting Point: 260 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• Refractive Index: 1.564
• Boiling Point: 483.9 °C at 760 mmHg
• PKA: 4.81±0.60(Predicted)
• Flash Point: 260.6 °C
• PSA: 54.37000
• Density: 1.17 g/cm³
• LogP: 4.21910
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 592

Purity/Quality:

99% ^*data from raw suppliers

3-Keto-4-etiocholenic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)O)CCC4=CC(=O)CCC34C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)O)CCC4=CC(=O)CC[C@]34C

Technology Process of Etienic acid

There total 46 articles about Etienic acid 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: 100.0%

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester (2681-55-2) → androst-4-en-3-one-17β-carboxylic acid (302-97-6)

Guidance literature:

With potassium hydroxide; In methanol; for 5h; Heating;

DOI:10.1016/S0968-0896(99)00169-8

Reference yield: 94.77%

3-hydroxy-5-androstene-17β-carboxylic acid → androst-4-en-3-one-17β-carboxylic acid (302-97-6)

Guidance literature:

3-hydroxy-5-androstene-17β-carboxylic acid; With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 24h; Large scale;

With hydrogenchloride; In water; for 2h; pH=1 - 2; Reagent/catalyst; Temperature; Time; Reflux; Large scale;

Reference yield: 93.84%

3-keto-4-androstene-17-aldehyde → androst-4-en-3-one-17β-carboxylic acid (302-97-6)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; acetonitrile; at 20 ℃;

upstream raw materials:

Progesterone

etienic acid

10,13-Dimethyl-17-vinyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

3-oxo-androst-4-ene-17β-carboxylic acid methyl ester

Downstream raw materials:

C₆₁H₁₀₄NO₁₀P

N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide

21-methylpregn-4-ene-3,20-dione

N,N-diethyl-3-oxo-4-aza-5α-androstane-17β-carboxamide

Refernces

• 1、 Smith,L.L.. "-". . p. 289 - 297. Retrieved 1967.
• 2、 Li, Na,Qian, Hao,Wang, Junru,Wang, Shijun,Yuan, Xiaorong. "Design, synthesis, and biological evaluation of two series of novel a-ring fused steroidal pyrazines as potential anticancer agents". . . Retrieved 2020/03/06.
• 3、 -. "Steroid compound as well as preparation method and application thereof (by machine translation)". Paragraph 0058-0059; 0066-0067. . Retrieved 2020/10/29.