Doisynolic acid

Base Information

• Chemical Name: Doisynolic acid
• CAS No.: 482-49-5
• Deprecated CAS: 21528-80-3,52484-75-0
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• UNII: CBJ6A3D19C
• Nikkaji Number: J62.755K
• Wikidata: Q27275385
• Wikipedia: Doisynolic_acid
• Mol file: 482-49-5.mol

Synonyms:doisynolic acid

Chemical Property of Doisynolic acid

Chemical Property:

• Vapor Pressure: 8.55E-10mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 474.1°Cat760mmHg
• Flash Point: 254.6°C
• PSA: 57.53000
• Density: 1.131g/cm³
• LogP: 3.94910
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 288.17254462
• Heavy Atom Count: 21
• Complexity: 407

Purity/Quality:

99% ^*data from raw suppliers

DOISYNOLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C2CCC3=C(C2CCC1(C)C(=O)O)C=CC(=C3)O
• Isomeric SMILES: CC[C@H]1[C@@H]2CCC3=C([C@H]2CC[C@]1(C)C(=O)O)C=CC(=C3)O

Technology Process of Doisynolic acid

There total 13 articles about Doisynolic 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: 30.0%

Estrone (53-16-7) → (+)-trans-doisynolic acid (482-49-5) + (1S,2S,4aS,10aR)-7-Hydroxy-1-[(E)-2-((8S,9S,13R,14S)-3-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)-vinyl]-2-methyl-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-2-carboxylic acid + (E)-(8R,9S,13S,14S,8'R,9'S,13'S,14'S)-3,3'-Dihydroxy-13,13'-dimethyl-7,8,9,11,12,13,14,15,6',7',8',9',11',12',13',14',15',16'-octadecahydro-6H-[16,17']bi[cyclopenta[a]phenanthrenyliden]-17-one

Guidance literature:

With potassium hydroxide; at 280 - 290 ℃; for 1.25h; Yields of byproduct given;

DOI:10.1016/0039-128X(94)00051-D

Reference yield:

→ (+)-lumidoisynolic acid (482-49-5,482-50-8,38778-15-3,109784-48-7)

Guidance literature:

With sodium methylate; at 190 - 200 ℃;

Reference yield:

→ rac-3-hydroxy-16.17-seco-8α-estratrien-(1.3.5(10))-oic acid-(18) (482-49-5,482-50-8,38778-15-3,109784-48-7)

Guidance literature:

With pyridine hydrochloride; at 180 ℃;

DOI:10.1002/hlca.19470300606

upstream raw materials:

estradiol

Estrone

3-methoxy-16.17-seco-estratrien-(A)-oic acid-⁽¹⁷⁾

3-methoxy-16.17-seco-estratriene-(1.3.5⁽¹⁰⁾)-dioic acid-(16.17)-17-methyl ester

Downstream raw materials:

d-1β-Aethyl-2β-methyl-7-oxo-1.2.3.4.4aα,4bβ,5,6,7,9,10,10aβ-decahydro-phenanthren-carbonsaeure-(2α)

Refernces

• 1、 Miescher. "-". . p. 1727,1730. Retrieved 1944.