2,3-Dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid

Base Information

• Chemical Name: 2,3-Dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
• CAS No.: 599-07-5
• Molecular Formula: C30H46O6
• Molecular Weight: 502.692
• NSC Number: 382025
• Wikidata: Q105111357
• Mol file: 599-07-5.mol

Synonyms:Catsanogenin;2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid;Olean-12-ene-23,28-dioic acid, 2,3-dihydroxy-, (2beta,3beta,4alpha)-;NSC382025;NSC-382025;CHEBI:177711;IDGXIXSKISLYAC-UHFFFAOYSA-N;AKOS037514734;FT-0776927;2,3-Dihydroxyolean-12-ene-23,28-dioic acid;2,3-Dihydroxyolean-12-ene-23,28-dioic acid #

Chemical Property of 2,3-Dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 7.62E-19mmHg at 25°C
• Melting Point: 380-382℃ (dec.)
• Boiling Point: 635.9°Cat760mmHg
• PKA: 4.30±0.70(Predicted)
• Flash Point: 352.4°C
• PSA: 115.06000
• Density: 1.23g/cm³
• LogP: 5.26910
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 502.32943918
• Heavy Atom Count: 36
• Complexity: 1020

Purity/Quality:

99%, ^*data from raw suppliers

Medicagenicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C(=O)O)O)O)C)C)C2C1)C)C(=O)O)C
• Uses: Medicagenic acid is a versatile compound extracted from some plants, such as the branches of Eucommia ulmoides. It has antifungal properties towards candida albicans.

Technology Process of 2,3-Dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid

There total 12 articles about 2,3-Dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic 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:

2-hydroxy-23-carboxy-3-O-[β-D-galactopyranosyl-(1->2)-β-D-glucuronopyranosyl]oleanolic acid (915138-26-0) → D-Galactose (59-23-4) + D-Glucuronic acid (6556-12-3,25249-06-3,25990-10-7,36562-70-6,36655-86-4) + 2β,3β-dihydroxy-olean-12-ene-23,28-dioic acid (599-07-5)

Guidance literature:

With water; Acidic conditions;

DOI:10.1080/14786410902833948

Reference yield:

asterbatanoside K → 2β,3β-dihydroxy-olean-12-ene-23,28-dioic acid (599-07-5)

Guidance literature:

With hydrogenchloride; In methanol; at 100 ℃; for 4h;

DOI:10.1016/0031-9422(95)00016-Z

Reference yield:

3β-O-(4-deoxy-β-D-hex-4-enopyranosyluronic acid), 2β-hydroxy-olean-12-en-23,18-dioic acid (108886-08-4) → 2β,3β-dihydroxy-olean-12-ene-23,28-dioic acid (599-07-5)

Guidance literature:

With perchloric acid; In water; at 135 ℃; for 2.5h;

upstream raw materials:

medicoside H

undeca-acetate of medicoside J

medicagenic acid 3-O-β-D-glucopyranosyl-28-O-β-D-glucopyranoside

3β-(β-D-Glucopyranosyl)-2β-hydroxy-Δ¹²-oleanene-23,28-dioic acid

Downstream raw materials:

3-hydroxy-2-carbonyl-23-norolean-3,12-diene-28-acid

di-(2-nitrobenzyl) 2β,3β-dihydroxy-Δ¹²-oleanene-23,28-dioate

Refernces

• 1、 Timbekova, A. E.,Abubakirov, N. K.. "TRITERPENE GLYCOSIDES OF ALFALFA. IV. MEDICOSIDE J.". . p. 574 - 577. Retrieved 1986.
• 2、 Timebekova, A. E.,Larin, M. F.,Yagudaev, M. R.,Abubakirov, N. K.. "TRITERPENE GLYCOSIDES OF ALFALFA". . p. 573 - 576. Retrieved 2007/10/02.