31297-79-7

Basic information

• Product Name: (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester
• Synonyms: (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester;24-Deoxysericoside;Arjunetin;ARJUNETIN(SH);(2α,3β,49α)- 2,3,19-Trihydroxyolean-12-en-28-oic acid β-D-glucopyranosyl ester
• CAS NO: 31297-79-7
• Molecular Formula: C36H58O10
• Molecular Weight: 651
• Mol File: 31297-79-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 744.5°Cat760mmHg
• Flash Point: 224.7°C
• Appearance: /
• Density: 1.31
• Vapor Pressure: 1.39E-25mmHg at 25°C
• Refractive Index: 1.605
• PKA: 12.52±0.70(Predicted)
• CAS DataBase Reference: (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester(31297-79-7)
• EPA Substance Registry System: (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester(31297-79-7)

Safety Data

• Hazardous Substances Data: 31297-79-7(Hazardous Substances Data)

Usage

General Description

(2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester is a complex organic compound known as a glycoside because it contains a sugar moiety, specifically a glucopyranosyl (a form of glucose). (2alpha,3beta,19alpha)-2,3,19-Trihydroxyolean-12-en-28-oic acid beta-D-glucopyranosyl ester, like others in the oleanolic acid family, is a triterpenoid, possessing a 30-carbon skeleton usually arranged in five or six rings. This particular variant also carries three hydroxy (OH) functional groups on its molecule and has a glucopyranosyl ester form. Triterpenoids such as this are often extracted from plants and are studied for potential medicinal properties, including anti-cancer and anti-inflammatory effects. The complete bioactivity of this specific compound is still under research.

InChI:InChI=1/C36H58O10/c1-31(2)11-13-35(30(44)46-29-27(42)26(41)25(40)22(17-37)45-29)14-12-33(5)19(20(35)15-31)7-8-24-34(33,6)10-9-23-32(3,4)28(43)21(39)16-36(23,24)18-38/h7,20-29,37-43H,8-18H2,1-6H3/t20-,21+,22-,23?,24-,25-,26+,27-,28-,29+,33-,34-,35+,36-/m1/s1

Upstream product

• 508-02-1 Oleanolic acid 

Downstream Products

• 31298-06-3 (2α,3β,19α)-2,3,19-trihydroxyolean-12-en-28-oic acid 

Relevant articles and documents

Biotransformation of oleanolic acid by Alternaria longipes and Penicillium adametzi

Microbial transformation of oleanolic acid (1) was carried out. Six transformed products (2-7) from 1 by Alternaria longipes and three transformed products (8-10) from 1 by Penicillium adametzi were isolated. Their structures were elucidated as 2,3,19-trihydroxy-ursolic acid-28-O - d-glucopyranoside (2), 2,3,19-trihydroxy-ursolic acid-28-O - d-glucopyranoside (3), oleanolic acid 28-O - d-glucopyranosyl ester (4), oleanolic acid-3-O - d-glucopyranoside (5), 3-O-(-d-glucopyranosyl)-oleanolic acid-28-O - d-glucopyranoside (6), 2,3,19a-trihydroxy-oleanolic acid-28-O - d-glucopyranoside (7), 21-hydroxyl oleanolic acid-28-O - d-glucopyranoside (8), 21-hydroxyl oleanolic acid (9), and 7,21-dihydroxyl oleanolic acid (10) based on the extensive NMR studies. Among them, 10 was a new compound and compounds 5 and 8-10 had stronger cytotoxic activities against Hela cell lines than the substrate. At the same time, it was reported for the first time in this paper that the skeletons of compounds 2 and 3 were changed from oleanane to uranane and seven glycosidation products were obtained by biotransformation.