915-32-2

Basic information

• Product Name: 3-HYDROXY-(3ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER
• Synonyms: 3-HYDROXY-(3ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER;10-Hydroxy-1,2,6A,6B,9,9,12A-heptamethyl-1,3,4,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-octadecahydro-2H-picene-4A-carboxylic acid methyl ester;3beta-Hydroxy-urs-12-en-28-oic acid methyl ester;Inchi=1/C31H50o3/C1-19-11-16-31(26(33)34-8)18-17-29(6)21(25(31)20(19)2)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/H9,19-20,22-25,32H,10-18H2,1-8H3/T19-,20+,22+,23-,24+,25+,28+,29-,30-,31+/m1/s;Methyl (3beta)-3-hydroxyurs-12-en-28-oate;Urs-12-en-28-oic acid, 3-hydroxy-, methyl ester, (3beta)-
• CAS NO: 915-32-2
• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.7269
• Mol File: 915-32-2.mol
• Article Data: 57

Chemical Properties

• Boiling Point: 529.2°Cat760mmHg
• Flash Point: 192.2°C
• Appearance: /
• Density: 1.06g/cm³
• CAS DataBase Reference: 3-HYDROXY-(3ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-(3ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER(915-32-2)
• EPA Substance Registry System: 3-HYDROXY-(3ALPHA)-URS-12-EN-28-OIC ACID METHYL ESTER(915-32-2)

Safety Data

• Hazardous Substances Data: 915-32-2(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 77-52-1 ursolic acid 
• 77-52-1 ursolic acid 
• 77-78-1 dimethyl sulfate 
• 117804-25-8 cynarasaponin A methyl ester 
• 75-36-5 acetyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 989-72-0 methyl ursonate 
• 915-79-7 (3β)-3-acetoxy-urs-12-en-28-carboxylic acid 
• 990-89-6 methyl 3-acetylursolate 
• 77-52-1 Ursolic acid 
• 77-52-1 Ursolic acid 

Downstream Products

• 989-72-0 methyl ursonate 
• 94482-50-5 methyl (3β)-3-(benzoyloxy)urs-12-en-28-oate 
• 987-94-0 urs-12-en-3,28-diol 
• 77-52-1 ursolic acid 
• 990-89-6 acetate of methyl ursolate 
• 990-89-6 methyl 3-acetylursolate 
• 545-46-0 uvaol 
• 42447-82-5 3-hydroxyimino-urs-12-en-28-oic acid methyl ester 
• 303174-78-9 methyl 23-benzyloxy-3-oxours-12-en-28-oate 
• 303174-79-0 methyl 23-benzyloxy-3α-hydroxyurs-12-en-28-oate 
• 303174-77-8 methyl 23-benzyloxy-3,3-ethylenedioxyurs-12-en-28-oate 
• 303174-81-4 methyl 23-benzyloxy-3α-(tert-butyldimethyl)silyloxyurs-12-en-28-oate 
• 4518-70-1 methyl corosolate 
• 52213-28-2 methyl 2α,3α-dihydroxyurs-12-en-28-oate 

Relevant articles and documents

Studies on the constituents of medicinal and related plants in Sri Lanka. I. New triterpenes from Hedyotis lawsoniae

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Pentacylic triterpenes from Lavandula coronopifolia: structure related inhibitory activity on α-glucosidase

Ten pentacyclic triterpenes (1-10) were isolated from Lavandula coronopifolia. We evaluated their α-glucosidase inhibitory activity, and found that the aglycones, 1, 2, 3, 4, 7 and 10 showed superior IC50 values to the positive control. In order to explain the structural requirements for α-glucosidase inhibitory activity, eleven derivatives were prepared, including one new compound, 2-formyl-(A)1–19α-hydroxy-1-norursane-2, 12-dien-28-oic acid 10c. The results demonstrated that a free hydroxyl at ring-A and a free carboxylic group at position 28 are key structural features for the α-glucosidase inhibitory activity, also that an ursane skeleton is optimum for the activity. Additionally, enzyme kinetic analysis of pomolic acid 2, the most potent compound, revealed that it inhibited α-glucosidase in a mixed-type manner. The molecular docking simulation validated this type of inhibition and highlighted the role of the C-3 hydroxyl and C-28 carboxylic groups in interaction with the enzyme in silico.

Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement

Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticancer activity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 and C-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGH of hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. New derivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomeric forms by the Barbier-Grignard procedure and three of them were found to be active toward all of the three targets. The implication of the transcriptional nuclear factor NF?κB in the mechanism of action was assessed for the more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpress NF?κB.