13850-16-3

Basic information

• Product Name: 2α,19α－Dihydroxyursolic acid
• Synonyms: 2α,19α－Dihydroxyursolic acid;2α,3β,19-Trihydroxyurs-12-en-28-oic acid;2α,3β,19α-Trihydroxy-19-methyl-30-noroleana-12-ene-28-oic acid;2α,3β,19α-Trihydroxyurs-12-en-28-oic acid;Tormentic acid
• CAS NO: 13850-16-3
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.69912
• Mol File: 13850-16-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 273 °C
• Boiling Point: 602.7 °C at 760 mmHg
• Flash Point: 332.3 °C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 4.86E-17mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Pyridine (Sparingly)
• PKA: 4.47±0.70(Predicted)
• CAS DataBase Reference: 2α,19α－Dihydroxyursolic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2α,19α－Dihydroxyursolic acid(13850-16-3)
• EPA Substance Registry System: 2α,19α－Dihydroxyursolic acid(13850-16-3)

Safety Data

• Hazardous Substances Data: 13850-16-3(Hazardous Substances Data)

Usage

Description

2α,19α-Dihydroxyursolic acid is a naturally occurring triterpenoid compound that can be found in various plant sources, including the rhizomes of Tormentil. It possesses a unique chemical structure characterized by two hydroxyl groups at the 2α and 19α positions, which may contribute to its potential biological activities.

Uses

Used in Anticancer Applications:
2α,19α-Dihydroxyursolic acid is used as an anticancer agent for its inhibitory effect on carcinogenesis. It may modulate various oncological signaling pathways, exerting inhibitory effects on tumor growth and progression. Additionally, it has the potential to demonstrate synergistic anticancer effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases.
Used in Hepatoprotective Applications:
2α,19α-Dihydroxyursolic acid is used as a hepatoprotective agent for the prevention of acetaminophen (APAP)-induced liver injury. It achieves this by inhibiting oxidative stress and inflammation, which are key factors in liver damage caused by APAP overdose or other hepatotoxic agents.
Used in Pharmaceutical Industry:
2α,19α-Dihydroxyursolic acid is used as a pharmaceutical candidate due to its potential therapeutic properties. Its unique chemical structure and biological activities make it a promising compound for the development of new drugs targeting various diseases, including cancer and liver disorders.
Used in Drug Delivery Systems:
Similar to gallotannin, 2α,19α-Dihydroxyursolic acid may also benefit from novel drug delivery systems to enhance its applications and efficacy against disease targets. Various organic and metallic nanoparticles could be employed as carriers for 2α,19α-Dihydroxyursolic acid delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

InChI:InChI=1/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23+,26+,27-,28-,29-,30+/m1/s1

Upstream product

• 121064-78-6 3-O-trans-p-coumaroyltormentic acid 
• 1309589-79-4 2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester 
• 52936-88-6 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid 
• 95298-47-8 2α,3α,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester 

Downstream Products

• 13850-15-2 methyl 2α,3β,19-trihydroxyurs-12-en-28-oate 
• 13849-91-7 polnolic acid 
• 1412898-52-2 (2R,19R)-methyl 2-acetyloxy-19-hydroxy-3-oxours-12-en-28-carboxylate 
• 97094-23-0 (2R,3R,19R)-3-acetyloxy-2,19-dihydroxyurs-12-en-28-carboxylic acid 
• 97094-22-9 (2R,3R,19R)-2-acetyloxy-3,19-dihydroxyurs-12-en-28-carboxylic acid 
• 63478-78-4 methyl 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oate 
• 14539-80-1 Diacetyl-tormentsaeure-methylester 
• 52936-89-7 methyl 2α,3α,19-trihydroxyurs-12-en-28-oate 
• 52936-88-6 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid 
• 13850-14-1 (2R,3R,19R)-2,3-bis(acetyloxy)-19-hydroxyurs-12-en-28-carboxylic acid 

Relevant articles and documents

Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis

Chaenomeles sinensis has been consumed traditionally for the treatment of throat diseases, diarrhea, inflammatory diseases, and dry beriberi. Repeated chromatography of the CHCl3-soluble fraction from the 80% MeOH extract of C. sinensis twigs led to the isolation of three new triterpenoids, sinenic acid A (1), 3β-O-cis-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (2), and 3β-O-cis-caffeoylbetulin (3), together with 20 analogues. The chemical structures of 1-3 were determined using diverse NMR techniques and HRMS data analysis, chemical methods, and computational approaches supported by advanced statistics (CP3). All the purified compounds were evaluated not only for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) but for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells. Their anti-inflammatory effects were also assessed by measuring nitric oxide levels in lipopolysaccharide-insulted murine microglia BV2 cells.

Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina

A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 μM), 28-O-β-d- glucopyranosyl pomolic acid (IC50 = 9.5 μM), rosamutin (IC 50 = 35.5 μM), and kaji-ichigoside F1 (IC50 = 14.1 μM), inhibited d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by d-GalN.

Retrovirus protease inhibitors

A compound composition and method of treating a retrovirus infection are disclosed. In particular, isolated triterpenes have been shown to have significant inhibitory activity against HIV-1.