U6753

Ursolic acid

≥90%

• Synonym(s): 3β-Hydroxy-12-ursen-28-ic acid
• Empirical Formula (Hill Notation): C₃₀H₄₈O₃
• CAS Number: 77-52-1
• Molecular Weight: 456.70
• Beilstein/REAXYS Number: 2228563
• EC Number: 201-034-0
• MDL number: MFCD00009621
• UNSPSC Code: 12352002
• PubChem Substance ID: 57654721
• NACRES: NA.22

Properties

• assay: ≥90%
• mp: 292 °C (dec.) (lit.)
• storage temp.: 2-8°C
• SMILES string: [H][C@@]12CC[C@]3(C)[C@]([H])(CC=C4[C@]5([H])[C@@H](C)[C@H](C)CC[C@@]5(CC[C@@]34C)C(O)=O)[C@@]1(C)CC[C@H](O)C2(C)C
• InChI: 1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
• InChI key: WCGUUGGRBIKTOS-GPOJBZKASA-N
• Gene Information: mouse ... Ifng(15978) , Nos2(18126)

Description

General description

Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial, anti-cancer, anti-oxidative and anti-inflammatory effects. It can also promote neuroregeneration after peripheral nerve injury. UA can enhance sleep duration by activating the GABAergic neurotransmitter system. [GABA= γ-aminobutyric acid]

Application

Ursolic acid can be used as a starting material to synthesize ethoxycarbonylmethyl ursolate (ECU) by reacting with ethyl chloroacetate. ECU is further used as a key intermediate in the total synthesis of a biologically important compound 3-acetyl-2-[(un)substituted phenyl]-2,3-dihydro-1,3,4-oxadiazol-5-Me 3-O-acetylursolate. Ursolic acid can also be used to prepare novel heterocyclic derivatives for various activity studies.

Biochem/physiol Actions

Triterpenoid found in a variety of fruits, including apples. Cardioprotective and anti-tumor agent. Under study as a potential Alzheimer′s disease therapeutic due to its inhibitory effect on the interactions between amyloid-β and the CD36 receptor.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: 580.5 °F
• flash_point_c: 304.7 °C
• ppe: Eyeshields, Gloves, type N95 (US)