U6753

Acide ursolique

≥90%

• Synonyme(s) : Acide 3β-hydroxy-12-ursen-28-ique
• Formule empirique (notation de Hill): C₃₀H₄₈O₃
• Numéro CAS: 77-52-1
• Poids moléculaire : 456.70
• Beilstein: 2228563
• Numéro CE : 201-034-0
• Numéro MDL: MFCD00009621
• Code UNSPSC : 12352002
• ID de substance PubChem : 57654721
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 100
• Essai: ≥90%
• Pf: 292 °C (dec.) (lit.)
• Température de stockage: 2-8°C
• Chaîne SMILES: [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
• Clé InChI: WCGUUGGRBIKTOS-GPOJBZKASA-N
• Informations sur le gène: mouse ... Ifng(15978) , Nos2(18126)

Description

Description générale

Ursolic acid (UA) is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits anti-bacterial,[1] anti-cancer,[2] anti-oxidative and anti-inflammatory effects.[3] It can also promote neuroregeneration after peripheral nerve injury.[3] UA can enhance sleep duration by activating the GABAergic neurotransmitter system.[4] [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.[5] Ursolic acid can also be used to prepare novel heterocyclic derivatives for various activity studies.[6]

Actions biochimiques/physiologiques

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 580.5 °F
• Point d'éclair (°C): 304.7 °C
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)