U6753
Ursolic acid
≥90%
Synonym(s):
3β-Hydroxy-12-ursen-28-ic acid
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About This Item
Empirical Formula (Hill Notation):
C30H48O3
CAS Number:
Molecular Weight:
456.70
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-034-0
Beilstein/REAXYS Number:
2228563
MDL number:
Assay:
≥90%
Quality Level
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)
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.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
580.5 °F
flash_point_c
304.7 °C
ppe
Eyeshields, Gloves, type N95 (US)
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Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats.
Shih YH, et al.
Neuroscience Letters, 363(2), 136-140 (2004)
Ursolic acid induces neural regeneration after sciatic nerve injury.
Liu B, et al.
Neural Regeneration Research, 8(27), 2510-2510 (2013)
Ursolic acid enhances pentobarbital-induced sleeping behaviors via GABAergic neurotransmission in mice.
Jeon, SJ, et al.
European Journal of Pharmacology, 762, 443-448 (2015)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| U6753-100MG | 04061835514328 |
| U6753-500MG | 04061837409998 |