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U6753

Sigma-Aldrich

Ursolic acid

≥90%

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

Quality Level

100

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)

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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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

580.5 °F

Flash Point(C)

304.7 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Ursolic acid enhances pentobarbital-induced sleeping behaviors via GABAergic neurotransmission in mice.
Jeon, SJ, et al.
European Journal of Pharmacology, 762, 443-448 (2015)
Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells
Leal AS, et al.
Bioorganic & Medicinal Chemistry, 20(19), 5774-5786 (2012)
Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats.
Shih YH, et al.
Neuroscience Letters, 363(2), 136-140 (2004)
Synthesis and anti-inflammatory activity of 3-acetyl-2-[(un) substituted phenyl]-2, 3-dihydro-1, 3, 4-oxadiazol-5-methyl 3-O-acetylursolate
Ding-Ju Y, et al.
Chinese Journal of Organic Chemistry, 28(6), 1055-1060 (2008)
Aljawharah AlQathama et al.
Biomolecules, 10(6) (2020-06-18)
We evaluate how 3-acetylation modulates the in vitro activity of ursolic acid in melanoma cells alone or in combination treatments with quercetin. Anti-proliferative studies on A375 cells and adult human dermal fibroblasts included analyses on cell cycle distribution, caspase activity
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