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Merck
모든 사진(1)

주요 문서

U6753

Sigma-Aldrich

Ursolic acid

≥90%

동의어(들):

3β-Hydroxy-12-ursen-28-ic acid

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About This Item

실험식(Hill 표기법):
C30H48O3
CAS Number:
Molecular Weight:
456.70
Beilstein:
2228563
EC Number:
MDL number:
UNSPSC 코드:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

≥90%

mp

292 °C (dec.) (lit.)

저장 온도

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

유전자 정보

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일반 설명

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]

애플리케이션

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.

생화학적/생리학적 작용

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

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


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문서 라이브러리 방문

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
Ursolic acid induces neural regeneration after sciatic nerve injury.
Liu B, et al.
Neural Regeneration Research, 8(27), 2510-2510 (2013)
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)
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)

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