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U6753

Acide ursolique

≥90%

Synonyme(s) :

Acide 3β-hydroxy-12-ursen-28-ique

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A propos de cet article

Formule empirique (notation de Hill) :
C30H48O3
Numéro CAS:
77-52-1
Poids moléculaire :
456.70
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
57654721
EC Number:
201-034-0
Beilstein/REAXYS Number:
2228563
MDL number:
MFCD00009621
Assay:
≥90%
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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)

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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Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
BCCP3004
BCCM8760
BCCK7788
BCCJ6581
BCCG0742

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Consulter la Bibliothèque de documents

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