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Fórmula empírica (notación de Hill):
C30H48O3
Número CAS:
Peso molecular:
456.70
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-034-0
Beilstein/REAXYS Number:
2228563
MDL number:
Assay:
≥90%
Servicio técnico
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Permítanos ayudarleQuality 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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Clase de almacenamiento
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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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 enhances pentobarbital-induced sleeping behaviors via GABAergic neurotransmission in mice.
Jeon, SJ, et al.
European Journal of Pharmacology, 762, 443-448 (2015)