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Merck
CN

U6628

Uvaol

≥95%

Synonym(s):

Urs-12-ene-3,28-diol

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About This Item

Empirical Formula (Hill Notation):
C30H50O2
CAS Number:
545-46-0
Molecular Weight:
442.72
NACRES:
NA.25
PubChem Substance ID:
24900437
UNSPSC Code:
12352103
EC Number:
208-888-3
MDL number:
MFCD00009620

Key Documents

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InChI

1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22+,23-,24+,25+,27+,28-,29-,30-/m1/s1

InChI key

XUARCIYIVXVTAE-ZAPOICBTSA-N

SMILES string

C[C@@H]1CC[C@]2(CO)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]2[C@H]1C

assay

≥95%

mp

223-225 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

100

Gene Information

mouse ... Nos2(18126)

Related Categories

General description

Uvaolis a pentacyclic triterpene compound usually extracted from plant leaves such as Apocynum venetum L., olive leaves (Olea europaea L.), and oregano (Origanum vulgare L.).

Application

Uvaol has been used as retinoic acid receptor-related orphan receptor gamma t (RORγt) inhibitor to study the role of cardiac glycoside reductase 2 (Cgr2) enzyme on its metabolism.

Biochem/physiol Actions

Uvaolexerts pharmacological properties such as antioxidant, anticancer, anti-inflammatory, and wound healing. It also displays vasodilator, hepatoprotective, and antimicrobial effects. Uvaol has inhibitory effects on nitric oxide (NO) release.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6817
BCCM0149
BCCJ3037
BCCF6195
BCCD6167

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B S Min et al.
Planta medica, 65(4), 374-375 (1999-06-12)
The methanol extracts of the leaves of Crataegus pinnatifida showed potent inhibitory activities against HIV-1 protease at a concentration of 100 micrograms/ml. The subsequent fractionation and isolation of the extract gave two active compounds. Their structures were identified as uvaol
Lei Liu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 32(17), 1762-1765 (2007-11-13)
To investigate the chemical constituents of Pyrola calliatha. The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data. Ten compounds were isolated and identified as chimaphilin (1), uvaol(2), ursolic acid (3), 2beta,3beta,23-trihydroxy-12-ene-28-ursolic acid
X Z Xu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 25(4), 225-226 (2003-01-07)
To study the chemical components of Gentiana tizuensis distributed in Qinghai Province. Chromatography and spectral analyses were used to isolate the constituents and elucidate their structure. Four compounds were isolated and identified as uvaol, L-(+)-l-O-methyl-myo-inositol, ursolic acid,beta-sitosterol. All these components
De-Hong Huang et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 34(3), 375-378 (2011-08-10)
To study the chemical constituents of Coleus forskohlii. Isolation and purification were carried out by silica gel column chromatographic and Toyopearl HW-40F. Compounds were identified and elucidated by spectral and chemical methods. Seven compounds were obtained from ethyl acetate extract
A Martins et al.
Anticancer research, 30(3), 829-835 (2010-04-16)
A bioassay-guided separation protocol, including the testing of the extracts, fractions and pure compounds for their ability to inhibit P-glycoprotein (the efflux pump responsible for the multidrug resistance of the used cell line) of mouse lymphoma cells containing the human
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