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U6628

Sigma-Aldrich

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
EC Number:
208-888-3
MDL number:
MFCD00009620
UNSPSC Code:
12352103
PubChem Substance ID:
24900437
NACRES:
NA.25

Assay

≥95%

mp

223-225 °C (lit.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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

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

Gene Information

mouse ... Nos2(18126)

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Emad M Hassan et al.
Planta medica, 74(14), 1749-1750 (2008-11-01)
Phytochemical investigation of the methanolic extract of Plumeria acutifolia (Apocynaceae) leaves has led to the isolation and identification by spectroscopic means of a new monoterpene alkaloid, (R)-4'-((S)-1-hydroxyethyl)-5,6-dihydro-5' H-spiro[cyclopenta[C]pyridine-7,2'-furan)-5'-one, for which the name plumerianine was adopted, the iridoid 15-demethylplumeride, and three
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
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
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
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
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