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Key Documents

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:
Molecular Weight:
442.72
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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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Guang-Bo Xie et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 32(18), 1890-1892 (2007-12-07)
To investigate the chemical constituents of Ilex pernyi. The chemical constituents were isolated by various column chromatographic methods. The structures were identified by spectral data. Eight triterpenoid compounds were isolated and identified as ursolic acid (1), lupeol (2), alpha-amyrin (3)
Sabira Begum et al.
Natural product research, 18(2), 135-140 (2004-02-27)
Five constituents including one new pentacyclic triterpenoid guajanoic acid (1) and four known compounds beta-sitosterol (2), uvaol (3), oleanolic acid (4), and ursolic acid (5) have been isolated from the leaves of Psidium guajava. The new constituent 1 has been
A Martins et al.
International journal of antimicrobial agents, 37(5), 438-444 (2011-03-18)
Several compounds isolated from the plant Carpobrotus edulis were evaluated for their activity against multidrug-resistant (MDR) bacteria and their efflux pump systems. Amongst the compounds isolated, six compounds were tested, namely uvaol, β-amyrin, oleanolic acid, catechin, epicatechin and monogalactosyldiacylglycerol. Oleanolic
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
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

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