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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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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)
Julianderson Carmo et al.
Molecules (Basel, Switzerland), 25(21) (2020-11-01)
Uvaol is a natural pentacyclic triterpene that is widely found in olives and virgin olive oil, exerting various pharmacological properties. However, information remains limited about how it affects fibroblasts and endothelial cells in events associated with wound healing. Here, we
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
L I Somova et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 11(2-3), 121-129 (2004-04-09)
The cardiotonic and antidysrhythmic effects of four triterpenoid derivatives, namely oleanolic acid (OA), ursolic acid (UA), and uvaol (UV), isolated from the leaves of African wild olive (Olea europaea, subsp. africana) as well as methyl maslinate (MM) isolated from the
Margaret Alexander et al.
Cell host & microbe, 30(1), 17-30 (2021-11-26)
Bacterial activation of T helper 17 (Th17) cells exacerbates mouse models of autoimmunity, but how human-associated bacteria impact Th17-driven disease remains elusive. We show that human gut Actinobacterium Eggerthella lenta induces intestinal Th17 activation by lifting inhibition of the Th17
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