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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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Product Name

Uvaol, ≥95%

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)

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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.

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.).

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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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
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
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
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
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
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