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SMB00948

Sigma-Aldrich

trans-Resveratrol 3-O-β-D-glucuronide

≥95% (HPLC)

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Synonym(s):
3-Hydroxy-5-[(1E )-2-(4-hydroxyphenyl)ethenyl]phenyl β-D-glucopyranosiduronic acid, trans-Resveratrol 3-O-glucuronide, trans-Resveratrol 3-glucuronide, RSV 3-O-glucuronide, RSV 3-glucuronide, RSV 3-glur, Resveratrol 3-O-β-D-glucuronide, Resveratrol 3-O-b-D-glucuronide, Resveratrol 3-O-glucuronide, Resveratrol 3-glucuronide
Empirical Formula (Hill Notation):
C20H20O9
CAS Number:
387372-17-0
Molecular Weight:
404.37
MDL number:
MFCD24386496
UNSPSC Code:
12352201
NACRES:
NA.25

biological source

synthetic

Quality Level

200

Assay

≥95% (HPLC)

form

solid

mol wt

403.37 g/mol

storage condition

(Tightly closed. Dry)

technique(s)

HPLC: suitable

color

white to beige

storage temp.

2-8°C

SMILES string

Canonical SMILES: C1=CC(=CC=C1C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)C(=O)O)O)O)O)O)OIsomeric SMILES: C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)C(=O)O)O)O)O)O)O

InChI

1S/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17+,18-,20+/m0/s1

InChI key

QWSAYEBSTMCFKY-OTPOQTMVSA-N

General description

Trans-Resveratrol 3-O-glucuronide, also known as Resveratrol 3-O-glucuronide, is a polyphenol belonging to the stilbenoid glycosides class, found in various plants and fruits. This natural compound is an active metabolite and glucuronide derivative of trans-resveratrol, a polyphenol present in grapes and other plants, known for potential health benefits. Extensive research indicates that it possess diverse biological activities including antioxidant, antiproliferative, anti-inflammatory, and anti-cancer properties. Further, It activates the sirtuin pathway, implicated in aging and metabolism regulation. While its mechanism of action is not fully elucidated, it is believed to engage the sirtuin pathway and inhibit enzymes involved in inflammatory mediator production. Notably, it exhibits inhibitory effects on specific cancer cell proliferation and bacterial growth.Furthermore, it also exerts inhibitory effects on specific cancer cell proliferation and bacterial growth. This active form undergoes various metabolic transformations, including hydrolysis, oxidation, reduction, and glucuronidation, exhibiting frequent interaction with human erythrocytes. Such characteristics make it crucial for biochemical and metabolomics research.

Application

trans-Resveratrol 3-O-β-ᴅ-glucuronide is a metabolite that finds application in metabolomics and biochemical research.

Features and Benefits

  • High-purity compound suitable for a wide variety of research applications

Other Notes

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WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Susan J Zunino et al.
Oncology letters, 14(2), 2517-2522 (2017-08-07)
Resveratrol has been reported to inhibit or induce DNA damage, depending upon the type of cell and the experimental conditions. Dietary resveratrol is present in the body predominantly as metabolites and limited data is available concerning the activities of these
Juan Antonio Giménez-Bastida et al.
Molecular nutrition & food research, 63(22), e1900629-e1900629 (2019-08-24)
Recent evidence demonstrates that resveratrol (RSV) metabolites, but not free RSV, reach malignant tumors (MT) in breast cancer (BC) patients. Since these metabolites, as detected in MT, do not exert short-term antiproliferative or estrogenic/antiestrogenic activities, long-term tumor-senescent chemoprevention has been
Ljubica Svilar et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1104, 119-129 (2018-11-20)
Trans-resveratrol is a stilbene polyphenol with a large spectrum of biological activities. This is why it is widely studied in terms of activities, bioavailability and quantitation in different foods, beverages and biological matrices. Different analytical methods are employed for its

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