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SML0032

Sigma-Aldrich

Triacetyl resveratrol

≥98% (HPLC)

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Synonym(s):
3,5,4′-Tri-O-acetylresveratrol, 5-[(1E)-2-[4-(acetyloxy)phenyl]ethenyl]-1,3-Benzenediol-1,3-diacetate
Empirical Formula (Hill Notation):
C20H18O6
CAS Number:
42206-94-0
Molecular Weight:
354.35
MDL number:
MFCD01546481
UNSPSC Code:
12352200
PubChem Substance ID:
329825102
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to tan

solubility

DMSO: ≥18 mg/mL

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

room temp

SMILES string

CC(=O)Oc1ccc(cc1)\C=C\c2cc(OC(C)=O)cc(OC(C)=O)c2

InChI

1S/C20H18O6/c1-13(21)24-18-8-6-16(7-9-18)4-5-17-10-19(25-14(2)22)12-20(11-17)26-15(3)23/h4-12H,1-3H3/b5-4+

InChI key

PDAYUJSOJIMKIS-SNAWJCMRSA-N

General description

Resveratrol (RSV) is a natural polyphenolic antioxidant.

Biochem/physiol Actions

Resveratrol prodrug. SIRT inhibitor
Resveratrol (RSV) plays a protective role on the nervous and cardiovascular systems. It is considered as a modulator of energetic metabolism as it controls glucose homeostasis in obese mice, improves fatty acid oxidation (FAO) and promotes the expression of genes that participate in mitochondrial biogenesis.
Triacetyl resveratrol displays superior bioavailability to the parent compound, resveratrol. The compound induces p53 activity and inhibits proliferation in breast and prostate tumor cell lines.

WGK

WGK 3

Regulatory Information

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Resveratrol induces a mitochondrial complex I dependent increase in NADH oxidation responsible for sirtuin activation in liver cells.
Desquiret-Dumas V, et al.
The Journal of Biological Chemistry, 2013 (2013)
Liqiong Ding et al.
Biochemical pharmacology, 171, 113691-113691 (2019-11-11)
Resveratrol is a natural compound found in many plant species that has broad therapeutic benefits. Here, we investigated the effects of resveratrol on the replication of HSV-2. We found that resveratrol accelerated replication of HSV-2 and increased release of progeny
Tammy R Dugas et al.
Journal of biomedical materials research. Part B, Applied biomaterials, 107(3), 646-651 (2018-08-10)
Peripheral artery disease is a cardiovascular disease characterized by a narrowing of arteries that supply blood to the extremities, particularly, the legs. When surgical intervention is warranted, the primary approach is balloon angioplasty. Drug coated balloons (DCB) designed to release
Xiaoyun Zeng et al.
Journal of agricultural and food chemistry, 65(22), 4384-4394 (2017-05-05)
The persistence of latent HIV reservoirs presents a significant challenge to viral eradication. Effective latency reversing agents (LRAs) based on "shock and kill" strategy are urgently needed. The natural phytoalexin resveratrol has been demonstrated to enhance HIV gene expression, although
Hyeanjeong Jeong et al.
International journal of molecular sciences, 20(17) (2019-09-05)
Epigenetic remodeling via histone acetylation has become a popular therapeutic strategy to treat Alzheimer's disease (AD). In particular, histone deacetylase (HDAC) inhibitors including M344 and SAHA have been elucidated to be new drug candidates for AD, improving cognitive abilities impaired
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