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ChemicalBook--->CAS DataBase List--->58436-28-5

58436-28-5

58436-28-5 Structure

58436-28-5 Structure
IdentificationBack Directory
[Name]

Dihydroresveratrol
[CAS]

58436-28-5
[Synonyms]

Dihydroresveratol
Dihydroresveratrol
a, b-Dihydroresveratrol
3,3',5-trihydroxybibenzyl
3,4',5-Trihydroxybibenzyl
3,5,4'-Trihydroxybibenzyl
α,β-Dihydrostilbene-3,4',5-triol
4-[2-(3,5-Dihydroxyphenyl)ethyl]phenol
5-[2-(4-Hydroxyphenyl)ethyl]benzene-1,3-diol
5-[2-(4-hydroxyphenyl)ethyl]-1,3-benzenediol
Resveratrol Impurity 12(Dihydro Resveratrol)
1,3-Benzenediol, 5-[2-(4-hydroxyphenyl)ethyl]-
[Molecular Formula]

C14H14O3
[MDL Number]

MFCD11974971
[MOL File]

58436-28-5.mol
[Molecular Weight]

230.26
Chemical PropertiesBack Directory
[Melting point ]

155-157°C
[Boiling point ]

430.3±14.0 °C(Predicted)
[density ]

1.291±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 30 mg/ml).
[form ]

solid
[pka]

9.51±0.10(Predicted)
[color ]

Off-white
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
Hazard InformationBack Directory
[Description]

Dihydroresveratrol (58436-28-5) is a metabolite of resveratrol produced by gut microbiota.1-3?Glucoronide conjugates are found in human urine after oral intake of resveratrol-containing dietary supplements.4?Dihydroresveratrol glucoside is a potent melanogenesis inhibitor in B16F0 melanoma cells.5?Inactive analog of resveratrol in induction of premature senescence.6
[Uses]

Dihydroresveratrol is a major metabolite of resveratrol that is produced by animal-associated bacteria, including the gut microbiota. Dihydroresveratrol and dihydroresveratrol monosulfate are detectable in urine. The physiological effects of dihydroresveratrol have not been investigated.
[Definition]

ChEBI: Dihydroresveratrol is a stilbenol that is 1,1'-ethane-1,2-diyldibenzene with hydroxy groups at positions 1, 3 and 4'. It has a role as a xenobiotic metabolite and a plant metabolite.
[References]

1) Jung?et al.?(2009),?Interaction of dietary resveratrol with animal-associated bacteria; FEMS Microbiol. Lett.,?297?266 2) Bode?et al.?(2013),?In vivo and in vitro metabolism of trans-resveratrol by human gut microbiota; Am. J. Clin. Nutr.,?97?295 3) Jarosova?et al.?(2019),?Metabolism of Stilbenoids by Human Faecal Microbiota; Molecules,?24?E1155 4) Radco?et al.?(2013),?Semi-preparative isolation of dihydroresveratrol-3-O-?-d-glucuronide and four resveratrol conjugates from human urine after oral intake of a resveratrol-containing dietary supplement; J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 930?54 5) Oode?et al.?(2014),?Synthesis of dihydroresveratrol glycosides and evaluation of their activity against melanogenesis in B16F0 melanoma cells; Eur. J. Med. Chem.,?87?862 6) Faragher?et al.?(2011),?Resveratrol, but not dihydroresveratrol, induces premature senescence in primary human fibroblasts; Age (Dordr.),?33?555
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