Dihydroresveratrol Chemical Properties

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).

pka

9.51±0.10(Predicted)

form 

solid

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.

InChI

InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2

InChIKey

HITJFUSPLYBJPE-UHFFFAOYSA-N

SMILES

C1(O)=CC(CCC2=CC=C(O)C=C2)=CC(O)=C1

Dihydroresveratrol Usage And Synthesis

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.

Uses

Dihydroresveratrol is a natural phytoestrogen.

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] CARINA M. JUNG. Interaction of dietary resveratrol with animal-associated bacteria[J]. Fems Microbiology Letters, 2009, 297 2: 266-273. DOI:10.1111/j.1574-6968.2009.01691.x
[2] LISA M BODE. In vivo and in vitro metabolism of trans-resveratrol by human gut microbiota123[J]. American Journal of Clinical Nutrition, 2013, 97 2: Pages 295-309. DOI:10.3945/ajcn.112.049379
[3] VERONIKA JAROSOVA. Metabolism of Stilbenoids by Human Faecal Microbiota.[J]. Molecules, 2019, 24 6. DOI:10.3390/molecules24061155
[4] YULIA RADKO  Lars P C  Kathrine B Christensen. Semi-preparative isolation of dihydroresveratrol-3-O-β-d-glucuronide and four resveratrol conjugates from human urine after oral intake of a resveratrol-containing dietary supplement[J]. Journal of Chromatography B, 2013, 930: Pages 54-61. DOI:10.1016/j.jchromb.2013.05.002
[5] CHISATO OODE . Synthesis of dihydroresveratrol glycosides and evaluation of their activity against melanogenesis in B16F0 melanoma cells[J]. European Journal of Medicinal Chemistry, 2014, 87: Pages 862-867. DOI:10.1016/j.ejmech.2014.09.092
[6] RICHARD G A FARAGHER. Resveratrol, but not dihydroresveratrol, induces premature senescence in primary human fibroblasts.[J]. AGE, 2011, 33 4: 555-564. DOI:10.1007/s11357-010-9201-5

Dihydroresveratrol(58436-28-5)Related Product Information

• CIS-TRIMETHOXY STILBENE
• trans Resveratrol 3-O-β-D-Glucuronide
• Resveratrol-3-4'-Disulfate
• 3,4',5-TRIMETHOXY-TRANS-STILBENE
• Punicalagin
• 1,3,6-TRI-O-GALLOYL-B-D-GLUCOSE
• (-)-Epigallocatechin gallate
• punicalin
• L-Epicatechin
• (-)-Epigallocatechin
• (-)-EGCG-3''-O-ME
• 1,2,3,4,6-PENTA-O-GALLOYL-BETA-D-GLUCOPYRANOSE
• (+)-GALLOCATECHIN
• (-)-Epicatechin gallate
• Resveratrol
• Azo-Resveratrol
• trans/cis Resveratrol-D4
• Oxyresveratrol