Dihydroresveratrol

Base Information

• Chemical Name: Dihydroresveratrol
• CAS No.: 58436-28-5
• Molecular Formula: C14H14O3
• Molecular Weight: 230.263
• Hs Code.: 2907299090
• European Community (EC) Number: 611-651-0
• NSC Number: 723534
• UNII: CBY43AY0TT
• DSSTox Substance ID: DTXSID60973983
• Nikkaji Number: J391.840H
• Wikipedia: Dihydro-resveratrol
• Wikidata: Q5276414
• Metabolomics Workbench ID: 27976
• ChEMBL ID: CHEMBL111234
• Mol file: 58436-28-5.mol

Synonyms:dihydro-resveratrol;dihydroresveratrol

Chemical Property of Dihydroresveratrol

Chemical Property:

• Vapor Pressure: 5.23E-08mmHg at 25°C
• Refractive Index: 1.661
• Boiling Point: 430.3 °C at 760 mmHg
• PKA: 9.51±0.10(Predicted)
• Flash Point: 210.9 °C
• PSA: 60.69000
• Density: 1.291 g/cm³
• LogP: 2.58860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 30 mg/ml).
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 214

Purity/Quality:

99%, ^*data from raw suppliers

Dihydroresveratrol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCC2=CC(=CC(=C2)O)O)O
• 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. Dihydroresveratrol is a natural phytoestrogen.

Technology Process of Dihydroresveratrol

There total 7 articles about Dihydroresveratrol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) → dihydroresveratrol (58436-28-5)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/j.bmc.2005.09.070

Reference yield: 95.0%

resveratrol (501-36-0,61434-67-1,133294-37-8) → dihydroresveratrol (58436-28-5)

Guidance literature:

With 5% Pd(II)/C(eggshell); hydrogen; In methanol; at 20 ℃; for 12h; under 760.051 Torr;

DOI:10.1002/cbdv.200800229

Reference yield: 84.0%

1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethane (83638-45-3) → dihydroresveratrol (58436-28-5)

Guidance literature:

With hydrogen bromide; acetic acid; In water; for 3h; Reflux;

DOI:10.1021/acs.jnatprod.7b00129

upstream raw materials:

resveratrol

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

3,5,4'-trimethoxystilbene

1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethane

Downstream raw materials:

3,5-di-O-methyldihydroresveratrol

α,β-dihydro-3,5-dihydroxy-4'-methoxystilbene

1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethane

4-{4-[2-(3,5-dihydroxyphenyl)ethyl]phenoxy}-5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol

Refernces

• 1、 Oode, Chisato,Shimada, Wataru,Izutsu, Yukiko,Yokota, Mariko,Iwadate, Takehiro,Nihei, Ken Ichi. "Synthesis of dihydroresveratrol glycosides and evaluation of their activity against melanogenesis in B16F0 melanoma cells". . p. 862 - 867. Retrieved 2014.
• 2、 Tamboli, Vajir,Defant, Andrea,Mancini, Ines,Tosi, Paolo. "A study of resveratrol-copper complexes by electrospray ionization mass spectrometry and density functional theory calculations". . p. 526 - 532. Retrieved 2011.
• 3、 -. "TERPENOPHENOLIC COMPOUNDS AND THEIR USE". Paragraph 0108; 0109. . Retrieved 2021/10/11.
• 4、 -. "The transparent or translucent cosmetic". Paragraph 0016. . Retrieved 2019/07/03.