Дигидрорезвератрол

Identification

Dihydroresveratrol (3,5,4'-trihydroxybibenzyl; English Dihydroresveratrol, CAS 58436-28-5) is a saturated stilbenoid, a product of the reduction of the double bond of resveratrol. Synonyms: resorcinol 5-(p-hydroxyphenethyl)-, 3,4',5-trihydroxybibenzyl. Chemical formula C14H14O3.

Molecular parameters

• Molecular weight: 230.262; exact weight: 230.26
• EU number: 611-651-0
• UNII: CBY43AY0TT
• NSC number: 723534
• HS code: 2907299090
• PSA specifications: 60.7
• XLogP3: 3.1

Physico-chemical properties

• Density: 1.3±0.1 g/cm3
• Flash point: 210.9±14.7°C
• Refractive index: 1.662

Scope of application

Dihydroresveratrol is formed in the body as a metabolite of resveratrol under the influence of intestinal microbiota - reduction of the alkene bridge between two aromatic rings converts stilbene into a bibenzyl structure. The compound retains a phenolic antioxidant framework and is being studied in studies of the bioavailability, metabolism and antioxidant activity of stilbene polyphenols. Used as an analytical reference standard in the study of resveratrol metabolites in biological samples by chromatography and mass spectrometry, as well as in nutraceutical and pharmacological studies of polyphenols. Saturation of the alkene bridge changes the geometry of the molecule and, according to metabolic studies, reduces some of the biological activity inherent in the parent resveratrol, which makes dihydroresveratrol a convenient standard for distinguishing between the effects of the “parent” stilbene and its microbial metabolites. Resveratrol is one of the most studied natural polyphenols, the source of which is grape skin, peanut nuts and Japanese knotweed root (Polygonum cuspidatum); dihydroform is formed at the final stage of its microbial transformation in the human intestine, therefore its presence in biological samples is used as a marker of completed metabolism of the original stilbene. Intestinal bacteria reduce the alkene bridge of resveratrol in a stepwise manner, and the accumulation of the dihydro form, and not intermediate products, indicates the complete completion of this stage of biotransformation in a particular individual or in a particular microbiota culture. Differences in microbiota composition between individuals explain the wide interindividual variability in dihydroresveratrol concentrations found in plasma and urine after ingestion of resveratrol-containing supplements or products.

Security and storage

Hazard classification data and transport codes are not provided in the dump; information on this metabolite as a separate commercial product is published to a limited extent. As a phenolic solid, dihydroresveratrol is stored in an airtight container, in a dry place, protected from light and elevated temperatures (flash point greater than 210°C indicates a low fire hazard under normal storage conditions), away from strong oxidizing agents. When packaging the powder, use gloves to avoid dust formation; After sampling, re-close the container as quickly as possible.