253435-07-3

Basic information

• Product Name: Viniferin
• Synonyms: rel-5-[(2R,3R)-2,3-Dihydro-6-hydroxy-2-(4-hydroxyphenyl)-4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-3-benzofuranyl]-1,3-benzenediol
• CAS NO: 253435-07-3
• Molecular Formula: C28H22O6
• Molecular Weight: 454.47
• Mol File: 253435-07-3.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Viniferin(CAS DataBase Reference)
• NIST Chemistry Reference: Viniferin(253435-07-3)
• EPA Substance Registry System: Viniferin(253435-07-3)

Safety Data

• Hazardous Substances Data: 253435-07-3(Hazardous Substances Data)

Upstream product

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 412004-56-9 4-bromo-1-(cyclopropylmethoxy)benzene 
• 540-38-5 p-Iodophenol 
• 106-41-2 4-bromo-phenol 
• 20469-65-2 1-bromo-3,5-dimethoxybenzene 
• 39151-19-4 1-(3,5-dimethoxyphenyl)ethan-1-one 
• 855400-66-7 3-bromo-5-methoxyphenol 
• 33527-94-5 4-acetoxyiodobenzene 
• 50841-50-4 (2-bromo-1-(3,5-dimethoxyphenyl)ethanone) 

Downstream Products

• 872357-75-0 (+)-cis-ε-viniferin 
• 223558-50-7 trans-ε-viniferin pentaacetate 
• 1527502-97-1 C₂₁H₁₆O₂ 
• 1527502-99-3 C₂₈H₂₂O 
• 1527503-02-1 C₃₃H₁₇F₁₅O₁₆S₅ 
• 165883-77-2 (-)-vitisin B 
• 165883-77-2 (+)-vitisin C 

Relevant articles and documents

Identification of isomers of resveratrol dimer and their analogues from wine grapes by HPLC/MSn and HPLC/DAD-UV

A facile method based on HPLC/(-)ESI-MSn is established for the analysis of seven isomers of resveratrol dimers and three of their analogues in Xinjiang wine grapes. The structures of these compounds are positively or tentatively determined. Among them, three are tentatively identified as new compounds. MSn experiments on the [M-H]- ions provide abundant structural information, especially regarding the relative abundance of the key product ions, m/z 333 and 369 (385 in compound 3), which can be utilised to distinguish whether or not the compound identified contains the scaffold of the isomer of a resveratrol dimer. The relative abundance of key product ions remains unchanged as collision energy varies from 0.60 to 0.95 V. All the trans-, and cis-isomers could be identified by HPLC/DAD-UV spectra. The UV spectra of compounds 2 and 9 tentatively show cis and trans- configurations, respectively.

Investigation of monomeric and oligomeric wine stilbenoids in red wines by ultra-high-performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry

RATIONALE Stilbenoids are secondary plant metabolites responsible for the protection of multiple plant species including grape vine from bacterial and fungal infection. Red wine has been shown to be a major source of these compounds in the human diet, where they display an array of health benefits. Providing a more complete profile of the stilbenoids present in red wine, this study detects 41 stilbenoid compounds, 23 of which have never before been detected in red wine. METHODS Red wine extracts were scanned using an ultra-high-performance liquid chromatograph coupled to a hybrid quadrupole time-of-flight mass analyzer. Multiple targeted MS/MS precursor ion scan experiments were performed using electrospray ionization operated in negative mode. Precursor ion masses were scanned for the monomeric and oligomeric stilbenoids, as well as modifications such as O-glycosylation, methoxylation and oxidation products of these compounds. Accurate mass precursor and characteristic product ions afforded partial structural elucidation and assignment of these compounds. RESULTS A total of 41 (both known and novel) stilbenoids were detected in extracted red wine. In addition to the well-known monomeric stilbenes, several resveratrol-resveratrol homodimers (m/z 453.1344), resveratrol-piceatannol heterodimers (m/z 469.1293) and piceatannol-piceatannol homodimers (m/z 485.1236) were detected. Modified dimers of resveratrol including O-glycosylated (m/z 615.1872), methoxylated (m/z 485.1606) and oxidized (m/z 471.1449) dimers were also detected. Multiple trimers of resveratrol (m/z 679.1978) were detected for the first time in red wine, as well as some known and some novel stilbenoid tetramers (m/z 905.2604). CONCLUSIONS In summary, 41 stilbenoids were detected in red wine, 23 for the first time. Both monomeric and oligomeric stilbenoids were partially identified and assigned by their accurate mass precursor ions and characteristic stilbenoid fragmentation patterns. Knowledge gained from these experiments contributes to a more complete understanding of the origin of the beneficial properties of red wine. Copyright

Viniferin derivatives, preparation method thereof and composition for preventing or treating infection caused by pneumococcal biofilm comprising the same as an active ingredient

The present invention relates to a viniferin derivative compound represented by chemical formula 1 to chemical formula 4; a method for producing the same; a composition for preventing or treating an infection caused by a pneumococcal biofilm, wherein the composition comprises the viniferin derivative compound as an active ingredient; an antibacterial composition for Streptococcus pneumoniae; and a coating composition for inhibiting pneumococcal biofilm formation. The pharmaceutical composition, the antibacterial composition, and the coating composition of the present invention have excellent antibacterial effects.

Plant-derived purification, chemical synthesis, and in vitro/in vivo evaluation of a resveratrol dimer, viniferin, as an HCV Replication inhibitor

Oligostilbenoid compounds, a group of resveratrol multimers, display several anti-microbial activities through the neutralization of cytotoxic oxidants, and by inhibiting essential host and viral enzymes. In our previous study, we identified a series of oligostilbenoid compounds as potent hepatitis C virus (HCV) replication inhibitors. In particular, vitisin B, a resveratrol tetramer, exhibited the most dramatic anti-HCV activity (EC50 = 6 nM and CC50 > 10 μ M) via the disruption of the viral helicase NS3 (IC50 = 3 nM). However, its further development as an HCV drug candidate was halted due to its intrinsic drawbacks, such as poor stability, low water solubility, and restricted in vivo absorption. In order to overcome these limitations, we focused on (+)-"-viniferin, a resveratrol dimer, as an alternative. We prepared three different versions of (+)-"-viniferin, including one which was extracted from the grapevine root (EVF) and two which were chemically synthesized with either penta-acetylation (SVF-5Ac) or no acetylation (SVF) using a newly established synthesis method. We confirmed their anti-HCV replication activities and minimal cytotoxicity by using genotype 1b and 2a HCV replicon cells. Their anti-HCV replication action also translated into a significant reduction of viral protein expression. Anti-HCV NS3 helicase activity by EVF was also verified in vitro. Finally, we demonstrated that SVF has improved pharmacokinetic properties over vitisin B. Overall, the favorable antiviral and pharmacokinetic properties of these three versions of viniferin warrant their further study as members of a promising new class of anti-HCV therapeutics.