(±)-ε-Viniferin is a racemic form of ε-Viniferin. (±)-ε-Viniferin has P450 inhibitory antioxidant as well as hepatoprotective and antibacterial activities. (±)-ε-Viniferin has antibacterial and antibiofilm activities against Gram-positive bacteria Streptococcus pneumoniae with a MIC of 20 μM.

Physicochemical Properties

Molecular Formula	C28H22O6
Molecular Weight	454.47
Exact Mass	454.141
Elemental Analysis	C, 74.00; H, 4.88; O, 21.12
CAS #	253435-07-3
PubChem CID	366354
Appearance	Typically exists as solid at room temperature
Density	1.5±0.1 g/cm3
Boiling Point	694.8±55.0 °C at 760 mmHg
Flash Point	374.0±31.5 °C
Vapour Pressure	0.0±2.3 mmHg at 25°C
Index of Refraction	1.777
LogP	4.6
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Heavy Atom Count	34
Complexity	672
Defined Atom Stereocenter Count	0
SMILES	C1=CC(=CC=C1C=CC2=C3C(C(OC3=CC(=C2)O)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O
InChi Key	FQWLMRXWKZGLFI-UHFFFAOYSA-N
InChi Code	InChI=1S/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H
Chemical Name	5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Synonyms	5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol; 253435-07-3; Cis-epsilon-viniferin; Cis-?-viniferin; SCHEMBL1903054; MCA25012
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Antimicrobial agent targeting Streptococcus pneumoniae biofilm formation (no specific molecular target identified) [1]
ln Vitro	(±)-ε-Viniferin exhibited potent antibacterial activity against Streptococcus pneumoniae with MIC (minimum inhibitory concentration) = 16 μg/mL and MBC (minimum bactericidal concentration) = 32 μg/mL [1] Significantly inhibited biofilm formation at sub-MIC concentrations (4 and 8 μg/mL), reducing biofilm biomass by 40% and 60% respectively vs. untreated controls (p<0.01) [1] Disrupted pre-formed pneumococcal biofilms by 50% at 32 μg/mL after 24h treatment (crystal violet assay) [1]
Cell Assay	Biofilm formation assay: S. pneumoniae strains cultured in tryptic soy broth + 1% glucose. Bacterial suspensions (10⁶ CFU/mL) treated with (±)-ε-Viniferin (0-32 μg/mL) in 96-well plates. After 24h incubation, biofilms stained with 0.1% crystal violet, dissolved in ethanol, and quantified at OD570nm [1] Pre-formed biofilm disruption: Mature biofilms grown for 24h before (±)-ε-Viniferin treatment (16-32 μg/mL). Biofilm integrity assessed via crystal violet staining after 24h exposure [1]
References	[1].Ruthenium Chloride-Induced Oxidative Cyclization of Trans-Resveratrol to (±)-ε-Viniferin and Antimicrobial and Antibiofilm Activity Against Streptococcus pneumonia. Front Pharmacol. 2019 Aug 14:10:890.
Additional Infomation	(±)-ε-Viniferin was synthesized via ruthenium chloride-catalyzed oxidative cyclization of trans-resveratrol, yielding a racemic mixture [1] Mechanism: Disrupts extracellular polymeric substance (EPS) matrix in pneumococcal biofilms, enhancing susceptibility to conventional antibiotics [1] Potential application: Adjuvant therapy for drug-resistant S. pneumoniae infections by targeting biofilm-mediated resistance [1] 5-[6-Hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol has been reported in Vitis betulifolia, Vitis riparia, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

Typically soluble in DMSO (e.g. 10 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.2004 mL	11.0018 mL	22.0037 mL
	5 mM	0.4401 mL	2.2004 mL	4.4007 mL
	10 mM	0.2200 mL	1.1002 mL	2.2004 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.