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malvidin-3-glucoside
3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloride

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Name:(3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
CAS Number: 7228-78-6Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:230-631-9
FDA UNII: B34F52D7NB
MDL:MFCD00185576
Molecular Weight:528.89465000
Formula:C23 H25 Cl O12
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
Soluble in:
 water, 300.7 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Malvidin 3-glucoside
Carbosynth
For experimental / research use only.
Malvidin-3-glucoside
ExtraSynthese
For experimental / research use only.
Oenin chloride (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Oenin chloride ≥90%
Sigma-Aldrich: Sigma
For experimental / research use only.
Oenin chloride ≥90% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for malvidin-3-glucoside usage levels up to:
 not for fragrance use.
 
Recommendation for malvidin-3-glucoside flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :65178
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
Chemidplus:0007228786
 
References:
 (3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):65178
Pubchem (sid):135021573
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C12140
HMDB (The Human Metabolome Database):HMDB30777
FooDB:FDB002714
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bean black bean seed
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 bean field bean
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 bilberry fruit
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 bilberry leaf
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 blueberry fruit
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 grape
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 grape exocarp
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 grape fruit
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 grape pericarp
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 vaccinium spp.
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 wine red wine
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Synonyms:
(3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloride
 malvidin-3-O-glucoside chloride
 oenin
 oenin chloride
 

Articles:

PubMed:Targeted analysis of bioactive phenolic compounds and antioxidant activity of Macedonian red wines.
PubMed:Anti-inflammatory effect of the blueberry anthocyanins malvidin-3-glucoside and malvidin-3-galactoside in endothelial cells.
PubMed:Tracing flavonoid degradation in grapes by MS filtering with stable isotopes.
PubMed:The protective effects of berry-derived anthocyanins against visible light-induced damage in human retinal pigment epithelial cells.
PubMed:In Silico Insight into Potent of Anthocyanin Regulation of FKBP52 to Prevent Alzheimer's Disease.
PubMed:NMR methodologies in the analysis of blueberries.
PubMed:Berry anthocyanins suppress the expression and secretion of proinflammatory mediators in macrophages by inhibiting nuclear translocation of NF-κB independent of NRF2-mediated mechanism.
PubMed:Isolation of high-purity anthocyanin mixtures and monomers from blueberries using combined chromatographic techniques.
PubMed:Inhibitory effects of wild blueberry anthocyanins and other flavonoids on biomarkers of acute and chronic inflammation in vitro.
PubMed:Antioxidant features of red wine pyranoanthocyanins: experimental and theoretical approaches.
PubMed:Antioxidative and cardioprotective properties of anthocyanins from defatted dabai extracts.
PubMed:Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids.
PubMed:Anthocyanin determination in blueberry extracts from various cultivars and their antiproliferative and apoptotic properties in B16-F10 metastatic murine melanoma cells.
PubMed:The identification of degradation products and degradation pathway of malvidin-3-glucoside and malvidin-3,5-diglucoside under microwave treatment.
PubMed:Structural characterization of a A-type linked trimeric anthocyanin derived pigment occurring in a young Port wine.
PubMed:Structural features of copigmentation of oenin with different polyphenol copigments.
PubMed:Malvidin-3-O-β glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats.
PubMed:Pre-clinical anti-inflammatory aspects of a cuisine and medicinal millennial herb: Malva sylvestris L.
PubMed:Efficient quantification of the health-relevant anthocyanin and phenolic acid profiles in commercial cultivars and breeding selections of blueberries ( Vaccinium spp.).
PubMed:Supplementation of a grape seed and grape marc meal extract decreases activities of the oxidative stress-responsive transcription factors NF-κB and Nrf2 in the duodenal mucosa of pigs.
PubMed:Identification and quantification of anthocyanins in Kyoho grape juice-making pomace, Cabernet Sauvignon grape winemaking pomace and their fresh skin.
PubMed:Different phenolic compounds activate distinct human bitter taste receptors.
PubMed:Degradation kinetics of malvidin-3-glucoside and malvidin-3,5-diglucoside exposed to microwave treatment.
PubMed:Phenolic profiles and antioxidant activity of litchi (Litchi Chinensis Sonn.) fruit pericarp from different commercially available cultivars.
PubMed:Inhibitory effects of anthocyanins on secretion of Helicobacter pylori CagA and VacA toxins.
PubMed:The anthocyanin metabolites gallic acid, 3-O-methylgallic acid, and 2,4,6-trihydroxybenzaldehyde decrease human colon cancer cell viability by regulating pro-oncogenic signals.
PubMed:Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease.
PubMed:Bog bilberry anthocyanin extract improves motor functional recovery by multifaceted effects in spinal cord injury.
PubMed:Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation.
PubMed:The effect of self-aggregation on the determination of the kinetic and thermodynamic constants of the network of chemical reactions in 3-glucoside anthocyanins.
PubMed:Identification by mass spectrometry of new compounds arising from the reactions involving malvidin-3-glucoside-(O)-catechin, catechin and malvidin-3-glucoside.
PubMed:On the bioavailability of flavanols and anthocyanins: flavanol-anthocyanin dimers.
PubMed:Protective role of malvidin-3-glucoside on peroxynitrite-induced damage in endothelial cells by counteracting reactive species formation and apoptotic mitochondrial pathway.
PubMed:Optimization of the Extraction of Anthocyanins from the Fruit Skin of Rhodomyrtus tomentosa (Ait.) Hassk and Identification of Anthocyanins in the Extract Using High-Performance Liquid Chromatography-Electrospray Ionization-Mass Spectrometry (HPLC-ESI-MS).
PubMed:Formation of vitisins and anthocyanin-flavanol adducts during red grape drying.
PubMed:Direct effects of Vaccinium myrtillus L. fruit extracts on rat heart mitochondrial functions.
PubMed:Metabolism of anthocyanins by human gut microflora and their influence on gut bacterial growth.
PubMed:A new approach on the gastric absorption of anthocyanins.
PubMed:Comprehensive colorimetric study of anthocyanic copigmentation in model solutions. Effects of pH and molar ratio.
PubMed:Survey of antioxidant capacity and phenolic composition of blueberry, blackberry, and strawberry in Nanjing.
PubMed:Antiradical properties of red wine portisins.
PubMed:Phenolic composition and antioxidant activity in seed coats of 60 Chinese black soybean (Glycine max L. Merr.) varieties.
PubMed:Characteristic phenolic composition of single-cultivar red wines of the Canary Islands (Spain).
PubMed:Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
PubMed:Rapid methods to determine procyanidins, anthocyanins, theobromine and caffeine in rat tissues by liquid chromatography-tandem mass spectrometry.
PubMed:New phenolic grape skin products from Vitis vinifera cv. Pinot Noir.
PubMed:Characterization and quantification of polyphenols in Amazon grape (Pourouma cecropiifolia Martius).
PubMed:Thermodynamic and kinetic properties of a red wine pigment: catechin-(4,8)-malvidin-3-O-glucoside.
PubMed:Modulation of flavonoid biosynthetic pathway genes and anthocyanins due to virus infection in grapevine (Vitis vinifera L.) leaves.
PubMed:Physico-chemical and chromatic characterization of malvidin 3-glucoside-vinylcatechol and malvidin 3-glucoside-vinylguaiacol wine pigments.
PubMed:Comparison of high-performance liquid chromatography separation of red wine anthocyanins on a mixed-mode ion-exchange reversed-phase and on a reversed-phase column.
PubMed:Inhibition of Ca2+-activated Cl- channels by gallotannins as a possible molecular basis for health benefits of red wine and green tea.
PubMed:Bog bilberry (Vaccinium uliginosum L.) extract reduces cultured Hep-G2, Caco-2, and 3T3-L1 cell viability, affects cell cycle progression, and has variable effects on membrane permeability.
PubMed:Isolation and structural characterization of anthocyanin-furfuryl pigments.
PubMed:Vinylcatechin dimers are much better copigments for anthocyanins than catechin dimer procyanidin b3.
PubMed:Stability of meoru (Vitis coignetiea) anthocyanins under photochemically produced singlet oxygen by riboflavin.
PubMed:Phenolic characterization of malbec wines from mendoza province (Argentina).
PubMed:A new class of anthocyanin-procyanidin condensation products detected in red wine by electrospray ionization multi-stage mass spectrometry analysis.
PubMed:Berry anthocyanins and anthocyanidins exhibit distinct affinities for the efflux transporters BCRP and MDR1.
PubMed:Absorption of anthocyanins through intestinal epithelial cells - Putative involvement of GLUT2.
PubMed:Induction of apoptosis and inhibition of invasion in human hepatoma cells by anthocyanins from meoru.
PubMed:Irrigation and rootstock effects on the phenolic concentration and aroma potential of Vitis vinifera L. cv. cabernet sauvignon grapes.
PubMed:Red wine phenolic complexes and their in vitro antioxidant activity.
PubMed:Expression of bilitranslocase in the vascular endothelium and its function as a flavonoid transporter.
PubMed:Distribution and excretion of bilberry anthocyanins [corrected] in mice.
PubMed:Dealcoholized wines by spinning cone column distillation: phenolic compounds and antioxidant activity measured by the 1,1-diphenyl-2-picrylhydrazyl method.
PubMed:An unusual acylated malvidin 3-glucoside from flowers of Impatiens textori Miq. (Balsaminaceae).
PubMed:Hypoglycemic activity of a novel anthocyanin-rich formulation from lowbush blueberry, Vaccinium angustifolium Aiton.
PubMed:Bog blueberry anthocyanins alleviate photoaging in ultraviolet-B irradiation-induced human dermal fibroblasts.
PubMed:Post-veraison sunlight exposure induces MYB-mediated transcriptional regulation of anthocyanin and flavonol synthesis in berry skins of Vitis vinifera.
PubMed:Singlet oxygen quenching by anthocyanin's flavylium cations.
PubMed:Role of vinylcatechin in the formation of pyranomalvidin-3-glucoside-+-catechin.
PubMed:Volatile and color composition of young and model-aged Shiraz wines as affected by diammonium phosphate supplementation before alcoholic fermentation.
PubMed:Simulated digestion and antioxidant activity of red wine fractions separated by high speed countercurrent chromatography.
PubMed:Identification of Cabernet Sauvignon anthocyanin gut microflora metabolites.
PubMed:Uptake of grape anthocyanins into the rat kidney and the involvement of bilitranslocase.
PubMed:Contribution of anthocyanin fraction to the antioxidant properties of wine.
PubMed:Principal components of phenolics to characterize red Vinho Verde grapes: anthocyanins or non-coloured compounds?
PubMed:Characterization and quantification of anthocyanins in grape juices obtained from the grapes cultivated in Korea by HPLC/DAD, HPLC/MS, and HPLC/MS/MS.
PubMed:New compounds obtained by evolution and oxidation of malvidin 3-O-glucoside in ethanolic medium.
PubMed:Saskatoon and wild blueberries have higher anthocyanin contents than other Manitoba berries.
PubMed:Entropy-driven complex formation of malvidin-3-O-glucoside with common polyphenols in ethanol-water binary solutions.
PubMed:Effect of the solvatation shell exchange on the formation of malvidin-3-O-glucoside-ellagic acid complexes.
PubMed:Different sorption behaviors for wine polyphenols in contact with oak wood.
PubMed:Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary alpha-amylase (HSA) by fluorescence quenching.
PubMed:Reaction between hydroxycinnamic acids and anthocyanin-pyruvic acid adducts yielding new portisins.
PubMed:High-performance liquid chromatography/electrospray ionization mass spectrometric characterization of new products formed by the reaction between flavanols and malvidin 3-glucoside in the presence of acetaldehyde.
PubMed:Formation of hydroxyphenyl-pyranoanthocyanins in Grenache wines: precursor levels and evolution during aging.
PubMed:Anthocyanone A: a quinone methide derivative resulting from malvidin 3-O-glucoside degradation.
PubMed:Glyceraldehyde bridging between flavanols and malvidin-3-glucoside in model solutions.
PubMed:Influence of different phenolic copigments on the color of malvidin 3-glucoside.
PubMed:Determination of the thermodynamic parameters of the complex formation between malvidin-3-O-glucoside and polyphenols. Copigmentation effect in red wines.
PubMed:UV-visible spectroscopic investigation of the 8,8-methylmethine catechin-malvidin 3-glucoside pigments in aqueous solution: structural transformations and molecular complexation with chlorogenic acid.
PubMed:Effect of copigments and grape cultivar on the color of red wines fermented after the addition of copigments.
PubMed:Isolation of flavanol-anthocyanin adducts by countercurrent chromatography.
PubMed:Effects of anthocyanidin on the inhibition of proliferation and induction of apoptosis in human gastric adenocarcinoma cells.
PubMed:In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.
PubMed:Determination of anthocyanins in wine by direct injection liquid chromatography-diode array detection-mass spectrometry and classification of wines using discriminant analysis.
PubMed:Anthocyanins are efficiently absorbed from the small intestine in rats.
PubMed:Structural characterization of new malvidin 3-glucoside-catechin aryl/alkyl-linked pigments.
PubMed:Analysis of flavonoids and other phenolic compounds using high-performance liquid chromatography with coulometric array detection: relationship to antioxidant activity.
PubMed:Liquid chromatography with mass spectrometry in tandem mode applied for the identification of wine markers in residues from ancient Egyptian vessels.
PubMed:Occurrence of pyranoanthocyanins in sparkling wines manufactured with red grape varieties.
PubMed:Investigations on anthocyanins in wines from Vitis vinifera cv. pinotage: factors influencing the formation of pinotin A and its correlation with wine age.
PubMed:Reactions of anthocyanins and tannins in model solutions.
PubMed:Vitisin A content in Chilean wines from Vitis vinifera Cv. Cabernet Sauvignon and contribution to the color of aged red wines.
PubMed:Manipulating anthocyanin composition in Vitis vinifera suspension cultures by elicitation with jasmonic acid and light irradiation.
PubMed:Charge equilibria and pK(a) of malvidin-3-glucoside by electrophoresis.
PubMed:The stomach as a site for anthocyanins absorption from food.
PubMed:Characterization of a colorless anthocyanin-flavan-3-ol dimer containing both carbon-carbon and ether interflavanoid linkages by NMR and mass spectrometry.
PubMed:Absorption of anthocyanins from blueberries and serum antioxidant status in human subjects.
PubMed:Synergistic antioxidant effect of catechin and malvidin 3-glucoside on free radical-initiated peroxidation of linoleic acid in micelles.
PubMed:Anthocyanin color behavior and stability during storage: effect of intermolecular copigmentation.
PubMed:Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS.
PubMed:Interactions between cyanidin 3-O-glucoside and furfural derivatives and their impact on food color changes.
PubMed:Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of fruit-derived foods.
PubMed:Blackberry anthocyanins are slightly bioavailable in rats.
PubMed:Influence of storage conditions on the stability of monomeric anthocyanins studied by reversed-phase high-performance liquid chromatography.
PubMed:Enzymatic synthesis of [3'-O-methyl-(3)H]malvidin-3-glucoside from petunidin-3-glucoside.
PubMed:Identification of anthocyanin-flavanol pigments in red wines by NMR and mass spectrometry.
PubMed:Inhibitory effects of anthocyanins and other phenolic compounds on nitric oxide production in LPS/IFN-gamma-activated RAW 264.7 macrophages.
PubMed:Evolution and stability of anthocyanin-derived pigments during Port wine aging.
PubMed:Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice.
PubMed:Occurrence of anthocyanin-derived pigments in red wines.
PubMed:Antioxidant capacities and phenolics levels of French wines from different varieties and vintages.
PubMed:Preparative isolation of anthocyanins by high-speed countercurrent chromatography and application of the color activity concept to red wine.
PubMed:Determination of anthocyanins in wine based on flow-injection, liquid--solid extraction, continuous evaporation and high-performance liquid chromatography--photometric detection.
PubMed:Effect of postharvest ultraviolet irradiation on resveratrol and other phenolics of cv. Napoleon table grapes.
PubMed:Effect of storage temperature and pyruvate on kinetics of anthocyanin degradation, vitisin A derivative formation, and color characteristics of model solutions.
PubMed:Interactions between grape anthocyanins and pyruvic acid, with effect of pH and acid concentration on anthocyanin composition and color in model solutions.
PubMed:PH-dependent forms of red wine anthocyanins as antioxidants.
PubMed:Kinetics of thermal degradation of the anthocyanins delphinidin-3-rutinoside and malvidin-3-glucoside.
 
Notes:
Pigment of skins of black grapes, also in other plants. Found in red wine
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