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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H25O12.Cl
Molecular Weight 528.89
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MALVIDIN 3-GLUCOSIDE

SMILES

[Cl-].COC1=CC(=CC(OC)=C1O)C2=[O+]C3=C(C=C2O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(O)=CC(O)=C3

InChI

InChIKey=YDIKCZBMBPOGFT-DIONPBRTSA-N
InChI=1S/C23H24O12.ClH/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23;/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27);1H/t17-,19-,20+,21-,23-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H24O12
Molecular Weight 492.4295
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Malvidin-3-O-glucoside is a polyphenolic anthocyanin. Anthocyanins are flavonoids widely distributed in fruits and vegetables that exhibit antioxidative and anti-inflammatory bioactivities. Among other polyphenolic components, malvidin-3-glucoside is present in ViNitrox™ a natural dietary supplement from apple and grape, it offers a number of exceptional sports nutrition properties including enhanced and lasting performance.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
35.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ViNitrox
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Vinitrox™, supplied by Nexira (France) is a combination of specific profile polyphenols from grape and apple. Vinitrox™ is a purified extract with low lipids, fibers and proteins content (respectively 0.5%, 1.4% and 5.5%) and more than 60% of total polyphenols (Folin method—expressed as gallic acid equivalent) with antioxidant properties demonstrated by ORAC value (12,000 μMtrolox equivalent per gram of ingredient). The main polyphenol classes are proanthocyanidins (as catechins, B2 dimer), phenolic acids (as chlorogenic acids, gallic acids) and anthocyanins (as malvidin-3-glucoside). Nexira’s latest clinical study on 50 athletes, 25-45 years old, demonstrated that under intensive effort, 500 mg/day of ViNitrox™ improves physical capabilities: increases physical training time by 10%, delays the fatigue barrier by 13%.
Route of Administration: Oral
In Vitro Use Guide
1 mg/mL blueberry extract significantly reduced LPS-induced nitric oxide release in BV-2 mouse microglia; this concentration of blueberry extract contains 2.6 μM malvidin-3-O-glucoside, but when malvidin-3-O-glucoside was tested individually, 20 μM was necessary to observe a significant reduction in nitric oxide release.
Substance Class Chemical
Record UNII
B34F52D7NB
Record Status Validated (UNII)
Record Version