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Sigma-Aldrich

Oenin chloride

≥90% (HPLC)

Synonym(s):

Cyclamin chloride, Enin chloride, Malvidin 3-β-D-glucopyranoside, Malvidin-3-O-glucoside chloride

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About This Item

Empirical Formula (Hill Notation):
C23H25ClO12
CAS Number:
7228-78-6
Molecular Weight:
528.89
EC Number:
230-631-9
MDL number:
MFCD00185576
UNSPSC Code:
12352200
PubChem Substance ID:
57652436
NACRES:
NA.25

Assay

≥90% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

[Cl-].COc1cc(cc(OC)c1O)-c2[o+]c3cc(O)cc(O)c3cc2O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

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

InChI key

YDIKCZBMBPOGFT-DIONPBRTSA-N

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General description

Oenin chloride/malvidin-3-O-glucoside is an anthocyanin content, present at high level in Vitis vinifera young red wines. It helps in defining the colour of wine.

Biochem/physiol Actions

Anthocyanin. Studied for its neuroprotective properties.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oenin and Quercetin Copigmentation: Highlights From Density Functional Theory
Li Y, et al.
Frontiers in Chemistry, 6, 245-245 (2018)
Baoshan Sun et al.
Journal of agricultural and food chemistry, 57(18), 8623-8627 (2009-09-01)
Phenolic complexes are a major group of polyphenols in aged red wine. The objective of this work was to evaluate the in vitro antioxidant activity of the phenolic complexes. Thus, red wine polyphenols were fractionated into various fractions including monomers
Joana Paixão et al.
Oxidative medicine and cellular longevity, 2012, 428538-428538 (2012-07-14)
The health-promoted benefits of anthocyanins, including vascular protective effects and antiatherogenic properties, have now been recognized, but the involved molecular mechanisms have not been well elucidated. Following our previous work on cytoprotective mechanisms of some anthocyanins against apoptosis triggered by
Iva Fernandes et al.
Food & function, 3(5), 508-516 (2012-03-07)
The bioavailability of anthocyanins is the most difficult one to assess amongst all flavonoid compounds as a result of their occurrence under different structures in equilibrium depending on pH. Due to their rapid appearance in plasma, the absorption of anthocyanins
Luís Cruz et al.
Rapid communications in mass spectrometry : RCM, 26(18), 2123-2130 (2012-08-14)
The aim of this work was to study the putative reactions that could occur in red wines between malvidin-3-glucoside-(O)-catechin (mv3glc-(O)-cat) adduct and catechin (cat) or malvidin-3-glucoside (mv3glc) in presence of acetaldehyde. Mv3glc-(O)-cat adduct (1 mM) was incubated with catechin (or
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