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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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Delphinidin 3-glucoside chloride phyproof® Reference Substance

PHL89627

Delphinidin 3-glucoside chloride

Oenin and Quercetin Copigmentation: Highlights From Density Functional Theory
Li Y, et al.
Frontiers in Chemistry, 6, 245-245 (2018)
Luis Cruz et al.
Journal of agricultural and food chemistry, 56(22), 10980-10987 (2008-10-31)
Reactions between malvidin-3-glucoside (mv3glc) and 8-vinylcatechin were carried out to synthesize pyranomv3glc-(+)-catechin pigment and to study the formation of intermediates. A rapid decrease of mv3glc content concomitant with the formation of more complex structures such as mv3glc-vinylcatechin [precursor of pyranomv3glc-(+)-catechin
Linga R Gutha et al.
BMC plant biology, 10, 187-187 (2010-08-25)
Symptoms of grapevine leafroll disease (GLRD) in red-fruited wine grape (Vitis vinifera L.) cultivars consist of green veins and red and reddish-purple discoloration of inter-veinal areas of leaves. The reddish-purple color of symptomatic leaves may be due to the accumulation
Joana Paixão et al.
Chemico-biological interactions, 199(3), 192-200 (2012-09-11)
Anthocyanins are the most abundant flavonoid constituents of fruits and vegetables and several epidemiological studies suggest that the consumption of these compounds protect against several diseases, including vascular disorders. Previously, we have reported that anthocyanins are able to counteract peroxynitrite-induced
Sandor Kunsagi-Maté et al.
The journal of physical chemistry. B, 111(40), 11750-11755 (2007-09-15)
The interaction of malvidin-3-O-glucoside with ellagic acid was studied in aqueous solutions in dependence of the ethanol content of the samples. The results show significant changes of the thermodynamic parameters when the ethanol content exceeds 8%vol. The quantum chemical calculations
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