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Key Documents

40796

Sigma-Aldrich

Peonidin 3-O-glucoside chloride

≥95% (HPLC)

Synonym(s):

3-(Glucosyloxy)-4′,5,7-trihydroxy-3′-methoxyflavylium chloride, Glucopeonidin chloride

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About This Item

Empirical Formula (Hill Notation):
C22H23ClO11
CAS Number:
Molecular Weight:
498.86
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

biological source

synthetic

Assay

≥95% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

[Cl-].COc1cc(ccc1O)-c2[o+]c3cc(O)cc(O)c3cc2O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

InChI

1S/C22H22O11.ClH/c1-30-15-4-9(2-3-12(15)25)21-16(7-11-13(26)5-10(24)6-14(11)31-21)32-22-20(29)19(28)18(27)17(8-23)33-22;/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26);1H/t17-,18-,19+,20-,22-;/m1./s1

InChI key

VDTNZDSOEFSAIZ-VXZFYHBOSA-N

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General description

Peonidin 3-O-glucoside is an anthocyanin, which is present in fruits and vegetables as natural colorants. It can also be found in red wine and black rice.

Application

Peonidin 3-O-glucoside chloride (P3G) has been used as a phytochemical and inflammasome modulator to test its inhibitory effects on Melanoma 2 (AIM2) inflammasome.

Biochem/physiol Actions

Peonidin 3-O-glucoside chloride (PNG) exerts antioxidant and anti-inflammatory activities and together with lutein showed additive effects on Caco-2 cells. It has free radical scavenging capacities. Peonidin 3-O-glucoside is investigated for inhibition of tumor cell growth and reduction of metastasis of lung cancer cells. It shows inhibitory activity against aldose reductase.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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Accumulation of peonidin 3-glucoside enhanced by osmotic stress in grape (Vitis vinifera L.) cell suspension.
Do, C.B. and Cormier, F.
Plant Cell, Tissue and Organ Culture, 24, 49-54 (1991)
N Landrault et al.
Journal of agricultural and food chemistry, 49(7), 3341-3348 (2001-07-17)
Phenolics from grapes and wines can play a role against oxidation and development of atherosclerosis. Levels of phenolics, major catechins [(+)-catechin, (-)-epicatechin, procyanidin dimers B1, B2, B3, and B4], phenolic acids (gallic acid and caffeic acid), caftaric acid, malvidin-3-glucoside, peonidin-3-glucoside
Natasha Sharma et al.
Molecules (Basel, Switzerland), 25(24) (2020-12-12)
The present study aimed to analyze the antioxidant and antimicrobial activity of anthocyanins extracted from colored wheat flour and wheat-grass juice against human pathogens. The total anthocyanin content and antioxidant potential in colored wheat flour and wheat-grass juice extracts were
Mao-Lin Ho et al.
Nutrition and cancer, 62(4), 505-516 (2010-05-01)
Anthocyanins, present in various vegetables and fruits as a nature colorant, have broad activities including anticarcinogenesis and antimutagenesis, which are generally attributed to their antioxidant activities. However, limited studies have been available concerning the inhibitory effect of peonidin 3-glucoside (P3G)
Pei-Ni Chen et al.
Nutrition and cancer, 53(2), 232-243 (2006-04-01)
Dietary polyphenols, including anthocyanins, are suggested to be involved in the protective effects of fruits and vegetables against cancer. However, anticancer effects of peonidin 3-glucoside have not been clearly demonstrated, with only limited studies being available concerning the inhibitory effect

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