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16733

Sigma-Aldrich

Quercetin 3-O-(6″-O-malonyl)-β-D-glucoside

≥85% (HPLC)

Synonym(s):

Quercetin 3-O-malonylglucoside

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About This Item

Empirical Formula (Hill Notation):
C24H22O15
CAS Number:
96862-01-0
Molecular Weight:
550.42
Beilstein:
6625918
MDL number:
MFCD20527305
UNSPSC Code:
12352201
PubChem Substance ID:
329751366
NACRES:
NA.25

Quality Level

100

Assay

≥85% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@@H]1O

InChI

1S/C24H22O15/c25-9-4-12(28)17-13(5-9)37-22(8-1-2-10(26)11(27)3-8)23(19(17)33)39-24-21(35)20(34)18(32)14(38-24)7-36-16(31)6-15(29)30/h1-5,14,18,20-21,24-28,32,34-35H,6-7H2,(H,29,30)/t14-,18-,20+,21-,24+/m1/s1

InChI key

NBQPHANHNTWDML-UJKBSQBPSA-N

General description

The flavonoid quercetin 3-O-(6-O-malonyl)glucoside, a conjugate of quercetin, was identified in the green-leafed lettuce Lactuca sativum.

Biochem/physiol Actions

Metabolite in flavone and flavonol biosynthesis, is found in plants like the fruit peel of Sicana odorifera and mulberry leaves, shows antioxidant activity. Q3MG also potentially has antiatherogenic protective effects; and found to improve hyperglycemia in obese mice and reduced oxidative stress in the liver.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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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Katherine Jaramillo et al.
Journal of agricultural and food chemistry, 59(3), 975-983 (2011-01-20)
Ten flavonols and three anthocyanins were identified in the fruit peel of melón de olor (Sicana odorifera), and their structures were established by spectrometric and spectroscopic (ESI-MS and NMR) techniques. One of the identified flavonols, quercetin 3-O-(6''-O-malonyl)-β-D-glucopyranoside 4'-O-β-D-glucopyranoside, has not
Takuya Katsube et al.
Journal of the science of food and agriculture, 90(14), 2386-2392 (2010-07-22)
Mulberry therapies on type 2 diabetic patients or streptozotocin-induced diabetic rats have been reported to improve fasting blood glucose levels. We investigated the effects of dietary consumption of mulberry-leaf powder and purified quercetin 3-(6-malonylglucoside), the quantitatively major flavonol glycoside in
M S DuPont et al.
Journal of agricultural and food chemistry, 48(9), 3957-3964 (2000-09-20)
Eight varieties of lettuce (Lactuca sativum) and three varieties of endive (Cichorium endivia) were analyzed for flavonoid composition and content. Total flavonoid contents, expressed as units of aglycon for fresh material, were in the ranges of 0.3-229 microg/g for lettuce
Byambaa Enkhmaa et al.
The Journal of nutrition, 135(4), 729-734 (2005-03-30)
The effects of dietary consumption of mulberry (Morus alba L.) leaves and their major flavonol glycoside, quercetin 3-(6-malonylglucoside) (Q3MG), on the development of atherosclerotic lesions, in relation to the susceptibility of plasma LDL to oxidative modification, was studied in LDL

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