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90081

Sigma-Aldrich

3-O-Methylquercetin

≥97% (HPLC)

Synonym(s):

5,7,3′ ,4′ -Tetrahydroxy-3-methoxyflavone, Quercetin 3-O-methyl ether

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About This Item

Empirical Formula (Hill Notation):
C16H12O7
CAS Number:
1486-70-0
Molecular Weight:
316.26
Beilstein:
324509
MDL number:
MFCD00210588
UNSPSC Code:
12352202
PubChem Substance ID:
329769845
NACRES:
NA.32

Quality Level

100

Assay

≥97% (HPLC)

form

powder

SMILES string

COC1=C(Oc2cc(O)cc(O)c2C1=O)c3ccc(O)c(O)c3

InChI

1S/C16H12O7/c1-22-16-14(21)13-11(20)5-8(17)6-12(13)23-15(16)7-2-3-9(18)10(19)4-7/h2-6,17-20H,1H3

InChI key

WEPBGSIAWZTEJR-UHFFFAOYSA-N

Biochem/physiol Actions

3-O-Methylquercetin significantly inhibits cyclic adenosine monophosphate- (cAMP-) and cyclic guanosine monophosphate- (cGMP-) phosphodiesterase activity. It possess anti-inflammatory, bronchodilating properties and used in treatment of asthma. It suppresses the total inflammatory cells, tumor necrosis factor-α (TNF-α) and attenuates the production of interleukins.
3-O-Methylquercetin is a metabolite in flavone and flavonol biosynthesis. It is a naturally occurring compound present in various plants, and was shown to have potent anticancer-promoting, antioxidant, antiallergy, and antimicrobial activity, and showed strong anti-viral activity inhibition of tomato ringspot virus.

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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Mechanisms of suppression of nitric oxide production by 3-O-methylquercetin in RAW 264.7 cells
Jiang JS, et al.
Journal of Ethnopharmacology, 103(2), 281-287 (2006)
Inhibition of tomato ringspot virus by flavonoids.
Malhotraa, B. , et al.
Phytochemistry, 43, 1271-1276 (1996)
3-O-methylquercetin more selectively inhibits phosphodiesterase subtype 3
Ko WC, et al.
Planta Medica, 69(04), 310-315 (2003)
Clement K Ameho et al.
The Journal of nutritional biochemistry, 19(7), 467-474 (2007-10-02)
Dietary antioxidants interact in a dynamic fashion, including recycling and sparing one another, to decrease oxidative stress. Limited information is available regarding the interrelationships in vivo between quercetin and vitamin E. We investigated the antioxidant activity and metabolism of quercetin
Jixia Li et al.
Carcinogenesis, 33(2), 459-465 (2011-12-06)
Chemoprevention has been acknowledged as an important and practical strategy for the management of skin cancer. Quercetin-3-methyl ether, a naturally occurring compound present in various plants, has potent anticancer-promoting activity. We identified this compound by in silico virtual screening of
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