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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)

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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
Ana Paula Preczenhak et al.
Food chemistry, 286, 600-607 (2019-03-05)
This study investigated the effectiveness of cysteine in conservation of bioactive compounds and the antioxidant capacity of minimally processed red beet. After red beet minimal processing increasing cysteine concentrations were applied, corresponding to control, 2 mM, 4 mM, 8 mM and 16 mM. Assay
3-O-methylquercetin more selectively inhibits phosphodiesterase subtype 3
Ko WC, et al.
Planta Medica, 69(04), 310-315 (2003)
Inhibition of tomato ringspot virus by flavonoids.
Malhotraa, B. , et al.
Phytochemistry, 43, 1271-1276 (1996)
L Van Puyvelde et al.
Journal of natural products, 52(3), 629-633 (1989-05-01)
3,5-Dihydroxy-6,7,8-trimethoxyflavone, 3-O-methylquercetin, and helichrysetin were isolated from the flowers of the Rwandese medicinal plant, Helichrysum odoratissimum. Because of inconsistencies of the mp of the latter chalcone, a synthesis of helichrysetin was developed. 3-O-Methylquercetin was shown to be an active principle
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