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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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1 MG
₪1,251.00
5 MG
₪3,051.00

₪1,251.00

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1 MG
₪1,251.00
5 MG
₪3,051.00

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

₪1,251.00

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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.[1] 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.[2]
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[3], antioxidant[4], antiallergy[5], and antimicrobial activity[6], and showed strong anti-viral activity inhibition of tomato ringspot virus[7].

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8030
BCCH2859
BCBW5668
BCBV1478
BCBP5687V

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C Angeloni et al.
Biochimie, 89(1), 73-82 (2006-10-19)
The aim of this study was to investigate the potential of quercetin and two of its "in vivo" metabolites, 3'-O-methyl quercetin and 4'-O-methyl quercetin, to protect H9c2 cardiomyoblasts against H(2)O(2)-induced oxidative stress. As limited data are available regarding the potential
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
3-O-methylquercetin more selectively inhibits phosphodiesterase subtype 3
Ko WC, et al.
Planta Medica, 69(04), 310-315 (2003)
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
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
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Questions

  1. is this product also called Isorhamnetin?

    1 answer

    1. Isorhamnetin shares structural similarities with 3-O-methylquercetin. They are structural isomers, sharing similar chemical compositions but differing in the arrangement of atoms. Both compounds belong to the flavonoid family and have various dietary sources.

      For Item 90081, the structure and properties (SMILES string, InChI, InChI key) are of 3-O-methylquercetin per PubChem: https://pubchem.ncbi.nlm.nih.gov/compound/5280681.

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