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90081

Sigma-Aldrich

3-O-Methylquercetin

≥97% (HPLC)

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C16H12O7
Número CAS:
1486-70-0
Peso molecular:
316.26
Beilstein:
324509
Número MDL:
MFCD00210588
Código UNSPSC:
12352202
ID de substância PubChem:
329769845
NACRES:
NA.32
Preço e disponibilidade não estão disponíveis no momento.

Ensaio

≥97% (HPLC)

Formulário

powder

cadeia de caracteres SMILES

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

chave InChI

WEPBGSIAWZTEJR-UHFFFAOYSA-N

Ações bioquímicas/fisiológicas

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].

Embalagem

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Frases de perigo

H301

Declarações de precaução

P301 + P310

Classificações de perigo

Acute Tox. 3 Oral

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
BCCL8030
BCCH2859
BCBW5668
BCBV1478
BCBP5687V

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Sigma-Aldrich

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Quercetina

Hyang Dok-Go et al.
Brain research, 965(1-2), 130-136 (2003-02-20)
The flavonoids quercetin, (+)-dihydroquercetin, and quercetin 3-methyl ether were isolated from the ethyl acetate fractions of the fruits and stems of Opuntia ficus-indica var. saboten. In the present study, we evaluated their protective effects against oxidative neuronal injuries induced in
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)
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
Inhibition of tomato ringspot virus by flavonoids.
Malhotraa, B. , et al.
Phytochemistry, 43, 1271-1276 (1996)
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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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.

      Helpful?

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