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Documentos Principais

T8951

Sigma-Aldrich

Tangeretin

≥95% (HPLC)

Sinônimo(s):

4′,5,6,7,8-Pentamethoxyflavone, 5,6,7,8-Tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, NSC 53909, NSC 618905, Ponkanetin

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About This Item

Fórmula empírica (Notação de Hill):
C20H20O7
Número CAS:
Peso molecular:
372.37
Beilstein:
351695
Número CE:
Número MDL:
Código UNSPSC:
12352205
ID de substância PubChem:
NACRES:
NA.25
Preço e disponibilidade não estão disponíveis no momento.

Ensaio

≥95% (HPLC)

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

cadeia de caracteres SMILES

COc1ccc(cc1)C2=CC(=O)c3c(OC)c(OC)c(OC)c(OC)c3O2

InChI

1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3

chave InChI

ULSUXBXHSYSGDT-UHFFFAOYSA-N

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Descrição geral

Tangeretin is a polymethoxyflavone extracted primarily from the peels of citrus fruits like Citrus sinensis and Citrus reticulata.[1][2]

Aplicação

Tangeretin has been used as an antioxidant and antifungal agent to test its effects on ferroptosis inhibition, conidial development, and appressorium formation against Magnaporthe oryzae.[3] It has also been used as a co-chemotherapeutics agent to study its cytotoxic effects in combination with 5-Fluorouracil (5-Fu) on WiDr colon cancer cells.[4]

Ações bioquímicas/fisiológicas

Tangeretin displays its anti-cancer effects by modulating different pathways in several cancer types in both in-vitro and in-vivo studies.[1][2] It also exerts antioxidant, anti-inflammatory, and estrogenic properties.[2]
Tangeretin is a flavonoid found in the peel of citrus fruits where it most likely provides natural resistance to fungi. Tangeretin has been shown to counteract tumor promoter-induced inhibition of intercellular communication and to inhibit cell proliferation in several cancer lines.

Pictogramas

Exclamation mark

Palavra indicadora

Warning

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Sigma-Aldrich

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Sigma-Aldrich

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Bergapten analytical standard

Supelco

69664

Bergapten

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Sigma-Aldrich

W530098

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Luteolin ≥98% (TLC), powder

Sigma-Aldrich

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Luteolin

Hesperetin analytical standard

Supelco

H4125

Hesperetin

Hideo Satsu et al.
Journal of agricultural and food chemistry, 56(13), 5366-5373 (2008-06-11)
The pregnane X receptor (PXR) is understood to be the key regulator for gene expression of such drug-metabolizing enzymes and transporters as multidrug-resistant protein 1 (MDR1) and the cytochrome P450 (CYP) family. We examined the effect of dietary phytochemicals on
Combination of Tangeretin and 5-Fluorouracil Modulates Cell Cycle and Induce Apoptosis on WiDr Cells
Indriyani L, et al.,
Indonesian Journal of Cancer Chemoprevention, 3(1), 364-369 (2012)
Hong-Yin Wu et al.
Journal of agricultural and food chemistry, 59(5), 1713-1722 (2011-02-15)
This study investigated the potential effects of natural products ursolic acid (UA) and oleanolic acid (OA) against HBx-mediated tumorigenic activities in vitro and in vivo. HBx transactivated Sp-1 and Smad 3/4 in Huh7 and FL83B hepatocytes and induced cell migration
John A Manthey et al.
Journal of agricultural and food chemistry, 59(1), 145-151 (2010-12-08)
Nobiletin (NOB) and tangeretin (TAN), two of the main polymethoxylated flavones (PMFs) in citrus, influence a number of key biological pathways in mammalian cells. Although the impacts of NOB and TAN on glucose homeostasis and cholesterol regulation have been investigated
Jérôme Quintin et al.
Bioorganic & medicinal chemistry letters, 19(1), 167-169 (2008-11-18)
A series of chalcones polyoxygenated on the ring A (with pentamethoxy or 2'-hydroxy-3',4',5',6'-tetramethoxy substitution patterns) was synthesized from tangeretin, a natural Citrus flavonoid. These chalcones were evaluated for their antiproliferative, activation of apoptosis, inhibition of tubulin assembly and antileishmanial activities.

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