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T8951

Sigma-Aldrich

Tangeretin

≥95% (HPLC)

Sinónimos:

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 (notación de Hill):
C20H20O7
Número de CAS:
481-53-8
Peso molecular:
372.37
Beilstein/REAXYS Number:
351695
EC Number:
207-570-1
MDL number:
MFCD00017438
UNSPSC Code:
12352205
PubChem Substance ID:
329826890
NACRES:
NA.25

Quality Level

100

assay

≥95% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

SMILES string

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

InChI key

ULSUXBXHSYSGDT-UHFFFAOYSA-N

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General description

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

Application

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. 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.

Biochem/physiol Actions

Tangeretin displays its anti-cancer effects by modulating different pathways in several cancer types in both in-vitro and in-vivo studies. It also exerts antioxidant, anti-inflammatory, and estrogenic properties.
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
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
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.
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
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