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Merck
CN

T8951

Tangeretin

≥95% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C20H20O7
CAS Number:
481-53-8
Molecular Weight:
372.37
UNSPSC Code:
12352205
NACRES:
NA.25
PubChem Substance ID:
329826890
EC Number:
207-570-1
Beilstein/REAXYS Number:
351695
MDL number:
MFCD00017438

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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

SMILES string

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

InChI key

ULSUXBXHSYSGDT-UHFFFAOYSA-N

assay

≥95% (HPLC)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Quality Level

100

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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

WGK 3

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7939
MKCV4639
MKCQ9014
MKCR8769
MKCN5545

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Meiling Liang et al.
Journal of integrative plant biology, 63(12), 2136-2149 (2021-09-28)
Flavonoids are polyphenolic secondary metabolites that function as signaling molecules, allopathic compounds, phytoalexins, detoxifying agents and antimicrobial defensive compounds in plants. Blast caused by the fungus Magnaporthe oryzae is a serious disease affecting rice cultivation. In this study, we revealed
Jérôme Quintin et al.
Bioorganic & medicinal chemistry letters, 19(13), 3502-3506 (2009-05-22)
A series of 3'-aminoflavones 5,6,7,8-tetra- or 5,7-dioxygenated on the A-ring was synthesized from tangeretin or naringin, two natural Citrus flavonoids. These flavones were evaluated for antiproliferative activity, activation of apoptosis, and inhibition of tubulin assembly. The most antiproliferative flavones exhibit
Christophe Tistaert et al.
Analytica chimica acta, 705(1-2), 111-122 (2011-10-04)
Extracts of Citri reticulatae pericarpium (PCR) are commonly used in the Traditional Chinese Medicine. The quality control of PCR is currently performed by single marker analysis, which can hardly describe the complexity of such natural samples. In this study, a
Juhee Seo et al.
European journal of pharmacology, 673(1-3), 56-64 (2011-11-02)
Tangeretin, a natural polymethoxylated flavone concentrated in the peel of citrus fruits, is known to have antiproliferative, antiinvasive, antimetastatic and antioxidant activities. However, the effect of tangeretin on vascular smooth muscle cells (VSMCs) is unknown. This study examined the effect
Z Cheng et al.
British journal of pharmacology, 162(8), 1781-1791 (2011-01-05)
The mechanisms by which the dietary compound tangeretin has anticancer effects may include acting as a prodrug, forming an antiproliferative product in cancer cells. Here we show that tangeretin also inhibits cell cycle progression in hepatocytes and investigate the role
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