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T8951

Sigma-Aldrich

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
Beilstein:
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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Guy Lewin et al.
Journal of natural products, 73(4), 702-706 (2010-04-02)
Semisynthesis of 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone (1), a natural flavone that binds with high affinity to tubulin, was performed from hesperidin, the very abundant Citrus flavanone, by a five-step sequence. The last step of the synthesis also gave rise to 5,3'-dihydroxy-3,6,7,4'-tetramethoxyflavone (= casticin
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
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
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