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T8951

Sigma-Aldrich

Tangeretin

≥95% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C20H20O7
Numéro CAS:
481-53-8
Poids moléculaire :
372.37
Beilstein:
351695
Numéro CE :
207-570-1
Numéro MDL:
MFCD00017438
Code UNSPSC :
12352205
ID de substance PubChem :
329826890
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Essai

≥95% (HPLC)

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne 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

Clé InChI

ULSUXBXHSYSGDT-UHFFFAOYSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCQ9014
MKCN5545
MKCL6626
MKCH5316
MKCD6142

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Bergapten analytical standard

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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
El-Shaimaa A Arafa et al.
Cancer research, 69(23), 8910-8917 (2009-11-12)
Combination of innocuous dietary components with anticancer drugs is an emerging new strategy for cancer chemotherapy to increase antitumor responses. Tangeretin is a citrus flavonoid known to inhibit cancer cell proliferation. Here, we show an enhanced response of A2780/CP70 and
Lun-zhao Yi et al.
Analytica chimica acta, 649(1), 43-51 (2009-08-12)
Tangerine peels are herbal materials of two coupled traditional Chinese medicines, Pericarpium Citri Reticulatae (PCR) and Pericarpium Citri Reticulatae Viride (PCRV). In this paper, high-performance liquid chromatographic fingerprints of tangerine peels during growth were firstly measured for deliberately collected 34
Ai Eguchi et al.
BioFactors (Oxford, England), 31(2), 107-116 (2008-09-23)
Unregulated uptake of oxidized low-density lipoproteins (ox-LDL) via macrophage scavenger receptors (SRs) is a key event in atherosclerosis. We previously reported that nobiletin (NOB), a citrus polymethoxylated flavone, markedly reduced 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced SRs and adhesion molecules mRNA expression and blockade
Ji Hye Yoon et al.
Journal of agricultural and food chemistry, 59(1), 222-228 (2010-12-04)
The present study examined the effects of tangeretin, a polymethoxylated flavonone present in citrus fruits, on ultraviolet B (UVB)-induced cyclooxygenase-2 (COX-2) expression in JB6 P+ mouse skin epidermal cells. Tangeretin suppressed UVB-induced COX-2 expression and transactivation of nuclear factor-κB and
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