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T8951

Sigma-Aldrich

Tangeretin

≥95% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C20H20O7
CAS-Nummer:
481-53-8
Molekulargewicht:
372.37
Beilstein:
351695
EG-Nummer:
207-570-1
MDL-Nummer:
MFCD00017438
UNSPSC-Code:
12352205
PubChem Substanz-ID:
329826890
NACRES:
NA.25

Assay

≥95% (HPLC)

Anwendung(en)

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

InChIKey

ULSUXBXHSYSGDT-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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. Wirkung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Sigma-Aldrich

SMB00540

Tricin 5-glucoside

Hesperetin ≥95%

Sigma-Aldrich

W431300

Hesperetin

Limonin from citrus seeds, >90% (HPLC)

Sigma-Aldrich

L9647

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Bergapten analytical standard

Supelco

69664

Bergapten

Naringenin natural (US), 98%

Sigma-Aldrich

W530098

Naringenin

Luteolin ≥98% (TLC), powder

Sigma-Aldrich

L9283

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Hesperetin analytical standard

Supelco

H4125

Hesperetin

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)
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.
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
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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