Tangeratin

Tangeratin
Compound Structure:
Synonyms: Tangeretin ;481-53-8 ;Tangeritin ;Ponkanetin ;Pentamethoxyflavone
Compound ID: NMPC-1510
PubChem ID:

68077

Molecular Formula: C20H20O7
Canonical SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC
InChIKey: ULSUXBXHSYSGDT-UHFFFAOYSA-N
About the compound:

Tangeretin, known scientifically as an O-polymethoxylated flavone, is a compound primarily found in tangerine and other citrus peels. It plays a crucial role in strengthening the cell walls of plants, serving as a defensive mechanism against disease-causing pathogens. Additionally, tangeretin has been utilized as a marker compound to identify contamination in citrus juices. Various methods have been employed to extract tangeretin from citrus peels effectively. These methods include:

1. Column chromatography.

2. Preparative-high performance liquid chromatography.

3. Supercritical fluid chromatography.

4. High-speed counter-current chromatography.

5. A combination of vacuum flash silica gel chromatography and flash C8 column chromatography.

6. Flash chromatography.

7. Isolation using ionic liquids followed by a cycle of centrifugation and decantation.

One of the major challenges in using tangeretin in laboratory settings and therapeutic applications is its low solubility, which significantly affects its bioavailability. This low solubility is a common issue with many flavonoids. However, ongoing research and testing of extraction methods aim to maximize efficiency and yield, especially as the potential therapeutic uses of tangeretin in treating cancer and other diseases are becoming more recognized.

Tangeretin is available commercially as a dietary supplement and has shown promise in various pharmaceutical, nutraceutical, and cosmetic applications. The compound is known by several synonyms in scientific literature, including Tangeritin and 5,6,7,8,4’-pentamethoxyflavone (VIII), reflecting its diverse presence and interest in research and industry. The exploration of tangeretin's properties and applications continues to be a significant area of study, particularly in relation to health and disease prevention.

GHS Hazard Statements

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

372.4 g/mol

XLogP3-AA

3

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

7

Rotatable Bond Count

6

Exact Mass

372.12090297 g/mol

Monoisotopic Mass

372.12090297 g/mol

Topological Polar Surface Area

72.4Ų

Heavy Atom Count

27

Formal Charge

0

Complexity

540

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid

Melting Point

154 °C

Source:PubChem

Source Species: Talinum triangulare
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