NOBILETIN Chemical Properties

Melting point:

136.0 to 140.0 °C

Boiling point:

587.9±50.0 °C(Predicted)

Density 

1.244±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

Soluble in DMSO (up to 10 mg/ml)

form 

Solid

color 

White

BRN 

360887

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

InChIKey

MRIAQLRQZPPODS-UHFFFAOYSA-N

CAS DataBase Reference

478-01-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

DJ3052200

HS Code 

29329990

NOBILETIN Usage And Synthesis

Description

Nobiletin (NOB) chemically known as 5,6,7,8,3′,4′-hexamethoxyflavone is a dietary polymethoxylated flavonoid found in Citrus fruits. Nobiletin is a flavonoid isolated from citrus peels. It is an O-methylated flavone that has the activity to rescue bulbectomy-induced memory impairment.

Source

Nobiletin is a nonpolar polymethoxylated flavone (PMFs) found in the citrus peel of various fruits, such as tangerine. Its chemical structure is similar to tangeretin, containing the typical flavonoid structure and six methoxyl groups (one more than tangeretin).

Uses

NOB is a multifunctional pharmaceutical agent. The various pharmacological activities of NOB include neuroprotection, cardiovascular protection, antimetabolic disorder, anticancer, anti-inflammation, and antioxidation.

structure and hydrogen bonding

The crystal structure study on NOB shows that the chromene and the arene rings are almost in the same plane. The C atoms of the two methoxy groups in the arene ring are also in the same plane, while the C atoms of four methoxy groups linking to the chromene ring are not in parallel. This conformational characteristic of chiral structure is indicated by the covalent bond rotation between the arene and the chromene rings and the conformational alternations of methoxy groups.

Application

Nobiletin has been shown to exhibit antioxidant, anti-inflammatory, antitumor/cancer, and antiangiogenic activity in vitro and in vivo. Animal and in vitro data also demonstrate nobiletin's potential ability to suppress bone loss, lower cholesterol and atherosclerosis, and improve hyperglycemia and insulin resistance.

Description

Nobiletin (478-01-3) is a natural product isolated from citrus peels.? It has recently been shown to possess circadian clock amplitude-enhancing properties and was able to prevent metabolic syndrome in mice?via?a?Clock?gene-dependent mechanism.1? Nobiletin directly bound to and activated RORα/γ.? Nobiletin has previously been shown to attenuate the effects of metabolic syndrome2, have anti-neuroinflammatory effects3, possess neurotrophic activity4, and be a cancer chemopreventative agent5.

Chemical Properties

White powder

Uses

matrix metaloproteinase inhibitor; antineoplastic

Uses

Nobiletin is an O-methylated flavone, a flavonoid isolated from citrus peels like in tangerine. It is a potent antioxidant with good bioavailability. Nobiletin directly inhibits the ATP-binding cassette proteins P-glycoprotein and breast cancer resistance protein.

Definition

ChEBI: A methoxyflavone that is flavone substituted by methoxy groups at positions 5, 6, 7, 8, 3' and 4' respectively.

benefits

Nobiletin improved cognitive deficits and the pathological features of AD, such as Aβ pathology, hyperphosphorylation of tau, and oxidative stress, in animal models of AD. In addition, nobiletin improved motor and cognitive deficits in PD animal models. These observations suggest that nobiletin has the potential to become a novel drug for the treatment and prevention of neurodegenerative diseases such as AD and PD.

References

1) He?et al.?(2016),?The Small Molecule Nobiletin Targets the Molecular Oscillator to Enhance Circadian Rhythms and Protect against Metabolic Syndrome; Cell Metabolism,?23?610 2) Mulvihill?et al.?(2011),?Nobiletin attenuates VLDL overproduction, dyslipidemia, and atherosclerosis in mice with diet-induced insulin resistance; Diabetes?60?1446 3) Cui?et al.?(2010),?Anti-neuroinflammatory activity of nobiletin on suppression of microglial activation; Biol. Pharm. Bull.,?33?1814 4) Nagase?et al.?(2005),?Mechanism of neurotrophic action of nobiletin in PC12D cells; Biochemistry?44?13683 5) Walle (2007),?Methoxylated flavones, a superior cancer chemopreventative flavonoid subclass?;?Semin. Cancer Biol.?17?354

NOBILETIN(478-01-3)Related Product Information

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• 3',4',5,7-TETRAMETHOXYFLAVONE
• 7,8-DIMETHOXYFLAVONE
• 6,7-DIMETHOXY-3',4',5-TRIHYDROXYFLAVONE
• 5-DEMETHYLNOBILETIN
• 2,3,4-Trimethoxyphenol
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• GARDENIN B
• 2,3,4,5-Tetramethoxytoluene
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• Nobiletin
• LYSIONOTIN
• 1,2,3,4-TETRAMETHOXYBENZENE
• 6-METHOXYLUTEOLIN
• NOBILETIN(P)
• FLAVONE
• PEDALITIN