Nobiletin

Base Information

• Chemical Name: Nobiletin
• CAS No.: 478-01-3
• Molecular Formula: C21H22O8
• Molecular Weight: 402.401
• Hs Code.: 29329990
• NSC Number: 618903,76751
• UNII: D65ILJ7WLY
• DSSTox Substance ID: DTXSID30197275
• Nikkaji Number: J12.548B
• Wikipedia: Nobiletin
• Wikidata: Q2402963
• Metabolomics Workbench ID: 24551
• ChEMBL ID: CHEMBL76447
• Mol file: 478-01-3.mol

Synonyms:hexamethoxyflavone;nobiletin

Chemical Property of Nobiletin

Chemical Property:

• Vapor Pressure: 8.39E-14mmHg at 25°C
• Melting Point: 136.0 to 140.0 °C
• Refractive Index: 1.558
• Boiling Point: 587.9 °C at 760 mmHg
• Flash Point: 256.5 °C
• PSA: 85.59000
• Density: 1.244 g/cm³
• LogP: 3.51160
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml)
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 402.13146766
• Heavy Atom Count: 29
• Complexity: 593

Purity/Quality:

99% ^*data from raw suppliers

Nobiletin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC
• Recent NIPH Clinical Trials: A study to examine the effects of food intake on relief from eye and nasal discomfort.
• 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. 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.
• Uses: NOB is a multifunctional pharmaceutical agent. The various pharmacological activities of NOB include neuroprotection, cardiovascular protection, antimetabolic disorder, anticancer, anti-inflammation, and antioxidation. matrix metaloproteinase inhibitor; antineoplastic 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.

Technology Process of Nobiletin

There total 58 articles about Nobiletin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(3,4-dimethoxyphenyl)-1,3-propanedione (654083-34-8) → nobiletin (478-01-3)

Guidance literature:

With trifluoroacetic acid; In methanol; at 20 - 50 ℃; for 24h;

DOI:10.1021/acs.oprd.9b00091

Reference yield: 87.0%

5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone (683278-67-3) + dimethyl sulfate (77-78-1) → nobiletin (478-01-3)

Guidance literature:

With potassium carbonate; In dichloromethane; acetone; for 6h; Heating;

DOI:10.1016/j.tet.2004.01.023

Reference yield: 80.0%

7-hydroxy-3’,4’,5,6,8-pentamethoxyflavone + dimethyl sulfate (77-78-1) → nobiletin (478-01-3)

Guidance literature:

With potassium carbonate; In acetone; at 65 ℃; for 5h;

DOI:10.1007/s00044-017-1871-4

upstream raw materials:

2',5'-dihydroxy-3',4',6'-trimethoxyacetophenone

3,4-dimethoxybenzoic anhydride

1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(3,4-dimethoxyphenyl)-1,3-propanedione

dimethyl sulfate

Downstream raw materials:

3,3',4',5,6,7,8-heptamethoxyflavone

5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone

3-(2-(4-chlorophenyl)-2-oxoethyl)-5,6,7-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

ethyl 2-(2-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-4-oxo-4H-chromen-3-yl)acetate

Refernces

• 1、 -. "preparing methods of nobiletin". Paragraph 0142-0143; 0175-0177; 0179-0180. . Retrieved 2021/08/24.
• 2、 Nguyen, Van-Son,Li, Wei,Li, Yue,Wang, Qiuan. "Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells". . p. 1585 - 1592. Retrieved 2017/06/05.