AMENTOFLAVONE

Base Information

• Chemical Name: AMENTOFLAVONE
• CAS No.: 1617-53-4
• Molecular Formula: C30H18O10
• Molecular Weight: 538.467
• Hs Code.: 29329990
• Mol file: 1617-53-4.mol

Synonyms:3''',8-Biflavone,4',4''',5,5'',7,7''-hexahydroxy- (7CI,8CI);Ginkgetin, didemethyl- (6CI);Amenthoflavone;I3',II8-Biapigenin;NSC 295677;Tridemethylsciadopitysin;

Chemical Property of AMENTOFLAVONE

Chemical Property:

• Appearance/Colour: Odourless Whitish Solid
• Vapor Pressure: 2.79E-35mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.793
• Boiling Point: 910.5 °C at 760 mmHg
• PKA: 6.01±0.40(Predicted)
• Flash Point: 308.4 °C
• PSA: 181.80000
• Density: 1.656 g/cm³
• LogP: 5.13400
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated), Pyridine (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Amentoflavone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Amentoflavone , a bisapigenin , is one of the best inhibitors in the class of flavonoids , since its active dose is about 0.12uM. Amentoflavone (C30H18O10) is a well-known biflavonoid occurring in many natural plants. This polyphenolic compound has been discovered to have some important bioactivities, including anti-inflammation, anti-oxidation, anti-diabetes, and anti-senescence effects on many important reactions in the cardiovascular and central nervous system, etc. Over 120 plants have been found to contain this bioactive component, such as Selaginellaceae, Cupressaceae, Euphorbiaceae, Podocarpaceae, and Calophyllaceae plant families. Amentoflavone is a natural product with several associated biological effects.Its ability to block NF-xβ is the key for its anti-inflammatory potential. BETs were identified as NF-xβ promoters, with JQ-1 being highly effective in psoriasis models. Amentoflavone is a biflavonoid originally isolated from Selaginella. It has a wide variety of biological effects including antibacterial, antioxidant, antiviral, antidiabetic, and neuroprotective activities. Amentoflavone has antiviral activity against the influenza A subtypes H1N1 and H3N2, influenza B, and herpes simplex virus 1 (EC50s = 3.1 and 4.3, 0.56, and 17.9 μg/ml, respectively). It has antidiabetic effects such that it dose-dependently increases insulin receptor phosphorylation and activation and inhibits hydrolysis of p-nitrophenyl phosphate (p-NPP) catalyzed by protein tyrosine phosphatase 1B (PTP1B; IC50 = 7.3 μM). Amentoflavone reduces the time mice spend immobile in the forced swim test, a measure of antidepressant efficacy, in a dose-dependent manner.
• Biological Functions: Amentoflavone is a biflavonoid originally isolated from Selaginella. It has a wide variety of biological effects including antibacterial, antioxidant, antiviral, antidiabetic, and neuroprotective activities. Amentoflavone has antiviral activity against the influenza A subtypes H1N1 and H3N2, influenza B, and herpes simplex virus 1 (EC50s = 3.1 and 4.3, 0.56, and 17.9 μg/ml, respectively). It has antidiabetic effects such that it dose-dependently increases insulin receptor phosphorylation and activation and inhibits hydrolysis of p-nitrophenyl phosphate (p-NPP) catalyzed by protein tyrosine phosphatase 1B (PTP1B; IC50 = 7.3 μM). Amentoflavone reduces the time mice spend immobile in the forced swim test, a measure of antidepressant efficacy, in a dose-dependent manner.
• Uses: Amentoflavone, is isolated from an Et acetate ext. of the whole plant of Selaginella tamariscina. It has been shown to have antitumor activity, such as mitochondria-mediated apoptotic cell death. Amentoflavone can interact with many medications by being a potent inhibitor of CYP3A4 and CYP2C9, which are enzymes responsible for the metabolism of some drugs in the body.

Technology Process of AMENTOFLAVONE

There total 9 articles about AMENTOFLAVONE 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:

isoginkgetin (548-19-6) → amentoflavone (1617-53-4)

Guidance literature:

With pyridine hydrochloride; at 180 ℃;

Reference yield:

amentoflavone 4’-O-α-L-rhamnopyranoside → L-rhamnose (6014-42-2) + amentoflavone (1617-53-4)

Guidance literature:

With hydrogenchloride; water; In methanol; for 2h; Reflux;

DOI:10.1080/14786419.2020.1789636

Reference yield:

5,7,4',5'',7'',4'''-hexahydroxy-2,3,2'',3''-tetrahydroamentoflavone (48236-96-0) → amentoflavone (1617-53-4)

Guidance literature:

With sulfuric acid; iodine; In dimethyl sulfoxide; at 100 ℃; for 1h;

DOI:10.1016/0031-9422(81)83061-0

upstream raw materials:

5,7,4',5'',7'',4'''-hexahydroxy-2,3,2'',3''-tetrahydroamentoflavone

isoginkgetin

Downstream raw materials:

amentoflavone hexaacetate

Amentoflavon

robustaflavone

7,4',7'',4'''-tetra-O-methylamentoflavone

Refernces

• 1、 Abo El-Seoud, Kamilia A.,El-Aasr, Mona,Kabbash, Amal,Kassab, Amira A.,Negm, Walaa A.. "Hepatoprotective, cytotoxic, antimicrobial and antioxidant activities of Dioon spinulosum leaves Dyer Ex Eichler and its isolated secondary metabolites". . p. 1 - 11. Retrieved 2020.
• 2、 -. "COMPOUNDS, COMPOSITION AND USES THEREOF FOR TREATING CANCER". Page/Page column 23-24. . Retrieved 2018/11/22.