3316-46-9

Usage

Uses

Used in Pharmaceutical Industry:
Apigenin Triacetate is used as an intermediate in the synthesis of Isorhoifolin (I819700), a naturally occurring flavonoid with potential antidiabetic, antihyperlipidemic, and antioxidant effects. This makes it a valuable compound in the development of new drugs for treating diabetes, hyperlipidemia, and other conditions related to oxidative stress.

InChI:InChI=1/C21H16O8/c1-11(22)26-15-6-4-14(5-7-15)18-10-17(25)21-19(28-13(3)24)8-16(27-12(2)23)9-20(21)29-18/h4-10H,1-3H3

Upstream product

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 108-24-7 acetic anhydride 
• 73111-01-0 4',5,7-triacetoxyflavan-4-one 
• 10236-47-2 naringin 
• 724434-08-6 dihydrokaempferol 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 127-08-2 potassium acetate 

Downstream Products

• 29781-25-7 apigenin 7-O-β-D-glucopyranosiduronic acid methyl ester 
• 29741-09-1 apigenin-7-O-β-D-glucuronide 
• 34340-20-0 5,4'-diacetoxyflavone-7-O-D-triacetoxyglucuronic acid methyl ester 
• 16280-23-2 4',5,-diacetoxy-7-methoxyflavone 
• 437-64-9 genkwanin 
• 5892-39-7 acacetin diacetate 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 1610737-95-5 5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-7-morpholino-4H-chromen-4-one 
• 1610737-91-1 5-(benzyloxy)-2-(4-(benzyloxy)phenyl)-4-oxo-4Hchromen-7-yl4-methylbenzenesulfonate 
• 1104802-77-8 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl-4-methylbenzenesulfonate 
• 1610737-85-3 4-(5-acetoxy-4-oxo-7-(tosyloxy)-4H-chromen-2-yl)phenyl acetate 
• 1610737-80-8 4-(5-acetoxy-7-(tert-butoxy)-4-oxo-4H-chromen-2-yl)phenyl acetate 
• 1610737-52-4 4-(5-acetoxy-7-((4-fluorobenzyl)oxy)-4-oxo-4H-chromen-2-yl)phenyl acetate 
• 1610737-74-0 5-hydroxy-2-(4-hydroxyphenyl)-7-morpholino-4H-chromen-4-one 

Relevant academic research and scientific papers

Extraction, Isolation and Characterization of Valuable Worked on Acacia Tortilis

Acacia tortilis is one of the important species of genus Acacia belonging to family Leguminaceae. Though there is no more study performed on this plant but it plays important role in the countries where it found. These countries include North Africa, Arabian Peninsula and Asian countries. The various part of Acacia tortilis plant say leaves, pods, gum exudates and bark were used as antidiabetic, antidiarrhoeal, antiasthmatic and also had several other medicinal benefits. The present discussion deals with the isolation and characterization of the following compounds from the leaves of Acacia tortilis. Lupan-3-ol, 12,20-diene, Lupan-12, 20-dien 3-one, Friedelin, ?-amyrin, ?- sitosterol, Apigenin, Luteolin, Quercetin, 5,7-dihydroxy-4-p-methyl benzylisoflavone, Vitexin, 2',6'-dihydroxy chalcone-4'-O-glucoside.

Site-selective synthesis of acacetin and genkwanin through lipase-catalyzed deacetylation of apigenin 5,7-diacetate and subsequent methylation

Candida antarctica lipase B-catalyzed deacetylation proceeded with high site-selectivity on the C-4′ acetyl group in apigenin triacetate to give apigenin 5,7-diacetate. Methylation of the liberated hydroxy group with the combination of trimethyloxonium tetrafluoroborate (Meerwein reagent) and 1,8-bis(dimethylamino)naphthalene (proton sponge) in CH2Cl2 proceeded in a quantitative manner to give the product methylated at the C-4′ hydroxy group (acacetin 5,7-diacetate). Even with the same precursor, a different methylation product at the C-7 hydroxy group (genkwanin 4′,5-diacetate) was obtained in 86% yield by applying iodomethane and Cs2CO3 in dimethyl sulfoxide (DMSO). The methylated products were deprotected to form acacetin and genkwanin. We inferred that the latter unexpected methylation was ascribable to the intermolecular migration of an acetyl group from C-7 to C-4′. DFT calculations indicated that the C-7 phenoxide ion was 12.6 kJ/mol more stable than the initially formed C-4′ phenoxide ion.

A 5, 4' - dihydroxy flavone - 7 - O - D - glucuronic acid preparation method

The invention relates to the drug synthesis technical field, and in particular, relates to a preparation method of 5,4'-dihydroxy flavone-7-O-D-glucuronic acid. The method comprises the following steps: taking a compound having a structure represented by the formula II, and under an alkaline condition, acylating to obtain a compound having a structure represented by the formula III; taking the compound having the structure represented by the formula III and alpha-bromo triacetoxy methyl glucuronate, and carrying out a glycosylation reaction, to obtain a compound having a structure represented by the formula IV; taking the compound having the structure represented by the formula IV, and hydrolyzing under an acidic condition, to obtain a compound having a structure represented by the formula V; and taking the compound having the structure represented by the formula V, hydrolyzing under an alkaline condition, and thus obtaining the product. The method provided by the invention has the advantages of cheap and easily obtained starting raw materials, less reaction steps, and simple and easily operated process, and is suitable for large-scale industrialized production; and through testing, the purity of the obtained product can reach more than 98%, and the total yield reaches up to 56%.

Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines

A series of flavone-7-phosphoramidate derivatives were synthesized and tested for their antiproliferative activity in vitro against human hepatoma cell line HepG2 and human normal hepatic cell line L-O2. Compound 8d, 16d and 17d, incorporating the amino acid alanine, exhibited high inhibitory activity on HepG2 cell line with IC50 values of 9.0 μmol/L, 5.5 μmol/L and 6.6 μmol/L. The introduction of acyl groups played a pivotal role in the selective inhibition toward human hepatoma HepG2 cells, except for compound 8a, 9a and 16b. Compound 8d, 16d and 17d could significantly induce G2/M arrest in HepG2 cells. Specially, Compound 16d could lead early apoptosis in HepG2 cells.

Design and discovery of flavonoid-based HIV-1 integrase inhibitors targeting both the active site and the interaction with LEDGF/p75

HIV integrase (IN) is an essential enzyme for the viral replication. Currently, three IN inhibitors have been approved for treating HIV-1 infection. All three drugs selectively inhibit the strand transfer reaction by chelating a divalent metal ion in the

The first total synthesis of 7-O-β-d-glucopyranosyl-4′-O-α-l-rhamnopyranosyl apigenin via a hexanoyl ester-based protection strategy

The first total synthesis of 7-O-β-d-glucopyranosyl-4′-O-α-l-rhamnopyranosyl apigenin 1, which exhibits good anti-hepatitis B virus and anti-stroke activities, was accomplished in six steps and 20% overall yield from apigenin. Another synthetic route, in which the target was obtained in seven steps, was also developed to prove the utility of a hexanoyl ester-based orthogonal protection strategy. The hexanoyl protection strategy provided all the flavonoid intermediates with good solubility and reactivity, enabled efficient selective protection and glycosylation, and provided a practical and effective synthetic strategy for flavonoids, starting from commercially available flavone.

Flavonoids from Acacia tortilis

A novel isoflavone, 5,7-dihydroxy-4′- p-methyl benzyl isoflavone 1a, and three known flavonoids apigenin, luteolin and quercetin have been isolated from the leaves of Acacia tortilis. Their structures were elucidated by chemical and physical data (IR, UV,

NIVYASIDE - A NEW GLYCOSIDE FROM Leucanthemum vulgare

From the ligulate flowers of Leucanthemum vulgare Lam. growing on the territory of the Georgian SSR a new glycoside has been isolated which has been called nivyaside and has the structure 8-(1-α-D-glucopyranosyl-5-deoxyquercit-5-yl)-4',5,7-trihydroxyflavone.