1258551-28-8

Basic information

• Product Name: acetic acid 3,5-diacetoxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl ester
• Synonyms: acetic acid 3,5-diacetoxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl ester
• CAS NO: 1258551-28-8
• Molecular Weight: 592.559
• Mol File: 1258551-28-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: acetic acid 3,5-diacetoxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: acetic acid 3,5-diacetoxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl ester(1258551-28-8)
• EPA Substance Registry System: acetic acid 3,5-diacetoxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-7-yl ester(1258551-28-8)

Safety Data

• Hazardous Substances Data: 1258551-28-8(Hazardous Substances Data)

Upstream product

• 2051-90-3 Dichlorodiphenylmethane 
• 117-39-5 quercetol 
• 108-24-7 acetic anhydride 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 

Downstream Products

• 1258551-29-9 acetic acid 5-acetoxy-7-hydroxy-2-(2-methyl-2-phenylbenzo-[1,3]dioxol-5-yl)-4-oxo-4H-chromen-3-yl ester 
• 1258551-30-2 acetic acid 5-acetoxy-7-benzyloxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-4-oxo-4H-chromen-3-yl ester 
• 49570-46-9 7-benzyloxy-2-(2,2-diphenyl-benzo[1,3]dioxol-5-yl)-3,5-dihydroxy-chromen-4-one 
• 1310686-94-2 C₂₀H₁₈O₁₀ 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 

Relevant articles and documents

New lipophenols prevent carbonyl and oxidative stresses involved in macular degeneration

Dry age-related macular degeneration and Stargardt disease undergo a known toxic mechanism caused by carbonyl and oxidative stresses (COS). This is responsible for accumulation in the retinal pigment epithelium (RPE) of A2E, a main toxic pyridinium bis-retinoid lipofuscin component. Previous studies have shown that carbonyl stress in retinal cells could be reduced by an alkyl-phloroglucinol-DHA conjugate (lipophenol). Here, we performed a rational design of different families of lipophenols to conserve anti-carbonyl stress activities and improve antioxidant properties. Five synthetic pathways leading to alkyl-(poly)phenol derivatives, with phloroglucinol, resveratrol, catechin and quercetin as the main backbone, linked to poly-unsaturated fatty acid, are presented. These lipophenols were evaluated in ARPE-19 cell line for their anti-COS properties and a structure-activity relationship study is proposed. Protection of ARPE-19 cells against A2E toxicity was assessed for the four best candidates. Finally, interesting anti-COS properties of the most promising quercetin lipophenol were confirmed in primary RPE cells.

LIPOPHENOLIC FLAVONOID DERIVATIVES USEFUL TO REDUCE CARBONYL AND OXIDATIVE STRESSES (COS)

The invention relates to compound of formula (I): in particular flavonoid derivatives (quercetin and catechin derivatives), for use in the prevention and/or the treatment of a disease or disorder involving both carbonyl and oxidative stresses.

Quercetin derivatives as novel antihypertensive agents: Synthesis and physiological characterization

The antihypertensive flavonol quercetin (Q1) is endowed with a cardioprotective effect against myocardial ischemic damage. Q1 inhibits angiotensin converting enzyme activity, improves vascular relaxation, and decreases oxidative stress and gene expression. However, the clinical application of this flavonol is limited by its poor bioavailability and low stability in aqueous medium. In the aim to overcome these drawbacks and preserve the cardioprotective effects of quercetin, the present study reports on the preparation of five different Q1 analogs, in which all OH groups were replaced by hydrophobic functional moieties. Q1 derivatives have been synthesized by optimizing previously reported procedures and analyzed by spectroscopic analysis. The cardiovascular properties of the obtained compounds were also investigated in order to evaluate whether chemical modification affects their biological efficacy. The interaction with β-adrenergic receptors was evaluated by molecular docking and the cardiovascular efficacy was investigated on the ex vivo Langendorff perfused rat heart. Furthermore, the bioavailability and the antihypertensive properties of the most active derivative were evaluated by in vitro studies and in vivo administration (1 month) on spontaneously hypertensive rats (SHRs), respectively. Among all studied Q1 derivatives, only the ethyl derivative reduced left ventricular pressure (at 10- 8 M ÷ 10- 6 M doses) and improved relaxation and coronary dilation. NOSs inhibition by L-NAME abolished inotropism, lusitropism and coronary effects. Chronic administration of high doses of this compound on SHR reduced systolic and diastolic pressure. Differently, the acetyl derivative induced negative inotropism and lusitropism (at 10- 10 M and 10- 8 ÷ 10- 6 M doses), without affecting coronary pressure. Accordingly, docking studies suggested that these compounds bind both β1/β2-adrenergic receptors. Taking into consideration all the obtained results, the replacement of OH with ethyl groups seems to improve Q1 bioavailability and stability; therefore, the ethyl derivative could represent a good candidate for clinical use in hypertension.