102036-28-2

Basic information

• Product Name: protosappanin A
• Synonyms: protosappanin A;Sappanol B;3,10,11-Trihydroxy-6H-dibenz[b,d]oxocin-7(8H)-one
• CAS NO: 102036-28-2
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25278
• Mol File: 102036-28-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 254-255 °C
• Boiling Point: 613.1°Cat760mmHg
• Flash Point: 238.8°C
• Appearance: /
• Density: 1.476g/cm³
• Vapor Pressure: 1.26E-15mmHg at 25°C
• Refractive Index: 1.689
• PKA: 9.01±0.20(Predicted)
• CAS DataBase Reference: protosappanin A(CAS DataBase Reference)
• NIST Chemistry Reference: protosappanin A(102036-28-2)
• EPA Substance Registry System: protosappanin A(102036-28-2)

Safety Data

• Hazardous Substances Data: 102036-28-2(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Caesalpinia sappan.

InChI:InChI=1/C15H12O5/c16-9-1-2-11-12-6-14(19)13(18)4-8(12)3-10(17)7-20-15(11)5-9/h1-2,4-6,16,18-19H,3,7H2

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 1835-02-5 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 
• 41046-70-2 2-iodo-5-methoxyphenol 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 150-19-6 O-methylresorcine 
• 868405-37-2 protosappanin A dimethyl acetal 

Downstream Products

• 4371-31-7 sappanin 
• 120-80-9 benzene-1,2-diol 
• 108-46-3 recorcinol 

Relevant articles and documents

Xanthine oxidase inhibitors from the heartwood of Vietnamese Caesalpinia sappan

From the MeOH extract of Vietnamese Caesalpinia sappan, a novel biogenetically exclusive benzindenopyran, with a new carbon framework, neoprotosappanin (1), and a new compound, protosappanin A dimethyl acetal (3), were isolated together with protosappanin E-2 (2), neosappanone A (4), and 13 previously reported phenolic compounds (5-17). Their structures were elucidated on the basis of spectroscopic data. Compounds 1-4, 7, 13, and 15-17 showed significant xanthine oxidase inhibitory activity in a concentration-dependent manner, and sappanchalcone (17) showed the most potent activity with an IC 50 value of 3.9 μM, comparable to that of positive control allopurinol (IC50, 2.5 μM). The kinetic study of these inhibitors indicated that they are competitive inhibitors, the same as allopurinol, except for 1 and 16 which are noncompetitive inhibitors.

A original haematoxylin A and its derivative chemical whole synthetic method

The invention discloses a biochemical total synthetic method for protosappanin A and derivatives thereof. The synthetic method for protosappanin A and derivatives thereof comprises the main steps: taking a dibenzo[d,f]oxepane-3-one compound as a raw material, performing cyan addition on carbonyl, performing reduction, Tiffeneau-Demjanov rearrangement, deprotection and other reactions, so as to synthesize the protosappanin A derivatives with the total yield of 85% or more. Chemical total synthesis of protosappanin A compounds is developed for the first time. The synthetic method is simple to operate, reduced in synthetic difficulty because routine chemical reaction methods are employed, mild in reaction conditions, friendly to environment, simple in post-treatment and high in yield, and has good industrialization production prospect.