436-32-8

Basic information

• Product Name: DIFFRACTIC ACID
• Synonyms: DIRHIZONIC ACID;DIFFRACTIC ACID;benzoicacid,2,4-dimethoxy-3,6-dimethyl-,4-carboxy-3-hydroxy-2,5-dimethylph;beta-resorcylicacid,3,6-dimethyl-,4-(2,4-dimethoxy-3,6-dimethylbenzoate);diffractaicacid;2-Hydroxy-4-(2,4-dimethoxy-3,6-dimethylbenzoyloxy)-3,6-dimethylbenzoic acid;4-(2,4-dimethoxy-3,6-dimethyl-benzoyl)oxy-2-hydroxy-3,6-dimethyl-benzoic acid;4-(2,4-dimethoxy-3,6-dimethylbenzoyl)oxy-2-hydroxy-3,6-dimethylbenzoic acid
• CAS NO: 436-32-8
• Molecular Formula: C₂₀H₂₂O₇
• Molecular Weight: 374.38
• Mol File: 436-32-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 189～190℃
• Boiling Point: 604.9°Cat760mmHg
• Flash Point: 214.2°C
• Appearance: /
• Density: 1.26g/cm³
• Vapor Pressure: 1.74E-15mmHg at 25°C
• Refractive Index: 1.583
• PKA: 2.66±0.25(Predicted)
• CAS DataBase Reference: DIFFRACTIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DIFFRACTIC ACID(436-32-8)
• EPA Substance Registry System: DIFFRACTIC ACID(436-32-8)

Safety Data

• Hazardous Substances Data: 436-32-8(Hazardous Substances Data)

Usage

Description

Diffractaic acid is a lichen metabolite that has been found in P. magellanica and has diverse biological activities. It is cytotoxic to HCT116, HeLa, and MCF-7 cancer cells (IC50s = 42.2, 64.6, and 93.4 μM, respectively). Diffractaic acid inhibits growth of M. tuberculosis (MIC = 41.7 μM). In vivo, diffractaic acid (25-200 mg/kg) reduces neutrophil infiltration, lipid peroxidation, myeloperoxidase (MPx) activity, and the number of gastric lesions as well as reverses decreases in superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities induced by indomethacin in rat gastric mucosa. Diffractaic acid also has analgesic activity, reducing acetic acid-induced writhing and increasing the pressure pain threshold in mice.

InChI:InChI=1/C20H22O7/c1-9-8-14(11(3)17(21)15(9)19(22)23)27-20(24)16-10(2)7-13(25-5)12(4)18(16)26-6/h7-8,21H,1-6H3,(H,22,23)

Upstream product

• 56410-30-1 benzyl 2,4-dihydroxy-3,6-dimethylbenzoate 
• 56410-34-5 2,4-O-dimethyl-β-orcinolcarboxylic acid 
• 31581-32-5 ethyl 2,4-dihydroxy-3,6-dimethylbenzoate 
• 56410-45-8 Benzyl diffractaiat 

Downstream Products

• 58062-15-0 4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-methoxy-3,6-dimethyl-benzoic acid methyl ester 
• 81050-84-2 4-(2,4-dimethoxy-3,6-dimethyl-benzoyloxy)-2-hydroxy-3,6-dimethyl-benzoic acid methyl ester 
• 488-87-9 2,5-dimethyl-1,3-benzenediol 
• 56410-34-5 2,4-O-dimethyl-β-orcinolcarboxylic acid 
• 4707-46-4 2,4-dihydroxy-3,6-dimethylbenzoic acid 

Relevant articles and documents

Depsides as non-redox inhibitors of leukotriene B4 biosynthesis and HaCaT cell growth. 1. Novel analogues of barbatic and diffractaic acid

A series of barbatic and diffractaic acid analogues has been synthesized and evaluated as inhibitors of leukotriene B4 (LTB4) biosynthesis and as antiproliferative agents. The 4-O-demethyl barbatic and diffractaic acid derivatives were among the most active compounds in both assays. In particular, ethyl 4-O-demethylbarbatate was the most potent LTB4 biosynthesis inhibitor of this series, with an IC50 value in the submicromolar range. Because the compounds did not show appreciable reactivity against a stable free radical, 2,2-diphenyl-1-picrylhydrazyl, and did not produce appreciable amounts of deoxyribose degradation as a measure of their potency to generate hydroxyl radicals, a simple redox effect could not explain their biological activity. Also, there was no nonspecific cytotoxicity as documented by the activity of lactate dehydrogenase released from the cytoplasm of keratinocytes, which was in the control range.