4707-49-7

Basic information

• Product Name: 2,4-dihydroxy-3-methylbenzoic acid
• Synonyms: 2,4-dihydroxy-3-methylbenzoic acid;3-Methyl-β-resorcylic acid
• CAS NO: 4707-49-7
• Molecular Formula: C₈H₈O₄
• Molecular Weight: 168.15
• Mol File: 4707-49-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 425.1°C at 760 mmHg
• Flash Point: 225°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 5.52E-08mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 2,4-dihydroxy-3-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dihydroxy-3-methylbenzoic acid(4707-49-7)
• EPA Substance Registry System: 2,4-dihydroxy-3-methylbenzoic acid(4707-49-7)

Safety Data

• Hazardous Substances Data: 4707-49-7(Hazardous Substances Data)

Usage

Uses

2,4-Dihydroxy-3-methylbenzoic acid is used in the synthesis of Averufin a useful intermediate in Aflatoxin B1 biosynthesis.

InChI:InChI=1/C8H8O4/c1-4-6(9)3-2-5(7(4)10)8(11)12/h2-3,9-10H,1H3,(H,11,12)

Upstream product

• 124-38-9 carbon dioxide 
• 608-25-3 2-methylbenzene-1,3-diol 
• 39503-26-9 5-carbomethoxy-6-hydroxysalicylaldehyde 
• 2150-47-2 methyl 2,4-dihydroxybenzoate 
• 15719-64-9 methylammonium carbonate 
• 33662-58-7 methyl 2,4-dihydroxy-3-methylbenzoate 

Downstream Products

• 608-25-3 2-methylbenzene-1,3-diol 
• 6688-71-7 methyl 2,4-dimethoxy-3-methylbenzoate 
• 116386-94-8 methyl 2-hydroxy-4-methoxy-3-methylbenzoate 
• 33662-58-7 methyl 2,4-dihydroxy-3-methylbenzoate 

Relevant articles and documents

Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base

The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.

Synthesis of Averufin and its Role in Aflatoxin B1 Biosynthesis

Described are two total syntheses of (+/-)-averufin (4) proceeding through a common intermediate and predicated on the efficient introduction of isotopic label(s) at side-chain and nuclear sites for the purpose of biosynthetic investigations of aflatoxin B1 (8).Using these methods, (+/-)--and --averufin, (65) and (68) respectively, and a 1:1 mixture of (+/-)-- and --averufin (71) were prepared and incorporated into aflatoxin B1 using mycelial suspensions of Aspergillus parasiticus (SU-1).In each instance efficient and specific utilization of label was observed in the product by (13)C-n.m.r.spectroscopy, demonstrating the intact incorporation of averufin.When compared with earlier observations of acetate incorporation, a complete correlation of the carbon skeleton from the intermediate anthraquinone stage of the four carbons lost in this overall process were unambiguously identified.In the formation of the dihydrobisfuran, the anthraquinone nucleus migrates to C-2' to branch the linear side-chain of averufin.Deuterium bound at C-1' in averufin is carried to C-13 of aflatoxin.Preparation from (+/-)-averufin (68) of (+/-)--averufin (73) and incorporation of the latter into versiconal acetate (5) demonstrated loss of the terminal two carbons of the averufin side-chain, presumably as acetate, by way of a Baeyer-Villiger-like oxidation.