79214-49-6

Basic information

• Product Name: Pyrenochaetic acid
• Synonyms: 3-Methoxy-4-(2-butenoyl)-5-methylbenzoic acid;4-(2-Butenoyl)-3-methoxy-5-methylbenzoic acid;Pyrenochaetic acid;Pyrenochaetic acid A
• CAS NO: 79214-49-6
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.24786
• Mol File: 79214-49-6.mol

Chemical Properties

• Boiling Point: 434.2°Cat760mmHg
• Flash Point: 167.2°C
• Appearance: /
• Density: 1.168g/cm³
• Vapor Pressure: 2.62E-08mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: Pyrenochaetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrenochaetic acid(79214-49-6)
• EPA Substance Registry System: Pyrenochaetic acid(79214-49-6)

Safety Data

• Hazardous Substances Data: 79214-49-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H14O4/c1-4-5-10(14)12-8(2)6-9(13(15)16)7-11(12)17-3/h4-7H,1-3H3,(H,15,16)/b5-4+

Upstream product

• 80597-52-0 ethyl 4-acetyl-3-methoxy-5-methylbenzoate 
• 79214-48-5 pyrenochaetic acid B 
• 76868-97-8 citreopyrone 
• 108-24-7 acetic anhydride 
• 116097-04-2 ethyl 4-(3-hydroxybutyryl)-3-methoxy-5-methylbenzoate 

Downstream Products

• 585-81-9 3-hydroxy-5-methylbenzoic acid 
• 79214-47-4 pyrenochaetic acid C 

Relevant articles and documents

Studies on Metabolites of Macrophoma commelinae. IV. Substrate Specificity in the Biotransformation of 2-Pyrones to Substituted Benzoic Acids

Substrate specificity in the novel biotransformation from 2-pyrone derivatives to substituted benzoic acids by Macrophoma commelinae (IFO 9570) was investigated by means of feeding experiments with various compounds.Among them, 2-pyrone derivatives substituted by an electron-donating group at C-4, by an electron-withdrawing group at C-5 and by an alkyl group at C-6 were converted to the corresponding benzoic acid derivatives in fairly good yields.The C3-unit precursors and intermediates were examined in stationary or shaking culture.Based on the experimental results obtained, a mechanism for this unique reaction is proposed. macrophoma commelinae IFO 9570; fungi; 2-pyrone; substituted benzoic acid; biotransformation; substrate specificity; aromatic ring formation; macrophomic acid

SYNTHESIS OF PYRENOCINES A, B AND PYRENOCHAETIC ACID A

Starting from 5-acetyl-4-hydroxy-6-methyl-α-pyrone, three phytotoxins, pyrenocines A, B and pyrenochaetic acid A were synthesized.Retro-Diels-Alder reaction was successfully applied in the synthesis of pyrenochaetic acid A.

Three New Phytotoxins Produced by Pyrenochaeta terrestris: Pyrenochaetic Acids A, B and C

Three phytotoxins named pyrenochaetic acids A, B and C were isolated from culture filtrates of Pyrenochaeta terrestris, and the structures were determined to be 4-crotonoyl-3-methoxy-5-methylbenzoic acid (I), 4-(3-hydroxybutyroyl)-3-methoxy-5-methylbenzoi