Macrophomic acid

Macrophomic acid
Names
Preferred IUPAC name
4-Acetyl-3-methoxy-5-methylbenzoic acid
Systematic IUPAC name
4-Ethanoyl-3-methoxy-5-methylbenzenecarboxylic acid
Identifiers
3D model (JSmol)
5743941
ChEBI
ChemSpider
UNII
  • InChI=1S/C11H12O4/c1-6-4-8(11(13)14)5-9(15-3)10(6)7(2)12/h4-5H,1-3H3,(H,13,14) N
    Key: GWSISRLRTQOQNE-UHFFFAOYSA-N N
  • InChI=1/C11H12O4/c1-6-4-8(11(13)14)5-9(15-3)10(6)7(2)12/h4-5H,1-3H3,(H,13,14)
    Key: GWSISRLRTQOQNE-UHFFFAOYAK
  • CC1=CC(=CC(=C1C(=O)C)OC)C(=O)O
Properties
C11H12O4
Molar mass 208.21 g/mol
Boiling point 385.3±42.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Macrophomic acid is a fungal metabolite isolated from the fungus Macrophoma commelinae. The enzyme macrophomate synthase converts 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid) through an unusual intermolecular Diels-Alder reaction (Scheme 1). The pathway to formation of macrophomic acid suggests that the enzyme is a natural Diels-Alderase. Formation of this type of aromatic ring compound normally proceeds via the shikimate and polyketide pathways; however, the production of macrophomic acid by macrophomate synthase proceeds totally differently. Learning about the production of macrophomic acid by a possible natural Diels-Alderase enzyme is important in understanding enzyme catalytic mechanisms. This knowledge can then be applied to organic synthesis.

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