6-Methoxymellein

Chemical compound From Wikipedia, the free encyclopedia

6-Methoxymellein is a dihydroisocoumarin, a phenolic compound found in carrots and carrot purées. It is responsible for bitterness in carrots.[1][2] It is a phytoalexin, induced in carrot slices by UV-C,[3] that allows resistance to Botrytis cinerea[4] and other microorganisms.[5]

Quick facts Names, Identifiers ...
6-Methoxymellein
Chemical structure of 6-Methoxymellein
Chemical structure of 6-Methoxymellein
Names
Preferred IUPAC name
8-Hydroxy-6-methoxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one
Other names
8-Hydroxy-6-methoxy-3-methylisochroman-1-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C11H12O4/c1-6-3-7-4-8(14-2)5-9(12)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3
    Key: AIFNAMVERSBWPS-UHFFFAOYSA-N
  • InChI=1/C11H12O4/c1-6-3-7-4-8(14-2)5-9(12)10(7)11(13)15-6/h4-6,12H,3H2,1-2H3
    Key: AIFNAMVERSBWPS-UHFFFAOYAL
  • COc1cc(O)c2C(=O)OC(C)Cc2c1
Properties
C11H12O4
Molar mass 208.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Biosynthesis

6-Methoxymellein is formed from S-adenosyl methionine and 6-hydroxymellein by the enzyme 6-hydroxymellein O-methyltransferase with secondary production of S-adenosylhomocysteine.[6]

References

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