6-Methoxymellein

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 °C [77 °F], 100 kPa).

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]

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

  1. ^ Czepa, A; Hofmann, T (June 2003). "Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree". J. Agric. Food Chem. 51: 3865–73. doi:10.1021/jf034085+. PMID 12797757.
  2. ^ Talcott, S. T. (1999). "Determination and Distribution of 6-Methoxymellein in Fresh and Processed Carrot Puree by a Rapid Spectrophotometric Assay". Journal of Agricultural and Food Chemistry. 47: 3237–3242. doi:10.1021/jf990288f.
  3. ^ Mercier, J. (1993). "Induction of 6-Methoxymellein and Resistance to Storage Pathogens in Carrot Slices by UV-C". Journal of Phytopathology. 137: 44–54. doi:10.1111/j.1439-0434.1993.tb01324.x.
  4. ^ Hoffman, R. (1987). "Cell death, 6-methoxymellein accumulation, and induced resistance to Botrytis cinerea in carrot root slices". Physiological and Molecular Plant Pathology. 30: 67–75. doi:10.1016/0885-5765(87)90083-X.
  5. ^ Kurosaki, Fumiya (1983). "Isolation and antimicrobial activity of the phytoalexin 6-methoxymellein from cultured carrot cells". Phytochemistry. 22: 669–672. doi:10.1016/S0031-9422(00)86959-9.
  6. ^ "MetaCyc 6-methoxymellein biosynthesis". www.biocyc.org.
allikas: https://en.wikipedia.org/wiki/6-Methoxymellein