6-Methoxymellein

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
CAS Number	13410-15-6 ;
3D model (JSmol)	Interactive image;
ChemSpider	83993;
PubChem CID	93040;
UNII	424N0263W4 ;
	InChI 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;
	SMILES COc1cc(O)c2C(=O)OC(C)Cc2c1;
Properties
Chemical formula	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). Infobox references

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

^ Structural and Sensory Characterization of Compounds Contributing to the Bitter Off-Taste of Carrots (Daucus carota L.) and Carrot Puree. Andreas Czepa and Thomas Hofmann, J. Agric. Food Chem., 2003, 51, pages 3865-3873, doi:10.1021/jf034085+ PMID 12797757
^ Determination and Distribution of 6-Methoxymellein in Fresh and Processed Carrot Puree by a Rapid Spectrophotometric Assay. S.T. Talcott and L.R. Howard, J. Agric. Food Chem., 1999, 47 (8), pages 3237–3242, doi:10.1021/jf990288f
^ Induction of 6-Methoxymellein and Resistance to Storage Pathogens in Carrot Slices by UV-C. J. Mercier, J. Arul, R. Ponnampalam and M. Boulet, Journal of Phytopathology, Volume 137, Issue 1, pages 44–54, January 1993, doi:10.1111/j.1439-0434.1993.tb01324.x
^ Cell death, 6-methoxymellein accumulation, and induced resistance to Botrytis cinerea in carrot root slices. R. Hoffman and J.B. Heale, Physiological and Molecular Plant Pathology, Volume 30, Issue 1, January 1987, Pages 67–75, doi:10.1016/0885-5765(87)90083-X
^ Isolation and antimicrobial activity of the phytoalexin 6-methoxymellein from cultured carrot cells. Fumiya Kurosaki and Arasuke Nishi, Phytochemistry, Volume 22, Issue 3, 1983, Pages 669–672, doi:10.1016/S0031-9422(00)86959-9
^ "MetaCyc 6-methoxymellein biosynthesis". www.biocyc.org.

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