Mellein
Chemical structure of mellein
Names
IUPAC name
8-Hydroxy-3-methyl-3,4-dihydroisochromen-1-one
Other names
(−)-Mellein
(R)-(−)-Mellein
Ochracin
3,4-Dihydro-8-hydroxy-3-methyl-1H-2-benzopyran-1-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C10H10O3/c1-6-5-7-3-2-4-8(11)9(7)10(12)13-6/h2-4,6,11H,5H2,1H3
    Key: KWILGNNWGSNMPA-UHFFFAOYSA-N
  • CC1CC2=C(C(=CC=C2)O)C(=O)O1
Properties
C10H10O3
Molar mass 178.187 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mellein is a dihydroisocoumarin, a phenolic compound produced by the mold species Aspergillus ochraceus.[1]

Derivatives

4-Hydroxymellein is also produced by Aspergillus ochraceus.[1]

6-Hydroxymellein, together with S-adenosyl methionine, is a substrate of the enzyme 6-hydroxymellein O-methyltransferase to form 6-methoxymellein and S-adenosylhomocysteine in Apiaceae.[2] 6-Methoxymellein is one of the compounds responsible for bitterness in carrots.

References

  1. 1 2 Moore, J. H.; Davis, N. D.; Diener, U. L. (1972). "Mellein and 4-hydroxymellein production by Aspergillus ochraceus Wilhelm". Applied Microbiology. 23 (6): 1067–1072. doi:10.1128/AEM.23.6.1067-1072.1972. PMC 380508. PMID 5064985.
  2. ↑ 6-methoxymellein biosynthesis pathway on www.biocyc.org


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