Mellein

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
CAS Number	480-33-1
ChEBI	CHEBI:38760
ChEMBL	ChEMBL226090
ChemSpider	26529
Jmol interactive 3D	Image
PubChem	28516
InChI 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
SMILES CC1CC2=C(C(=CC=C2)O)C(=O)O1
Properties
Chemical formula	C₁₀H₁₀O₃
Molar mass	178.18 g/mol
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 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 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. PMC 380508. PMID 5064985.
↑ 6-methoxymellein biosynthesis pathway on www.biocyc.org

Types of isocoumarins

Aglycones	Bergenon Thunberginol A and B

Dihydroisocoumarins	Hydrangenol Mellein 6-Hydroxymellein 6-Methoxymellein Monocerin Phyllodulcin Thunberginol C, D, E and G

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