Mellein
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Names | |
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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 | |
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3D model (JSmol) |
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ChEBI |
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ChEMBL |
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ChemSpider |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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 |
Chemical compound
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
- ^ a b 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.
- ^ 6-methoxymellein biosynthesis pathway on www.biocyc.org
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Types of isocoumarins
- Bergenon
- Thunberginol A and B
- Hydrangenol
- Mellein
- 6-Hydroxymellein
- 6-Methoxymellein
- Monocerin
- Phyllodulcin
- Thunberginol C, D, E and G
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