6-Hydroxymellein

6-Hydroxymellein
Chemical structure of 6-hydroxymellein
Names
Preferred IUPAC name
(3R)-6,8-Dihydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one
Other names
(R)-6-hydroxymellein
(−)-6-Hydroxymellein
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C10H10O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h3-5,11-12H,2H2,1H3
    Key: DHLPMLVSBRRUGA-UHFFFAOYSA-N
  • InChI=1/C10H10O4/c1-5-2-6-3-7(11)4-8(12)9(6)10(13)14-5/h3-5,11-12H,2H2,1H3
    Key: DHLPMLVSBRRUGA-UHFFFAOYAI
  • O=C1OC(Cc2cc(O)cc(O)c12)C
Properties
C10H10O4
Molar mass 194.18 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

6-Hydroxymellein is a dihydroisocoumarin, a phenolic compound found in carrots.[1] It has also been isolated in Aspergillus terreus and shows an inhibition of pollen development in Arabidopsis thaliana.[2]

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.[3]

References

  1. ^ Kurosaki, F.; Nishi, A. (1988). "A methyltransferase for synthesis of the phytoalexin 6-methoxymellein in carrot cells". FEBS Letters. 227 (2): 183. doi:10.1016/0014-5793(88)80894-9. S2CID 86402868.
  2. ^ Shimada, A.; Kusano, M.; Takeuchi, S.; Fujioka, S.; Inokuchi, T.; Kimura, Y. (2002). "Aspterric acid and 6-hydroxymellein, inhibitors of pollen development in Arabidopsis thaliana, produced by Aspergillus terreus". Zeitschrift für Naturforschung C. 57 (5–6): 459–464. doi:10.1515/znc-2002-5-610. PMID 12132685. S2CID 37714214.
  3. ^ 6-Hydroxymellein biosynthesis pathway on www.biocyc.org
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