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Eugenitin

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Eugenitin
Chemical structure of eugenitin
Chemical structure of eugenitin
Names
IUPAC name 5-Hydroxy-7-methoxy-2,6-dimethylchromen-4-one
Preferred IUPAC name 5-Hydroxy-7-methoxy-2,6-dimethyl-4H-1-benzopyran-4-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H12O4/c1-6-4-8(13)11-10(16-6)5-9(15-3)7(2)12(11)14/h4-5,14H,1-3H3Key: RGTSAUBIQAKKLC-UHFFFAOYSA-N
  • InChI=1/C12H12O4/c1-6-4-8(13)11-10(16-6)5-9(15-3)7(2)12(11)14/h4-5,14H,1-3H3Key: RGTSAUBIQAKKLC-UHFFFAOYAN
SMILES
  • O=C\1c2c(O)c(c(OC)cc2O/C(=C/1)C)C
Properties
Chemical formula C12H12O4
Molar mass 220.224 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Eugenitin is a chromone derivative, a type of phenolic compound found in cloves. It has also been isolated from the fungal species Cylindrocarpon sp. C.M.I. 127996.

Synthesis

Eugenitin has also synthethised using the Kostanecki sodium acetate-acetic anhydride cyclization of C-methylphloracetophenone in 1952 and from visnagin, khellin and khellol in 1953.

See also

References

  1. Coombe, RG; Lowe, HIC; Watson, TR (1972). "Fungal metabolites. I. Chromone and naphthoquinone metabolites from a Cylindrocarponspecies". Australian Journal of Chemistry. 25 (4): 875. doi:10.1071/CH9720875.
  2. Whalley, W. B. (1952). "A New Synthesis of Eugenitin". Journal of the American Chemical Society. 74 (22): 5795–5796. doi:10.1021/ja01142a530.
  3. Schönberg, Alexander; Badran, Nasry; Starkowsky, Nicolas A. (1953). "Furo-chromones and -Coumarins. VII. Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin". Journal of the American Chemical Society. 75 (20): 4992. doi:10.1021/ja01116a032.


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