Eugenitin

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	480-12-6^Y
3D model (JSmol)	Interactive image
ChemSpider	2340764^N
PubChem CID	3083581
CompTox Dashboard (EPA)	DTXSID30197376
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,1-3H3^N Key: RGTSAUBIQAKKLC-UHFFFAOYSA-N^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,1-3H3 Key: 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^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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.^[1]

Synthesis

Eugenitin has also synthethised using the Kostanecki sodium acetate-acetic anhydride cyclization of C-methylphloracetophenone in 1952^[2] and from visnagin, khellin and khellol in 1953.^[3]

See also

• Eugenin

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.