Eugenitin

Eugenitin
Names
	IUPAC name 5-hydroxy-7-methoxy-2,6-dimethylchromen-4-one
Identifiers
CAS Number	480-12-6;
3D model (JSmol)	Interactive image;
ChemSpider	2340764;
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 Key: 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,1-3H3 Key: RGTSAUBIQAKKLC-UHFFFAOYAN;
	SMILES O=C\1c2c(O)c(c(OC)cc2O/C(=C/1)C)C;
Properties
Chemical formula	C12H12O4
Molar mass	220.22 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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]

References

^ Fungal metabolites. I. Chromone and naphthoquinone metabolites from a Cylindrocarpon species. RG Coombe, HIC Lowe and TR Watson, Australian Journal of Chemistry 25(4) pp. 875-879, doi:10.1071/CH9720875
^ A New Synthesis of Eugenitin. B. Whalley, J. Am. Chem. Soc., 1952, 74 (22), pp 5795–5796, doi:10.1021/ja01142a530
^ Furo-chromones and -Coumarins. VII. Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin. Alexander Schönberg, Nasry Badran, Nicolas A. Starkowsky, J. Am. Chem. Soc., 1953, 75 (20), pp 4992–4995, doi:10.1021/ja01116a032

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[1] Fungal metabolites. I. Chromone and naphthoquinone metabolites from a Cylindrocarpon species. RG Coombe, HIC Lowe and TR Watson, Australian Journal of Chemistry 25(4) pp. 875-879, doi:10.1071/CH9720875

[2] A New Synthesis of Eugenitin. B. Whalley, J. Am. Chem. Soc., 1952, 74 (22), pp 5795–5796, doi:10.1021/ja01142a530

[3] Furo-chromones and -Coumarins. VII. Degradation of Visnagin, Khellin and Related Substances; Experiments with Chromic Acid and Hydrogen Peroxide; and a Synthesis of Eugenitin. Alexander Schönberg, Nasry Badran, Nicolas A. Starkowsky, J. Am. Chem. Soc., 1953, 75 (20), pp 4992–4995, doi:10.1021/ja01116a032

[1]

[2]

[3]

Synthesis

See also

References