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Kermesic acid

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Kermesic acid
Names

IUPAC name 3,5,6,8-Tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid
Other names C.I. Natural Red 3 1-Methyl-2-carboxy-3,5,6,8-tetrahydroxyanthraquinone
Identifiers
CAS Number	18499-92-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:90183
ChemSpider	9901950
KEGG	C22689
PubChem CID	11727234
UNII	2A580G9V9I
CompTox Dashboard(EPA)	DTXSID40471199
InChI InChI=1S/C16H10O8/c1-4-9-5(2-6(17)10(4)16(23)24)13(20)12-11(15(9)22)7(18)3-8(19)14(12)21/h2-3,17-19,21H,1H3,(H,23,24) Key: CXORMDKZEUMQHX-UHFFFAOYSA-N
SMILES CC1=C2C(=CC(=C1C(=O)O)O)C(=O)C3=C(C2=O)C(=CC(=C3O)O)O
Properties
Chemical formula	C₁₆H₁₀O₈
Molar mass	330.248 g·mol⁻¹
Appearance	Red crystalline needles^[1]
Melting point	320 °C (608 °F; 593 K) (decomp.)^[1]
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Kermesic acid is an anthraquinone derivative and the main component of the red dyekermes (false carmine). The compound is theaglycone ofcarminic acid, the main component of truecarmine. As a dye, it is known as Natural Red 3.

Kermesic acid, like carminic acid and thelaccaic acids, is an insect dye obtained fromscale insects. Kermesic acid is found in insects of the genusKermes. It is the only colored component of the dye kermes.^[2]

The chemical structure of kermesic acid was elucidated byOtto Dimroth in 1916.^[3]^[4]

References

[edit]

^^a ^b"Kermessäure".Römpp's Chemistry Lexicon.
^Mark C. Whiting (1981). "The dyes in early oriental carpets". In Society of German Chemists (ed.).Chemistry in our time. Weinheim: Verlag Chemie GmbH. pp. 179–189. 15th year, no. 6.
^Brigl, P. (1921).Die chemische Erforschung der Naturfarbstoffe.doi:10.1007/978-3-663-05096-4.ISBN 978-3-663-03907-5.
^Dimroth, Otto; Fick, Reinhold (1916). "I. Über den Farbstoff des Kermes".Justus Liebigs Annalen der Chemie.411 (3):315–338.doi:10.1002/jlac.19164110303.

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