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Carminic acid

Carminic acid^[1]

IUPAC name	7-α-D-Glucopyranosyl-9,10-dihydro- 3,5,6,8-tetrahydroxy-1-methyl-9,10- dioxoanthracenecarboxylic acid
Other names	Carminic acid C.I. Natural Red 4 C.I. 75470
Identifiers
CAS number	1260-17-9
SMILES	Cc1c(C(O)=O)c(O)cc2C(=O)c3c(O)c (O)c([C@H]4O[C@H](CO)[C@@H](O) [C@H](O)[C@H]4O)c(O)c3C(=O)c12
Properties
Molecular formula	C₂₂H₂₀O₁₃
Molar mass	492.38 g/mol
Density	? g/cm³
Melting point	120 °C (decomp.)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Carminic acid (C₂₂H₂₀O₁₃) is a red glucosidal hydroxyanthapurin that occurs naturally in some scale insects, such as the cochineal and the Polish cochineal. The insects produce the acid as a feeding deterrent. Carminic acid is the colouring agent in carmine. Synonyms are C.I. 75470 and C.I. Natural Red 4.

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The chemical structure of carminic acid consists of a core anthraquinone structure linked to a glucose sugar unit. Carminic acid was first synthesized by organic chemists in 1991.^[2]

References

^ Merck Index, 11th Edition, 1850.
^ Allevi, P. et al. 1991. The 1st Total Synthesis of Carminic Acid. Journal of the Chemical Society-Chemical Communications 18:1319-1320.

Bond:	O-glycosidic bond \| S-glycosidic bond \| N-glycosidic bond
Geometry:	α-Glycoside \| β-Glycoside \| 1,4-Glycoside \| 1,6-Glycoside
Glycone:	Glucoside \| Fructoside \| Glucuronide
Aglycone:	Alcoholic glycoside \| Anthraquinone glycoside \| Coumarin glycoside \| Cyanogenic glycoside \| Flavonoid glycoside \| Phenolic glycoside \| Saponin \| Cardiac glycoside \| Steviol glycoside \| Thioglycoside \| Glycosylamine \| Bufanolide \| Cardenolide