Carminic acid

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Carminic acid[1]
Chemical structure of carminic acid
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 hydroxyanthrapurin 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.

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]

[edit] References

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