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Carminic acid

From Wikipedia, the free encyclopedia

Carminic acid[1]
Chemical structure of carminic acid
Chemical 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
Chemical formula C22H20O13
Molecular mass 492.38 g/mol
CAS number [1260-17-9]
Density  ? g/cm3
Melting point 120 °C (decomp.)
SMILES O=C1C4=C(C(C)=C(C(O)=O)C(O)=C4)
C(C2=C1C(O)=C(O)[C@@]([C@@H]3[C@H](O)
[C@@H](O)[C@H](O)[C@@H](CO)O3)=C2O)=O
Disclaimer and references

Carminic acid (C22H20O13) is a red glucosidal hydroxyanthapurin that occurs naturally in the cochineal insect. The insect produces 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 anthroquinone 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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