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It:Carminic acid

From ChemWiki
Carminic Acid
Chemical structure of carminic acid
3D Structure
Chemical name 7-α-D-Glucopyranosyl-9,10-dihydro-
3,5,6,8-tetrahydroxy-1-methyl-9,10-
dioxoanthracenecarboxylic acid
Other names Carminic acid
Natural Red 4
Chemical formula C22H20O13
Colour and state Bright red, pink to magenta powder
Molecular mass 492.38 g/mol
CAS number 1260-17-9
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 the active ingredient in the food colorant cochineal.

Cochineal was first extracted by drying and crushing the female bodies of the cactus dwelling Dactylopius coccus insect. The dried cochineal contains 17-24% carminic acid which is then refined to get carmine.

Cochineal was once an extremely valuable commodity and at one point reaching higher value than that of gold. This method is still in practice, but due to the high cost and somewhat unsavoury method of extraction this colorant has now been synthesised (synthesis found below) or been replaced with other synthetic compounds. The first synthesis of the compound was published in 1991 by Pietro Allevi et al.

First Synthesis of Carminic Acid DOI: 10.1039/C39910001319

The compound is soluble in water, mineral acids, ether, alkali

Some spectroscopic data of the compound can be found by clicking links below.

IR of Carminic Acid


References

Merck Index

http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/22010

http://www.foodadditivesworld.com/carminic-acid.html

http://chemicalland21.com/lifescience/foco/CARMINIC%20ACID.htm

http://sci-toys.com/ingredients/carmine.html