Carminic acid

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Carminic acid[1]
Chemical structure of carminic acid[citation needed]
Ball-and-stick model of carminic acid[citation needed]
Names
IUPAC names
7-α-D-Glucopyranosyl-9,10-dihydro-
3,5,6,8-tetrahydroxy-1-methyl-9,10-
dioxoanthracenecarboxylic acid[citation needed]
Other names
Carminic acid
C.I. Natural Red 4
C.I. 75470
Identifiers
1260-17-9 YesY
ChEBI CHEBI:78310 N
ChEMBL ChEMBL263094 N
ChemSpider 14068 YesY
Jmol 3D model Interactive image
KEGG C11254 YesY
UNII CID8Z8N95N YesY
Properties
C22H20O13
Molar mass 492.38 g/mol
Density  ? g/cm3
Melting point 120 °C (248 °F; 393 K) (decomposes)
Acidity (pKa) 3.39, 5.78, 8.35, 10.27, 11.51[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Carminic acid (C22H20O13) is a red glucosidal hydroxyanthrapurin that occurs naturally in some scale insects, such as the cochineal, Armenian cochineal, and Polish cochineal. The insects produce the acid as a deterrent to predators. 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.[3]

References[edit]

  1. ^ Merck Index, 11th Edition, 1850.
  2. ^ Atabey, Hasan; Sari, Hayati; Al-Obaidi, Faisal N. (28 April 2012). "Protonation Equilibria of Carminic Acid and Stability Constants of Its Complexes with Some Divalent Metal Ions in Aqueous Solution". Journal of Solution Chemistry 41 (5): 793–803. doi:10.1007/s10953-012-9830-7. 
  3. ^ Allevi, P.; et al. (1991). "The First Total Synthesis of Carminic Acid". Journal of the Chemical Society-Chemical Communications 18: 1319–1320. doi:10.1039/C39910001319.