Carminic acid

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. An aluminum salt of carminic acid is the coloring agent in carmine, a pigment. Natives of Peru had been producing cochineal dyes for textiles since at least 700 CE.[3] Synonyms are C.I. 75470 and C.I. Natural Red 4.

Carminic acid[1]

Names
IUPAC name 7-(β-D-Glucopyranosyl)-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Other names Carminic acid C.I. Natural Red 4 C.I. 75470 CI 75470
Identifiers
CAS Number	1260-17-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:78310^N
ChEMBL	ChEMBL263094^N
ChemSpider	14068^Y
ECHA InfoCard	100.013.658
EC Number	215-023-3
E number	E120 (colours)
KEGG	C11254^Y
PubChem CID	14749
UNII	CID8Z8N95N^Y
CompTox Dashboard (EPA)	DTXSID9022817
InChI InChI=1S/C22H20O13/c1-4-8-5(2-6(24)9(4)22(33)34)13(25)10-11(15(8)27)16(28)12(18(30)17(10)29)21-20(32)19(31)14(26)7(3-23)35-21/h2,7,14,19-21,23-24,26,28-32H,3H2,1H3,(H,33,34)/t7-,14-,19+,20-,21-/m1/s1^Y Key: DGQLVPJVXFOQEV-NGOCYOHBSA-N^Y InChI=1/C22H20O13/c1-4-8-5(2-6(24)9(4)22(33)34)13(25)10-11(15(8)27)16(28)12(18(30)17(10)29)21-20(32)19(31)14(26)7(3-23)35-21/h2,7,14,19-21,23-24,26,28-32H,3H2,1H3,(H,33,34)/t7-,14-,19+,20-,21-/m1/s1 Key: DGQLVPJVXFOQEV-NGOCYOHBBS
SMILES O=C(O)c2c(c3C(=O)c1c(O)c(c(O)c(O)c1C(=O)c3cc2O)[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)CO)C
Properties
Chemical formula	C22H20O13
Molar mass	492.38 g/mol
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 ^YN ?)
Infobox references

The chemical structure of carminic acid consists of a core anthraquinone structure linked to a glucose sugar unit. Carminic acid was first synthesized in the laboratory by organic chemists in 1991.[4][5]

It was previously thought that it contains α-D-glucopyranosyl residue,[1] which was later redetermined to be the β-D-glucopyranosyl anomer.[6]

References

1. Merck Index, 11th Edition, 1989, 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. S2CID 95406643.
3. Jan Wouters, Noemi Rosario-Chirinos (1992). "Dye Analysis of Pre-Columbian Peruvian Textiles with High-Performance Liquid Chromatography and Diode-Array Detection". Journal of the American Institute for Conservation. The American Institute for Conservation of Historic &. 31 (2): 237–255. doi:10.2307/3179495. JSTOR 3179495.
4. Allevi, P.; et al. (1991). "The First Total Synthesis of Carminic Acid". Journal of the Chemical Society, Chemical Communications. 18 (18): 1319–1320. doi:10.1039/C39910001319.
5. Ishida, T.; Inoue, M.; Baba, K.; Kozawa, M.; Inoue, K.; Inouye, H. (1987). "Absolute configuration and structure of carminic acid existing as the potassium salt in Dactylopius cacti L". Acta Crystallographica Section C Crystal Structure Communications. 43 (8): 1541–1544. doi:10.1107/S0108270187091169.
6. Fiecchi, Alberto; Galli, Mario Anastasia Giovanni; Gariboldi, Pierluigi (1981-03-01). "Assignment of the β configuration to the C-glycosyl bond in carminic acid". The Journal of Organic Chemistry. 46 (7): 1511. doi:10.1021/jo00320a061. ISSN 0022-3263.