Carminic acid

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
	Systematic IUPAC name 3,5,6,8-Tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:78310 ;
ChEMBL	ChEMBL263094 ;
ChemSpider	14068 ;
ECHA InfoCard	100.013.658
EC Number	215-023-3;
E number	E120 (colours)
KEGG	C11254 ;
PubChem CID	14749;
UNII	CID8Z8N95N ;
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 Key: DGQLVPJVXFOQEV-NGOCYOHBSA-N ; 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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.^[3] An aluminum salt of carminic acid is the coloring agent in carmine, a pigment.^[4] Natives of Peru had been producing cochineal dyes for textiles since at least 700 CE.^[4] Synonyms are C.I. 75470 and C.I. Natural Red 4.^[5]

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.^[6]^[7] In 2018, researchers genetically engineered the microbe Aspergillus nidulans to produce carminic acid.^[8]

It was previously thought that it contains α-D-glucopyranosyl residue, which was later redetermined to be the β-D-glucopyranosyl anomer.^[9]

^ "Carminic Acid". The Merck Index. Royal Society of Chemistry. 2013.
^ 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.
^ Eisner, T.; Nowicki, S.; Goetz, M.; Meinwald, J. (1980). "Red Cochineal Dye (Carminic Acid): Its Role in Nature". Science. 208 (4447): 1039–1042. Bibcode:1980Sci...208.1039E. doi:10.1126/science.208.4447.1039. ISSN 0036-8075. PMID 17779027. S2CID 40209712.
^ ^a ^b 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. 31 (2). The American Institute for Conservation of Historic &: 237–255. doi:10.2307/3179495. JSTOR 3179495.
^ "Approved additives and E numbers". Food Standards Agency. Retrieved 2021-03-12.
^ 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.
^ 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.
^ Miller, Brittney J. (25 March 2022). "Cochineal, a red dye from bugs, moves to the lab". Knowable Magazine. doi:10.1146/knowable-032522-1. Retrieved 28 March 2022.
^ 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.

[merck11-1] "Carminic Acid". The Merck Index. Royal Society of Chemistry. 2013.

[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.

[Eisner-1980c-3] Eisner, T.; Nowicki, S.; Goetz, M.; Meinwald, J. (1980). "Red Cochineal Dye (Carminic Acid): Its Role in Nature". Science. 208 (4447): 1039–1042. Bibcode:1980Sci...208.1039E. doi:10.1126/science.208.4447.1039. ISSN 0036-8075. PMID 17779027. S2CID 40209712.

[Wouters-1992-4] 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. 31 (2). The American Institute for Conservation of Historic &: 237–255. doi:10.2307/3179495. JSTOR 3179495.

[5] "Approved additives and E numbers". Food Standards Agency. Retrieved 2021-03-12.

[6] 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.

[7] 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.

[Miller-8] Miller, Brittney J. (25 March 2022). "Cochineal, a red dye from bugs, moves to the lab". Knowable Magazine. doi:10.1146/knowable-032522-1. Retrieved 28 March 2022.

[9] 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

Names


IUPAC name 7-(β-D-Glucopyranosyl)-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid
Systematic IUPAC name 3,5,6,8-Tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-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 (pK_a)	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