Back کارمینیک اسید AZB Karminsäure German Ácido carmínico Spanish Azido karminiko Basque کارمینیک اسید Persian Karmiinihappo Finnish Acide carminique French Aigéad cairmíneach Irish Ácido carmínico Galician कार्मिनिक अम्ल Hindi

Carminic acid

Carminic acid[1]
Chemical structure of carminic acid[citation needed]
Ball-and-stick model of carminic acid[citation needed]
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.013.658 Edit this at Wikidata
EC Number
  • 215-023-3
E number E120 (colours)
KEGG
UNII
  • 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 checkY
    Key: DGQLVPJVXFOQEV-NGOCYOHBSA-N checkY
  • 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
  • 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
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 checkY☒N ?)

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]

Female Dactylopius coccus on prickly pear cactus photographed by Frank Vincentz.
  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.
  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.
  4. ^ 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.
  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. Bibcode:1987AcCrC..43.1541I. doi:10.1107/S0108270187091169.
  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.
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