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Chemical compound
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.
^"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.
^ abJan 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.
The insects produce the acid as a deterrent to predators. An aluminum salt of carminicacid is the coloring agent in carmine, a pigment. Natives of Peru...
aluminium complex derived from carminicacid. Specific code names for the pigment include natural red 4, C.I. 75470, or E120. Carmine is also a general term for...
the plants, and dried. The insect produces carminicacid that deters predation by other insects. Carminicacid, typically 17–24% of dried insects' weight...
guarded the secret of its production for centuries. Carminicacid, the organic compound which gives carmine its color, was synthesized in 1991. Researchers...
Kermesic acid is an anthraquinone derivative and the main component of the red dye kermes (false carmine). The compound is the aglycone of carminicacid, the...
scale insects such as carminicacid, kermesic acid, and laccaic acids. The colorant carmine with the main component carminicacid is used, for example...
the insect Kerria lacca, similar to carminicacid and kermesic acid. This article focuses primarily on laccaic acid A (LCA). The word varnish goes back...
vermilion. Carmine dyes, which give crimson and related red and purple colors, are based on an aluminium and calcium salt of carminicacid. Carmine lake is...
adult females release the bright red substance when crushed known as carminicacid. Most species belonging to this genus are covered in thin, sticky strands...
metabolites caused by its complex biosynthesis which resembles that of fatty acid synthesis. Because of this diversity, polyketides can have various medicinal...
on cactus plants. Cochineal insects produce carminicacid to deter predation by other insects. Carminicacid, which forms 17% to 24% of the weight of the...
in the cactus sap. The insect produces carminicacid, which deters predation by other insects. The carminicacid can be extracted from the insect's body...
Indigo carmine, or 5,5′-indigodisulfonic acid sodium salt, is an organic salt derived from indigo by aromatic sulfonation, which renders the compound soluble...
insects, the red coloring is derived from carminicacid with traces of kermesic acid. The Polish cochineal carminicacid content is approximately 0.6% of the...
been produced using the dye carmine, made from carminicacid extracted from the crushed bodies of the cochineal insect. Carmine was once the only bright...
predatory on Coccidae species. They feed on the eggs and young. It uses carminicacid, acquired from its prey, as a defence against its own predators. Moth...
out. Approved in the US. E111 Orange GGN Orange E120 Cochineal, Carminicacid, Carmine (Natural Red 4) Crimson Approved in the EU. Approved in the US....
scale insect Dactylopius coccus produces the brilliant red-coloured carminicacid to deter predators. Up to 100,000 scale insects need to be collected...
Carmine Falcone is a fictional supervillain in DC Comics, portrayed as a powerful mob boss, an enemy of Batman, and a friend of the Wayne family. He has...
Color Source(s) Red Insect-based colors, including: Carmine, also known as cochineal, where carminicacid from the Dactylopius coccus insect is mixed with...
and aristocrats wore scarlet clothing dyed with kermes, or carmine, made from the carminicacid in tiny female scale insects, which lived on the leaves of...
of Dactylopius opuntiae produce red glucosidal hydroxyanthrapurin (carminicacid), which occurs naturally within their body. Morphologically, all Dactylopius...
dyestuffs such as carmine (also called cochineal). The scale insect Dactylopius coccus produces the brilliant red-coloured carminicacid to deter predators...
more concentrated dye. The carmine dyestuff of Porphyrophora hamelii owes its red color almost entirely to carminicacid, making it difficult to distinguish...
C37H34N2Na2O9S3. Related dyes are C.I. acid green 3 (CAS#4680-78-8) and acid green 9 (CAS#4857-81-2). In these dyes, the 2-sulfonic acid group is replaced by H and...
soluble in alcohol. It is soluble in strong acids to form yellow solution, or in aqueous alkalis to form carmine red solutions. Due to this behaviour it can...
Global Information![Chemical structure of carminic acid[citation needed]](http://upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Carminic_acid_structure.svg/230px-Carminic_acid_structure.svg.png)
![Ball-and-stick model of carminic acid[citation needed]](http://upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Carminic-acid-3D-balls.png/240px-Carminic-acid-3D-balls.png)
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