Carmine

This article is about the pigment. For other uses, see Carmine (color) and Carmine (disambiguation).

Carmine (/ˈkɑːrmən, ˈkɑːrmaɪn/) – also called cochineal (when it is extracted from the cochineal insect), cochineal extract, crimson lake, or carmine lake – is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid.^[2] Specific code names for the pigment include natural red 4, C.I. 75470, or E120. Carmine is also a general term for a particularly deep-red color.

Carmine^[1]

Names
Systematic IUPAC name aluminum;calcium;1-methyl-3,5,6,8-tetraoxido-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylate
Other names carmine red cochineal crimson lake carmine lake
Identifiers
CAS Number	1390-65-4
ChemSpider	28296172
ECHA InfoCard	100.014.295
E number	E120 (colours)
PubChem CID	102004931
CompTox Dashboard (EPA)	DTXSID2044216
Properties
Chemical formula	C44H43AlCa2O30
Molar mass	1158.936 g·mol^−1
Melting point	298–300 °C (568–572 °F; 571–573 K)
Solubility in water	insoluble < pH 11
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Etymology

 

A cluster of Dactylopius coccus (cochineal scale) females growing in Barlovento, Canary Islands

The English word "carmine" is derived from the French word carmin (12th century), from Medieval Latin carminium, from Persian قرمز qirmiz ("crimson"), which itself derives from Middle Persian carmir ("red, crimson").^[3] The Persian term carmir is likely cognate with Sanskrit krimiga ("insect-produced"), from krmi ("worm, insect"). The Persian word for "worm, insect" is kirm, and in Iran (Persia) the red colorant carmine was extracted from the bodies of dead female insects such as Kermes vermilio and cochineal.^[4]: 131 The form of the term may also have been influenced in Latin by minium ("red lead, cinnabar"), said to be of Iberian origin. The word "carmine" has been used as a color name as early as 1799.^[5] It is a popular food color, used in yogurt, candy, gelatin, meat, and beverages including fruit juices.^[6][7][8]

Production

The pigment is produced from carminic acid, which is extracted from some scale insects such as the cochineal scale (Prima), and certain Porphyrophora species (Armenian cochineal and Polish cochineal). Carmine is a colorant used in the manufacture of artificial flowers, paints, crimson ink, rouge and other cosmetics, and some medications.^[9]

To prepare carmine, the powdered scale insect bodies are boiled in an ammonia or sodium carbonate solution. After separating the insoluble matter, the extract is treated with alum to precipitate the red solid. This precipitate is called "carmine lake" or "crimson lake". Purity of color is ensured by the absence of iron. Stannous chloride, citric acid, borax, or gelatin may be added to modify the precipitation. The traditional crimson color is affected not only by carminic acid but also by choice of its chelating metal salt ion. For shades of purple, lime is added to the alum.^[10][11]

•  

  Zapotec cochineal nests on Opuntia ficus-indica host cacti

•  

  Use of carmine as a staining agent in histology (here on a flatworm)

Properties and uses

As confirmed by reflectance spectroscopy, carmine reflects mostly red light, i.e., wavelengths longer than about 603 nm.^[12]

Carmine can be used in histology, as Best's carmine to stain glycogen, mucicarmine to stain acidic mucopolysaccharides, and carmalum to stain cell nuclei. In these applications, it is applied together with a mordant, usually an Al(III) salt.^{[citation needed]}

Carmine was used in dyeing textiles and in painting since antiquity.^[13] It is not very stable in oil paint, and its use ceased after new and better red pigments became available. Jacopo Tintoretto used carmine in several of his paintings, including Portrait of Vincenzo Morosini^[14] and Christ Washing the Feet of the Disciples.^[15]

Regulations for use in foods

 

The extract of carmine was used from the Middle Ages until the 19th century to make crimson dye. Now it is used as a coloring for yogurt and other food products

United States

In January 2006, the United States Food and Drug Administration (FDA) evaluated a proposal that would require food products containing carmine to list it by name on the ingredient label.^[16] It was also announced that the FDA will separately review the ingredient labels of prescription drugs that contain colorings derived from carmine. A request from the Center for Science in the Public Interest urging the FDA to require ingredient labels to explicitly state that carmine is derived from insects and may cause severe allergic reactions and anaphylactic shock was declined by the FDA.^[17][18] Food industries were aggressively opposed to the idea of writing "insect-based" on the label, and the FDA agreed to allow "cochineal extract" or "carmine".^[19]

European Union

In the European Union (EU), the use of carmine in foods is regulated under the European Commission's directives governing food additives in general^[20][21] and food dyes in particular^[22] and listed under the names Cochineal, Carminic acid, Carmines and Natural Red 4 as additive E 120 in the list of EU-approved food additives.^[23] The directive governing food dyes approves the use of carmine for certain groups of foods only^[24] and specifies a maximum amount which is permitted or restricts it to the quantum satis.^{[citation needed]}

The EU-Directive 2000/13/EC^[25] on food labeling mandates that carmines (like all food additives) must be included in the list of ingredients of a food product with its additive category and listed name or additive number, that is either as Food colour carmines or as Food colour E 120 in the local language(s) of the market(s) the product is sold in.^{[citation needed]}

As of January 2012^[update], EFSA has changed the way they allow use of Carmine E120 for pharmaceutical products. The EFSA had raised concerns over the increasing number of allergic reactions to carmine derived from insects (E120.360), when used within the British Pharmacopoeia. Pharmaceutical products which had previously contained insect-derived carmine, have been replaced with a synthesized version of the food colorant. Internal studies have shown that the new formulations of popular anti-nausea and weight-gain liquid medication had a significantly lower risk in terms of allergic reactions.^{[citation needed]} The new formulation is known to be of plant origin, using calcium oxide to gauge color depth.^{[further explanation needed]}

References

1. Dapson, Rw (2007-01-01). "The history, chemistry and modes of action of carmine and related dyes". Biotechnic & Histochemistry. 82 (4–5): 173–187. doi:10.1080/10520290701704188. ISSN 1052-0295. PMID 18074265.
2. Dapson, R. W.; Frank, M.; Penney, D. P.; Kiernan, J. A. (2007). "Revised procedures for the certification of carmine (C.I. 75470, Natural red 4) as a biological stain". Biotechnic & Histochemistry. 82 (1): 13–15. doi:10.1080/10520290701207364. PMID 17510809. S2CID 27643596.
3. Mackenzie, D. (1971). A Concise Pahlavi Dictionary. Oxford University Press. pp. 50–51.
4. Purinton, N., & Watters, M. (1991). A Study of the Materials Used by Medieval Persian Painters. Journal of the American Institute for Conservation, 30(2), 125-144.
5. "Online Etymology Dictionary". Etymonline.com. Retrieved 2013-10-04.
6. "Carmine Market: Global Size, Demand, Share, Trends, Analysis, Growth and Forecast 2022-2027". MarketWatch. February 1, 2022. Retrieved 29 March 2022.
7. 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.
8. Pearson, Gwen (September 10, 2015). "You Know What Makes Great Food Coloring? Bugs". Wired. Retrieved 29 March 2022.
9. Hunger, Klaus; Herbst, Willy (2000). "Pigments, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a20_371.
10. . Time Line of Fabric Information. Threads In Tyme. Archived from the original on 2004-08-23.
11. "E-numbers: E120: Carmine, Carminic acid, Cochineal". Food-Info.net. Retrieved 2013-10-04.
12. Bisulca, Christina (2008). "UV-Vis-NIR reflectance spectroscopy of red lakes in paintings" (PDF). 9th International Conference on NDT of Art. ndt.net. Retrieved 2013-06-19.
13. Schweppe, H.; Roosen-Runge, H. (1986). "Carmine – Cochineal Carmine and Kermes Carmine". In Feller, R. L. (ed.). Artists' Pigments: A Handbook of Their History and Characteristics. Vol. 1. Oxford University Press. pp. 255–298.
14. Tintoretto, Portrait of Vincenzo Morosini, at ColourLex
15. Plesters, Joyce (1980). "Tintoretto's Paintings in the National Gallery". National Gallery Technical Bulletin. 4: 32–47. JSTOR 42616257.
16. Docket No. 1998P–0724, formerly 98P–0724; RIN 0910–AF12. Listing of Color Additives Exempt From Certification; Food, Drug, and Cosmetic Labeling: Cochineal Extract and Carmine Declaration.
17. . Cspinet.org. 1998-08-24. Archived from the original on 2013-10-02. Retrieved 2013-10-04.
18. "Bug-Based Food Dye Should Be ... Exterminated, Says CSPI". Cspinet.org. 2006-05-01. Retrieved 2013-10-04.
19. "Summary of Color Additives for Use in the United States in Foods, Drugs, Cosmetics, and Medical Devices". US Food & Drug Administration. November 2017. Retrieved 10 August 2020.
20. "Food Additives in Europe". Foodlaw.rdg.ac.uk. Retrieved 2013-10-04.
21. (PDF). Archived from the original (PDF) on 2007-01-23. Retrieved 2007-01-02.{{cite web}}: CS1 maint: archived copy as title (link)
22. "European Parliament and Council Directive 94/36/EC of 30 June 1994 on colours for use in foodstuffs" (PDF). Food Safety authority of Ireland. Retrieved 2013-10-04.
23. "Food Standards Agency - Current EU approved additives and their E Numbers". Food.gov.uk. 2012-03-14. Retrieved 2013-10-04.
24. a list of approved uses is included in Annexes I and III of EU-Directive 94/36 [1]
25. (PDF). Archived from the original (PDF) on 2006-12-08. Retrieved 2007-01-02.{{cite web}}: CS1 maint: archived copy as title (link)

Attribution

•   This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). "Carmine". Encyclopædia Britannica (11th ed.). Cambridge University Press.

See also

• Red pigments

Further reading

• Dutton, LaVerne M. Cochineal: A Bright Red Animal Dye (Master's degree). Baylor University. Retrieved November 13, 2010.
• Greenfield, Amy Butler (2005). A Perfect Red: Empire, Espionage, and the Quest for the Color of Desire. New York: HarperCollins. ISBN 978-0-06-052275-9.

External links

 

Wikimedia Commons has media related to Carmine (dye).

• Carmine as pigment in painting, at ColourLex