 | |
| 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
| |
| Identifiers | |
| ChemSpider | |
| ECHA InfoCard | 100.014.295 |
| E number | E120(colours) |
| Properties | |
| C44H43AlCa2O30 | |
| Molar mass | 1158.936 g·mol−1 |
| Melting point | 298–300 °C (568–572 °F; 571–573 K) |
| insoluble < pH 11 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Carmine (/ˈkɑːrmən,ˈkɑːrmaɪn/) – also calledcochineal (when it is extracted from thecochineal insect),cochineal extract,crimsonlake, orcarmine lake – is apigment of a bright-red color obtained from the aluminiumcomplex derived fromcarminic acid.[2] Specific code names for the pigment includenatural red 4,C.I. 75470, orE120.Carmine is also a general term for a particularlydeep-red color.
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The English word "carmine" is derived from the French wordcarmin (12th century), fromMedieval Latincarminium, fromPersianقرمزqirmiz ("crimson") and fromArmenian կարմիր/carmir ("red"), which both derive fromMiddle Persiancarmir ("red, crimson").[3] The Persian termcarmir is likely cognate withSanskritkrimiga ("insect-produced"), fromkrmi ("worm, insect"). The Persian word for "worm, insect" iskirm, and inIran (Persia) the red colorant carmine was extracted from the bodies of dead female insects such asKermes vermilio andcochineal.[4]: 131 The form of the term may also have been influenced in Latin byminium ("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 inyogurt,candy,gelatin,meat, and beverages including fruit juices.[6][7][8]
FemaleDactylopius coccus (cochineal) insects were used for their red coloring power as early as 700 BC. American civilizations (from the American continent) crushed the bugs present on cacti to extract the carmine they contain. Carmine pigment was extensively used by theAztec civilization to dye textiles. It was imported later to Europe during the 16th century.[9]
Red is a color often associated with power and social status. Through the centuries, red has been worn by tribal chiefs, kings and queens, and military officers.[10]
Cochineal was a major source of income for the Spanish Crown. By weight, it was a far more valuable commodity than sugar, making it especially lucrative for overseas trade. As part of thetriangular trade, its production and consumption were intertwined with slavery.[11]
In European markets, the Spanish Crown had a monopoly on cochineal until 1820 when the French learned to cultivate them. Later, German and British scientists created a synthetic red dye that competed with carmine. The combination of these factors contributed to the end of the Spanish monopoly and considerably lowered the price of carmine, making it accessible to a wider audience.[citation needed]
 | This sectionis missing information about synthetic production (claimed to exist in later passage on EU medicine use). Please expand the section to include this information. Further details may exist on thetalk page.(June 2022) |
The pigment is produced fromcarminic acid, which is extracted from somescale insects such as thecochineal scale (Prima), and certainPorphyrophora species (Armenian cochineal andPolish cochineal). Attempts have been made tofarm cochineal.
Carmine is a colorant used in the manufacture of artificial flowers, paints,crimson ink, rouge and other cosmetics, and some medications.[12]
Synthetic carminic acid is complex and expensive to produce. Therefore, natural cochineal carmine is predominant on the market. Its instability presents challenges for use in art and textiles, but this is less of a hindrance in the context of cosmetics.[13] As its synthetic production is still largely experimental, ongoing research focuses on improving the efficiency and sustainability of the synthetic pathways.[14][15]
To prepare carmine, the powdered scale insect bodies are boiled in anammonia orsodium carbonate solution. After separating the insoluble matter, the extract is treated withalum to precipitate the red solid. This precipitate is called "carmine lake" or "crimson lake". Purity of color is ensured by the absence ofiron.Stannous chloride,citric acid,borax, orgelatin 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. Forshades of purple,lime is added to the alum.[16][17]
To obtain 1 pound (0.45 kilograms) of red dye, 70,000 cochineal insects are required.[18]
Scientists can detect the presence of carminic acid through liquid chromatography and a diode array detector combined with a mass spectrometer with a quadruple-time-of-flight analyzer (LC-DAD-QTOF). The process is used for identifying carmine in works of art.[19]
Scientific methods can also distinguish among the different species of cochineal used in artworks.[citation needed]
As confirmed byreflectance spectroscopy, carmine reflects mostly red light. Itshue ranges from 497 nm for a dark purplish red and 612 nm for a vibrant red.[20]
Carmine's hue is dependent on the metallic ions present in the pigment. For instance, carmine combined with zinc or aluminum yields a crimson hue.[21]
The translucence of carmine depends on its binding medium. Mixed with oil, carmine remains translucent and adequate for glazes. Combined withtempera or glue, carmine turns opaque.[20]
On theMunsell color scale, carmine's value can range between 3.32 and 6.35.[20]
Carmine is a fugitive color, whose fading is influenced by different factors such as light, humidity, or even the color of the glass of a frame.[22]: 140–152 It is highly sensitive to light and tends to fade into brownish tones.[22]: 141–144
In painting, its durability depends on the type of binding. For instance, pigments are more stable if mixed with linseed oil rather than withgum arabic.[23]: 1 It is especially sensitive to light in watercolor.[24] Carmine can be stabilized when precipitated with alum and when combined with tin salt mordants.[25]: 698–9
Carmine was used in dyeing textiles and in painting since antiquity. Numerous examples are found among Inca remains such as textile artifacts. The Aztecs also used carmine.
In Europe, the 16th century Italian painterJacopo Tintoretto used carmine in several of his paintings, the most notable beingPortrait of Vincenzo Morosini (1575-80) andChrist Washing the Feet of the Disciples(1575-80).[26][27]
Carmine was also used by nineteenth-century artists such asVincent van Gogh inBedroom in Arles (1889). The floor of the bedroom is painted with carmine cochineal lake, geranium lake and indigo. This produced a reddish color, which over time changed to blueish.[28]
Analysis ofJ. M. W. Turner's palettes found that he used cochineal carmine.[29] The fading of this pigment affected the appearance of the sky inThe Fighting Temeraire (1839).[30]
Carmine red has been used in military cartography at least since the 17th century.Sébastien Le Prestre de Vauban, General Engineer of France, recommended the use of this red pigment to represent fortifications (ramparts, wood timbers, and brick buildings being reddish).[31]: 70–71 This made buildings more distinct on maps[32]: 104
Carmine is present in numerous cosmetics because of its red color. This use has continued from antiquity to the present.[33] It can be found in lipstick, eye shadow, nail polish. It may cause allergies.[34]
Carmine can be used inhistology, asBest's carmine to stainglycogen,mucicarmine to stain acidicmucopolysaccharides, andcarmalum to staincell nuclei. In these applications, it is applied together with amordant, usually anAl(III) salt.[citation needed]
Cochineal, the insect used to make carmine, also has medical properties that were exploited by the Aztecs.[35] It is said to help cure wounds when mixed with vinegar and applied to lesions. Aztecs used it to clean teeth.[citation needed]
In January 2006, theUnited 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.[36] 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 theCenter 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.[37][38] 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".[39]
In theEuropean Union (EU), the use of carmine in foods is regulated under theEuropean Commission's directives governing food additives in general[40][41] and food dyes in particular[42] and listed under the namesCochineal,Carminic acid,Carmines andNatural Red 4 as additive E 120 in thelist of EU-approved food additives.[43] The directive governing food dyes approves the use of carmine for certain groups of foods only[44] and specifies a maximum amount which is permitted or restricts it to thequantum satis.[citation needed]
The EU-Directive 2000/13/EC[45] 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 asFood colour carmines or asFood 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 theBritish 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, usingcalcium oxide to gauge color depth.[further explanation needed]
This article incorporates text from a publication now in thepublic domain: Chisholm, Hugh, ed. (1911). "Carmine".Encyclopædia Britannica (11th ed.). Cambridge University Press.| Aspects ofinsects in culture |
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