COCHINEAL

CAS NUMBER: 1343-78-8

EC NUMBER: 215-724-4

MOLECULAR FORMULA: C22H20O13

MOLECULAR WEIGHT: 492.4

IUPAC NAME: 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid

The Cochineal (Dactylopius coccus) is a scale insect in the suborder Sternorrhyncha, from which the natural dye carmine is derived. 
A primarily sessile parasite native to tropical and subtropical South America through North America (Mexico and the Southwest United States), this insect lives on cacti in the genus Opuntia, feeding on plant moisture and nutrients. 
The insects are found on the pads of prickly pear cacti, collected by brushing them off the plants, and dried.

The insect produces carminic acid that deters predation by other insects. 
Carminic acid, typically 17–24% of dried insects' weight, can be extracted from the body and eggs, then mixed with aluminium or calcium salts to make carmine dye, also known as cochineal. 
Today, carmine is primarily used as a colorant in food and in lipstick (E120 or Natural Red 4).

The carmine dye was used in North America in the 15th century for coloring fabrics and became an important export good during the colonial period. 
After synthetic pigments and dyes such as alizarin were invented in the late 19th century, natural-dye production gradually diminished. 
Health fears over artificial food additives, however, have renewed the popularity of cochineal dyes, and the increased demand has made cultivation of the insect profitable again, with Peru being the largest exporter. Some towns in the Mexican state of Oaxaca are still working in handmade textiles using this cochineal.
Other species in the genus Dactylopius can be used to produce "cochineal extract", and are extremely difficult to distinguish from D. coccus, even for expert taxonomists; that scientific term from the binary nomenclature, and also the vernacular "cochineal insect", may be used (whether intentionally or casually, and whether or not with misleading effect) to refer to other biological species

Etymology:
Cochineal is derived from the French "cochenille", derived from Spanish "cochinilla", in turn derived from Latin "coccinus" meaning "scarlet-colored", or from the Latin "coccum", meaning "berry yielding scarlet dye". 
See also the related word kermes, which is the source of a similar but weaker Mediterranean dye also called crimson, which was used to color cloth red before discovery of cochineal in the New World. 
Some sources identify the Spanish source word for cochineal as cochinilla "wood louse".

History:
Cochineal dye was used by the Aztec and Maya peoples of North and Central America as early as the second century BC.
Eleven cities conquered by Montezuma in the 15th century paid a yearly tribute of 2000 decorated cotton blankets and 40 bags of cochineal dye each.
Production of cochineal is depicted in Codex Osuna. 
During the colonial period, the production of cochineal (grana fina) grew rapidly.
Produced almost exclusively in Oaxaca by indigenous producers, cochineal became Mexico's second-most valued export after silver.
Soon after the Spanish conquest of the Aztec Empire, it began to be exported to Spain, and by the 17th century was a commodity traded as far away as India.
The dyestuff was consumed throughout Europe and was so highly prized, its price was regularly quoted on the London and Amsterdam Commodity Exchanges (with the latter one beginning to record it in 1589).
In 1777, French botanist Nicolas-Joseph Thiéry de Menonville, presenting himself as a botanizing physician, smuggled the insects and pads of the Opuntia cactus to Saint Domingue. 
This particular collection failed to thrive and ultimately died out, leaving the Mexican monopoly intact.
After the Mexican War of Independence in 1810–1821, the Mexican monopoly on cochineal came to an end. 
Large-scale production of cochineal emerged, especially in Guatemala and the Canary Islands; it was also cultivated in Spain and North Africa.

Spain's conquest of a New World empire in the 16th century introduced new pigments and colors to peoples on both sides of the Atlantic. 
Carmine, a dye and pigment derived from cochineal insects in Central and South America, attained great status and value in Europe. 
Produced from harvested, dried, and crushed cochineal insects, carmine could be (and still is) used in fabric dye, food dye, body paint, or almost any kind of paint or cosmetic.

The Florentine Codex contains a variety of illustrations with multiple variations of the red pigments. Specifically in the case of achiotl (light red), technical analysis of the paint reveals multiple layers of the pigment although the layers of the pigment is not visible to the naked eye. 
Therefore, it proves that the process of applying multiple layers is more significant in comparison to the actual color itself. 
Furthermore, the process of layering the various hues of the same pigment on top of each other enabled the Aztec artists to create variations in the intensity of the subject matter. 
A bolder application of pigment draws the viewer's eye to the subject matter which commands attention and suggests a power of the viewer. 
A weaker application of pigment commands less attention and has less power. 
This would suggest that the Aztec associated the intensity of pigments with the idea of power and life.

Natives of Peru had been producing cochineal dyes for textiles since at least 700 CE, but Europeans had never seen the color before.
When the Spanish invaded the Aztec empire in what is now Mexico, they were quick to exploit the color for new trade opportunities. 
Carmine became the region's second-most-valuable export next to silver. 
Pigments produced from the cochineal insect gave the Catholic cardinals their vibrant robes and the English "Redcoats" their distinctive uniforms. 
That an insect was the true source of the pigment was kept secret until the 18th century, when biologists discovered the source.

The demand for cochineal fell sharply with the appearance on the market of alizarin crimson and many other artificial dyes discovered in Europe in the middle of the 19th century, causing a significant financial shock in Spain as a major industry almost ceased to exist.
The delicate manual labour required for the breeding of the insect could not compete with the modern methods of the new industry, and even less so with the lowering of production costs. 
The "tuna blood" dye (from the Mexican name for the Opuntia fruit) stopped being used and trade in cochineal almost totally disappeared in the course of the 20th century. 
In recent decades, the breeding of cochineal has been done mainly for the purposes of maintaining the tradition rather than to satisfy any sort of demand.
However, the product has become commercially valuable again.

Art:
Moctezuma dead in the waters of the grand canal
The carmine of antiquity (technically, crimson) also contains carminic acid, and was extracted from a similar insect, Kermes vermilio, which lives on Quercus coccifera oaks native to the Near East, and the European side of the Mediterranean Basin. 
Kermes extract was used as a dye and a laked pigment in ancient Egypt, Greece, Armenia and the Near East and is one of the oldest organic pigments.[16] Recipes for artists' use of crimson appear in many early painting and alchemical handbooks throughout the Middle Ages; the laking process for both crimson and carmine was improved in the 19th century. 
Carmine was not light-fast and was largely abandoned in art.
True carmine, when it was introduced later, saw its primary use in Europe as a dye rather than a pigment.

Spanish influence changed the way in which Aztecs used pigments, particularly in their manuscripts. For example, cochineal was replaced by Spanish dyes like minium and alizarin crimson.
The image of Moctezuma's death (seen to the right) uses both indigenous and Spanish pigments, and is therefore representative of the transition and influence between cultures

Biology:
Cochineal insects are soft-bodied, flat, oval-shaped scale insects. The females, wingless and about 5 mm (0.20 in) long, cluster on cactus pads. 
They penetrate the cactus with their beak-like mouthparts and feed on its juices, remaining immobile unless alarmed. 
After mating, the fertilised female increases in size and gives birth to tiny nymphs. 
The nymphs secrete a waxy white substance over their bodies for protection from water loss and excessive sun. 
This substance makes the cochineal insect appear white or grey from the outside, though the body of the insect and its nymphs produces the red pigment, which makes the insides of the insect look dark purple. 
Adult males can be distinguished from females in that males have wings, and are much smaller.

The cochineal disperses in the first nymph stage, called the "crawler" stage. The juveniles move to a feeding spot and produce long wax filaments. 
Later, they move to the edge of the cactus pad, where the wind catches the wax filaments and carries the insects to a new host. 
These individuals establish feeding sites on the new host and produce a new generation of cochineals.
Male nymphs feed on the cactus until they reach sexual maturity. 
At this time, they can no longer feed at all and live only long enough to fertilise the eggs.
They are, therefore, seldom observed.
In addition, females typically outnumber males due to environmental factors

Farming:
A nopal cactus farm for the production of cochineal is traditionally known as a nopalry.
The two methods of farming cochineal are traditional and controlled. 
Cochineals are farmed in the traditional method by planting infected cactus pads or infesting existing cacti with cochineals and harvesting the insects by hand. 
The controlled method uses small baskets called Zapotec nests placed on host cacti. 
The baskets contain clean, fertile females that leave the nests and settle on the cactus to await fertilization by the males. 
In both cases, the cochineals must be protected from predation, cold, and rain. 
The complete cycle lasts three months, during which time the cacti are kept at a constant temperature of 27 °C (81 °F). 
At the end of the cycle, the new cochineals are left to reproduce or are collected and dried for dye production.

To produce dye from cochineals, the insects are collected when they are around 90 days old. 
Harvesting the insects is labour-intensive, as they must be individually knocked, brushed, or picked from the cacti and placed into bags. 
The insects are gathered by small groups of collectors who sell them to local processors or exporters.

Several natural enemies can reduce the population of the insects on hosts. 
Of all the predators, insects seem to be the most important group. 
Insects and their larvae such as pyralid moths (order Lepidoptera), which destroy the cactus, and predators such as lady bugs (Coleoptera), various Diptera (such as Syrphidae and Chamaemyiidae), lacewings (Neuroptera), and ants (Hymenoptera) have been identified, as well as numerous parasitic wasps. Many birds, human-commensal rodents (especially rats) and reptiles also prey on cochineal insects. 
In regions dependent on cochineal production, pest control measures are taken seriously. 
For small-scale cultivation, manual methods of control have proved to be the safest and most effective. 
For large-scale cultivation, advanced pest control methods have to be developed, including alternative bioinsecticides or traps with pheromones

Failed farming in Australia:
Opuntia species, known commonly as prickly pears, were first brought to Australia in an attempt to start a cochineal dye industry in 1788. 
Captain Arthur Phillip collected a number of cochineal-infested plants from Brazil on his way to establish the first European settlement at Botany Bay, part of which is now Sydney, New South Wales. 
At that time, Spain and Portugal had a worldwide cochineal dye monopoly via their New World colonial sources, and the British desired a source under their own control, as the dye was important to their clothing and garment industries; it was used to color the British soldiers' red coats, for example.
The attempt was a failure in two ways: the Brazilian cochineal insects soon died off, but the cactus thrived, eventually overrunning about 100,000 sq mi (259,000 km2) of eastern Australia.
The cacti were eventually brought under control in the 1920s by the deliberate introduction of a South American moth, Cactoblastis cactorum, the larvae of which feed on the cactus.

Failed farming in Ethiopia:
The nopal pear has been traditionally eaten in parts of northern Ethiopia, where it is utilized more than cultivated. 
Carmine cochineal was introduced into northern Ethiopia early in the 2000s to be cultivated among farming communities. 
Foodsafe exported 2000 tons of dried carmine cochineal over 3 years.

A conflict of interest among communities led to closure of the cochineal business in Ethiopia, but the insect spread and became a pest. 
Cochineal infestation continued to expand after the cochineal business had ended. 
Control measures were unsuccessful and by 2014 about 16,000 hectares (62 sq mi) of cactus land had become infested with cochineal.

Dye:
Cochineal is extracted from the female cochineal insects and is treated to produce carmine, which can yield shades of red such as crimson and scarlet. 
The body of the insect is 19–22% carminic acid.
The insects are processed by immersion in hot water or exposure to sunlight, steam, or the heat of an oven. 
Each method produces a different color that results in the varied appearance of commercial cochineal. 
The insects must be dried to about 30% of their original body weight before they can be stored without decaying.
Cochineal takes about 80,000 to 100,000 insects to make one kilogram of cochineal dye.

The two principal forms of cochineal dye are cochineal extract, a coloring made from the raw dried and pulverised bodies of insects, and carmine, a more purified coloring made from the cochineal. 
To prepare carmine, the powdered insect bodies are boiled in ammonia or a sodium carbonate solution, the insoluble matter is removed by filtering, and alum is added to the clear salt solution of carminic acid to precipitate the red aluminium salt. 
Purity of color is ensured by the absence of iron. 
Stannous chloride, citric acid, borax, or gelatin may be added to regulate the formation of the precipitate. 
For shades of purple, lime is added to the alum.

As of 2005,[needs update] Peru produced 200 tons of cochineal dye per year and the Canary Islands produced 20 tons per year.
Chile and Mexico also export cochineal.
In Mexico, production and exportation of the dye has been found to lower poverty and improve female literacy.
France is believed to be the world's largest importer, and Japan and Italy also import the insect. 
Much of these imports are processed and re-exported to other developed economies.
As of 2005,[needs update] the market price of cochineal was between US$50 and 80 per kilogram, while synthetic raw food dyes are available at prices as low as $10–20 per kilogram.

Uses:
Cochineal use in histology: Carmine staining of a monogenean (parasitic worm)
Traditionally, cochineal was used for coloring fabrics. 
During the colonial period, with the introduction of sheep to Latin America, the use of cochineal increased, as it provided the most intense color and it set more firmly on woolen garments than on clothes made of materials of pre-Hispanic origin such as cotton or agave and yucca fibers. 
In general, cochineal is more successful on protein-based animal fibres (including silk) than plant-based material. 
Once the European market discovered the qualities of this product, the demand for it increased dramatically. 
By the beginning of the 17th century, it was traded internationally.
Carmine became strong competition for other colorants such as madder root, kermes, Polish cochineal, Armenian cochineal, brazilwood, and Tyrian purple, as they were used for dyeing the clothes of kings, nobles, and the clergy. 
For the past several centuries, it was the most important insect dye used in the production of hand-woven oriental rugs, almost completely displacing lac.
Cochineal was also used for painting, handicrafts, and tapestries.
Cochineal-colored wool and cotton are important materials for Mexican folk art and crafts.

Cochineal is used as a fabric and cosmetics dye and as a natural food coloring. 
Cochineal is also used in histology as a preparatory stain for the examination of tissues and carbohydrates.
In artists' paints, it has been replaced by synthetic reds and is largely unavailable for purchase due to poor lightfastness. 
Natural carmine dye used in food and cosmetics can render the product unacceptable to vegetarian or vegan consumers. 
Many Muslims consider carmine-containing food forbidden (haraam) because the dye is extracted from insects and all insects except the locust are haraam in Islam.
Jews also avoid food containing this additive, though it is not treif, and some authorities allow its use because the insect is dried and reduced to powder.

Cochineal is one of the few water-soluble colorants to resist degradation with time. 
Cochineal is one of the most light- and heat-stable and oxidation-resistant of all the natural organic colorants and is even more stable than many synthetic food colors.
The water-soluble form is used in alcoholic drinks with calcium carmine; the insoluble form is used in a wide variety of products. 
Together with ammonium carmine, they can be found in: 
-meat, 
-sausages, 
-processed poultry products (meat products cannot be colored in the United States unless they are labeled as such), 
-surimi, 
-marinades, 
-alcoholic drinks, 
-bakery products and toppings, 
-cookies, 
-desserts, 
-icings, 
-pie fillings, 
-jams, 
-preserves, 
-gelatin desserts, 
-juice beverages, 
-varieties of cheddar cheese and other dairy products, 
-sauces,
-sweets

Carmine is considered safe enough for cosmetic use in the eye area.
A significant proportion of the insoluble carmine pigment produced is used in: 
-the cosmetics industry for hair- and skin-care products, 
-lipsticks, 
-face powders, 
-rouges,
-blushes

A bright red dye and the stain carmine used in microbiology is often made from the carmine extract, too.
The pharmaceutical industry uses cochineal to color pills and ointments.

Cochineal, red dyestuff consisting of the dried, pulverized bodies of certain female scale insects, Dactylopius coccus, of the Coccidae family, cactus-eating insects native to tropical and subtropical America. 
Cochineal is used to produce scarlet, crimson, orange, and other tints and to prepare pigments such as lake and carmine (qq.v.). 
The dye was introduced into Europe from Mexico, where it had been used long before the coming of the Spaniards.

Cochineal has been replaced almost entirely by synthetic dyes, but it continues to be used principally as a colouring agent in cosmetics and beverages. 
Cochineal's dyeing power is attributed to cochinealin, or carminic acid, obtained by boiling cochineal in water. 
Cochineal also contains glyceryl myristate (a fat) and coccerin.

Cochineal, or carmine as it is commonly known, is a red insect dye that has been used for centuries to dye textiles, drugs, and cosmetics. 
In cosmetics, cochineal is used to dye lipstick, blush, and eyeshadow.
The color created from this cochineal dye is absolutely beautiful. 
Cochineal creates bright, bold and deep red colors. 
But perhaps the most stunning part of this incredible dye is where it originates. 
Cochineal red dye is actually the result of harvesting insects.

Cochineal is a red coloring material from the dried bodies of the female insect Coccus cacti and harvested from cultivated cacti. 
The raw material is obtained primarily from the Canary Islands and parts of South America. 
Boiling cochineal with mineral acid produces carmine red (ClH12O7). 
Precipitating a mixture of cochineal and alum produces a bright red pigment. 
Cochineal is used as a color additive in food, drugs and cosmetics. 
Cochineal is also used as a microscopic stain and biological marker.

Cochineal is a red colorant extracted from the dried bodies of the female insect coccus cacti. 
The coloring is carminic acid in which the water-soluble extract is. 
Cochineal precipitates at ph 3, has good stability at ph 4, and excellent stability at ph 5–8. 
Cochineal has low tinctorial strength and has excellent stability to heat and light. 
Cochineal is also stable in retorted protein systems where other food dyes are unstable. 
Cochineal is used in foods requiring red coloring.

PHYSICAL PROPERTIES:

-Molecular Weight: 492.4    

-XLogP3-AA: 0.5    

-Exact Mass: 492.09039069    

-Monoisotopic Mass: 492.09039069    

-Topological Polar Surface Area: 243 Ų    

-Heavy Atom Count: 35    

-Physical Description: Solid

-Melting Point: 136°C

-Solubility: 1.3 mg/mL

Cochineal is sourced from the female cochineal parasitic insect native to Mexico, Central and South America. 
Cochineal's origin as a red dye made from insects has spanned centuries. 
In fact, before the Spanish arrived in Mexico in the 1500s, the cochineal insect had already been in wide use as a dye by the native people of Oaxaca for centuries. 
Cochineal was the Spanish, however, that opened up the rest of the world to this incredible red insect dye, and it still remains as a choice red dye to this day.

Cochineal is a red substance that is used for colouring food.
Cochineal is the name of both an expensive crimson or carmine dye and the cochineal insect (Dactylopius coccus), from which the dye is derived. 
The cochineal insect is a scale insect in the suborder Sternorrhyncha, native to tropical and subtropical South America and Mexico.

The cochineal insect, a primarily sessile parasite, lives on cacti from the genus Opuntia, feeding on moisture and nutrients in the cacti. 
The insect produces carminic acid to deter predation by other insects. 
Carminic acid can be extracted from the insect's body and eggs to make the dye. 
Cochineal is primarily used as a food colouring and for cosmetics.

Coloring matter from the insect Coccus cacti L. 
Cochineal is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker

CHEMICAL PROEPRTIES:

-Hydrogen Bond Donor Count: 9

-Hydrogen Bond Acceptor Count: 13    

-Rotatable Bond Count: 3    

-Formal Charge: 0    

-Complexity: 864    

-Isotope Atom Count: 0    

-Defined Atom Stereocenter Count: 0    

-Undefined Atom Stereocenter Count: 5    

-Defined Bond Stereocenter Count: 0    

-Undefined Bond Stereocenter Count: 0    

-Covalently-Bonded Unit Count: 1    

-Compound Is Canonicalized: Yes

SYNONYMS:

Carmine
Cochineal
3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid
San-Ei Gen San Red 1
2-Anthracenecarboxylic acid, 7-.beta.-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-
2-Anthracenecarboxylic acid, 7-ss-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-
2-Anthracenecarboxylic acid,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-
7-Glucopyranosyl-3,4,5,8-tetrahydroxy-1-methylanthraquinone-2-carboxylic acid
1-Anthroic acid,10-dihydro-2,5,7,8-tetrahydroxy-4-methyl-9,10-dioxo-6-(2,3,4,5-tetrahydroxyhexanoy