CARMINIC ACİD

Carminic Acid is used for staining nuclei in histological sections.
Carminic Acid is used to prepare staining solutions.
Carminic Acid is used meat products, beverages, liqueurs, candies, dairy products, juices, jellies, cosmetics, pharmaceutical products, among others.

CAS Number: 1260-17-9
EC Number: 215-724-4
MDL Number: MFCD00167028
Molecular Formula: C₂₂H₂₀O₁₃
Molecular Weight: 492.39 g/mol

SYNONYMS:
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: ,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, Carminic acid, C.I. Natural Red 4, C.I. 75470, CI 75470, CARMINIC ACID, 1260-17-9, Natural red 4, Cochineal tincture, Sun Red No. 1, Sanred 1, CI Natural Red 4, Sun Red 1, San-Ei Gen San Red 1, C.I. Natural red 4, 2-Anthracenecarboxylic acid, 7-beta-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-, E 120 (dye), CI 75470, E 120, CID8Z8N95N, DTXSID9022817, C.I. 75470, E120, DTXCID902817, E-120, CHEBI:78310, INS-120, NSC-6196, NSC-326224, 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]anthracene-2-carboxylic acid, CI-(1975)-NO.75470, 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)anthracene-2-carboxylic acid, RefChem:918083, 2-Anthracenecarboxylic Acid, 7-Beta-D-Glucopyranosyl-9,10-Dihydro-, 215-023-3, Coccinellin, Carminic acid (E120), 3,5,6,8-Tetrahydroxy-1-methyl-9,10-dioxo-7-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-9,10-dihydroanthracene-2-carboxylic acid, MFCD00167028, carminate, CARMINIC ACID (NATURAL DYE), Carminic Acid, >70%, C22H20O13, DSSTox_CID_2817, DSSTox_RID_81084, DSSTox_GSID_45735, Carmine Red, (1S)-1,5-anhydro-1-(7-carboxy-1,3,4,6-tetrahydroxy-8-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-D-glucitol, CAS-1260-17-9, CAS-1343-78-8, CCRIS 1397, HSDB 912, CARMINE (ALUM LAKE), COCHINEAL RED PWD, NSC 6196, EINECS 215-023-3, UNII-CID8Z8N95N, NSC 326224, AI3-18242, NCGC00091708-04, 2-Anthracenecarboxylic acid, 7-.beta.-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-, 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, Cochineal Carmine Powder, Carminic Acid Natural dye, CI-NATURAL RED 4, CARMINIC ACID [MI], 2-Anthroic acid, 7-D-glucopyrosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-, 7-D-Glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthroic acid, CARMINE 5297, NATURAL RED 2180, CARMINIC ACID [HSDB], 7beta-D-Glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, MLS002472940, Carmine component carminic acid, Carminic acid, puriss., 95%, CHEMBL263094, orb1297117, SCHEMBL1808534, SCHEMBL29388396, SCHEMBL29664249, SCHEMBL30287626, MSK2433, Carminic acid, analytical standard, HMS2205G17, HY-N8407, Tox21_111163, Tox21_201979, Tox21_300294, AKOS015894273, Tox21_111163_1, MC30619, NCGC00247988-01, NCGC00247988-02, NCGC00247988-03, NCGC00254004-01, NCGC00259528-01, 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid, AS-76171, BP-41794, SMR001397048, CS-0144108, D89264, 10.14272/DGQLVPJVXFOQEV-JNVSTXMASA-N.1, Q416860, doi:10.14272/DGQLVPJVXFOQEV-JNVSTXMASA-N.1, Carminic acid, primary pharmaceutical reference standard, Carminic acid (E120) 100 microg/mL in Acetonitrile:Methanol, 2-Anthracenecarboxylic acid, 7-|A-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-, 3,5,6,8-Tetrahydroxy-1-methyl-9,10-dioxo-7-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-9,10-dihydroanthracene-2-carboxylicacid, 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]anthracene-2-carboxylic acid, 7- b- D- Glucopyranosyl- 9, 10- dihydro- 3, 5, 6, 8- tetrahydroxy- 1- methyl- 9, 10- dioxo-2- anthracenecarboxylic acid, 7-Carboxy-4,6-dihydroxy-8-methyl-9,10-dioxo-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-1,3-diolate, 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid, -anhydro-1-(7-carboxy-1,3,4,6-tetrahydroxy-8-methyl-9,10-dioxo-9,10-dihydro-2-anthracenyl)-D-glucitol, (1R)-1,5-anhydro-1-(7-carboxy-1,3,4,6-tetrahydroxy-8-methyl-9,10-dioxo-9,10-dihydroanthracen-2-yl)-D-glucitol, 2-anthroic acid, 7-D-glucopyrosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-, c.i. 75470, carmine acid, ci 75470, CI natural red 4, cochineal extract, D-glucitol, 1,5-anhydro-1-C-(7-carboxy-9,10-dihydro-1,3,4,6-tetrahydroxy-8-methyl-9,10-dioxo-2-anthracenyl)-, (1R)-, 7-a-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, 7beta-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthracenecarboxylic acid, 7-D-glucopyranosyl-9,10-dihydro-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-2-anthroic acid, natural red 4, sun red 1, sun red no. 1, 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acid, 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-9,10-dihydro-2-anthracenecarboxylic acid, 7-[(5S,2R,3R,4R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrahydropyran-2-yl)]-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid, CI 75470, coccinic acid, E120, CARMINE RED, CARMINE ALUMINUM LAKE, Carminic, NSC 326224, CARMINE 2G, CARMINE 40, Karminsure, carminic acid cochineal extract san-ei gen san red 1 coccinellin sun red 1 carmine stain C.I. natural red 4 sanred 1 sun red no. 1 CI natural red 4, Carminic acid, Cochineal acid, Natural Red 4 (component), CI 75470 (component), E120 (component), Carmine acid, Dactylopius coccus extract (active component), C.I. Natural Red 4 acid form

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 Carminic Acid as a deterrent to predators.
An aluminum salt of carminic acid is the coloring agent in carmine, a pigment.

Natives of Peru had been producing cochineal dyes for textiles since at least 700 CE.
Synonyms of Carminic Acid are C.I. 75470 and C.I. Natural Red 4.
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.
In 2018, researchers genetically engineered the microbe Aspergillus nidulans to produce carminic acid.
Carminic Acid was previously thought that it contains α-D-glucopyranosyl residue, which was later redetermined to be the β-D-glucopyranosyl anomer

Carminic Acid is a tetrahydroxyanthraquinone that is that is 1,3,4,6-tetrahydroxy-9,10-anthraquinone substituted by a methyl group at position 8, a carboxy group at position 7 and a 1,5-anhydro-D-glucitol moiety at position 2 via a C-gly osidic linkage.
Carminic Acid is a natural dye isolated from several insects such as Dactylopius coccus.

Carminic Acid is a dark purplish-brown mass or bright red or dark red powder.
Carminic Acid is soluble in water.
Carminic acid is a natural anthraquinone glycoside responsible for the characteristic red color of cochineal-derived pigments.

Carminic Acid is extracted from the dried bodies of the female Dactylopius coccus insect.
As the principal chromophore in carmine, carminic acid has been widely used historically and continues to be important in modern applications where natural colorants are preferred over synthetic dyes.
Carminic acid appears as dark purplish-brown mass or bright red or dark red powder.

Carminic Acid darkens at 248 °F.
Carminic Acid is a deep red color in water.
Carminic Acid is yellow to violet in acidic aqueous solutions.

Carminic acid is a tetrahydroxyanthraquinone that is that is 1,3,4,6-tetrahydroxy-9,10-anthraquinone substituted by a methyl group at position 8, a carboxy group at position 7 and a 1,5-anhydro-D-glucitol moiety at position 2 via a C-glycosidic linkage.
Carminic Acid is a natural dye isolated from several insects such as Dactylopius coccus.

Carminic Acid has a role as an animal metabolite and a histological dye.
Carminic Acid is a C-glycosyl compound, a monocarboxylic acid and a tetrahydroxyanthraquinone.
Carminic Acid is a conjugate acid of a carminate(2-).

Carminic acid is a naturally occurring organic molecule whose structure consists of 9,10-anthraquinone-2-carboxylic acid “decorated” with a methyl group, a glucopyranose, and four hydroxyls.
Carminic Acid is found in several species of scale insects known as cochineals, including Dactylopius coccus (Western Hemisphere), Porphyrophora hamelii (Armenia), and Porphyrophora polonica (north-central Europe).
In 1894, noted British dye chemist Henry Edward Schunk, working in Germany, isolated carminic acid from cochineals.

German chemist Otto Dimroth reported Carminic Acid's structure in 1920; and Indian chemists S. B. Bhatia and K. Venkataraman corrected the placement of the carboxyl group in Dimro
Carminic acid is a natural pigment derived from the cochineal insect, widely recognized for its vibrant red color.
Carminic Acid is primarily used in the food and cosmetic industries as a colorant, offering a safe and effective alternative to synthetic dyes.

Its unique properties allow Carminic Acid to impart a rich hue to a variety of products, including beverages, dairy items, and confectionery, while also being utilized in cosmetics and personal care formulations.
Carminic acid is valued not only for its aesthetic appeal but also for its stability and compatibility with various formulations, making it a preferred choice among manufacturers seeking to enhance product quality and consumer appeal.

Carminic acid, the well-known red dyestuff from cochineal insects (Dactylopius spp.), is a potent feeding deterrent to ants.
Carminic acid is an antioxidant to protect erythrocytes and DNA against radical-induced oxidation, it also has antitumor activity.
Carminic acid is a natural pigment, which is a red dye obtained from the cochineal insect, Dactylopius coccus.

Carminic Acid is extracted through the processing of these insects, which are primarily harvested from cacti.
The mode of action of carminic acid involves its ability to bind with proteins and metal ions, creating a stable colorant that is resistant to heat and light.
This stability makes Carminic Acid particularly valuable in applications requiring long-lasting pigmentation.

Carminic acid (C22H20O13) is a red glucosidal hydroxyanthrapurin that occurs naturally in some scale insects, such as the cochineal, Armenian cochineal, and Polish cochineal, which the insects produce as a deterrent to predators.
An aluminum salt of carminic acid is the coloring agent in carmine, a pigment.

USES and APPLICATIONS of CARMINIC ACİD:
Main applications of Carminic Acid: meat products, beverages, liqueurs, candies, dairy products, juices, jellies, cosmetics, pharmaceutical products, among others.
A red glucosidal hydroxyanthrapurin, Carminic Acid is produced naturally within some insects as a defense mechanism.
Carminic Acid is used for staining nuclei in histological sections.

Carminic Acid is used to prepare staining solutions.
Uses of Carminic Acid: antineoplastic, glucosyltransferase inhibitor
Cochineal insects use carminic acid to repel other insects.

But for centuries, cochineals have been valuable to humans for providing carminic acid to use on its own or to make cochineal dyes.
When carminic acid is treated with with aluminum and/or calcium salts, it forms complexes that are familiarly called carmine, carmine lake, crimson lake, or even the eponymous cochineal1.
Carminic Acid is used for textiles and as a US Food and Drug Administration–approved food, cosmetic, and drug colorant, although some people exhibit allergic reactions to it.

Free carminic acid has been used as a bacteriological stain, an ingredient for artists’ paints, and a pigment for inks.
In its cochineal dye form, you can even use Carminic Acid to make your own colored paper for cards and envelopes for Valentine’s Day!
In addition to its coloring properties, carminic acid exhibits potential applications in the pharmaceutical industry, where it can be used as a natural dye in drug formulations.

Its biocompatibility and low toxicity profile make Carminic Acid suitable for use in health-related products.
Researchers are also exploring Carminic Acid's antioxidant properties, which could offer additional benefits in various applications.
With its natural origin and versatility, carminic acid stands out as a valuable ingredient for industries aiming to meet the growing demand for natural and sustainable products.

Carminic acid is extensively used in the food and cosmetic industries due to its vibrant red hue and the fact that it is considered a natural additive.
In the food industry, Carminic Acid is commonly used to color products such as beverages, confectionery, and dairy items.
In cosmetics, Carminic Acid provides coloration for products like lipsticks and blushes.

Additionally, Carminic Acid is employed in the pharmaceutical industry as a coloring agent for medicines.
Its natural origin and safety profile when used as a colorant make Carminic Acid a versatile and widely used compound in various scientific and industrial applications.

Carminic acid is a widely used and orally active natural red pigment that can be used in industries such as food, cosmetics, and pharmaceuticals.
In addition, carminic acid has anti-inflammatory and antioxidant activities.

-Use of Carminic Acid as a deterrent:
For many scaled insects of the genus Dactylopius, carminic acid, thoroughly documented by Thomas Eisner, has been shown to be a highly potent feeding deterrent against ants.
In Eisner's 1980 paper, he notes that the red colour of the carminic acid released when the cochineals are crushed could also be a visual aposematic deterrent for predators as well.

However, he notes that tests have not been done on vertebrates to provide any support to that theory.
In the same paper however, Eisner mentions that cochineals were bitter when tasted by humans
Like other compounds housed in various plants, predators which are able to overcome the deterrent are able to sequester carminic acid in their flesh and utilize the deterrent for their own defense.

The pyralid moth larva (Laetilia coccidivora) is one such predator which feeds on cochineals, sequestering their prey's carminic acid in their own body for defense against predators.
The ability to sequester carminic acid has also been seen in several other larval bearing species (Hyperaspis, Leucopis, etc.).
Eisner remarks that the ability to sequester the compound likely arose due to ants being a common predator amongst larvae.

HOW IS CARMINIC ACID COMMERCIALLY USED NOWADAYS?
Carminic acid is a pH-dependent molecule.
This means that depending on the pH there are several forms of the molecule possible based on whether it is deprotonated or protonated.
Across the pH range, Carminic Acid contains five removable protons.

These include the carboxylic acid proton in position 1, in addition to four hydroxyl protons in positions 2, 3, 4, and 5.
This can cause significant colour variations.
For example, in acidic solutions, Carminic Acid appears orange, whereas, in basic conditions, it appears violet.

Such variations are not desirable, especially in commercial settings where consistency is key.
Well, to lock in carminic acid’s colour, it is usually complexed with aluminium and calcium to produce carmine; an intensely red and stable precipitate.
Carmine consists of two carminic acid molecules bridged by an aluminium metal, in addition to surrounding calcium.

Specifically, the carminic acid molecules behave as bidentate ligands, donating electrons to the metal to form a stable coordination complex.
This chelation results in carmine being less prone to colour changes and ensures a consistent red colour between pH 4-10.
This is in comparison to carminic acid which only maintains a persistent red colour between pH 4-7.

CAN CARMINIC ACID HELP IN FOOD PRESERVATION?
Carminic acid is a naturally occurring red pigment extracted from the cochineal insect (Dactylopius coccus).
For centuries, Carminic Acid has been used as a food colorant, especially in the form of E120 carmine, valued for its rich tone and stability in various formulations.
But in a new twist, researchers have uncovered an entirely different application: using carminic acid as an indicator of freshness in cheese packaging.
This innovation could mark a turning point in the way food manufacturers and consumers assess spoilage and ensure safety.

Carmine and Carminic acid are the most reliable natural coloring obtained from the cochineal.
Carminic Acid is obtained as a liquid and powder form.
Our carmines are soluble in water, alcohol and dispersible in oil, with several shades of red, yellow and blue.
The carminic acid is water soluble at high concentration, obtaining products resistant to the acid pH.

PROPERTIES of CARMINIC ACİD:
CHEMICAL
Carminic acid turns dark when heated close to its decomposition point.

PHYSICAL
Carminic acid is a dark red powder, though its shade varies on multiple factors.
Aqueous solutions are deep red in color, while acidic solutions tend to be yellow or violet.
Carminic Acid is only slightly soluble in cold water, and a bit more soluble in hot water.

AVAILABILITY of CARMINIC ACİD:
Carminic acid can be extracted from the female members of the scale insects, such as the cochineal, Armenian cochineal, and Polish cochineal.
Carminic Acid is purified by removing the insect bits, and washed.
Lastly, Carminic Acid can be bought from chemical suppliers.

PREPARATION of CARMINIC ACİD:
Synthesis of Carminic Acid is complicated and expensive, and it's just cheaper to extract it from insects.
However, this requires one to know how to grow and harvest the cochineal insects first, before doing any chemical extraction

HARVESTING FROM COCHINEALS:
Carminic acid is commonly harvested from an American species scaled insects called Dactylopius coccus (or cochineals).
Cochineals are parasitic scaled insects which are abundantly found on their host plants, the prickly pear cactus native to Mexico and South America.
The insects are either cultivated or harvested from wild populations, mainly for the wingless females of the species which attach themselves to the cactus and outnumber the winged males of the species two hundred to one.

Classically, cultivated species were grown from eggs placed by workers onto the cactus leaves and left to grow.
There the female cochineals would remain immobile for about 3 months until being brushed off, collected, and dried for shipping.
Females possess concentrations of about 1.5% bodyweight of carminic acid and newborns about 3.0%.
The carminic acid is then extracted by soaking the dried cochineals in water, and additives are then added to alter dye colour and enable the dye to adhere to objects.

CHEMICAL PROPERTIES of CARMINIC ACİD:
Carminic Acid is a red to dark red crystalline powder
Cochineal extract is a concentrated solution obtained after removing alcohol from an aqueous–alcoholic extract of cochineal (Dactylopius coccus Costa, also called Coccus cati L.).
This extract is used as a color additive, the primary colorant being carminic acid.

HISTORY of CARMINIC ACİD:
Carminic Acid is a red dye occurring as a glycoside in the body of the cochineal insect Dactylopius coccus of the order Homoptera, family Coccidae.
This insect is native to Central and South America.
The Aztecs had extracted the dye from the insect centuries before the coming of the Spaniards.

For breeding purposes, the insects were collected in the autumn and carefully protected during the winter months.
Cochineal was harvested after three months, and then the bugs were killed by immersion in hot water, by placing in hot ovens, or by exposure to the hot sun.
The latter method produced the highest quality dye.

At present, Peru and the Canary Islands are the main source of the dye.
Until the advent of synthetic dyes, the principal use for carminic acid was for dyeing tin-mordanted wool or silk.
Carminic Acid's aluminum lake, carmine, finds use in the coloring of foods.

BIOSYNTHESIS OF CARMINIC ACID:
Carminic acid is a polyketide secondary metabolite produced by the scale insect Dacylopius coccus.
In terms of its biosynthetic origin, the structure of carminic acid was speculated to be either from type ll polyketide or shikimate pathways.
This claim was not disputed until a key intermediate exclusive to the polyketide pathway was isolated.

Until then, a detailed biosynthetic mechanism had not been formally proposed.
The biosynthesis of carminic acid can be divided into three stages.
The initiation stage involves transferases that load acetyl (AT) and malonyl-CoA (MCAT) to the acyl carrier protein (ACP) forming acetyl and malonyl-ACP, respectively.

The acetyl-ACP acts as a priming unit for the decarboxylative condensation with malonyl-CoA catalyzed by a ketoacyl synthase (KS) protein.
The resulting acetoacetyl ACP is the simplest polyketide produced by this pathway, and it is subsequently condensed with six more malonyl-ACP units before cyclizing.
The elongation stage consists of the repeated decarboxylative condensation by a ketoacyl synthase/chain length factor heterodimer that monitors the length of the growing polyketide.

The resulting octaketide is then aromatized by a cyclase domain which catalyzes an aldol-like cyclization reaction resulting in the formation of a flavokermesic acid anthrone (FKA).
In any polyketide-based pathway, flavokermesic acid anthrone is the first cyclic intermediate.
It was the successful isolation and characterization of FKA in wild type coccids that strengthened the evidence of a polyketide mediated biosynthetic pathway.

The reactions that follow the formation of FKA consist of the aromatization and functionalization stages.
FKA is subjected to two rounds of hydroxylation catalyzed by two distinct P450 monooxygenases forming flavokermesic acid and kermesic acid, respectively.
Whether these monooxygenases are oxygen or flavin dependent is to be determined.

The first monooxygenation occurs in the central aromatic ring carbon, C10 while the second occurs in the C4 position.
The final attachment of a carbohydrate onto the C2 position C-glycosylation reaction is catalyzed by a UDP-glucose dependent membrane bound glucosyltransferase.
The order of the last two steps has not been determined due to lack of experimental kinetic data.

REACTIVITY PROFILE of CARMINIC ACİD:
Carminic Acid neutralizes bases in exothermic reactions.
Carminic Acid is incompatible with strong oxidizing agents.

PURIFICATION METHODS of CARMINIC ACİD:
Carminic acid forms red prisms from EtOH.
Carminic Acid gives a red colour in Ac2O and yellow to violet in acidic solution.
UV: max (H2O) 500nm ( 6,800); (0.02N HCl) 490-500nm ( 5,800) and (0.0001N NaOH) 540nm ( 3,450).
IR: max (Nujol) 1708s, 1693s, 1677m, 1648m, 1632m, 1606s, 1566s, 1509 cm-1.
Periodate oxidation is complete after 4hours at 0o with the consumption of 6.2 mols.
The tetra-O-methyl carminate has m 186-188o (yellow needles from *C6H6/pet ether).

HOW IS CARMINIC ACID OBTAINED?
Cochineal insects live and feed on the leaves of the prickly pear cactus.
They can be easily mistaken for fungus as they exude a cottony white coating to protect themselves.
Currently, Peru is the largest commercial producer of the insect, with plantations dedicated to growing cacti for the sole purpose of harvesting cochineal.
The traditional and still widely used method begins by scraping cochineal off the cactus leaves.
These insects are then dried and ground into a red powder mainly consisting of crude carminic acid.

HOW WAS CARMINIC ACID DISCOVERED?
Using ground-up dried insects to make pigments has been known since antiquity, but when the Spanish conquered the Aztec Empire in the early 1500's, they encountered Aztec warriors dressed in a bright crimson colour that was brighter and more vivid than any dye they'd seen before.
This was due to the cochineal insect (Dactylopius coccus) which was native to South America.

The Spanish started shipping the dried insects back to Europe, and by the mid 1500's, tons of cochineal were being shipped to Europe for use in dyes.
After silver, Carminic Acid became Spain's second most valuable export from the New World, and it contributed to Spain becoming one of the wealthiest and most powerful countries in Europe.
The Spanish guarded the secret of Carminic Acid's production carefully for centuries, and had a monopoly on the red pigment that was envied all over Europe.

PHYSICAL and CHEMICAL PROPERTIES of CARMINIC ACİD:
Chemical formula: 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
Molecular Formula / Molecular Weight: C22H20O13 = 492.39
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 1260-17-9
PubChem Substance ID: 87565853

Merck Index (14): 1843
Colour Index: 75470
MDL Number: MFCD00167028
Molecular Weight: 492.4 g/mol
XLogP3-AA: 0.5
Hydrogen Bond Donor Count: 9
Hydrogen Bond Acceptor Count: 13
Rotatable Bond Count: 3

Exact Mass: 492.09039069 Da
Monoisotopic Mass: 492.09039069 Da
Topological Polar Surface Area: 243 Ų
Heavy Atom Count: 35
Formal Charge: 0
Complexity: 864
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0

Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Other (deleted CASRN): 1389-34-0
ECHA EINECS - REACH Pre-Reg: 215-023-3
FDA UNII: CID8Z8N95N
Nikkaji Web: J3.366I

Beilstein Number: 071651
MDL: MFCD00167028
XlogP3-AA: 0.50 (est)
Molecular Weight: 492.39100000
Formula: C22H20O13
Assay: 96.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 136.00 °C @ 760.00 mm Hg
Boiling Point: 907.00 to 908.00 °C @ 760.00 mm Hg (est)

Flash Point: 601.00 °F TCC (316.10 °C) (est)
logP (o/w): 1.532 (est)
Soluble in: water, 1300 mg/L @ 25 °C (exp)
CBNumber: CB1428489
Molecular Formula: C22H20O13
Molecular Weight: 492.39
MDL Number: MFCD00167028
MOL File: 1260-17-9.mol
Melting point: 136 °C
alpha: 15654 +51.6° (water)

Boiling point: 506.2°C (rough estimate)
Density: 1.4504 (rough estimate)
bulk density: 490kg/m3
refractive index: 1.6000 (estimate)
Flash point: 12℃
storage temp.: room temp
solubility: 30g/l
Colour Index: 75470
form: Crystalline Powder
pka: 1.62±0.20(Predicted)

color: Red to dark red
PH: 1.6 (10g/l, H2O, 20℃)
Odor: Odorless
PH Range: 4.8 - 6.2
optical activity: [α]20/D +3.1°, c = 1 in H2O
Water Solubility: 1.298g/L(room temperature)
λmax: 495 nm
ε(extinction coefficient): ≥13000 at 222-228 nm in ethanol at 0.03g/L
ε(extinction coefficient): ≥18000 at 275-281nm in ethanol at 0.03g/L

Merck: 14,1843
BRN: 71651
Major Application: diagnostic assay manufacturing
hematology
histology
InChIKey: DGQLVPJVXFOQEV-JNVSTXMASA-N
SMILES: Cc1c(C(O)=O)c(O)cc2C(=O)c3c(O)c(O)c([C@@H]4OC@H
C@@H
C@H
[C@H]4O)c(O)c3C(=O)c12
LogP: 1.532 (est)

CAS DataBase Reference: 1260-17-9
Substances Added to Food (formerly EAFUS): COCHINEAL EXTRACT (COCCUS CACTI L.)
FDA UNII: CID8Z8N95N
EPA Substance Registry System: C.I. Natural Red 4 (1260-17-9)
UNSPSC Code: 85151701
NACRES: NA.47
Physical state: solid
CAS Number: 1260-17-9
IUPAC Name: 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracene-2-carboxylic acid
Molecular Formula: C22H20O13

InChI Key: DGQLVPJVXFOQEV-NGOCYOHBSA-N
SMILES: CC1=C(C(O)=O)C(O)=CC2=C1C(=O)C1=C(O)C([C@H]3OC@H
C@@H
C@H
[C@H]3O)=C(O)C(O)=C1C2=O
Molecular Weight (g/mol): 492.39
Infrared spectrum: Conforms
Appearance (Form): Crystalline powder
Appearance (Color): Red
HPLC: >=70 %

Synonyms: Natural red 4
CAS Number: 1260-17-9
Purity: ≥ 95% (Dye content)
Molecular Formula: C22H20O13
Molecular Weight: 492.39
MDL Number: MFCD00167028
PubChem ID: 14950
Appearance: Red to purple powder or crystalline powder
Optical Rotation: [a]20D = 3.1 ° (C=1 in H2O)
Conditions: Store at RT
CAS No: 1260-17-9

Synonyms: 7- b- D- Glucopyranosyl- 9, 10- dihydro- 3, 5, 6, 8- tetrahydroxy- 1- methyl- 9, 10- dioxo-2- anthracenecarboxylic acid
Product Code: MC30619
MDL No: MFCD00167028
MOL file: Download
Chemical Formula: C22H20O13
Molecular Weight: 492.39 g/mol
Smiles: CC1=C2C(=CC(=C1C(=O)O)O)C(=O)C3=C(C2=O)C(=C(C(=C3O)O)[C@H]4C@@HO)O
Long Term Storage: store at 10°C - 25°C, protect from light
Color: No data available

Odor: No data available
Melting point/freezing point: Melting point: 136 °C
Initial boiling point and boiling range: No data available
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits: No data available
Flash point: No data available
Autoignition temperature: No data available
Decomposition temperature: No data available

pH: No data available
Viscosity: Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water solubility: No data available
Partition coefficient: n-octanol/water: log Pow: ca.1,62 at 25 °C - Bioaccumulation is not expected.
Vapor pressure: No data available
Density: No data available
Relative density: No data available
Relative vapor density: No data available

Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: none
Other safety information: No data available
CAS Number: 1260-17-9
EC Number: 215-724-4
MDL No: MFCD00167028
Molecular Formula: C22H20O13
Molecular Weight: 492.39 g/mol

FIRST AID MEASURES of CARMINIC ACİD:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of CARMINIC ACİD:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of CARMINIC ACİD:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of CARMINIC ACİD:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of CARMINIC ACİD:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of CARMINIC ACİD:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available