Carmine
Basic information
- CAS
1260-17-9- Standard SMILES
Cc1c(C(=O)O)c(O)cc2c1C(=O)c1c(O)c([C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c(O)c1C2=O- InChIKey
DGQLVPJVXFOQEV-NGOCYOHBSA-N- Molecular formula
- C22H20O13
- Average molar mass
- 492.4 g/mol
- Monoisotopic mass
- 492.09039069
Overview
Coloring matter from the insect Coccus cacti L. It is used in foods, pharmaceuticals, toiletries, etc., as a dye, and also has use as a microscopic stain and biological marker.
Names & identifiers
- Preferred name
- Carmine
- IUPAC
- 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
- English name
- Carminic Acid
- Molecular formula
- C22H20O13
- Molecular weight
- 492.39
Names & synonyms
CarmineB Rose liquidCochineal Dye1390-65-4Dye, CochinealCarmine (Coccus cacti L.)Cochineal (Coccus cacti L.)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 acid3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-((2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)anthracene-2-carboxylic acidRefChem:574680DTXSID20442167-glucopyranosyl-3,5,6,8-tetrahydroxyl-1-methyl-9,10-dioxoanthracene-2-carboxylic acid
Show more names
CI 75470E120coccinic acidCARMINE ALUMINUM LAKECarminicC.I.Naturalred4NSC 326224CARMINE 2GCARMINE 40
215-724-4Carmine RedST0693397-[(5S,2R,3R,4R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrahydropy ran-2-yl)]-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic aci dNSC326224NCGC00091708-04SCHEMBL34094orb1218979
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 243 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 3
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 864
Experimental & physicochemical properties
Chemical ClassesDyes -> Anthraquinone Dyes
CosmeticsCosmetic colorant
Food Additives
Foods, Drugs, Cosmetics -> FDA Regulatory Status of Color Additives
Foods, Drugs -> FDA Regulatory Status of Color Additives
COLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Physical DescriptionRed crystals in methanol; bright red powder; deep red color in water; [HSDB]
Physicochemical properties
- Melting point
- 136 °C · 136 °C
- alpha
- 15654 · 15654 +51.6° (water)
- Boiling point
- 506.2 °C · 506.2°C (rough estimate)
- Density
- 1.4504 · 1.4504 (rough estimate)
- bulk density
- 490 kg/m3 · 490kg/m3
- refractive index
- 1.6 · 1.6000 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (298 of 298) of all reports.
Not Classified
Aggregated GHS information provided per 298 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Carmine
REACH registered substance: Carmine (EC: 215-724-4)
Carmine: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Anthraquinones are toxic by ingestion and may cause vomiting, diarrhea, kidney and liver damage, and coma; Deaths have been reported after children ingested Rhamnus berries; [HSDB] Occupational asthma confirmed in workers in dye manufacturing plant; [Malo] Cochineal is the dried bodies of the female insect coccus cacti. Carminic acid is the active coloring material, and carmine is the aluminum lake of carminic acid. [HSDB] See Carminic acid and Cochineal.
Hazard Classes and CategoriesNot Classified
Toxicology
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Natural or synthetic dyes used as coloring agents in processed foods.
Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS.
Uses & manufacturing
Uses
Used in inks, dyes, food coloring, photography, paints, microbiological stains, and chemical reagents; [HSDB] Carmine is used as a microscopic stain of chromatin. [Ullmann]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
Household Products
Information on 77 consumer products that contain Carmine in the following categories is provided:
Information on 2 consumer products that contain C.I. 75470 in the following categories is provided:
Use ClassificationCosmetics -> Cosmetic colorant
Applications
HistoryCI Natural Red 4(CI 75470), 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. Its aluminum lake, carmine, finds use in the coloring of foods.
Related reactions
1 records
Compound notes
Loading…