Basic information
- 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
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
Carmine1390-65-4B Rose liquid3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-7-[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]anthracene-2-carboxylic acidCarmine (Coccus cacti L.)Cochineal (Coccus cacti L.)Cochineal DyeDye, Cochineal3,5,6,8-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
Database identifiers
- CAS
1260-17-9、1390-65-4- PubChem CID
- 14749
- ChEMBL
CHEMBL1366408- EC Number
- 215-724-4
- Nikkaji
- J3.366I
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
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)
- Flash point
- 12 ℃ · 12℃
- storage temp.
- room temp
- solubility
- 30 g/l · 30g/l
- Colour Index
- 75470 · 75470
- form
- Crystalline Powder
- pka
- 1.62 · 1.62±0.20(Predicted)
- color
- Red to dark red
- PH
- 1.6 · 1.6 (10g/l, H2O, 20℃)
- Odor
- Odorless
- PH Range
- 4.8 · 4.8 - 6.2
- optical activity
- 20 · [α]20/D +3.1°, c = 1 in H2O
- Water Solubility
- 1.298 g/L · 1.298g/L(room temperature)
- λmax
- 495 nm · 495 nm
- ε(extinction coefficient)
- 13000 at · ≥13000 at 222-228 nm in ethanol at 0.03g/L≥18000 at 275-281nm in ethanol at 0.03g/L
- Merck
- 14 · 14,1843
- BRN
- 71651 · 71651
- Major Application
- diagnostic assay manufacturinghematologyhistology
- InChIKey
- DGQLVPJVXFOQEV-JNVSTXMASA-N
- SMILES
- Cc1c(C(O)=O)c(O)cc2C(=O)c3c(O)c(O)c([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(O)c3C(=O)c12
- LogP
- 1.532 · 1.532 (est)
- CAS DataBase Reference
- 1260 · 1260-17-9
- Substances Added to Food (formerly EAFUS)
- COCHINEAL EXTRACT (COCCUS CACTI L.)
- FDA UNII
- 8 Z8N95N · CID8Z8N95N
- EPA Substance Registry System
- 4 · C.I. Natural Red 4 (1260-17-9)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 260 · P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 2 · 2
- TSCA
- TSCA listed
- HS Code
- 32129000 · 32129000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazardous Substances Data
- 1260 · 1260-17-9(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (298 of 298) of all reports.
Not Classified；Reported as not meeting GHS hazard criteria by 298 of 298 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 298 reports by companies from 1 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 298 of 298 reports by companies.；There are 0 notifications provided by 0 of 298 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: Carmine
Status: Active Update: 13-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/28382
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 Effects
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.；Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Regulatory information
Regulatory Information
Chemical: Carmine
Status: Active Update: 13-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/28382
Carmine: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 32129000
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H314
- Precautionary statements
- P260-P264-P280-P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P305+P351+P338-P405-P501
- Hazardous Substances Data
- 1260-17-9(Hazardous Substances Data)
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]；Photographic Processing [Category: Other]；Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
Household Products
Information on 77 consumer products that contain Carmine in the following categories is provided:；• Personal Care
Information on 2 consumer products that contain C.I. 75470 in the following categories is provided:；• Personal Care
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.
UsesA red glucosidal hydroxyanthrapurin, it is produced naturally within some insects as a defense mechanism.
UsesCarminic acid (C.I. 75470) For staining nuclei in histological sections. Used to prepare staining solutions. CAS 1260-17-9, pH 1.6 (10g/l, HO, 20°C).
Usesantineoplastic, glucosyltransferase inhibitor
General DescriptionDark purplish-brown mass or bright red or dark red powder. Darkens at 248°F. Deep red color in water. Yellow to violet in acidic aqueous solutions.
Upstream & downstream products
Downstream products
Suppliers50 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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九鼎化学（上海）科技有限公司4009209199 · [email protected]
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Additional notes
DefinitionChEBI: 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. It is a natural dye isolated from several insects such as Dactylopius coccus.
Related reactions
1 records
Linked notes
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