| Record Information |
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| Version | 2.0 |
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| Created at | 2024-09-11 11:20:17 UTC |
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| Updated at | 2024-09-11 11:20:18 UTC |
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| NP-MRD ID | NP0337549 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Cochineal Red A |
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| Description | Cochineal Red A, also known as coccine or acid scarlet 3R, belongs to the class of organic compounds known as 1,1'-azonaphthalenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to the 1-position of a naphthalene ring system. Naphthalene is a compound made up of two fused benzene rings. The production process may result in unsulphonated aromatic amines present in concentrations of up to 100 mg/kg which may be linked to cancer. Ponceau 4R (known by more than 100 synonyms, including as C.I. 16255, Cochineal Red A, C.I. Acid Red 18, Brilliant Scarlet 3R, Brilliant Scarlet 4R, New Coccine, is a synthetic colourant that may be used as a food colouring. The lake pigment form of the colour additive can also increase the intake of aluminium beyond the tolerable weekly intake (TWI) of 1 mg/kg/week. Cochineal Red A is an extremely weak basic (essentially neutral) compound (based on its pKa). It is used in Europe, Asia and Australia, but has not been approved for human consumption by the United States Food and Drug Administration. Ponceau (17th century French for "poppy-coloured") is the generic name for a family of azo dyes. There is no evidence to support broad claims that food colouring causes food intolerance and ADHD-like behaviour in children. These concerns have led the FDA and other food safety authorities to regularly review the scientific literature, and led the UK FSA to commission a study by researchers at Southampton University of the effect of a mixture of six food dyes (Tartrazine, Allura Red AC, Ponceau 4R, Quinoline Yellow WS, Sunset Yellow and Carmoisine (dubbed the "Southampton 6")) and sodium benzoate (a preservative) on children in the general population, who consumed them in beverages; the study published in 2007. There is no evidence of carcinogenicity, genotoxicity, neurotoxicity, or reproductive and developmental toxicity at the permitted dietary exposures; the European acceptable daily intake (ADI) is 0.7 Mg/kg and the WHO/FAO ADI is 4 mg/kg. |
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| Structure | OC1=C(\N=N\C2=CC=C(C3=CC=CC=C23)S(O)(=O)=O)C2=C(C=C(C=C2C=C1)S(O)(=O)=O)S(O)(=O)=O InChI=1S/C20H14N2O10S3/c23-16-7-5-11-9-12(33(24,25)26)10-18(35(30,31)32)19(11)20(16)22-21-15-6-8-17(34(27,28)29)14-4-2-1-3-13(14)15/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32)/b22-21+ |
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| Synonyms | | Value | Source |
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| 7-Hydroxy-8-[(4-sulfO-1-naphthalenyl)azo]-1,3-naphthalenedisulfonic acid, 9ci | HMDB | | Acid scarlet 3R | HMDB | | Brilliant ponceau 3R | HMDB | | Brilliant scarlet 3R | HMDB | | C.I. 16255 | HMDB | | C.I. acid red 18 | HMDB | | C.I. FOOD red 7 | HMDB | | Coccine | HMDB | | e124 | HMDB | | FOOD Red no. 102 | HMDB | | Kayaku acid brilliant scarlet 3R | HMDB | | Naphthalene scarlet 4R | HMDB | | Neucoccin | HMDB | | New coccine | HMDB | | Ponceau 4R | HMDB | | Strawberry red | HMDB | | 7-Hydroxy-8-[(e)-2-(4-sulfonaphthalen-1-yl)diazen-1-yl]naphthalene-1,3-disulfonate | Generator | | 7-Hydroxy-8-[(e)-2-(4-sulphonaphthalen-1-yl)diazen-1-yl]naphthalene-1,3-disulphonate | Generator | | 7-Hydroxy-8-[(e)-2-(4-sulphonaphthalen-1-yl)diazen-1-yl]naphthalene-1,3-disulphonic acid | Generator |
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| Chemical Formula | C20H14N2O10S3 |
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| Average Mass | 538.5280 Da |
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| Monoisotopic Mass | 537.98106 Da |
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| IUPAC Name | 7-hydroxy-8-[(E)-2-(4-sulfonaphthalen-1-yl)diazen-1-yl]naphthalene-1,3-disulfonic acid |
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| Traditional Name | 7-hydroxy-8-[(E)-2-(4-sulfonaphthalen-1-yl)diazen-1-yl]naphthalene-1,3-disulfonic acid |
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| CAS Registry Number | Not Available |
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| SMILES | OC1=C(\N=N\C2=CC=C(C3=CC=CC=C23)S(O)(=O)=O)C2=C(C=C(C=C2C=C1)S(O)(=O)=O)S(O)(=O)=O |
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| InChI Identifier | InChI=1S/C20H14N2O10S3/c23-16-7-5-11-9-12(33(24,25)26)10-18(35(30,31)32)19(11)20(16)22-21-15-6-8-17(34(27,28)29)14-4-2-1-3-13(14)15/h1-10,23H,(H,24,25,26)(H,27,28,29)(H,30,31,32)/b22-21+ |
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| InChI Key | JZGWEIPJUAIDHM-QURGRASLSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as 1,1'-azonaphthalenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to the 1-position of a naphthalene ring system. Naphthalene is a compound made up of two fused benzene rings. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Naphthalenes |
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| Sub Class | 1,1'-azonaphthalenes |
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| Direct Parent | 1,1'-azonaphthalenes |
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| Alternative Parents | |
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| Substituents | - 1,1'-azonaphthalene
- 2-naphthalene sulfonate
- 1-naphthalene sulfonate
- Naphthalene sulfonic acid or derivatives
- 2-naphthalene sulfonic acid or derivatives
- 1-naphthalene sulfonic acid or derivatives
- Naphthalene sulfonate
- 2-naphthol
- Arylsulfonic acid or derivatives
- 1-sulfo,2-unsubstituted aromatic compound
- 1-hydroxy-2-unsubstituted benzenoid
- Organic sulfonic acid or derivatives
- Organosulfonic acid or derivatives
- Organosulfonic acid
- Sulfonyl
- Azo compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Hydrocarbon derivative
- Organic oxide
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Organic nitrogen compound
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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