| Common Name |
Erythrosine
| Description |
Erythrosine is a dye used in food and feed additives. Prohibited in U.S.A. and Norway Erythrosine is a cherry-pink synthetic fluorone food coloring. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation.[citation needed]; It is used as a food coloring, in printing inks, as a biological stain, a dental plaque disclosing agent and a radiopaque medium. It is commonly used in sweets and foods marketed to children such as cake icing and cake-decorating gels. It is also used to color pistachio shells. While commonly used in most countries of the world, erythrosine is rarely used in the United States due to its known hazards, with Allura Red AC (Red #40) being generally used instead. However, Allura Red AC is banned in many European countries because it is an azo dye, despite the fact that it has fewer known health risks than Erythrosine.Erythrosine has been shown to exhibit anti-microbial function (PMID 21180961 ).Erythrosine belongs to the family of Xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29702 (Erythrosine)
| Synonyms |
| Value |
Source |
e127ChEMBL
2',4',5',7'-TetraiodofluoresceinHMDB
2, 4,5,7-TetraiodofluoresceinHMDB
2,4,5,7-ErythrosinHMDB
2,4,5,7-TetraiodofluoresceinHMDB
3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'(9H)-xanthen]-3-one, 9ciHMDB
Aizen erythrosineHMDB
C.I. 45430HMDB
C.I. acid red 51HMDB
C.I. FOOD red 14HMDB
CeplacHMDB
Cogilor orange 211.10HMDB
Cogilor orange 312.42HMDB
Dianthine bHMDB
Erythrosine acidHMDB
Erythrosine, phenolicHMDB
FD And C red no. 3HMDB
FeluminHMDB
FOOD Red no. 3HMDB
IodeosinHMDB
Iodeosine bHMDB
IodofluoresceinHMDB
Pyrosine bHMDB
Red 1427HMDB
TetraiodofluoresceinHMDB
TraceHMDB
| Chemical Formlia |
C20H8I4O5
| Average Molecliar Weight |
835.8924
| Monoisotopic Molecliar Weight |
835.655047046
| IUPAC Name |
3,6-dihydroxy-2,4,5,7-tetraiodo-3H-spiro[2-benzofuran-1,9-xanthene]-3-one
| Traditional Name |
erythrosine
| CAS Registry Number |
15905-32-5
| SMILES |
OC1=C(I)C2=C(C=C1I)C1(OC(=O)C3=C1C=CC=C3)C1=CC(I)=C(O)C(I)=C1O2
| InChI Identifier |
InChI=1S/C20H8I4O5/c21-11-5-9-17(13(23)15(11)25)28-18-10(6-12(22)16(26)14(18)24)20(9)8-4-2-1-3-7(8)19(27)29-20/h1-6,25-26H
| InChI Key |
OALHHIHQOFIMEF-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
| Kingdom |
Organic compounds
| Super Class |
Organoheterocyclic compounds
| Class |
Benzopyrans
| Sub Class |
1-benzopyrans
| Direct Parent |
Xanthenes
| Alternative Parents |
Diarylethers
Phthalides
Benzofuranones
O-iodophenols
Iodobenzenes
Aryl iodides
Lactones
Carboxylic acid esters
Oxacyclic compounds
Monocarboxylic acids and derivatives
Organoiodides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Xanthene
Diaryl ether
Phthalide
Benzofuranone
2-iodophenol
2-halophenol
Iodobenzene
Benzenoid
Aryl iodide
Aryl halide
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organoiodide
Organohalogen compound
Carbonyl group
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
Not Available
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
anti-microbial
| Application |
Dye / Coloring Agent
| Cellliar locations |
Membrane (predicted from logP)
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point303 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.7 mg/mLNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.0034 mg/mLALOGPS
logP4.87ALOGPS
logP7.6ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)6.5ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity144.67 m3·mol-1ChemAxon
Polarizability55.06 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB000892
| KNApSAcK ID |
Not Available
| Chemspider ID |
Not Available
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Erythrosine
| NuGOwiki Link |
HMDB29702
| Metagene Link |
HMDB29702
| METLIN ID |
Not Available
| PubChem Compound |
Not Available
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Calcipotriol Impurity C
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Costa AC, Chibebe Junior J, Pereira CA, Machado AK, Beltrame Junior M, Junqueira JC, Jorge AO: Susceptibility of planktonic cultures of Streptococcus mutans to photodynamic therapy with a light-emitting diode. Braz Oral Res. 2010 Oct-Dec;24(4):413-8. [PubMed:21180961 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 14751870