Basic information
- Standard SMILES
O=C1OC2(c3ccccc31)c1cc(I)c(O)c(I)c1Oc1c2cc(I)c(O)c1I- InChIKey
OALHHIHQOFIMEF-UHFFFAOYSA-N- Molecular formula
- C20H8I4O5
- Average molar mass
- 835.9 g/mol
- Monoisotopic mass
- 835.65506536
Overview
Fd&c red no. 3 is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]").<br /> Fd&c red no. 3 belongs to the family of Xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene ring joined to each other by a pyran ring.
Names & identifiers
- Preferred name
- Erythrosine
- IUPAC
- 3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one
- English name
- ERYTHROSIN B
- Molecular formula
- C20H8I4O5
- Molecular weight
- 835.89
Names & synonyms
ERYTHROSINEE1273',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-oneFD & C red no. 33',6'-dihydroxy-2',4',5',7'-tetraiodospiro(2-benzofuran-3,9'-xanthene)-1-oneFDC Red No. 3RefChem:591122Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt16423-68-0Erythrosine, sodium anhydrousNSC-36685Erythrosin B
Show more names
ERYTHROSINtraiodo-Nsc328781cherry redBErythrosiIODOEOSINECI 45430:2tetraiodo-
Tetraiodofluorescein15905-32-5Solvent Red 140IodeosinErythrosine acidErythrosine, phenolic2',4',5',7'-Tetraiodofluorescein2,4,5,7-Erythrosin
Database identifiers
- CAS
15905-32-5、16423-68-0- PubChem CID
- 3259
- DTXSID
DTXSID7044843- ChEMBL
CHEMBL1332616- UNII
- 1A878FZQ9B
- EC Number
- 240-046-0
- Nikkaji
- J25.137B
Properties
Computed structural properties
- XLogP
- 6
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 645
Experimental & physicochemical properties
CosmeticsHair dyeing; Cosmetic colorant
Solubility0.7 mg/mL
Melting Point303 °C
Physical Description
Liquid; Other Solid
Red powder or granules.
Solid
Collision Cross Section217.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID7021233]
Physicochemical properties
- Melting point
- 303 °C · 303 °C (dec.)(lit.)
- Boiling point
- 628.3 · 628.3±55.0 °C(Predicted)
- Density
- 2.4391 · 2.4391 (estimate)
- storage temp.
- room temp
- solubility
- spirit: soluble
- form
- powder
- pka
- 7.21 · 7.21±0.20(Predicted)
- Colour Index
- 45430 · 45430:2
- color
- Red
- Water Solubility
- Soluble in water, spirit, methanol, methyl cellosolve and ethanol.
- ε(extinction coefficient)
- 102000 at · ≥102000 at 526-534nm at 0.005g/L (95% Methanol 5% 0.1M Na2CO3)≥13000 at 310-318nm in 1 M NH4OH at 0.005g/L (95% Methanol 5% 0.1M Na2CO3)≥32000 at 258-266nm at 0.005g/L (95% Methanol 5% 0.1M Na2CO3)
- Major Application
- diagnostic assay manufacturinghematologyhistology
- 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
- InChIKey
- OALHHIHQOFIMEF-UHFFFAOYSA-N
- SMILES
- Oc1c(I)cc2c(Oc3c(I)c(O)c(I)cc3C24OC(=O)c5ccccc45)c1I
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 A878FZQ9B · 1A878FZQ9B
- EPA Substance Registry System
- 2 · 2',4',5',7'-Tetraiodofluorescein (15905-32-5)
- UNSPSC Code
- 12171500 · 12171500
- NACRES
- 47 · NA.47
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314-H290
- Precautionary statements
- 501 · P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 2 · 2
- RTECS
- 5940000 · LM5940000
- TSCA
- TSCA listed
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 in · A food color formerly approved for use in the United States and Europe. It was used primarily in jams and marmalades, maraschino cherries, pickles and relishes, etc. The LD50 in rats is 150 mg/kg, i.p., and 600 mg/kg, p.o. Erythrosine has a variety of actions in vitro due in large measure to its ability to affect biological membranes and lipophilic sites of enzymes. Such data have led to the hypothesis that erythrosine could be neurotoxic, but both clinical and preclinical data have suggested that erythrosine is not likely to be neurotoxic at doses that might be encountered. Two other toxicological issues have been raised with this food color. It has been suggested to be a potential, if weak, carcinogen, and it may also contribute to potential thyroid toxicity resulting from release of iodine.
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 94.9% (37 of 39) of all reports.
Not Classified
Aggregated GHS information provided per 39 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, disodium salt
Regulation (EC) No 1333/2008 (amended)
Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, sodium salt (1:2) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, sodium salt (1:2) are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Erythrosine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified
Toxicology
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- LM5940000
- hs_code
- 29329990
- Toxicity
- A food color formerly approved for use in the United States and Europe. It was used primarily in jams and marmalades, maraschino cherries, pickles and relishes, etc. The LD50 in rats is 150 mg/kg, i.p., and 600 mg/kg, p.o. Erythrosine has a variety of actions in vitro due in large measure to its ability to affect biological membranes and lipophilic sites of enzymes. Such data have led to the hypothesis that erythrosine could be neurotoxic, but both clinical and preclinical data have suggested that erythrosine is not likely to be neurotoxic at doses that might be encountered. Two other toxicological issues have been raised with this food color. It has been suggested to be a potential, if weak, carcinogen, and it may also contribute to potential thyroid toxicity resulting from release of iodine.
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H314-H290
- Precautionary statements
- P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Cellular LocationsMembrane
Uses & manufacturing
U.S. Production2023: 108,000 lb
Consumer UsesPigment
Use Classification
Food additives
Food Additives -> COLOUR -> JECFA Functional Classes
Food Additives -> COLOUR -> JECFA Functional Classes
Food Additives -> COLOUR -> JECFA Functional Classes
Cosmetics -> Hair dyeing; Cosmetic colorant
General Manufacturing Information
Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-: ACTIVE
Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 3',6'-dihydroxy-2',4',5',7'-tetraiodo-, sodium salt (1:2): ACTIVE
Applications
UsesIndicator in analytical chemistry.
UsesErythrosin B is used as a red coloring in some foods such as cherries and fish. It is used as printing ink, dental plaque disclosing agent and biological stain. It finds application as a radiopaque medium and sensitizer for orthochromatic photographic films. It is utilized as a cake-decorating gel. In addition to this, it is used in sweets such as candies and popsicles.
UsesErythrosin B has been used as a dye in fluorescence lifetime imaging.
Preparation methods
PreparationFluorescein (C.I.Acid Yellow 73, C.L 45350) in aqueous solution or Tetraiodide in ethanol, and made the free acid form.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
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Related reactions
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