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Allura red AC (CHEM003816)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (1)XML
Record Information
Version1.0
Creation Date2014-09-11 05:19:39 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003816
Identification
Common NameAllura red AC
ClassSmall Molecule
DescriptionColour additive used in gelatins, puddings, custards, beverages, sauces, toppings, fruits, dairy products, bakery products, jams, jellies, condiments, meat and poultry Allura Red AC is a red azo dye that goes by several names including: Allura Red, Food Red 17, C.I. 16035, FD&C Red 40, 2-naphthalenesulfonic acid, 6-hydroxy-5-((2-methoxy-5-methyl-4-sulfophenyl)azo)-, disodium salt, and disodium 6-hydroxy-5-((2-methoxy-5-methyl-4-sulfophenyl)azo)-2-naphthalene-sulfonate. It is used as a food dye and has the E number E129. Allura Red AC was originally introduced in the United States as a replacement for the use of amaranth as a food coloring. Allura Red AC is one of many High Production Volume Chemicals. Some manufacturers of Allura Red AC include: Asim Products, Sanchi Chemicals Pvt. Ltd., and Warner-Jenkinson Europe Ltd. Upon its introduction into the market, there were fears that Allura Red AC was carcinogenic; however, studies have since shown that this is not the case.[citation needed] The initial reports of its consumption causing tumors have since been shown to have been caused by the presence of para-cresidine.[citation needed] Although para-cresidine is an important reactant in the manufacture of Allura Red AC and is a known carcinogen, further studies conducted since have found no trace of para-cresidine to be present in food-grade Allura Red AC.[citation needed].
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Dye
  • Ether
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Hydroxy-5-[(2-methoxy-5-methyl-4-sulfophenyl)azo]-2-naphthalenesulfonic acid, 9ciHMDB
Allura redHMDB
Allura red ac dyeHMDB
C.I. 16035HMDB
C.I. FOOD red 17HMDB
Curry redHMDB
e129HMDB
FD & C red no. 40HMDB
FD And C red no. 40HMDB
FD&C red no. 40HMDB
FOOD Red 17HMDB
FOOD Red no. 40HMDB
Red no. 40HMDB
6-Hydroxy-5-[(e)-2-(2-methoxy-5-methyl-4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonateGenerator
6-Hydroxy-5-[(e)-2-(2-methoxy-5-methyl-4-sulphophenyl)diazen-1-yl]naphthalene-2-sulphonateGenerator
6-Hydroxy-5-[(e)-2-(2-methoxy-5-methyl-4-sulphophenyl)diazen-1-yl]naphthalene-2-sulphonic acidGenerator
Chemical FormulaC18H16N2O8S2
Average Molecular Mass452.458 g/mol
Monoisotopic Mass452.035 g/mol
CAS Registry Number25956-17-6
IUPAC Name6-hydroxy-5-[(E)-2-(2-methoxy-5-methyl-4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonic acid
Traditional Name6-hydroxy-5-[(E)-2-(2-methoxy-5-methyl-4-sulfophenyl)diazen-1-yl]naphthalene-2-sulfonic acid
SMILESCOC1=C(C=C(C)C(=C1)S(O)(=O)=O)\N=N\C1=C(O)C=CC2=CC(=CC=C12)S(O)(=O)=O
InChI IdentifierInChI=1S/C18H16N2O8S2/c1-10-7-14(16(28-2)9-17(10)30(25,26)27)19-20-18-13-5-4-12(29(22,23)24)8-11(13)3-6-15(18)21/h3-9,21H,1-2H3,(H,22,23,24)(H,25,26,27)/b20-19+
InChI KeyUQWIHFJXDRNUDP-FMQUCBEESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 2-position. Naphthalene is a bicyclic compound that is made up of two fused benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthalene sulfonic acids and derivatives
Direct Parent2-naphthalene sulfonates
Alternative Parents
Substituents
  • 2-naphthalene sulfonic acid or derivatives
  • 2-naphthalene sulfonate
  • 2-naphthol
  • Benzenesulfonate
  • Arylsulfonic acid or derivatives
  • Benzenesulfonyl group
  • 1-sulfo,2-unsubstituted aromatic compound
  • Methoxyaniline
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Monocyclic benzene moiety
  • Organic sulfonic acid or derivatives
  • Sulfonyl
  • Organosulfonic acid
  • Organosulfonic acid or derivatives
  • Azo compound
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point300 °C
Boiling PointNot Available
Solubility225 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP-0.35ALOGPS
logP-0.44ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)-3ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area162.92 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity111.56 m³·mol⁻¹ChemAxon
Polarizability43.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0079-0194400000-18e286940f518096ed97View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-01vo-3154920000-1e2da1baaba41d420686View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-d0a5b7281767780579c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0312900000-ad84ed764e2434380742View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avl-2329000000-6bd858afebf71d6ff8e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-c1fb3bb729e1a24a69cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0115900000-08ef62471db37994b26cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fl0-0390000000-50ed853957d4d7d0df44View in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0032884
FooDB IDFDB010866
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAllura Red AC
Chemspider ID26351025
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.