Allura red AC (T3D4860)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2014-09-11 05:19:39 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4860
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].
Compound Type
  • Dye
  • Ether
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
6-Hydroxy-5-[(2-methoxy-5-methyl-4-sulfophenyl)azo]-2-naphthalenesulfonic acid, 9CI
Allura Red
Allura red ac
Allura red ac dye
C.I. 16035
C.I. Food Red 17
Curry red
E129
FD & C Red no. 40
FD and C Red No. 40
FD&C RED NO. 40
Food Red 17
Food Red No. 40
Red No. 40
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=CC(=C(C)C=C1\N=N\C1=C(O)C=CC2=CC(=CC=C12)S(O)(=O)=O)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 KeyInChIKey=UQWIHFJXDRNUDP-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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP-0.35ALOGPS
logP-0.44ChemAxon
logS-4.4ALOGPS
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 KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0194400000-18e286940f518096ed972017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01vo-3154920000-1e2da1baaba41d4206862017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000900000-d0a5b7281767780579c92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0312900000-ad84ed764e24343807422016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avl-2329000000-6bd858afebf71d6ff8e42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-c1fb3bb729e1a24a69cd2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-0115900000-08ef62471db37994b26c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fl0-0390000000-50ed853957d4d7d0df442016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fki-0083900000-d4e076cb60a93b75d0122021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0292200000-daf149179f0b507d5cf42021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0072-0942000000-b6dbb62519877fe6bee22021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-fbbfdc64fa7f94cc59b52021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1031900000-29caa7d0b05ab522ca452021-09-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9864200000-14a17bd14e7cde4184ea2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32884
PubChem Compound IDNot Available
ChEMBL IDNot Available
ChemSpider ID26351025
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkAllura_red_AC
References
Synthesis ReferenceNot Available
MSDST3D4860.pdf
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. D(2) dopamine receptor
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC507.36 uMNVS_GPCR_hDRD2sNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]