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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:28 UTC
Update Date2022-03-07 02:53:30 UTC
HMDB IDHMDB0032884
Secondary Accession Numbers
  • HMDB32884
Metabolite Identification
Common NameAllura red AC
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].
Structure
Data?1563862321
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 Weight452.458
Monoisotopic Molecular Weight452.034806878
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
CAS Registry Number25956-17-6
SMILES
COC1=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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility225 mg/mL at 25 °CNot Available
LogP-0.550The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-225.83330932474
DeepCCS[M+Na]+201.25830932474
AllCCS[M+H]+199.832859911
AllCCS[M+H-H2O]+197.432859911
AllCCS[M+NH4]+201.932859911
AllCCS[M+Na]+202.532859911
AllCCS[M-H]-190.532859911
AllCCS[M+Na-2H]-190.232859911
AllCCS[M+HCOO]-189.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Allura red ACCOC1=C(C=C(C)C(=C1)S(O)(=O)=O)\N=N\C1=C(O)C=CC2=CC(=CC=C12)S(O)(=O)=O5895.2Standard polar33892256
Allura red ACCOC1=C(C=C(C)C(=C1)S(O)(=O)=O)\N=N\C1=C(O)C=CC2=CC(=CC=C12)S(O)(=O)=O3229.3Standard non polar33892256
Allura red ACCOC1=C(C=C(C)C(=C1)S(O)(=O)=O)\N=N\C1=C(O)C=CC2=CC(=CC=C12)S(O)(=O)=O4205.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Allura red AC,1TMS,isomer #1COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O)=CC=C124061.1Semi standard non polar33892256
Allura red AC,1TMS,isomer #2COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O)=CC=C123976.5Semi standard non polar33892256
Allura red AC,1TMS,isomer #3COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123919.7Semi standard non polar33892256
Allura red AC,2TMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O)=CC=C123878.7Semi standard non polar33892256
Allura red AC,2TMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O)=CC=C123919.1Standard non polar33892256
Allura red AC,2TMS,isomer #2COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123847.2Semi standard non polar33892256
Allura red AC,2TMS,isomer #2COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123929.5Standard non polar33892256
Allura red AC,2TMS,isomer #3COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123745.7Semi standard non polar33892256
Allura red AC,2TMS,isomer #3COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123879.3Standard non polar33892256
Allura red AC,3TMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123742.9Semi standard non polar33892256
Allura red AC,3TMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C)=CC=C123995.3Standard non polar33892256
Allura red AC,1TBDMS,isomer #1COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O)=CC=C124295.5Semi standard non polar33892256
Allura red AC,1TBDMS,isomer #2COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O)=CC=C124218.9Semi standard non polar33892256
Allura red AC,1TBDMS,isomer #3COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124156.4Semi standard non polar33892256
Allura red AC,2TBDMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O)=CC=C124335.7Semi standard non polar33892256
Allura red AC,2TBDMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O)=CC=C124422.1Standard non polar33892256
Allura red AC,2TBDMS,isomer #2COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124306.1Semi standard non polar33892256
Allura red AC,2TBDMS,isomer #2COC1=CC(S(=O)(=O)O)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124441.6Standard non polar33892256
Allura red AC,2TBDMS,isomer #3COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124219.1Semi standard non polar33892256
Allura red AC,2TBDMS,isomer #3COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124418.5Standard non polar33892256
Allura red AC,3TBDMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124387.9Semi standard non polar33892256
Allura red AC,3TBDMS,isomer #1COC1=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=C(C)C=C1/N=N/C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=CC(S(=O)(=O)O[Si](C)(C)C(C)(C)C)=CC=C124787.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Allura red AC GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0194400000-18e286940f518096ed972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allura red AC GC-MS (1 TMS) - 70eV, Positivesplash10-01vo-3154920000-1e2da1baaba41d4206862017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Allura red AC GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 10V, Positive-QTOFsplash10-0udi-0000900000-d0a5b7281767780579c92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 20V, Positive-QTOFsplash10-0udi-0312900000-ad84ed764e24343807422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 40V, Positive-QTOFsplash10-0avl-2329000000-6bd858afebf71d6ff8e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 10V, Negative-QTOFsplash10-0udi-0001900000-c1fb3bb729e1a24a69cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 20V, Negative-QTOFsplash10-0uk9-0115900000-08ef62471db37994b26c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 40V, Negative-QTOFsplash10-0fl0-0390000000-50ed853957d4d7d0df442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 10V, Positive-QTOFsplash10-0fki-0083900000-d4e076cb60a93b75d0122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 20V, Positive-QTOFsplash10-000i-0292200000-daf149179f0b507d5cf42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 40V, Positive-QTOFsplash10-0072-0942000000-b6dbb62519877fe6bee22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 10V, Negative-QTOFsplash10-0udi-0000900000-fbbfdc64fa7f94cc59b52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 20V, Negative-QTOFsplash10-0udi-1031900000-29caa7d0b05ab522ca452021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Allura red AC 40V, Negative-QTOFsplash10-001i-9864200000-14a17bd14e7cde4184ea2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010866
KNApSAcK IDNot Available
Chemspider ID10677559
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllura Red AC
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1300031
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .