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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:58:19 UTC
Update Date2019-01-11 19:52:25 UTC
HMDB IDHMDB0036795
Secondary Accession Numbers
  • HMDB36795
Metabolite Identification
Common NameAzorubine
DescriptionAzorubine is a food dye Azorubine is commonly used in the UK and in several other countries in a popular soda brand, but it is a prohibited food additive in Canada, Japan, Norway, Sweden and the United States. Azorubine, carmoisine, food Red 3, Azorubin S, Brillantcarmoisin O, Acid Red 14, or C.I. 14720 is a synthetic red food dye from the azo dye group. It usually comes as a disodium salt. It is a red to maroon powder. It is used for the purposes where the food is heat-treated after fermentation. It has E number E122. Some of the foods it can be present in are blancmange, marzipan, Swiss roll, jams, preserves, yoghurts, jellies, breadcrumbs, and cheesecake mixes. It is also present in Oraldene Mouthwash. It is one of the colourants that the Hyperactive Children's Support Group recommends be eliminated from the diet of children.
Structure
Data?1547236345
Synonyms
ValueSource
4-Hydroxy-3-[(4-sulfO-1-naphthalenyl)azo]-1-naphthalenesulfonic acid, 9ciHMDB
Acetacid red bHMDB
Acid brilliant rubine 2gHMDB
Acid brilliant rubine 2GTHMDB
Acid brilliant rubine a2g CONC.HMDB
Acid chrome blue 2RHMDB
Acid chrome blue baHMDB
Acid chrome blue ba-CFHMDB
Acid chrome blue FBSHMDB
Acid fast red FBHMDB
Acid red 14HMDB
Acid red 26HMDB
Acid red 2CHMDB
Acid red 2SHMDB
Acid rubineHMDB
Acid rubine extraHMDB
Airedale carmoisineHMDB
Amacid carmoisine bHMDB
Amacid chrome blue RHMDB
Atul acid crystal redHMDB
Atul crystal red FHMDB
azo Rubin extraHMDB
azo Rubin SHMDB
azo Rubin XXHMDB
azo RubineHMDB
azo Rubine (biological stain)HMDB
azo Rubine afHMDB
azo Rubine extra LCHMDB
azo Rubine for FOODHMDB
azo Rubine LZHMDB
azo Rubine S specially pureHMDB
azo Rubine XXHMDB
AzorubinHMDB
Brasilan azo rubine 2NSHMDB
Brilliant acid rubine mHMDB
Brilliant carmoisineHMDB
Brilliant crimson 2R.fqHMDB
Brilliant crimson redHMDB
Bucacid azo rubineHMDB
C.I. acid red 14HMDB
C.I. acid red 14, disodium saltHMDB
C.I. acid red no. 14HMDB
C.I. chromotrope FBHMDB
C.I. FOOD red 3HMDB
C.I. mordant blue 79HMDB
Calcocid rubine XXHMDB
CarmoisineHMDB
Carmoisine aluminium lakeHMDB
Carmoisine aluminum lakeHMDB
Carmoisine baHMDB
Carmoisine ba-CFHMDB
Carmoisine BSSHMDB
Carmoisine fuHMDB
Carmoisine GRNHMDB
Carmoisine lasHMDB
Carmoisine SHMDB
Carmoisine supraHMDB
Carmoisine WHMDB
Carmoisine WSHMDB
Certicol carmoisine SHMDB
Chrome fast blue 2RHMDB
Chromotrop FBHMDB
Chromotrope FBHMDB
Cilefa rubine RHMDB
Crimson 2EMBLHMDB
Crimson emblHMDB
Diadem chrome blue gHMDB
Diadem chrome blue RHMDB
Disodium 2-(4-sulfO-1-naphthylazo)-1-naphthol-4-sulfonateHMDB
e122HMDB
Edicol supra carmoisine WHMDB
Edicol supra carmoisine WSHMDB
Eniacid brilliant rubine 3bHMDB
erio Rubine bHMDB
Eurocert azorubineHMDB
Ext D and C red no. 10HMDB
Ext. D & C red no. 10HMDB
Extract D and C red no. 10HMDB
fenazo Red cHMDB
FOOD Red 5HMDB
Fruit red a extra yellowish geigyHMDB
HD CarmoisineHMDB
HD Carmoisine supraHMDB
Hexacol carmoisineHMDB
Hexacol carmoisine CONC.HMDB
Hidacid azo rubineHMDB
Hispacid rubine FHMDB
Java rubine NHMDB
KarmesinHMDB
Kenachrome blue 2RHMDB
Kiton crimson 2RHMDB
Kiton rubine RHMDB
Lighthouse chrome blue 2RHMDB
Lissamine red WHMDB
NacaratHMDB
Nacarat a exportHMDB
Nacarat extra pure aHMDB
Neklacid azorubine WHMDB
Neklacid rubine WHMDB
Nylomine acid red P4bHMDB
Pontacyl rubine RHMDB
Solar rubineHMDB
Solochrome blue FBHMDB
Solochrome brilliant blueHMDB
Standacol carmoisineHMDB
Tertracid red caHMDB
Tertrochrome blue FBHMDB
Chemical FormulaC20H14N2O7S2
Average Molecular Weight458.464
Monoisotopic Molecular Weight458.024242192
IUPAC Name4-hydroxy-3-[(Z)-2-(4-sulfonaphthalen-1-yl)diazen-1-yl]naphthalene-1-sulfonic acid
Traditional Name4-hydroxy-3-[(Z)-2-(4-sulfonaphthalen-1-yl)diazen-1-yl]naphthalene-1-sulfonic acid
CAS Registry Number3567-69-9
SMILES
OC1=C(C=C(C2=CC=CC=C12)S(O)(=O)=O)\N=N/C1=CC=C(C2=CC=CC=C12)S(O)(=O)=O
InChI Identifier
InChI=1S/C20H14N2O7S2/c23-20-15-8-4-3-7-14(15)19(31(27,28)29)11-17(20)22-21-16-9-10-18(30(24,25)26)13-6-2-1-5-12(13)16/h1-11,23H,(H,24,25,26)(H,27,28,29)/b22-21-
InChI KeyTVWOWDDBXAFQDG-DQRAZIAOSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1-naphthalene sulfonates. These are organic aromatic compounds that contain a naphthalene moiety that carries a sulfonic acid group at the 1-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 Parent1-naphthalene sulfonates
Alternative Parents
Substituents
  • 1-naphthalene sulfonate
  • 1-naphthalene sulfonic acid or derivatives
  • 1-naphthol
  • Arylsulfonic acid or derivatives
  • 1-sulfo,2-unsubstituted aromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organosulfonic acid
  • Sulfonyl
  • Azo compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point> 300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility30 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP-0.06ALOGPS
logP0.49ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)-3.2ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area153.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.5 m³·mol⁻¹ChemAxon
Polarizability42.52 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-0193300000-e70ea6560beecd501ec8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3092410000-78801168d8e43a586b06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0042900000-1ca6efe37beefa4ac9a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0397300000-2be370a6ebe3f9576cc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aba-0691000000-767d8a2cac2ccd089219View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-1091700000-d59ac9f6004d97f50e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057s-5397500000-6b01550285f08626f009View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9170000000-63a0e6db01fb16d89f9aView in MoNA
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
FoodDB IDFDB015741
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAzorubine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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.. .