Rose bengal (CHEM030278)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:47:12 UTC
Update Date2016-11-09 01:19:02 UTC
Accession NumberCHEM030278
Identification
Common NameRose bengal
ClassSmall Molecule
DescriptionA xanthene dye that is fluorescein bearing bromine substituents at positions 2', 4', 5' and 7' (on the xanthene ring) and iodine substituents at position 2, 3, 4, and 5 (on the phenyl ring). The dipotassium salt is the biological stain 'rose bengal'.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2',4',5',7'-Tetrabromo-2,3,4,5-tetraiodofluoresceinChEBI
3,4,5,6-tetrachloro-2',4',5',7'-Tetraiodofluorescein, 8ciHMDB
4,5,6,7-tetrachloro-3',6'-Dihydroxy-2',4',5',7'-tetraiodospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 9ciHMDB
Ak-rose liq 1%HMDB
C.I. 45440HMDB
C.I. solvent red 141HMDB
Bengal, roseMeSH
Rose bengalMeSH
Rose bengal sodium I 125MeSH
Rose bengal sodium I 131MeSH
Chemical FormulaC20H4Cl4I4O5
Average Molecular Mass973.673 g/mol
Monoisotopic Mass971.499 g/mol
CAS Registry Number11121-48-5
IUPAC Name2,3,4,5-tetrachloro-6-(6-hydroxy-2,4,5,7-tetraiodo-3-oxo-3H-xanthen-9-yl)benzoic acid
Traditional Namerose bengal
SMILESOC(=O)C1=C(C(Cl)=C(Cl)C(Cl)=C1Cl)C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C12
InChI IdentifierInChI=1S/C20H4Cl4I4O5/c21-10-8(9(20(31)32)11(22)13(24)12(10)23)7-3-1-5(25)16(29)14(27)18(3)33-19-4(7)2-6(26)17(30)15(19)28/h1-2,29H,(H,31,32)
InChI KeyVDNLFJGJEQUWRB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentXanthenes
Alternative Parents
Substituents
  • Xanthene
  • 2-halobenzoic acid or derivatives
  • 3-halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 2-halobenzoic acid
  • 3-halobenzoic acid
  • 4-halobenzoic acid
  • Halobenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzoyl
  • 2-iodophenol
  • 1-carboxy-2-haloaromatic compound
  • Chlorobenzene
  • Halobenzene
  • Monocyclic benzene moiety
  • Aryl iodide
  • Aryl halide
  • Benzenoid
  • Aryl chloride
  • Vinylogous halide
  • Heteroaromatic compound
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organochloride
  • Organoiodide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00068 g/LALOGPS
logP6.02ALOGPS
logP9.26ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)2.52ChemAxon
pKa (Strongest Basic)1.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity176.05 m³·mol⁻¹ChemAxon
Polarizability63.8 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000009-f3bf8c5a3e0f0a0853fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000009-66093dd459c6362a7d97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-1000000009-2e8b9a120af756884330Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000009-db1a74d9f739e534146dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-0000000009-29def3b73f15b66f7561Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-0000000019-a195e1189bd1f1119c6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000000009-4d514593d08da0819fbaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000000009-cb8d88946ddbbd8b9e9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0000000119-bd361297dc21f404f385Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000000009-f3e6775ccbb7efabbbe2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000000009-6240466616fe0b78d3a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v4l-0000000019-0a9443190bf8c294261bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036613
FooDB IDFDB015529
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRose bengal
Chemspider ID23774
ChEBI ID87202
PubChem Compound ID25474
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Roat MI, Romanowski E, Araullo-Cruz T, Gordon YJ: The antiviral effects of rose bengal and fluorescein. Arch Ophthalmol. 1987 Oct;105(10):1415-7.
2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.