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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:27 UTC
Update Date2020-06-24 19:24:19 UTC
HMDB IDHMDB0031786
Secondary Accession Numbers
  • HMDB31786
Metabolite Identification
Common NameRhodamine B
DescriptionRhodamine B (RhB), also known as rhodamine 610 chloride (CAS: 81-88-9), 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. Rhodamine B is a highly-soluble, basic, red, synthetic dye that is widely used in many industries (e.g. paper, plastic, textiles, ceramics, cosmetics). In the past, it was used extensively as a low-cost food colourant (e.g. in paprika- and chilli-containing foods) but it has since been prohibited for use as a food additive due to its carcinogenicity, reproductive and developmental toxicity, and neurotoxicity (PMID: 30463493 ). Due to its photostability and solubility, rhodamine B is also used as a fluorescent dye to stain biological tissues (PMID: 28957318 ).
Structure
Data?1593026659
Synonyms
ValueSource
Rhodamine b cationChEBI
81-88-9 (CHLORIDE)HMDB
9-(2-Carboxyphenyl)-3,6-bis(diethylamino)-xanthyliumHMDB
9-(2-Carboxyphenyl)-3,6-bis(diethylamino)xanthyliumHMDB
9-(2-Carboxyphenyl)-3,6-bis(diethylamino)xanthylium(1+), 9ciHMDB
Basazol red 71PHMDB
Basic rose redHMDB
Basic violet 10HMDB
C.I. 45170HMDB
C.I. basic violet 10HMDB
C.I. FOOD red 15HMDB
C.I. solvent red 49HMDB
Calcozine red BXHMDB
Calcozine rhodamine BXPHMDB
Cerise toner X 1127HMDB
D And C red 19HMDB
Eriosin rhodamine bHMDB
FOOD Red 15HMDB
N-[9-(2-Carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminium(1+), 9ciHMDB
Pilot 578HMDB
RhodamineHMDB
Rhodamine 610HMDB
Rhodamine b monocationHMDB
Rhodamine b(1+)HMDB
Rhodamine lake red bHMDB
TetraethylrhodamineHMDB
Rhodamine bHMDB
RhodaminesMeSH
Chemical FormulaC28H31N2O3
Average Molecular Weight443.5573
Monoisotopic Molecular Weight443.233467868
IUPAC Name9-(2-carboxyphenyl)-6-(diethylamino)-N,N-diethyl-3H-xanthen-3-iminium
Traditional Namerhodamine B(1+)
CAS Registry Number64381-98-2
SMILES
CCN(CC)C1=CC2=[O+]C3=CC(=CC=C3C(=C2C=C1)C1=C(C=CC=C1)C(O)=O)N(CC)CC
InChI Identifier
InChI=1S/C28H30N2O3/c1-5-29(6-2)19-13-15-23-25(17-19)33-26-18-20(30(7-3)8-4)14-16-24(26)27(23)21-11-9-10-12-22(21)28(31)32/h9-18H,5-8H2,1-4H3/p+1
InChI KeyCVAVMIODJQHEEH-UHFFFAOYSA-O
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
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Tertiary aliphatic/aromatic amine
  • Dialkylarylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Tertiary amine
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Role

Industrial application:

Indirect biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00046 g/LALOGPS
logP5.95ALOGPS
logP1.78ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.5ChemAxon
pKa (Strongest Basic)4.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.78 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity157.92 m³·mol⁻¹ChemAxon
Polarizability51.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0201900000-6ddae7ec527f63d82258Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004s-2000910000-f514b6402bfea591b5c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-2fdde36060a9fe440262Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kg-0000900000-9c87be1c845dc583a654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ba-6113900000-d8bc00aae3733b299974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-410660bd6e9676b52deaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1000900000-eb15465a3f6f966326f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9002400000-16b1da2c93179f10c79bSpectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB008459
KNApSAcK IDNot Available
Chemspider ID6440
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRhodamine B
METLIN IDNot Available
PubChem Compound6695
PDB IDNot Available
ChEBI ID52896
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wang M, Nie X, Tian L, Hu J, Yin D, Qiao H, Li T, Li Y: Rhodamine B in spices determined by a sensitive UPLC-MS/MS method. Food Addit Contam Part B Surveill. 2019 Mar;12(1):59-64. doi: 10.1080/19393210.2018.1548504. Epub 2018 Nov 21. [PubMed:30463493 ]
  2. Johnson BJ, Mitchell SN, Paton CJ, Stevenson J, Staunton KM, Snoad N, Beebe N, White BJ, Ritchie SA: Use of rhodamine B to mark the body and seminal fluid of male Aedes aegypti for mark-release-recapture experiments and estimating efficacy of sterile male releases. PLoS Negl Trop Dis. 2017 Sep 28;11(9):e0005902. doi: 10.1371/journal.pntd.0005902. eCollection 2017 Sep. [PubMed:28957318 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .