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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:27 UTC
Update Date2022-03-07 02:53:07 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
N-[9-(2-Carboxyphenyl)-6-(diethylamino)-3H-xanthen-3-ylidene]-N-ethylethanaminiumChEBI
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
RhodaminesHMDB
Rhodamine bHMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.79431661259
DarkChem[M-H]-202.59631661259
DeepCCS[M+H]+210.15430932474
DeepCCS[M-H]-207.75830932474
DeepCCS[M-2H]-240.64230932474
DeepCCS[M+Na]+216.06630932474
AllCCS[M+H]+206.832859911
AllCCS[M+H-H2O]+204.432859911
AllCCS[M+NH4]+208.932859911
AllCCS[M+Na]+209.532859911
AllCCS[M-H]-209.832859911
AllCCS[M+Na-2H]-210.332859911
AllCCS[M+HCOO]-211.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Rhodamine BCCN(CC)C1=CC2=[O+]C3=CC(=CC=C3C(=C2C=C1)C1=C(C=CC=C1)C(O)=O)N(CC)CC4921.0Standard polar33892256
Rhodamine BCCN(CC)C1=CC2=[O+]C3=CC(=CC=C3C(=C2C=C1)C1=C(C=CC=C1)C(O)=O)N(CC)CC3640.5Standard non polar33892256
Rhodamine BCCN(CC)C1=CC2=[O+]C3=CC(=CC=C3C(=C2C=C1)C1=C(C=CC=C1)C(O)=O)N(CC)CC3938.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rhodamine B,1TMS,isomer #1CCN(CC)C1=CC=C2C(C3=CC=CC=C3C(=O)O[Si](C)(C)C)=C3C=CC(N(CC)CC)=CC3=[O+]C2=C13682.8Semi standard non polar33892256
Rhodamine B,1TBDMS,isomer #1CCN(CC)C1=CC=C2C(C3=CC=CC=C3C(=O)O[Si](C)(C)C(C)(C)C)=C3C=CC(N(CC)CC)=CC3=[O+]C2=C13876.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rhodamine B GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0201900000-6ddae7ec527f63d822582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rhodamine B GC-MS (1 TMS) - 70eV, Positivesplash10-004s-2000910000-f514b6402bfea591b5c42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rhodamine B 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 - Rhodamine B 10V, Positive-QTOFsplash10-0006-0000900000-2fdde36060a9fe4402622016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 20V, Positive-QTOFsplash10-00kg-0000900000-9c87be1c845dc583a6542016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 40V, Positive-QTOFsplash10-00ba-6113900000-d8bc00aae3733b2999742016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 10V, Negative-QTOFsplash10-0006-0000900000-410660bd6e9676b52dea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 20V, Negative-QTOFsplash10-0006-1000900000-eb15465a3f6f966326f32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 40V, Negative-QTOFsplash10-006x-9002400000-16b1da2c93179f10c79b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 10V, Positive-QTOFsplash10-00kg-0003900000-580a90bf751eaa24e3252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 20V, Positive-QTOFsplash10-0007-0006900000-7a20165467799e0cafd72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rhodamine B 40V, Positive-QTOFsplash10-01ta-0009200000-b43e0a84f39a698847132021-09-23Wishart LabView Spectrum
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 IDNot Available
Good Scents IDNot Available
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.. .