Orcein (CHEM033097)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:55:43 UTC
Update Date2016-11-09 01:20:51 UTC
Accession NumberCHEM033097
Identification
Common NameOrcein
ClassSmall Molecule
DescriptionOrcein, also archil, orchil, lacmus and C.I. Natural Red 28, are names for dyes extracted from several species of lichen, commonly known as "orchella weeds", found in various parts of the world. A major source is the archil lichen, Roccella tinctoria. Orcinol is extracted from such lichens. It is then converted to orcein by ammonia and air. In traditional dye-making methods, urine was used as the ammonia source. If the conversion is carried out in the presence of potassium carbonate, calcium hydroxide, and calcium sulfate (in the form of potash, lime, and gypsum in traditional dye-making methods), the result is litmus, a more complex molecule. The manufacture was described by Cocq in 1812 and in the UK in 1874. Edmund Roberts noted orchilla as a principal export of the Cape Verde islands, superior to the same kind of "moss" found in Italy or the Canary Islands, that in 1832 was yielding an annual revenue of $200,000.: pp.14, 15  Commercial archil is either a powder (called cudbear) or a paste. It is red in acidic pH and blue in alkaline pH.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
PAceinMeSH
C.I. natural red 28HMDB
NSC 610930ChEBI
OrceinMeSH
Chemical FormulaC28H24N2O7
Average Molecular Mass500.499 g/mol
Monoisotopic Mass500.158 g/mol
CAS Registry NumberNot Available
IUPAC Name4,12-bis[(2,4-dihydroxy-6-methylphenyl)amino]-3,13-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1,3,6,9,12-pentaene-5,11-dione
Traditional Name4,12-bis[(2,4-dihydroxy-6-methylphenyl)amino]-3,13-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1,3,6,9,12-pentaene-5,11-dione
SMILESCC1=CC(O)=CC(O)=C1NC1=C(C)C2=C3C(OC2=CC1=O)=CC(=O)C(NC1=C(O)C=C(O)C=C1C)=C3C
InChI IdentifierInChI=1S/C28H24N2O7/c1-11-5-15(31)7-17(33)25(11)29-27-13(3)23-21(9-19(27)35)37-22-10-20(36)28(14(4)24(22)23)30-26-12(2)6-16(32)8-18(26)34/h5-10,29-34H,1-4H3
InChI KeyVPEASJIRGSVXBF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • P-aminophenol
  • O-aminophenol
  • Aminotoluene
  • Aniline or substituted anilines
  • Resorcinol
  • M-cresol
  • Aminophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Secondary ketimine
  • Furan
  • Azomethine
  • Cyclic ketone
  • Ketone
  • Ketimine
  • Oxacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.039 g/LALOGPS
logP4.14ALOGPS
logP3.17ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.35 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity146.3 m³·mol⁻¹ChemAxon
Polarizability53.16 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0632920000-123dd4ad3a506a96a39dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-2330029000-852e97f1e2e24eb53623Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000190000-36b73a203923997d9eccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0225790000-14fd8705726174ab45bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1904400000-ab7844f6af08a959f022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-04502af16d5e9088017cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0001900000-a135eb875b7008ed9040Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3900300000-0ede7f8faee4e358d05fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000090000-8aee1d79240e4c0d58aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0202490000-8255fed7cac1bd77a92bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ei-0305900000-cf3c7de19607cd988dc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0001900000-93cbe327dbf43898f8ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0000900000-90727d3b11cb75be3cafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1009400000-742fe1b2998d483ad751Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOrcein
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID72685
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available