9,10-Anthracenedione, 1,2-dihydroxy- (CHEM014788)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:36:01 UTC
Update Date2016-11-09 01:15:05 UTC
Accession NumberCHEM014788
Identification
Common Name9,10-Anthracenedione, 1,2-dihydroxy-
ClassSmall Molecule
DescriptionA dihydroxyanthraquinone that is anthracene-9,10-dione in which the two hydroxy groups are located at positions 1 and 2.
Contaminant Sources
  • HPV EPA Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-AnthraquinonediolChEBI
1,2-Dihydroxy-9,10-anthraquinoneChEBI
1,2-Dihydroxyanthra-9,10-quinoneChEBI
1,2-DihydroxyanthraquinoneChEBI
Alizarin bChEBI
Alizarin redChEBI
AzChEBI
C.I. 58000ChEBI
Dihydroxy-9,10-anthracenedioneChEBI
DihydroxyanthraquinoneChEBI
Mordant red 11ChEBI
Pigment red 83ChEBI
Turkey redChEBI
AlizarineHMDB
Chemical FormulaC14H8O4
Average Molecular Mass240.214 g/mol
Monoisotopic Mass240.042 g/mol
CAS Registry Number72-48-0
IUPAC Name1,2-dihydroxy-9,10-dihydroanthracene-9,10-dione
Traditional Namealizarin
SMILESOC1=C(O)C2=C(C=C1)C(=O)C1=CC=CC=C1C2=O
InChI IdentifierInChI=1S/C14H8O4/c15-10-6-5-9-11(14(10)18)13(17)8-4-2-1-3-7(8)12(9)16/h1-6,15,18H
InChI KeyRGCKGOZRHPZPFP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentHydroxyanthraquinones
Alternative Parents
Substituents
  • Hydroxyanthraquinone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Vinylogous acid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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 Solubility0.27 g/LALOGPS
logP3.03ALOGPS
logP2.96ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.5ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.11 m³·mol⁻¹ChemAxon
Polarizability23.33 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dr-0690000000-80a87c0c266307f6a3dbSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0090000000-a13edc68da0469d9a585Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-9a7be129e70f277530d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0290000000-ac4df11c5e3ccdbd6771Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0090000000-9f0abc04c948c3b0bf15Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03di-0890000000-9d29746b8cec88a717e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-0900000000-af9c6be9864c111515b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-0980000000-da2637905a1280746099Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0790000000-4a1cf7ad94370666ff5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-a2f666ff7db73d22d0caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-697c72cc8f95edcc45ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5i-2940000000-250411d89e3ab5eab95aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-ffc6344f48ef3652df86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-ffc6344f48ef3652df86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0920000000-be1440062c576addc535Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-ed2dff1a72ec211ca300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0590000000-4534979944e608528f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-107i-5930000000-a9f254df85164444e7acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-8c788adea9f79f33ff40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0090000000-8c788adea9f79f33ff40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1159-5960000000-141a3df76daddcfe388eSpectrum
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 IDHMDB0248144
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002785
BiGG IDNot Available
BioCyc IDALIZARIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlizarin
Chemspider ID6056
ChEBI ID16866
PubChem Compound ID6293
Kegg Compound IDC01474
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14500876
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1650428
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16851024
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23225693
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25025314
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25497981
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25651191
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=26178874
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=26763935
10. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.