Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-02-24 19:10:33 UTC
Primary IDFDB002584
Secondary Accession Numbers
  • FDB006850
Chemical Information
FooDB NameChrysophanol
DescriptionChrysophanol, also known as chrysophanic acid or 3-methylchrysazin, belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Thus, chrysophanol is considered to be an aromatic polyketide lipid molecule. Chrysophanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Chrysophanol has been detected, but not quantified in, a few different foods, such as docks, garden rhubarbs, and sorrels. This could make chrysophanol a potential biomarker for the consumption of these foods.
CAS Number481-74-3
Structure
Thumb
Synonyms
SynonymSource
1,8-Dihydroxy-3-methyl-9,10-anthracenedioneChEBI
1,8-Dihydroxy-3-methylanthraquinoneChEBI
3-MethylchrysazinChEBI
Chrysophanic acidChEBI
ChrysophansaeureChEBI
ChrysophanateGenerator
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9ciHMDB
1,8-Dihydroxy-3-methyl-9,10-anthraquinoneHMDB
1,8-Dihydroxy-3-methyl-anthraquinoneHMDB
1,8-Dihydroxy-3-methylanthra-9,10-quinoneHMDB
2-Methyl-4,5-dihydroxyanthraquinoneHMDB
3-Methyl-1, 8-dihydroxyanthraquinoneHMDB
3-Methyl-1,8-dihydroxyanthraquinoneHMDB
4, 5-Dihydroxy-2-methylanthraquinoneHMDB
4,5-Dihydroxy-2-methylanthraquinoneHMDB
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9ci)HMDB
ArchininHMDB
C.I. natural yellow 23HMDB
Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)HMDB
Crysophanic acidHMDB
CrysophanolHMDB
Rheic acidHMDB
RumicinHMDB
Turkey rhubarbHMDB
Chrysophanic acid, ion (1-)HMDB
1,8-dihydroxy-3-methyl-9,10-anthracenedionebiospider
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9CIdb_source
1,8-dihydroxy-3-methyl-9,10-anthraquinonebiospider
1,8-dihydroxy-3-methylanthra-9,10-quinonebiospider
9,10-Anthracenedione, 1, 8-dihydroxy-3-methyl-biospider
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl-biospider
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9CI)biospider
Anthraquinone, 1,8-dihydroxy-3-methyl-biospider
C.I. Natural Yellow 23biospider
Chrysophanoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP3.08ALOGPS
logP4.12ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.14ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.15 m³·mol⁻¹ChemAxon
Polarizability25.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H10O4
IUPAC name1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
InChI IdentifierInChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
InChI KeyLQGUBLBATBMXHT-UHFFFAOYSA-N
Isomeric SMILESCC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O
Average Molecular Weight254.2375
Monoisotopic Molecular Weight254.057908808
Classification
Description belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentAnthraquinones
Alternative Parents
Substituents
  • Anthraquinone
  • 9,10-anthraquinone
  • 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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.86%; H 3.96%; O 25.17%DFC
Melting PointMp 200-201° (196°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 8.91 (20°, H2O)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data450 (sh) (e ) (MeOH) (Derep)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fc0-0690000000-d56c5b4fdcc7de967ecfJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05gi-2359000000-d3bd8223a5923410d2a4JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-0a16efeb6df65aacacefJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0190000000-10812e976b35a4eda862JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0490000000-c9aef7073169bd80cd2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-9ac1e0a42128dea2cf82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0900000000-cff9163f34bb1966a807JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-e07dfb1bc89242872bd7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-15cdaa0757dfee20a1ccJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-5950000000-e1a059b73e79aff8e23eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-82cd0ac4ea31f7614f40JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-d6372d233a8f6a5cbadbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-4970000000-8ac19f70333bd7440cefJSpectraViewer
ChemSpider ID9793
ChEMBL IDCHEMBL41092
KEGG Compound IDC10315
Pubchem Compound ID10208
Pubchem Substance IDNot Available
ChEBI ID3687
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30670
CRC / DFC (Dictionary of Food Compounds) IDCMM74-G:CMM74-G
EAFUS IDNot Available
Dr. Duke IDCHRYSOPHANOL|CHRYSOPHANIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000568
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
candidicideDUKE
cathartic75325 Any substance that accelerates defecation. Compare with laxatives, which are substances that ease defecation (usually by softening faeces). A substance can be both a laxative and a cathartic.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
hemostatDUKE
keratitigenicDUKE
occuloirritantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
purgative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
termitifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.