Showing Compound Chrysophanol (FDB002584)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:26 UTC

Update date

2020-02-24 19:10:33 UTC

Primary ID

FDB002584

Secondary Accession Numbers

FDB006850

Chemical Information

FooDB Name

Chrysophanol

Description

Chrysophanol, 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. Chrysophanol has been detected, but not quantified in, a few different foods, such as docks (Rumex), garden rhubarbs (Rheum rhabarbarum), and sorrels (Rumex acetosa). This could make chrysophanol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Chrysophanol.

CAS Number

481-74-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,8-Dihydroxy-3-methyl-9,10-anthracenedione	ChEBI
1,8-Dihydroxy-3-methylanthraquinone	ChEBI
3-Methylchrysazin	ChEBI
Chrysophanic acid	ChEBI
Chrysophansaeure	ChEBI
Chrysophanate	Generator
2-Methyl-4,5-dihydroxyanthraquinone	MeSH
3-Methyl-1,8-dihydroxyanthraquinone	MeSH
Chrysophanic acid, ion (1-)	MeSH
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9ci	HMDB
1,8-Dihydroxy-3-methyl-9,10-anthraquinone	HMDB
1,8-Dihydroxy-3-methyl-anthraquinone	HMDB
1,8-Dihydroxy-3-methylanthra-9,10-quinone	HMDB
3-Methyl-1, 8-dihydroxyanthraquinone	HMDB
4, 5-Dihydroxy-2-methylanthraquinone	HMDB
4,5-Dihydroxy-2-methylanthraquinone	HMDB
9,10-Anthracenedione, 1,8-dihydroxy-3-methyl- (9ci)	HMDB
Archinin	HMDB
C.I. natural yellow 23	HMDB
Chrysophanic acid (1,8-dihydroxy-3-methylanthraquinone)	HMDB
Crysophanic acid	HMDB
Crysophanol	HMDB
Rheic acid	HMDB
Rumicin	HMDB
Turkey rhubarb	HMDB
1,8-dihydroxy-3-methyl-9,10-anthracenedione	biospider
1,8-Dihydroxy-3-methyl-9,10-anthracenedione, 9CI	db_source
1,8-dihydroxy-3-methyl-9,10-anthraquinone	biospider
1,8-dihydroxy-3-methylanthra-9,10-quinone	biospider
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 23	biospider
Chrysophanol	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.08	ALOGPS
logP	4.12	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.15 m³·mol⁻¹	ChemAxon
Polarizability	25.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H10O4

IUPAC name

1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

InChI Identifier

InChI=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 Key

LQGUBLBATBMXHT-UHFFFAOYSA-N

Isomeric SMILES

CC1=CC2=C(C(O)=C1)C(=O)C1=C(C=CC=C1O)C2=O

Average Molecular Weight

254.2375

Monoisotopic Molecular Weight

254.057908808

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homopolycyclic compounds

External Descriptors

hydroxyanthraquinones (CHEBI:3687 )
Anthracenes and phenanthrenes (C10315 )
Anthraquinone type (C10315 )
Anthracenes and phenanthrenes (LMPK13040006 )
a hydroxyanthraquinone (CPD-8216 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Plant

Role

Industrial application:

Pharmaceutical industry:

Anti-inflammatory

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 70.86%; H 3.96%; O 25.17%	DFC
Melting Point	Mp 200-201° (196°)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa 8.91 (20°, H2O)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	450 (sh) (e ) (MeOH) (Derep)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Chrysophanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fc0-0690000000-d56c5b4fdcc7de967ecf	Spectrum
Predicted GC-MS	Chrysophanol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05gi-2359000000-d3bd8223a5923410d2a4	Spectrum
Predicted GC-MS	Chrysophanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0090000000-0a16efeb6df65aacacef	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0190000000-10812e976b35a4eda862	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0490000000-c9aef7073169bd80cd2e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-9ac1e0a42128dea2cf82	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0900000000-cff9163f34bb1966a807	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0190000000-10812e976b35a4eda862	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0490000000-c9aef7073169bd80cd2e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-d81a22c668d9038b248b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-9ac1e0a42128dea2cf82	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-cff9163f34bb1966a807	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-e07dfb1bc89242872bd7	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-15cdaa0757dfee20a1cc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-5950000000-e1a059b73e79aff8e23e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-82cd0ac4ea31f7614f40	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-d6372d233a8f6a5cbadb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbc-4970000000-8ac19f70333bd7440cef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-88382720cb3b98a4d462	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-e08fea207b7939b57f6d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1940000000-45b0989f4038017840e8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-ff2e7266db5d933feb85	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-ff2e7266db5d933feb85	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0h00-0590000000-c8e0292c61de829d2a42	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

3687

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30670

CRC / DFC (Dictionary of Food Compounds) ID

CMM74-G:CMM74-G

EAFUS ID

Not Available

Dr. Duke ID

CHRYSOPHANOL|CHRYSOPHANIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00000568

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
candidicide			DUKE
cathartic	75325	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
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hemostat			DUKE
keratitigenic			DUKE
occuloirritant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
pigment	26130	An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.	DUKE
purgative	50503	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
termitifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE