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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O4
Molecular Weight 254.2375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHRYSOPHANIC ACID

SMILES

CC1=CC(O)=C2C(=O)C3=C(C=CC=C3O)C(=O)C2=C1

InChI

InChIKey=LQGUBLBATBMXHT-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H10O4
Molecular Weight 254.2375
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Chrysophanic acid (Chrysophanol) is a member of the anthraquinone family abundant in rhubarb, a widely used herb for obesity treatment in Traditional Korean Medicine. Chrysophanol has been shown to induce cell death in different types of cancer cells. Chrysophanol inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol also effectively suppresses breast cancer cell proliferation and facilitates chemosentivity through modulation of the NF-κB signaling pathway. A treatment of chrysophanol could reduce significantly the clinical signs and the levels of inflammatory mediators in a colitis model caused by DSS treatment. The anti-inflammatory activities of chrysophanol could be attributed, at least in part, to the inhibition of proinflammatory cytokine production (TNF-α and IL-6), COX-2, and iNOS protein expression. These effects of chrysophanol are caused by the inhibition of LPS-induced NF-κB activation, IκB-α degradation, and caspase-1 activation. These results provide experimental evidence showing that chrysophanol might prove useful in the treatment of inflammatory diseases.

Approval Year

TargetsConditions
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
11.7%
CHRYSOPHANIC ACID plasma
Homo sapiens
PubMed

PubMed

TitleDatePubMed
Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus.
1992 Jan
[Studies on the chemical constituents of Evodia rutaecarpa (Juss.) Benth. var. officinalis (Dode) Huang].
2001 Oct
[Studies on the chemical constituents in root of Rheum rhizastachyum].
2002 Apr
Emodin induces apoptosis in human promyeloleukemic HL-60 cells accompanied by activation of caspase 3 cascade but independent of reactive oxygen species production.
2002 Dec 15
[Studies on the chemical constituents of the stems of Alyxia sinensis (I)].
2002 Feb
[Study on the quantitative change of anthraquinonoids of Rhei in the preparation of dachengqi].
2002 Jan
Simultaneous determination of hydroxyanthraquinones in rhubarb and experimental animal bodies by high-performance liquid chromatography.
2003 Aug
Sulfemodin 8-O-beta-D-glucoside, a new sulfated anthraquinone glycoside, and antioxidant phenolic compounds from Rheum emodi.
2003 Aug
Cynodontin: a fungal metabolite with antifungal properties.
2003 Aug 13
Transcriptional suppression of the HIV promoter by natural compounds.
2003 Mar
Bhimamycin A to approximately E and bhimanone: isolation, structure elucidation and biological activity of novel quinone antibiotics from a terrestrial Streptomycete.
2003 Nov
[Study on releasing rate of chrysophanol from Ruyi Jinhuang plaster].
2004 Aug
Microbial glycosylation of four free anthraquinones by Absidia coerulea.
2004 Jan
Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru.
2004 Mar
Evaluation of Rhubarb using antioxidative activity as an index of pharmacological usefulness.
2004 Mar
Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process.
2004 Nov 19
Chrysophanol glycosides from callus cultures of monocotyledonous Kniphofia spp. (Asphodelaceae).
2004 Oct
Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography.
2004 Oct 15
[Studies on the chemical constituents in herb of Mentha haplocalyx].
2005 Jul
[Influence of processing rhubarb on it's anthraquinone contents].
2005 Jun
[Study on the optimal harvesting time of Rumex gmelini by analyzing the contents of principal components].
2005 Jun
High-performance thin layer chromatography method for quantitative determination of four major anthraquinone derivatives in Rheum emodi.
2005 Jun 10
Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis.
2005 May
[Study on the selection of crude drugs of rhubarb dispensing granule].
2006 Apr
PTP1B inhibitors from Saussrurea lappa.
2006 Apr-May
Determination of five anthraquinones in medicinal plants by capillary zone electrophoresis with beta-cyclodextrin addition.
2006 Aug 4
[Comparative studies on purgative potency among three spieces of certified rhubarb].
2006 Dec
[Studies on chemical constituents of hairy root of Cassia obtusifolia].
2006 Feb
[Simultaneous determination of resveratrol, emodin, chrysophanol, physcion, in root of Polygonam cuspidatum and its extract by HPLC].
2006 Feb
[Simultaneous determination of three kinds of components in sanhuang tablets by high-performance liquid chromatography].
2006 Mar
[Isolation of the chemical constituents from Shuanghuanglian injection and their structural identification].
2006 Oct
Isolation and synthesis of analgesic and anti-inflammatory compounds from Ochna squarrosa L.
2006 Oct 15
Preparative isolation and purification of hydroxyanthraquinones from Rheum tanguticum Maxim. on normal phase silica gel: using a Flash Master Personal system.
2007
[Comparative study on in vitro drug-release between Tuizhang ophthalmic gel and Tuizhang oculentum].
2007 Apr
Efficient isolation of anthraquinone-derivatives from Trichoderma harzianum ETS 323.
2007 Apr 10
Ferulic acid esters from Euphorbia hylonoma.
2007 Jan
Monodictyquinone A: a new antimicrobial anthraquinone from a sea urchin-derived fungus Monodictys sp.
2007 Jul
Simultaneous determination and pharmacokinetic studies of aloe emodin and chrysophanol in rats after oral administration of Da-Cheng-Qi decoction by high-performance liquid chromatography.
2007 Jul
Alvaradoins E-N, antitumor and cytotoxic anthracenone C-glycosides from the leaves of Alvaradoa haitiensis.
2007 Jun
Antiprotozoal activity of Senna racemosa.
2007 Jun 13
Chemical constituents from the roots of Homonoia riparia.
2007 Mar
Simultaneous determination of anthraquinones in rhubarb by high-performance liquid chromatography and capillary electrophoresis.
2007 Mar 23
Anthraquinones, Cdc25B phosphatase inhibitors, isolated from the roots of Polygonum multiflorum Thunb.
2007 May 20
Preparation of 1,8-di-O-alkylaloe-emodins and 15-amino-, 15-thiocyano-, and 15-selenocyanochrysophanol derivatives from aloe-emodin and studying their cytotoxic effects.
2008 Apr
Simultaneous determination of eight major bioactive compounds in Dachengqi Tang (DT) by high-performance liquid chromatography.
2008 Apr 29
Development and validation of a UPLC method for quality control of rhubarb-based medicine: fast simultaneous determination of five anthraquinone derivatives.
2008 Aug 5
Determination of pharmacologically active compounds in root extracts of Cassia alata L. by use of high performance liquid chromatography.
2008 Jan 15
Paeciloxanthone, a new cytotoxic xanthone from the marine mangrove fungus Paecilomyces sp. (Tree1-7).
2008 Jan-Feb
Simultaneous determination of anthraquinones in radix Polygoni multiflori by capillary gas chromatography coupled with flame ionization and mass spectrometric detection.
2008 Jul 18
Lipoxygenase inhibitory constituents from rhubarb.
2008 May
Patents

Sample Use Guides

Experimental colitis in mice was induced by a 5% DSS dissolved in the drinking water for 7 days. Chrysophanol was administered at doses of 5 mg/kg once a day for 7 days prior to 5% DSS supplement.
Route of Administration: Oral
Chrysophanol (80 and 120 uM) significantly blocks cell proliferation when combined with the mTOR inhibitor, Rapamycin. Chrysophanol inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K, and significantly blocks cell proliferation. Chrysophanol dose dependently decreases CCK-8 and the viability of EGFR-overexpressing SNU-C5 cells. Chrysophanol treatment dose-dependently decreases EGF induced phosphorylation of EGFR at Tyr1068. Chrysophanol (80 and 120 uM) reduces the phosphorylation levels of mTOR at Ser2448. Chrysophanol (80 and 120 uM) also decreases the phosphorylation levels of p70S6K at Thr389.
Substance Class Chemical
Created
by admin
on Wed Apr 02 17:55:58 GMT 2025
Edited
by admin
on Wed Apr 02 17:55:58 GMT 2025
Record UNII
N1ST8V8RR2
Record Status Validated (UNII)
Record Version
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Name Type Language
CHRYSOPHANOL
INCI  
Preferred Name English
CHRYSOPHANIC ACID
MI   WHO-DD  
Common Name English
CHRYSOPHANIC ACID [MI]
Common Name English
4,5-DIHYDROXY-2-METHYLANTHRAQUINONE
Systematic Name English
3-METHYLCHRYSAZIN
Common Name English
1,8-DIHYDROXY-3-METHYL-9,10-ANTHRACENEDIONE
Systematic Name English
NSC-37132
Code English
C.I. NATURAL YELLOW 23
Code English
NSC-646567
Code English
2-METHYL-4,5-DIHYDROXYANTHRAQUINONE
Systematic Name English
C.I. 75400
Code English
Chrysophanic acid [WHO-DD]
Common Name English
1,8-DIHYDROXY-3-METHYLANTHRAQUINONE
Systematic Name English
3-METHYL-1,8-DIHYDROXYANTHRAQUINONE
Systematic Name English
Code System Code Type Description
MERCK INDEX
m3532
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID6024832
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
FDA UNII
N1ST8V8RR2
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
MESH
C027113
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
CHEBI
3687
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
SMS_ID
100000126027
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
CAS
481-74-3
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-572-2
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
PUBCHEM
10208
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
NSC
37132
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
WIKIPEDIA
Chrysophanic acid
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
EVMPD
SUB33000
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
NSC
646567
Created by admin on Wed Apr 02 17:55:58 GMT 2025 , Edited by admin on Wed Apr 02 17:55:58 GMT 2025
PRIMARY
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