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

• ChemBase ID: 73025
• Molecular Formular: C15H10O4
• Molecular Mass: 254.2375
• Monoisotopic Mass: 254.0579088
• SMILES: c1cc(c2c(c1)C(=O)c1c(C2=O)c(cc(c1)C)O)O
• Canonical SMILES: Cc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)ccc1
• InChI: 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
• InChIKey: LQGUBLBATBMXHT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
• IUPAC Traditional name: turkey rhubarb; 1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
• Synonyms: Chrysophanol; NSC 37132; NSC 646567; Chrysophanic acid; Chrysophanic acid; 1,8-Dihydroxy-3-methylanthraquinone; 1,8-Dihydroxy-3-methyl-9,10-anthracenedione; 1,8-Dihydroxy-3-methylanthraquinone; 3-Methylchrysazin; Rheic acid; Archinin; Rumicin; Chrysophanol

Database IDs

• CAS Number: 481-74-3
• EC Number: 207-572-2
• MDL Number: MFCD00001208
• Beilstein Number: 1252300
• PubChem SID: 24853726; 162037945
• PubChem CID: 10208

CALCULATED PROPERTIES

• Acid pKa: 7.9404755
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.1234355
• LogD (pH = 7.4): 4.0098643
• Log P: 4.1249967
• Molar Refractivity: 70.154 cm^3
• Polarizability: 26.28563 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Yellow powder

Safety Information

• Storage Condition: -20°C
• RTECS: CB6725000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: EGFR(HER) / mTOR
• Gene Information: human ... ELA2(1991)
• Mechanism of Action: Inhibitor of phosphoinositide- 3-kinase (PI3K)/AKT; Monoamine oxidase inhibitor

Product Information

• Purity: 98%
• Salt Data: Free Base
• Biological Source: Constit. of Cassia, Rumex, Rheum, Asphodelus and Muehlenbeckia spp., etc. Also isol. from Monilinia fructicola. V. widely distributed
• Application(s): Antimicrobial; Cathartic agent
• Empirical Formula (Hill Notation): C15H10O4

DETAILS

MP Biomedicals - 05203909

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2406

Research Area: Cancer
Biological Activity:
Chrysophanic acid (Chrysophanol) is a EGFR/mTOR pathway inhibitor. Chrysophanic acid (Chrysophanol) is a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid (Chrysophanol) preferentially blocked proliferation in SNU-C5 cells but not in other cell lines (HT7, HT29, KM12C, SW480, HCT116 and SNU-C4) with low levels of EGFR expression. Chrysophanic acid (Chrysophanol) treatment in SNU-C5 cells inhibited EGF-induced phosphorylation of EGFR and suppressed activation of downstream signaling molecules, such as AKT, extracellular signal-regulated kinase (ERK) and the mammalian target of rapamycin (mTOR)/ribosomal protein S6 kinase (p70S6K). Chrysophanic acid (80 and 120 µM) significantly blocked cell proliferation when combined with the mTOR inhibitor, rapamycin. [1]References on Chrysophanic acid (Chrysophanol)[1] Phytother. Res, 2010,

Sigma Aldrich - 229075

Packaging
1 g in glass bottle
50 mg in glass bottle
Application
Chrysophanic acid, a natural anthraquinone, is used to study anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells 1. It is also used to study the inhibition of replication of poliovirus types 2 and 3 (Picornaviridae) in vitro 2.
Biochem/physiol Actions
Anticancer activity for chrysophanic acid is via the EGFR/mTOR mediated signaling transduction pathway 1. Chrysophanic acid has two hydrophobic positions on the molecule (C-6 and the methyl group attached to C-3) which are responsible for the compound′s activity against poliovirus 2.

Toronto Research Chemicals - C432675

A topical ointment used in the treatment of dermal conditions such as eczema and herpes.

REFERENCES

• Lee MS et al. Phytother Res. 2010 Nov 19. doi: 10.1002/ptr.3323.
• McDougall, G., et al.: Food Chem., 119, 758 (2009)
• Lu, B., et al.: Phytochem. Anal., 20, 385 (2009)
• Liang, X., et al.: J. Pharm. Biomed. Anal., 51, 565 (2009)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 88A, (ir)
• King, F.E. et al., J.C.S., 1952, 4580, (synth)
• Bloom, H. et al., J.C.S., 1959, 178, (ir)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, no. 1254, (occur)
• Labadie, R.P., Pharm. Weekbl., 1972, 107, 535, (occur)
• Rizk, A.M. et al., Phytochemistry, 1972, 11, 2122, (deriv)
• Banville, J. et al., Can. J. Chem., 1974, 52, 80, (synth, uv, pmr)
• Harris, T.M. et al., J.A.C.S., 1976, 98, 6065, (synth)
• Kraus, G.A. et al., J.O.C., 1983, 48, 3439, (synth)
• Kelly, T.R. et al., J.O.C., 1983, 48, 3573, (isol)
• Anderson, J.A. et al., Phytochemistry, 1986, 25, 103, (biosynth)
• Ahmed, S.A. et al., Chem. Comm., 1987, 883, (synth)
• Thomson, W.H., Naturally Occurring Quinones, Recent Advances, Chapman and Hall, 1987, (occur)
• Sassa, T. et al., Agric. Biol. Chem., 1991, 55, 95, (isol)
• Danielsen, K. et al., Magn. Reson. Chem., 1992, 30, 359, (pmr, cmr)
• Schmidt, R.R. et al., Synthesis, 1994, 255, (synth, pmr)
• Schripsema, J. et al., Phytochemistry, 1996, 42, 177, (pmr, struct)