Chrysophanic acid

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MedKoo CAT#: 401220

CAS#: 481-74-3

Description: Chrysophanic acid (Chrysophanol ) is a a natural anthraquinone, has anticancer activity in EGFR-overexpressing SNU-C5 human colon cancer cells. Chrysophanic acid 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 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. These findings offer the first evidence of anticancer activity for chrysophanic acid via EGFR/mTOR mediated signaling transduction pathway.

Chemical Structure

Chrysophanic acid
CAS# 481-74-3

Theoretical Analysis

MedKoo Cat#: 401220
Name: Chrysophanic acid
CAS#: 481-74-3
Chemical Formula: C15H10O4
Exact Mass: 254.06
Molecular Weight: 254.238
Elemental Analysis: C, 70.86; H, 3.96; O, 25.17

Price and Availability

Size Price Availability Quantity
100mg USD 350
200mg USD 550
500mg USD 950
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Synonym: Chrysophanol; Chrysophanic acid

IUPAC/Chemical Name: 1,8-dihydroxy-3-methylanthracene-9,10-dione

InChi Key: 1,8-dihydroxy-3-methylanthracene-9,10-dione

InChi Code: 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

SMILES Code: O=C1C2=C(C=CC=C2O)C(C3=CC(C)=CC(O)=C13)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:          

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 254.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Seo EJ, Ngoc TM, Lee SM, Kim YS, Jung YS. Chrysophanol-8-O-glucoside, an Anthraquinone Derivative in Rhubarb, Has Antiplatelet and Anticoagulant Activities. J Pharmacol Sci. 2012 Feb 3. [Epub ahead of print] PubMed PMID: 22302018.

2: Qian ZJ, Zhang C, Li YX, Je JY, Kim SK, Jung WK. Protective Effects of Emodin and Chrysophanol Isolated from Marine Fungus Aspergillus sp. on Ethanol-Induced Toxicity in HepG2/CYP2E1 Cells. Evid Based Complement Alternat Med. 2011;2011:452621. Epub 2011 Sep 6. PubMed PMID: 21912566; PubMed Central PMCID: PMC3168298.

3: Huang X, Zhong G, Zhang X, Zhang Y. [Determination of aurantio-obtusin and chrysophanol in cassiae semen by HPLC]. Zhongguo Zhong Yao Za Zhi. 2010 Aug;35(16):2065-7. Chinese. PubMed PMID: 21046729.

4: Kim SJ, Kim MC, Lee BJ, Park DH, Hong SH, Um JY. Anti-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation in vitro and in vivo. Molecules. 2010 Sep 16;15(9):6436-51. PubMed PMID: 20877234.

5: Lu CC, Yang JS, Huang AC, Hsia TC, Chou ST, Kuo CL, Lu HF, Lee TH, Wood WG, Chung JG. Chrysophanol induces necrosis through the production of ROS and alteration of ATP levels in J5 human liver cancer cells. Mol Nutr Food Res. 2010 Jul;54(7):967-76. PubMed PMID: 20169580; PubMed Central PMCID: PMC3031088.

6: Genovese S, Tammaro F, Menghini L, Carlucci G, Epifano F, Locatelli M. Comparison of three different extraction methods and HPLC determination of the anthraquinones aloe-emodine, emodine, rheine, chrysophanol and physcione in the bark of Rhamnus alpinus L. (Rhamnaceae). Phytochem Anal. 2010 May;21(3):261-7. PubMed PMID: 20024894.

7: Bringmann G, Gulder TA, Hamm A, Goodfellow M, Fiedler HP. Multiple convergence in polyketide biosynthesis: a third folding mode to the anthraquinone chrysophanol. Chem Commun (Camb). 2009 Nov 28;(44):6810-2. Epub 2009 Oct 5. PubMed PMID: 19885487.

8: Zhao X, Zheng Z, Feng S, Shi Z, Chen D. A TD-DFT study on the photo-physicochemical properties of chrysophanol from rheum. Int J Mol Sci. 2009 Jul 13;10(7):3186-93. PubMed PMID: 19742131; PubMed Central PMCID: PMC2738918.

9: Jiao Y, Zuo Y. Ultrasonic extraction and HPLC determination of anthraquinones, aloe-emodine, emodine, rheine, chrysophanol and physcione, in roots of Polygoni multiflori. Phytochem Anal. 2009 Jul;20(4):272-8. PubMed PMID: 19402184.

10: Lee MS, Sohn CB. Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome. Biol Pharm Bull. 2008 Nov;31(11):2154-7. PubMed PMID: 18981591.