481-74-3

Golden yellow plates or brown powder. Melting point 196°C. Slightly soluble in water. Pale yellow aqueous solutions turn red on addition of alkali. Solutions in concentrated sulfuric acid are red.

CHRYSOPHANIC ACID(481-74-3) is incompatible with strong oxidizing agents.

Insoluble in water.

Flash point data for this chemical are not available; however, CHRYSOPHANIC ACID is probably combustible.

Chrysophanol is an anthraquinone that has been found in R. palmatum and has diverse biological activities. It induces necrosis in J5 human liver cancer cells when used at concentrations of 25, 50, 75, 100, and 200 μM. Chrysophanol (5, 10, and 50 μM) reduces LPS-induced production of nitric oxide (NO) and prostaglandin E₂ (PGE₂; Item No. 14010) and inhibits LPS-induced DNA oxidation in BV-2 microglia. In vivo, chrysophanol (5 mg/kg) decreases colonic levels of IL-6 and activation of NF-κB and reduces weight loss, diarrhea, and rectal bleeding in a mouse model of colitis induced by dextran sulfate (DSS; Item No. 23250). Chrysophanol (0.1, 1, and 10 mg/kg) increases survival, reduces brain tissue loss, and ameliorates motor balance deficits in a mouse model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).

yellow crystalline solid or brown powder

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

antineoplastic, antibacterial

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.

ChEBI: A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity.

Tetrahedron Letters, 20, p. 4911, 1979 DOI: 10.1016/S0040-4039(01)86747-2

Crystallise chrysophanic acid from EtOH or *benzene and has m 195.6-196.2o, after sublimation it in a vacuum. The yellow mono-acetate has m 188-190o (from MeOH or Me2CO). It forms Ni2+, Co2+ and Cu2+ complexes. [Beilstein 8 H 470, 8 I 725, 8 II 510, 8 III 3808, 8 IV 3277.]

[1] F H QI. Traditional Chinese medicine and related active compounds: a review of their role on hepatitis B virus infection.[J]. Drug Discoveries and Therapeutics, 2013, 7 6: 212-224. DOI: 10.5582/ddt.2013.v7.6.212
[2] CHI-CHENG LU. Chrysophanol induces necrosis through the production of ROS and alteration of ATP levels in J5 human liver cancer cells[J]. Molecular Nutrition & Food Research, 2010, 54 7: 967-976. DOI: 10.1002/mnfr.200900265
[3] FUQING LIN. Chrysophanol affords neuroprotection against microglial activation and free radical-mediated oxidative damage in BV2 murine microglia.[J]. International journal of clinical and experimental medicine, 2015, 8 3: 3447-3455.
[4] SU-JIN KIM. Anti-Inflammatory activity of chrysophanol through the suppression of NF-kappaB/caspase-1 activation in vitro and in vivo.[J]. Molecules, 2010, 15 9: 6436-6451. DOI: 10.3390/molecules15096436
[5] YONGMEI ZHAO . Neuroprotective effects of Chrysophanol against inflammation in middle cerebral artery occlusion mice[J]. Neuroscience Letters, 2016, 630: Pages 16-22. DOI: 10.1016/j.neulet.2016.07.036