Chrysophanic acid Property

Melting point:

194-198 °C

Boiling point:

357.45°C (rough estimate)

Density 

1.2693 (rough estimate)

refractive index 

1.4872 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

chloroform: soluble1%

form 

crystalline

pka

6.63±0.20(Predicted)

color 

yellow-orange

Water Solubility 

<0.1 g/100 mL at 18 ºC

λmax

429nm(MeOH)(lit.)

Merck 

14,2258

BRN 

1252300

Stability:

Stable. Incompatible with strong oxidizing agents.

LogP

4.720 (est)

CAS DataBase Reference

481-74-3(CAS DataBase Reference)

EPA Substance Registry System

Chrysophanic acid (481-74-3)

Safety

Hazard Codes 

Xi

Risk Statements 

36/38-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

CB6725000

F 

8-10

HS Code 

29146990

Hazardous Substances Data

481-74-3(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Chrysophanic acid Chemical Properties,Usage,Production

Description

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; ) 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; ). 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).

Chemical Properties

yellow crystalline solid or brown powder

Uses

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.

Uses

antineoplastic, antibacterial

Uses

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

Definition

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.

Synthesis Reference(s)

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

General Description

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.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Chrysophanic acid is incompatible with strong oxidizing agents.

Fire Hazard

Flash point data for Chrysophanic acid are not available; however, Chrysophanic acid is probably combustible.

Purification Methods

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.]