| Identification | More | [Name]
Chrysophanic acid | [CAS]
481-74-3 | [Synonyms]
1,8-DIHYDROXY-3-METHYL-9,10-ANTHRACENEDIONE
1,8-DIHYDROXY-3-METHYLANTHRAQUINONE
3-METHYLCHRYSAZIN
3-METHYLCHRYSAZINE
9,10-ANTHRACENEDIONE,1,8-DIHYDROXY-3-METHYL
CHRYSOPHANIC ACID
CHRYSOPHANOL
RHUBARB EXTRACT
1,8-dihydroxy-3-methyl-10-anthracenedione
1,8-Dihydroxy-3-methyl-9,10-anthraquinone
1,8-dihydroxy-3-methyl-anthraquinon
2-Methyl-4,5-dihydroxyanthraquinone
3-Methyl-1,8-dihydroxyanthraquinone
4,5-Dihydroxy-2-methylanthraquinone
Anthraquinone,1,8-dihydroxy-3-methyl-
c.i.75400
c.i.naturalyellow23
Chrysophansαure
turkeyrhubarb
CHRYSOPHANOL:9,10-ANTHRACENEDIONE,1,8-DIHYDROXY-3-METHYL | [EINECS(EC#)]
207-572-2 | [Molecular Formula]
C15H10O4 | [MDL Number]
MFCD00001208 | [Molecular Weight]
254.24 | [MOL File]
481-74-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline solid or brown powder | [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 | [Stability:]
Stable. Incompatible with strong oxidizing agents. | [Water Solubility ]
<0.1 g/100 mL at 18 ºC | [λmax]
429nm(MeOH)(lit.) | [Merck ]
13,2280 | [BRN ]
1252300 | [LogP]
4.720 (est) | [CAS DataBase Reference]
481-74-3(CAS DataBase Reference) | [EPA Substance Registry System]
481-74-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/38:Irritating to eyes and skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
CB6725000
| [F ]
8-10 | [HS Code ]
29146990 | [Hazardous Substances Data]
481-74-3(Hazardous Substances Data) |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
CHRYSOPHANIC ACID(481-74-3) is incompatible with strong oxidizing agents. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
Flash point data for this chemical are not available; however, CHRYSOPHANIC ACID is probably combustible. | [Description]
Chrysophanol is an anthraquinone that has been found in R. palmatum and has diverse biological activities.1,2,3 It induces necrosis in J5 human liver cancer cells when used at concentrations of 25, 50, 75, 100, and 200 μM.2 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.3 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).4 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).5 | [Chemical Properties]
yellow crystalline solid or brown powder | [Uses]
A topical ointment used in the treatment of dermal conditions such as eczema and herpes. | [Uses]
antineoplastic, antibacterial | [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. | [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 | [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.] |
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