Chrysophanic acid CAS 481-74-3

Introduction：Basic information about Chrysophanic acid CAS 481-74-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Chrysophanic acid Basic information

• Product Name: Chrysophanic acid
• Synonyms: 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
• CAS: 481-74-3
• MF: C15H10O4
• MW: 254.24
• EINECS: 207-572-2
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Aloe Vera;Bioactive Small Molecules;Building Blocks;C15 to C38;Carbonyl Compounds;Cell Biology;Chemical Synthesis;DIG-DY;Ketones;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);The group of Polydatin;Anthraquinones, Hydroquinones and Quinones;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 481-74-3.mol

Chrysophanic acid Chemical Properties

• 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.
• 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
• SMILES: Cc1cc(O)c2C(=O)c3c(O)cccc3C(=O)c2c1
• LogP: 4.720 (est)
• CAS DataBase Reference: 481-74-3(CAS DataBase Reference)
• EPA Substance Registry System: Chrysophanic acid (481-74-3)

Safety Information

• 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
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
• Hazardous Substances Data: 481-74-3(Hazardous Substances Data)

Chrysophanic acid Usage And Synthesis

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.]

References

[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