Chrysophanol

Base Information

• Chemical Name: Chrysophanol
• CAS No.: 481-74-3
• Molecular Formula: C15H10O4
• Molecular Weight: 254.242
• Hs Code.: 29146990
• European Community (EC) Number: 207-572-2
• NSC Number: 646567,37132
• UNII: N1ST8V8RR2
• DSSTox Substance ID: DTXSID6024832
• Nikkaji Number: J1.547D
• Wikipedia: Chrysophanol
• Wikidata: Q15410875
• Metabolomics Workbench ID: 27920
• ChEMBL ID: CHEMBL41092
• Mol file: 481-74-3.mol

Synonyms:2-methyl-4,5-dihydroxyanthraquinone;3-methyl-1,8-dihydroxyanthraquinone;chrysophanic acid;chrysophanic acid, ion (1-);chrysophanol

Chemical Property of Chrysophanol

Chemical Property:

• Appearance/Colour: yellow crystalline solid or brown powder
• Vapor Pressure: 3.31E-10mmHg at 25°C
• Melting Point: 194-198 °C
• Refractive Index: 1.709
• Boiling Point: 489.495 °C at 760 mmHg
• PKA: 6.63±0.20(Predicted)
• Flash Point: 263.939 °C
• PSA: 74.60000
• Density: 1.476 g/cm³
• LogP: 2.18160
• Storage Temp.: 2-8°C
• Solubility.: chloroform: soluble1%
• Water Solubility.: <0.1 g/100 mL at 18℃
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 254.05790880
• Heavy Atom Count: 19
• Complexity: 405

Purity/Quality:

98% ^*data from raw suppliers

Chrysophanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
• 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).
• 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. antineoplastic, antibacterial A topical ointment used in the treatment of dermal conditions such as eczema and herpes.

Technology Process of Chrysophanol

There total 90 articles about Chrysophanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione (67116-22-7) → Chrysophanol (481-74-3)

Guidance literature:

With hydrogen bromide; In acetic acid; for 5h; Heating;

DOI:10.1016/S0040-4020(01)91537-6

Reference yield: 98.0%

Chrysophanol 8-O-beta-D-glucopyranoside (13241-28-6,67492-66-4) → Chrysophanol (481-74-3)

Guidance literature:

With acetate buffer; β-glucosidase; In water; at 37 ℃; for 16h; pH=5.0;

DOI:10.1016/S0968-0896(00)00215-7

Reference yield: 96.0%

(1R,4aS,9aR)-9a-Chloro-8-hydroxy-1-methoxy-3-methyl-1-trimethylsilanyloxy-1,4,4a,9a-tetrahydro-anthraquinone (108637-78-1) → Chrysophanol (481-74-3) + 8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione (67116-22-7)

Guidance literature:

1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)85117-5

upstream raw materials:

1,8-diacetoxy-3-methyl-anthraquinone

8-O-methylchrysophanol

1,8-dihydroxy-3-methylanthracen-9(10H)-one

cephalanone F

Downstream raw materials:

1,8-dihydroxy-3-methylanthracen-9(10H)-one

islandicin

chrysophanol 1-O-β-gentiobioside

Chrysophanol 8-O-beta-D-glucopyranoside

Refernces

• 1、 Anderson, John A.. "CONVERSION OF EMODIN TO CHRYSOPHANOL IN A CELL-FREE SYSTEM FROM PYRENOCHAETA TERRESTRIS". . p. 103 - 106. Retrieved 1986.
• 2、 Mondal, Amit,Singh, Shailesh Kumar,Saha, Nirmal,Husain, Syed Masood. "A Biomimetic Synthesis of Racemic Dihydroanthracen-1(2H)-ones Using Sodium Borohydride in Water". . p. 2425 - 2430. Retrieved 2020.
• 3、 Anderson, John A.,Lin, Bor-Kang. "NADPD ISOTOPE EFFECT ON ACTIVITY OF EMODIN DEOXYGENASE". . p. 811 - 812. Retrieved 1993.
• 4、 Birch,Powell. "". . p. 3467. Retrieved 1970.
• 5、 Gartman, Jackson A.,Tambar, Uttam K.. "Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C". . p. 11237 - 11262. Retrieved 2021/08/16.
• 6、 Mondal, Amit,Singh, Shailesh Kumar,Manna, Tanaya,Husain, Syed Masood. "Chemoenzymatic, biomimetic total synthesis of (-)-rugulosin B, C and rugulin analogues and their biosynthetic implications". supporting information. p. 3337 - 3340. Retrieved 2020/04/02.