Emodin

Base Information

• Chemical Name: Emodin
• CAS No.: 518-82-1
• Molecular Formula: C15H10O5
• Molecular Weight: 270.241
• Hs Code.: 29146990
• European Community (EC) Number: 208-258-8
• NSC Number: 622947,408120
• UNII: KA46RNI6HN
• DSSTox Substance ID: DTXSID5025231
• Nikkaji Number: J6.587K
• Wikipedia: Emodin
• Wikidata: Q4348178
• NCI Thesaurus Code: C466
• Pharos Ligand ID: PUW5W92PY6JC
• Metabolomics Workbench ID: 27922
• ChEMBL ID: CHEMBL289277
• Mol file: 518-82-1.mol

Synonyms:Archin;Casanthranol;Emodin;Emodin, Frangula;Emodin, Rheum;Frangula Emodin;Frangulic Acid;Peristim;Rheum Emodin

Chemical Property of Emodin

Chemical Property:

• Appearance/Colour: red-orange powder
• Melting Point: 255 °C (dec.)(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 586.9 °C at 760 mmHg
• PKA: 6.39±0.20(Predicted)
• Flash Point: 322.8 °C
• PSA: 94.83000
• Density: 1.583 g/cm³
• LogP: 1.88720
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 270.05282342
• Heavy Atom Count: 20
• Complexity: 434

Purity/Quality:

99%, ^*data from raw suppliers

Emodin ^*data from reagent suppliers

Safty Information:

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

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=C(C=C3O)O
• Recent ClinicalTrials: Randomized Clinical Trial of Triptolide Woldifii for Autosomal Dominant Polycystic Kidney Disease
• Uses: 1. The product can be used as a laxative. As it is susceptible to oxidative damage within the body, its diarrhea activity is actually very weak. However, it can be compounded with glucose to form a glycoside with diarrhea activity. Both emodin-1-O-β-D-glucoside and emodin-8-O-β-D-glucoside are glycosides formed through combination of emodin and glucose.? The only different between the two are the binding sites.? The two glycosides coexist in Radix et Rhizoma Rhei. 2. intermediate;health products material. Occurs mostly as the rhamnoside (see Frangulin) in rhubarb root. Cathartic. antibacterial, antineoplastic, cathartic, tyrosine kinase inhibitor Emodin has been used:to investigate its regulatory mechanisms on lipopolysaccharide (LPS)-induced inflammatory injury in myocarditisas a reference standard for the development and validation of high performance liquid chromatography (HPLC)-photodiode array (PDA) assay methodto inhibit Tau aggregationfor direct binding assay
• Production method: Emodin is a plant laxative widely present in plant organs such as roots of Radix et Rhizoma Rhei, bark and root bark of buckthorn and cassia seeds. Emodin can be extracted from roots and rhizomes of Radix et Rhizoma Rhei. It also can be obtained by synthesis, for example, using 2-methyl-anthraquinone, or 3, 5-nitro-phthalic anhydride and m-cresol as the raw material.

Technology Process of Emodin

There total 37 articles about Emodin 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%

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone (6030-60-0) → 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1)

Guidance literature:

With sodium hydroxide; at 80 ℃; for 2h;

DOI:10.1002/jlcr.2580360811

Reference yield: 98.0%

physcion (521-61-9) → 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.151004

Reference yield: 72.0%

(R)-3,8,9,10-tetrahydroxy-6-methyl-3,4-dihydroanthracen-1(2H)-one (1396259-15-6) → Chrysophanol (481-74-3) + 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1) + (?)-flavoskyrin (39546-16-2,115729-00-5)

Guidance literature:

With oxygen; In aq. phosphate buffer; acetonitrile; at 10 ℃; for 10h; pH=6; Solvent;

DOI:10.1021/acs.orglett.0c03121

upstream raw materials:

physcion

1,3,8-trimethoxy-6-methyl-9,10-anthraquinone

endocrocin

2-(2-hydroxy-4-methyl-benzoyl)-3,5-dimethoxy-benzoic acid

Downstream raw materials:

1,6,8-triacetoxy-3-methyl-9,10-anthraquinone

1,3,8-Trihydroxy-2-chlor-6-methylanthrachinon

1,3-dichloro-2,4,5-trihydroxy-7-methylanthracene-9,10-dione

2-methylanthracene

Refernces

• 1、 Hadj-Hamdri,Vidal-Cros,Gaudry,Sobrio,Rousseau. "Synthesis of high specific radioactivity [3H]emodin". . p. 795 - 799. Retrieved 1995.
• 2、 Bennett, Graham J.,Lee, Hiok-Huang,Lowrey, Timothy K.. "Novel metabolites from ploiarium alternifolium: A bixanthone and two anthraquinonylxanthones". . p. 751 - 754. Retrieved 1990.
• 3、 Adomako-Bonsu, Amma G.,Maser, Edmund,Thiele, Solveig,Westermann, Magdalena,?i?ek, Serhat Sezai,Martin, Hans-J?rg. "Inhibition of human carbonyl reducing enzymes by plant anthrone and anthraquinone derivatives". . . Retrieved 2022/02/03.
• 4、 Mondal, Amit,De, Arijit,Husain, Syed Masood. "Synthesis of (-)-Flavoskyrins by Catalyst-Free Oxidation of (R)-Configured Dihydroanthracenones in Aqueous Media and Its (Bio)synthetic Implications". supporting information. p. 8511 - 8515. Retrieved 2020/11/12.