Rhein

Base Information

• Chemical Name: Rhein
• CAS No.: 478-43-3
• Molecular Formula: C15H8O6
• Molecular Weight: 284.225
• Hs Code.: 29189900
• European Community (EC) Number: 207-521-4
• NSC Number: 38629
• UNII: YM64C2P6UX
• DSSTox Substance ID: DTXSID4026000
• Nikkaji Number: J12.584I
• Wikipedia: Rhein_(molecule)
• Wikidata: Q720356
• Metabolomics Workbench ID: 27929
• ChEMBL ID: CHEMBL418068
• Mol file: 478-43-3.mol

Synonyms:1,8-dihydroxy-3-carboxyl-9,10-anthraquinone;4,5-dihydroxyanthraquinone-2-carboxylic acid;dipropionyl rhein;rhein

Chemical Property of Rhein

Chemical Property:

• Appearance/Colour: Yellowish brown solid
• Vapor Pressure: 3.85E-15mmHg at 25°C
• Melting Point: ≥300 °C(lit.)
• Refractive Index: 1.4413 (estimate)
• Boiling Point: 597.8 °C at 760 mmHg
• PKA: 3.17±0.20(Predicted)
• Flash Point: 329.4 °C
• PSA: 111.90000
• Density: 1.687 g/cm³
• LogP: 1.57140
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 17℃
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 284.03208797
• Heavy Atom Count: 21
• Complexity: 487

Purity/Quality:

Rhubarb 0.3% phenol ^*data from raw suppliers

Rhein ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)C(=O)O
• Uses: Medical intermediate;raw materials of health food. Rhein is used to inhibit growth factor beta-1 induced plasminogen activator inhibitor-1 in endothelial cells. It acts as an antibacterial agent against Staphylococcus aureus. It is also used as a laxative. Further, it is employed as a pharmaceutical intermediate. Rhein was used to induce necrosis-apoptosis switch in injured pancreatic acinar cells.

Technology Process of Rhein

There total 59 articles about Rhein 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%

diacetylrhein (13739-02-1) → 1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3)

Guidance literature:

With sodium carbonate; In water;

DOI:10.1016/S0960-894X(97)00102-9

Reference yield: 98.0%

Chrysophanol (481-74-3) → 1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3)

Guidance literature:

Chrysophanol; With chromium(VI) oxide; In acetic anhydride; acetic acid; at 65 ℃; for 8h;

With sodium carbonate; In water;

Reference yield: 96.0%

Rhein methyl ester (6155-37-9) → 1,8-dihydroxy-3-carboxy-anthraquinone (478-43-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo00341a050

upstream raw materials:

diacetylrhein

1,8,9-triacetoxy-3-methyl-anthracene

sennidin B

(+)-4,5,4',5'-tetrahydroxy-10,10'-dioxo-9,10,9',10'-tetrahydro-[9,9']bianthryl-2,2'-dicarboxylic acid

Downstream raw materials:

rhein anthrone

Rhein methyl ester

Refernces

• 1、 Fairbairn,El-Muhtadi. "". . p. 263,267. Retrieved 1972.
• 2、 Das, Kiran,De, Arijit,Husain, Syed Masood,Maity, Biswanath,Mondal, Amit,Rajput, Anshul. "A biocatalytic approach towards the preparation of natural deoxyanthraquinones and their impact on cellular viability". . p. 3087 - 3090. Retrieved 2022/02/21.
• 3、 Liu, Kai-Jian,Jiang, Si,Lu, Ling-Hui,Tang, Ling-Li,Tang, Shan-Shan,Tang, Hai-Shan,Tang, Zilong,He, Wei-Min,Xu, Xinhua. "Bis(methoxypropyl) ether-promoted oxidation of aromatic alcohols into aromatic carboxylic acids and aromatic ketones with O2 under metal- and base-free conditions". supporting information. p. 3038 - 3043. Retrieved 2018/07/13.