71013-35-9

Basic information

• Product Name: chrysophanol dimethyl ether
• Synonyms: chrysophanol dimethyl ether
• CAS NO: 71013-35-9
• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.294
• Mol File: 71013-35-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 474.1°C at 760 mmHg
• Flash Point: 212.3°C
• Appearance: /
• Density: 1.263g/cm³
• Vapor Pressure: 3.73E-09mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: chrysophanol dimethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: chrysophanol dimethyl ether(71013-35-9)
• EPA Substance Registry System: chrysophanol dimethyl ether(71013-35-9)

Safety Data

• Hazardous Substances Data: 71013-35-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H14O4/c1-9-7-11-15(13(8-9)21-3)17(19)14-10(16(11)18)5-4-6-12(14)20-2/h4-8H,1-3H3

Upstream product

• 481-74-3 Chrysophanol 
• 74-88-4 methyl iodide 
• 2398-37-0 3-methoxyphenyl bromide 
• 111210-21-0 1,3-dihydro-4-methoxy-6-methyl-3-oxo-1-isobenzofurancarbonitrile 
• 77-78-1 dimethyl sulfate 
• 14963-96-3 3-methoxyphthalic anhydride 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 14963-97-4 3-methoxyphthalic acid 
• 2944-49-2 2,3-dimethylanisole 
• 526-75-0 2,3-Dimethylphenol 
• 210752-19-5 1,8,9,10-Tetramethoxy-3-methyl-anthracene 
• 67-64-1 acetone 
• 121275-42-1 4,5-dimethoxy-2-methylanthracene-9(10H)-one 
• 73909-16-7 2-chloro-5-methylanisole 

Downstream Products

• 481-74-3 Chrysophanol 
• 111822-93-6 3-[N,N-Bis(2-chloroethyl)amino]methyl-1,8-dihydroxy-9,10-anthraquinone 
• 72036-12-5 2-bromomethyl-9,10-dihydro-4,5-dihydroxy-9,10-dioxoanthracene 

Relevant articles and documents

An anthraquinone and three naphthopyrone derivatives from Cassia pudibunda.

Chemical examination of the methanolic extract of the roots of Cassia pudibunda led to isolation of the new rubrofusarin-6-O-beta-D-glucopyranoside, quinquangulin-6-O-beta- D-apiofuranosyl-(1----6)-O-beta-D-glucopyranoside, quinquangulin-6-O-beta-D-glucopyranoside and chrysophanol dimethyl ether. Moreover the known chrysophanol, physcion, cis-3,3',5,5'-tetrahydroxy-4-methoxystilbene, trans-3,3',5,5' -tetrahydroxy-4-methoxystilbene, and cassiaside B were identified. The antimicrobial activity of some of these compounds is also reported.

Intercalating agents with covalent bond forming capability. A novel type of potential anticancer agents. 2. Derivatives of chrysophanol and emodin

Fifty-one new C-methyl-modified derivatives of the anthraquinones chrysophanol and emodin or their various methyl ethers were prepared for structure-activity relationship studies of anticancer activity against mouse leukemia L1210 and human leukemia HL-60 cells. Representative compounds were spectrophotometrically studied for their capacity to interact with natural and denatured DNA. In general, those anthraquinones bearing an amino function interact with DNA. 1,8-Dimethoxyanthraquinones are incapable of intercalating into DNA. 1- or 8-Monohydroxymonomethoxyanthraquinones, however, interact with DNA to some extent. No straightforward correlation is apparent between the DNA-affinity data of the compounds studied spectrophotometrically and their cytotoxic effects. Cytotoxic potencies of these compounds on cell growth inhibition during a 72-h period are inversely correlated to their potencies when inhibiting [3H]TdR incorporation into DNA during the initial 30 min of exposure. Surprisingly, some compounds that showed more cytotoxicity did not inhibit initial TdR incorporation (0-30 min), while some others that strongly inhibited TdR incorporation initially did not exhibit cytotoxicity in 72 h. The results suggest that the cytotoxicity produced by these compounds is time dependent and is not a direct result of initial inhibition of DNA replication.

Total synthesis process of rhein

The invention relates to a total synthesis process of rhein. The process includes: adopting methoxy phthalic anhydride and a Grignard reaction liquid as the raw materials, and carrying out condensation, dehydration cyclization, methoxylation, oxidation and demethylation reaction so as to obtain rhein.

Total synthesis of (-)-balanol

The efficient total synthesis of (-)-balanol, a potent inhibitor of the protein kinase C, is described (-)-Balanol consists of a chiral hexahydroazepine-containing fragment and a benzophenone fragment, both of which were prepared via novel synthetic routes. The hxahydroazepine fragment was prepared in racemic form through either Bu3SnH- or SmI2-promoted radical cyclization of oxime ethers 2ab intramolecularly connected with the formyl group. SmI2-promoted radical cyclization of 2b was found to be particularly successful in the selective synthesis of the seven-membered trans-amino alcohol 8b. Preparation of the enantiomerically pure hexahydroazepine-containing fragment was achieved through the enantioselective enzymatic acetylation of racemic alcohol 9, employing the immobilized lipase from Pseudomonas sp. The benzophenone fragment was prepared in short steps through a biomimetic oxidative anthraquinone ring cleavage starting from commercially available natural chrysophanic acid 15c. This reaction proceeded via [4 + 2]-cycloaddition of single of oxygen to anthracene derivative 17c, followed by Baeyer-Villiger-type rearrangement of the resulting hydroperoxide to afford the benzophenone derivatives 22 and 23.