31179-82-5

Basic information

• Product Name: (1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione
• Synonyms: 9,10-Anthracenedione, 1,2,3,4-tetrahydro-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-, (1.alpha.,2.beta.,3.beta.,4.alpha.)-
• CAS NO: 31179-82-5
• Molecular Formula: C₁₆H₁₆O₈
• Molecular Weight: 336.2934
• Mol File: 31179-82-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 656.9°C at 760 mmHg
• Flash Point: 246.5°C
• Density: 1.7g/cm³
• Vapor Pressure: 3.77E-18mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: (1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione(31179-82-5)
• EPA Substance Registry System: (1R,2S,3R,4S)-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-1,2,3,4-tetrahydroanthracene-9,10-dione(31179-82-5)

Safety Data

• Hazardous Substances Data: 31179-82-5(Hazardous Substances Data)

Upstream product

• 119644-07-4 alterporriol D 
• 65120-69-6 3-chloro-5-hydroxy-7-methoxy-1,4-naphthoquinone 
• 116948-37-9 (1RS,2RS,3RS,4RS)-3,4-epoxy-1,2,3,4-tetrahydro-2,5-dihydroxy-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 
• 70063-61-5 5-hydroxy-7-methoxy-1,4-naphthoquinone 
• 116888-93-8 5-acetoxy-7-methoxy-1,4-naphthoquinone 
• 116889-01-1 (1RS,2RS)-1,2-dihydro-2,5-dihydroxy-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 
• 116888-94-9 (1RS,4aRS,9aRS)-5-acetoxy-1,4,4a,9a-tetrahydro-7-methoxy-1-(trimethylsiloxy)-9,10-anthraquinone 
• 116888-97-2 (1RS,2RS,3RS,4aRS,9aRS)-5-acetoxy-2,3-epoxy-1,2,3,4,4a,9a-hexahydro-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 
• 116889-06-6 (1RS,2RS,3SR,4SR)-3,4-epoxy-1,2,3,4-tetrahydro-2,5-dihydroxy-7-methoxy-2-methyl-1-(trimethylsiloxy)-9,10-anthraquinone 

Relevant articles and documents

First enantioselective total synthesis of altersolanol A

The first enantioselective total synthesis of altersolanol A, a secondary metabolite from the endophytic fungi Stemphylium globuliferum and Alternaria solani, is described. The key step towards the tetrahydroanthraquinone core was an asymmetric Diels-Alder (D-A) cycloaddition promoted by (R)-3,3′-diphenyl-BINOL/boron Lewis acid with good to excellent yields and excellent diastereo- and enantioselectivity (>95 : 5 dr and 98 : 2 er).

rac-Altersolanol A and Related Tetrahydroanthraquinones, Total Synthesis and Cytotoxic Properties

A key step in the first synthesis of racemic altersolanol A (1a) is the regioselective Diels-Alder reaction of 5-acetoxy-7-methoxy-1,4-naphthoquinone (12) with 2-methyl-1-(trimethylsiloxy)-1,3-butadiene (13) to afford the adduct 14.The structure of 14 has been confirmed by X-ray measurements.The hydroxy groups of ring A are introduced by epoxidation of 14 to 20, rearrangement to the allylic alcohol 26, epoxidation to 31, and opening of the oxirane to rac-altersolanol A (1a).Similar products were obtained starting from juglone (15).Many of the intermediate epoxidesand also compounds 42-44 show remarkable cytotoxicity in cell cultures but all compounds were too toxic to be useful as anticancer agents.