71524-16-8

Basic information

• Product Name: meso-1,4-bis(4-acetoxy-3-methoxyphenyl)-(2R,3S)-dimethylbutane
• Synonyms: meso-1,4-bis(4-acetoxy-3-methoxyphenyl)-(2R,3S)-dimethylbutane
• CAS NO: 71524-16-8
• Molecular Weight: 414.499
• Mol File: 71524-16-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: meso-1,4-bis(4-acetoxy-3-methoxyphenyl)-(2R,3S)-dimethylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: meso-1,4-bis(4-acetoxy-3-methoxyphenyl)-(2R,3S)-dimethylbutane(71524-16-8)
• EPA Substance Registry System: meso-1,4-bis(4-acetoxy-3-methoxyphenyl)-(2R,3S)-dimethylbutane(71524-16-8)

Safety Data

• Hazardous Substances Data: 71524-16-8(Hazardous Substances Data)

Upstream product

• 36469-60-0 (8R,8'S)-dihydroguaiaretic acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 

Downstream Products

• 36469-60-0 (8R,8'S)-dihydroguaiaretic acid 

Relevant articles and documents

meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity

Thirty-three meso-dihydroguaiaretic acid (meso-DGA) derivatives bearing esters, ethers, and amino-ethers were synthesized. All derivatives were tested against twelve drug-resistant clinical isolates of Gram-positive and Gram-negative bacteria, including sensitive (H37Rv) and multidrug-resistant Mycobacterium tuberculosis strains. Among the tested compounds, four esters (7, 11, 13, and 17), one ether (23), and three amino-ethers (30, 31, and 33) exhibited moderate activity against methicillin-resistant Staphylococcus aureus, whereas 30 and 31 showed better results than levofloxacin against vancomycin-resistant Enterococcus faecium. Additionally, nineteen meso-DGA derivatives displayed moderate to potent activity against M. tuberculosis H37Rv with minimum inhibitory concentration (MIC) values ranging from 3.125 to 50 μg/mL. Seven meso-DGA derivatives bearing amino-ethers (26–31 and 33) exhibited the lowest MICs against M. tuberculosis H37Rv and G122 strains, with 31 being as potent as ethambutol (MICs of 3.125 and 6.25 μg/mL). The presence of positively charged group precursors possessing steric and hydrophobic features (e.g. N-ethylpiperidine moieties in meso-31) resulted essential to significantly increase the antimycobacterial properties of parent meso-DGA as supported by the R-group pharmacophoric and field-based QSAR analyses. To investigate the safety profile of the antimycobacterial compounds, cytotoxicity on Vero cells was determined. The amino-ether 31 exhibited a selectivity index value of 23, which indicate it was more toxic to M. tuberculosis than to mammalian cells. Therefore, 31 can be considered as a promising antitubercular agent for further studies.