634205-22-4

Basic information

• Product Name: Benzoic acid, 2-methyl-6-(2-propenyloxy)-, ethyl ester
• CAS NO: 634205-22-4
• Molecular Formula: C13H16O3
• Molecular Weight: 220.268
• Mol File: 634205-22-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-methyl-6-(2-propenyloxy)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-methyl-6-(2-propenyloxy)-, ethyl ester(634205-22-4)
• EPA Substance Registry System: Benzoic acid, 2-methyl-6-(2-propenyloxy)-, ethyl ester(634205-22-4)

Safety Data

• Hazardous Substances Data: 634205-22-4(Hazardous Substances Data)

Upstream product

• 6555-40-4 ethyl 2-hydroxy-6-methylbenzoate 
• 106-95-6 allyl bromide 

Downstream Products

• 1383427-48-2 ingenol-5,20-acetonide-3-(2-hydroxy-6-methyl-benzoate) 
• 1383427-47-1 ingenol-5,20-acetonide-3-(2-allyloxy-6-methyl-benzoate) 
• 1383427-01-7 ingenol-3-(2-hydroxy-6-methyl-benzoate) 
• 634205-29-1 (R)-6-[1-(2-allyloxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid allyl ester 
• 634205-30-4 (S)-6-[1-(2-allyloxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid allyl ester 
• 634205-26-8 6-[1-(2-allyloxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid allyl ester 
• 81645-10-5 (R)-6-[1-(2-hydroxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid 
• 81645-10-5 (S)-6-[1-(2-hydroxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid 
• 81645-10-5 saphenamycin 
• 634205-23-5 2-allyloxy-6-methylbenzoic acid 

Relevant articles and documents

Synthesis, biological evaluation and SAR of 3-benzoates of ingenol for treatment of actinic keratosis and non-melanoma skin cancer

Ingenol 3-benzoates were investigated with respect to chemical stability, pro-inflammatory effects, cell death induction and PKCδ activation. A correlation between structure, chemical stability and biological activity was found and compared to ingenol mebutate (ingenol 3-angelate) used for field treatment of actinic keratosis. We also provided further support for involvement of PKCδ for induction of oxidative burst and cytokine release. Molecular modeling and dynamics calculations corroborated the essential interactions between key compounds and C1 domain of PKCδ.

First synthesis of racemic saphenamycin and its enantiomers. Investigation of biological activity

The natural antibiotic saphenamycin, 6-[1-(2-hydroxy-6-methyl-benzoyloxy)-ethyl]-phenazine-1-carboxylic acid, was synthesized from saphenic acid using temporary allyl protection of carboxy and phenoxy functionalities. Resolution of racemic saphenic acid was performed by crystallization of the corresponding (-)-brucine diastereomeric salts and the absolute configuration of (-)-brucinium (-)-saphenate was determined by X-ray crystallography to have R-configuration. This also proved to be the configuration of natural saphenic acid. Enantiomers of saphenamycin were obtained from resolved saphenic acid and screened against a range of skin flora and resistant Staphylococcus aureus strains. Biological activities of saphenamycin enantiomers were compared with that of the synthetic racemate as well as earlier reported activities of saphenamycin isolated from natural sources. No significant difference was observed in activity of the enantiomers of saphenamycin, which revealed that the chirality of saphenamycin has no consequences for the antibiotic activity. Saphenamycin proved to be a potent antibiotic against fusidic acid and rifampicin resistant S. aureus strains showing MIC of 0.1-0.2 μg/mL. 2002 Elsevier Science. All rights reserved.