Benzoic acid, C9-11 , C10-rich, branched alkyl esters

Endpoint summary

Key value for chemical safety assessment

Bioaccumulation potential:

no bioaccumulation potential

Additional information

Adsorption, distribution, metabolism and excretion are important components in developing an understanding of the potential health effects of a material and of extrapolating data between studies, between routes of administration and between compounds. In the case of CAS RN 131298-44-7, some generalities are useful in understanding the interrelationships of the components that comprise the alkyl benzyl ester molecule. Hydrolysis of isodecyl benzoate would release the benzoic acid and primary C10 alcohol.

 

Isodecyl Benzoate (IDB) (CAS RN 131298) is an alkyl benzyl ester, also referred to as a carboxylic ester (R-C(O)-OR’) produced by reaction with benzoic acid and isodecyl (C10) alcohol. An important feature is that such esters are poorly soluble in water. Esters are reactive with water and can hydrolyze under either acidic or basic conditions. The expected rapid hydrolysis of IDB would be a reverse of the esterification process (generally catalyzed via an esterase) and would produce benzoic acid and primary C10 alcohol. Metabolism and excretion are expected to occur rapidly. 

 

Benzoic acid is metabolised to either benzoyl glucuronide or hippuric acid. Benzoyl glucuronide is produced by the reaction of benzoic acid with glucuronic acid, which accounts for 10-20% of benzoic acid elimination. Hippuric acid is also known as benzoylglycine and is produced from benzoic acid in two steps: first benzoic acid is converted to benzoyl-CoA by the enzyme benzoyl-CoA synthase; then benzoyl-CoA is converted to hippuric acid by benzoyl-CoA:glycine N-acyltransferase. Excretion of hippuric acid is via the urine. 

 

The primary C10 alcohol would likely be broken down by mitochondrial beta-oxidation or by cytochrome P450-mediated ω- and ω-1-oxidation (may be followed by β-oxidation). The alcohol undergoes various oxidative steps to yield other alcohols, ketones, aldehydes, carboxylic acids and carbon dioxide. Data for monohydric, saturated alcohols show a systematic variation according to molecular weight in a manner similar to many other homologous series. The analogs 1-hexanol and 1-dodecanol follow similar metabolic pathways by undergoing oxidative steps to yield aldehydes, carboxylic acid and eventually undergoing intermediary metabolism. The body handles aliphatic hydrocarbons in a similar manner via oxidative conversion to alcohols, ketones, and eventual elimination as carbon dioxide and carboxylic acids. The undegraded alcohols can be conjugated either directly or as a metabolite with glucuronic acid, sulfuric acid, or glycine and are rapidly excreted. Glucuronidation and glutathione conjugation are possible means of rapid elimination. 

Discussion on bioaccumulation potential result:

Adsorption, distribution, metabolism and excretion are important components in developing an understanding of the potential health effects of a material and of extrapolating data between studies, between routes of administration and between compounds. In the case of CAS RN 131298-44-7, some generalities are useful in understanding the interrelationships of the components that comprise the alkyl benzyl ester molecule. Hydrolysis of isodecyl benzoate would release the benzoic acid and primary C10 alcohol.

 

Isodecyl Benzoate (IDB) (CAS RN 131298) is an alkyl benzyl ester, also referred to as a carboxylic ester (R-C(O)-OR’) produced by reaction with benzoic acid and isodecyl (C10) alcohol. An important feature is that such esters are poorly soluble in water. Esters are reactive with water and can hydrolyze under either acidic or basic conditions. The expected rapid hydrolysis of IDB would be a reverse of the esterification process (generally catalyzed via an esterase) and would produce benzoic acid and primary C10 alcohol. Metabolism and excretion are expected to occur rapidly. 

 

Benzoic acid is metabolised to either benzoyl glucuronide or hippuric acid. Benzoyl glucuronide is produced by the reaction of benzoic acid with glucuronic acid, which accounts for 10-20% of benzoic acid elimination. Hippuric acid is also known as benzoylglycine and is produced from benzoic acid in two steps: first benzoic acid is converted to benzoyl-CoA by the enzyme benzoyl-CoA synthase; then benzoyl-CoA is converted to hippuric acid by benzoyl-CoA:glycine N-acyltransferase. Excretion of hippuric acid is via the urine. 

 

The primary C10 alcohol would likely be broken down by mitochondrial beta-oxidation or by cytochrome P450-mediated ω- and ω-1-oxidation (may be followed by β-oxidation). The alcohol undergoes various oxidative steps to yield other alcohols, ketones, aldehydes, carboxylic acids and carbon dioxide. Data for monohydric, saturated alcohols show a systematic variation according to molecular weight in a manner similar to many other homologous series. The analogs 1-hexanol and 1-dodecanol follow similar metabolic pathways by undergoing oxidative steps to yield aldehydes, carboxylic acid and eventually undergoing intermediary metabolism. The body handles aliphatic hydrocarbons in a similar manner via oxidative conversion to alcohols, ketones, and eventual elimination as carbon dioxide and carboxylic acids. The undegraded alcohols can be conjugated either directly or as a metabolite with glucuronic acid, sulfuric acid, or glycine and are rapidly excreted. Glucuronidation and glutathione conjugation are possible means of rapid elimination.