92418-59-2

Basic information

• Product Name: (2,2-diMethyl-1,3-dioxolane-4-yl)Methyl n-butanoate
• Synonyms: (2,2-DiMethyl-1,3-dioxolan-4-yl)Methyl butyrate;(2,2-diMethyl-1,3-dioxolane-4-yl)Methyl n-butanoate
• CAS NO: 92418-59-2
• Molecular Formula: C₁₀H₁₈O₄
• Molecular Weight: 202.24752
• Mol File: 92418-59-2.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2,2-diMethyl-1,3-dioxolane-4-yl)Methyl n-butanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (2,2-diMethyl-1,3-dioxolane-4-yl)Methyl n-butanoate(92418-59-2)
• EPA Substance Registry System: (2,2-diMethyl-1,3-dioxolane-4-yl)Methyl n-butanoate(92418-59-2)

Safety Data

• Hazardous Substances Data: 92418-59-2(Hazardous Substances Data)

Usage

General Description

(2,2-diMethyl-1,3-dioxolane-4-yl)Methyl n-butanoate is an organic compound with the chemical formula C10H18O4. It is a colorless liquid with a fruity odor, commonly used as a flavor and fragrance ingredient in the food and cosmetic industries. The compound is derived from the esterification of (2,2-diMethyl-1,3-dioxolane-4-yl)methanol with n-butanoic acid, resulting in a compound with a pleasant, fruity aroma reminiscent of apple and pear. Due to its low volatility and stability, it is often used in perfumes, lotions, and various food products as a flavor enhancer. Additionally, it is considered safe for use in these applications by regulatory agencies such as the US Food and Drug Administration.

Upstream product

• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 106-31-0 butanoic acid anhydride 
• 123-20-6 vinyl n-butyrate 

Downstream Products

• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 107-92-6 butyric acid 
• 557-25-5 1-monobutyrin 
• 119238-14-1 (S)-2,2-dimethyl-1,3-dioxolane-4-methanol butanoate 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 

Relevant articles and documents

Lipases aided esterification of (2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Racemic solketal (2,2-Dimethyl-1,3-dioxolan-4-yl)methanol 1, was treated with carboxylic acids of varying chain length or their vinyl esters in the presence of different lipases. The esterification reaction was carried out in n-hexane or diisopropyl ether as a solvent. The yield of the solketal esters and their enantiopurity were satisfactory, as indicated by gas chromatography using chiral column. Lipases from Rhizopus oryzae and Pseudomonas fluorescence gave the best enantiomeric excess (ee) when the solketal was treated with vinyl butyrate in a solution of diisopropyl ether at room temperature.

Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides

Chirazyme L-2 (Candida antarctica) catalyzed esterification of glycerol with aromatic and aliphatic anhydrides in 1,4-dioxane is described. All the aromatic monoacylglycerols (MAGs) were produced as (R)-enantiomers, while aliphatic MAGs were obtained either as racemic mixtures or the (S)-enantiomers. The influence of substituted aromatic rings, chain length, and presence of a conjugated double bond in the acyl donor moiety on the enantiotopic selectivity as well as the efficiency of the enzyme was studied.

Quantitative screening of hydrolase libraries using pH indicators: Identifying active and enantioselective hydrolases

The slowest step in finding a selective hydrolase for synthesis is often the screening step. Researchers must run small test reactions and measure the amounts of stereoisomers formed by HPLC, GC, or NMR. We have developed a colorimetric method to speed up this screening. We quantitatively detect ester hydrolysis using a pH indicator, 4-nitrophenol. We estimate the selectivity by measuring the initial rates of hydrolysis for pure stereoisomers separately. To demonstrate the utility of this method, we screened seventy-two commercial enzymes for enantioselective hydrolysis of racemic solketal butyrate, an important chiral building block. First, we eliminated the twenty hydrolases that did not catalyze hydrolysis of either enantiomer. Next, we measured initial rates of hydrolysis of the pure enantiomers of solketal butyrate. For horse-liver esterase, these initial rates differed by a factor of twelve. Subsequent GC experiments confirmed an enantiomeric ratio of fifteen for this hydrolase. Although this enantioselectivity is moderate, it is the highest enantioselectivity reported for a hydrolysis of solketal esters.