10415-88-0

Basic information

• Product Name: 4-PHENYL-2-BUTYL ACETATE
• Synonyms: 2-Butanol, 4-phenyl-, acetate;alpha-methyl-benzenepropanoacetate;Benzenepropanol, alpha-methyl-, acetate;Benzenepropanol,.alpha.-methyl-,acetate;CH3C(O)OCH(CH3)CH2CH2C6H5;Phenylpropanol, alpha-methyl, acetate;1-METHYL-3-PHENYLPROPYL ACETATE;4-PHENYL-2-BUTYL ACETATE
• CAS NO: 10415-88-0
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25
• EINECS: 233-890-6
• Mol File: 10415-88-0.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 72-74 °C
• Flash Point: 112.8 °C
• Appearance: /
• Density: 0.99
• Vapor Pressure: 0.00547mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• CAS DataBase Reference: 4-PHENYL-2-BUTYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENYL-2-BUTYL ACETATE(10415-88-0)
• EPA Substance Registry System: 4-PHENYL-2-BUTYL ACETATE(10415-88-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 10415-88-0(Hazardous Substances Data)

Usage

Description

4-Phenyl-2-butyl acetate is an organic compound with a mild, green, fruity odor and a sweet, fruity taste. It is a colorless to pale yellow liquid at room temperature and is soluble in organic solvents.

Uses

Used in Flavor Industry:
4-Phenyl-2-butyl acetate is used as a flavoring agent for its distinct sweet, fruity taste. It is commonly utilized in the creation of artificial flavors for the food and beverage industry, particularly in products that require a green, fruity note.
Used in Fragrance Industry:
In the fragrance industry, 4-Phenyl-2-butyl acetate is used as a fixative agent. Its mild, green, fruity odor helps to enhance and prolong the scent of perfumes and other fragrance products, providing a pleasant and lasting aroma.
Used in Cosmetics Industry:
4-Phenyl-2-butyl acetate is also used in the cosmetics industry, where it serves as a fragrance ingredient in various personal care products such as lotions, creams, and shampoos. Its fruity scent adds a pleasant aroma to these products, making them more appealing to consumers.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 4-Phenyl-2-butyl acetate may have potential applications in the pharmaceutical industry as a solvent or carrier for certain drugs, due to its solubility in organic solvents and its compatibility with various substances. Further research and development would be required to explore these possibilities.

Preparation

By acetylation of the corresponding alcohol; the racemic and the dextrorotatory forms are known.

InChI:InChI=1/C12H16O2/c1-10(14-11(2)13)8-9-12-6-4-3-5-7-12/h3-7,10H,8-9H2,1-2H3/t10-/m1/s1

Upstream product

• 2754-27-0 trimethylsilyl acetate 
• 141809-67-8 1-methyl-3-phenylpropyl trimethylsilyl ether 
• 34688-55-6 1,3-diacetoxy-1-phenyl-butane 
• 2344-70-9 1-phenyl-3-butanol 
• 123-54-6 acetylacetone 
• 62692-57-3 4-phenyl but-1-en-2-yl acetate 
• 108-24-7 acetic anhydride 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 2550-26-7 4-Phenyl-2-butanone 
• 141-78-6 ethyl acetate 
• 75178-12-0 2,2'-bipyridyl-6-yl acetate 
• 1117-31-3 1,3-diacetoxybutane 
• 71-43-2 benzene 
• 581-55-5 benzylidene 1,1-diacetate 

Downstream Products

• 2344-70-9 1-phenyl-3-butanol 
• 2550-26-7 4-Phenyl-2-butanone 
• 2344-70-9 (+)-(S)-4-phenylbutan-2-ol 
• 61836-03-1 (rac)-(4-phenylbutan-2-ylthio)benzene 
• 2344-70-9 (R)-4-phenyl-2-butanol 
• 131029-06-6 Acetic acid (S)-1-methyl-3-((R)-1-phenyl-ethylcarbamoyl)-propyl ester 
• 40654-82-8 4-phenyl-2-methylbutanal 
• 104-51-8 1-butylbenzene 
• 1929-33-5 triphenylsilyl acetate 

Relevant articles and documents

Highly enantioselective aminoacylase-catalyzed transesterification of secondary alcohols

The aminoacylase (N-acyl-L-amino acid amidohydrolase; E.C. 3.5.1.14) from Aspergillus melleus, a readily available inexpensive enzyme, catalyzes the transesterification of a wide range of chiral secondary arylalkanols with essentially absolute stereoselectivity (E> 500). Moreover, the productivities obtained with 1-phenylethanol, 1-phenylpropanol, 1-(1-naphthyl)ethanol and 1- (2-naphthyl)ethanol were substantially higher than those in the corresponding lipase-catalyzed transesterifications. (C) 2000 Elsevier Science Ltd.

CO2-expanded bio-based liquids as novel solvents for enantioselective biocatalysis

For the first time, CO2-expanded bio-based liquids were reported as novel and sustainable solvents for biocatalysis. Herein, it was found that by expansion with CO2, 2-methyltetrahydrofuran (MeTHF), and other bio-based liquids, which were not favorable solvents for immobilized Candida antarctica lipase B (Novozym 435) catalyzed transesterification, were tuned into excellent reaction media. Especially, for the kinetic resolution of challenging bulky secondary substrates such as rac-1-adamantylethanol, the lipase displayed very high activity with excellent enantioselectivity (E value > 200) in CO2-expanded MeTHF (MeTHF concentration 10% v/v, 6 MPa), whereas there was almost no activity observed in conventional organic solvents.

CALB immobilized onto magnetic nanoparticles for efficient kinetic resolution of racemic secondary alcohols: Long-term stability and reusability

In this study, an immobilization strategy for magnetic cross-linking enzyme aggregates of lipase B from Candida antarctica (CALB) was developed and investigated. Magnetic particles were prepared by conventional co-precipitation. The magnetic nanoparticles were modified with 3-aminopropyltriethoxysilane (APTES) to obtain surface amino-functionalized magnetic nanoparticles (APTES–Fe3O4) as immobilization materials. Glutaraldehyde was used as a crosslinker to covalently bind CALB to APTES–Fe3O4. The optimal conditions of immobilization of lipase and resolution of racemic 1-phenylethanol were investigated. Under optimal conditions, esters could be obtained with conversion of 50%, enantiomeric excess of product (eep) > 99%, enantiomeric excess of substrate (ees) > 99%, and enantiomeric ratio (E) > 1000. The magnetic CALB CLEAs were successfully used for enzymatic kinetic resolution of fifteen secondary alcohols. Compared with Novozym 435, the magnetic CALB CLEAs exhibited a better enantioselectivity for most substrates. The conversion was still greater than 49% after the magnetic CALB CLEAs had been reused 10 times in a 48 h reaction cycle; both ees and eep were close to 99%. Furthermore, there was little decrease in catalytic activity and enantioselectivity after being stored at ?20 ?C for 90 days.

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols

Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.