1851-86-1

Usage

Uses

Used in Food Industry:
3-Hydroxybutyl acetate is used as a flavoring agent for its fruity, sweet aroma reminiscent of pineapple and apricot, enhancing the taste and aroma of various food products.
Used in Cosmetic Industry:
3-Hydroxybutyl acetate is used as a fragrance ingredient in perfumes, colognes, and other scented products, providing a pleasant and attractive scent.
Used in Manufacturing Industry:
3-Hydroxybutyl acetate is used as a solvent in the production of coatings, adhesives, and chemical intermediates, contributing to the manufacturing process and improving product performance.
Used in Natural Sources:
3-Hydroxybutyl acetate can be found in various natural sources such as fruits and flowers, where it contributes to their distinct aroma and flavor profiles.

InChI:InChI=1/C6H12O3/c1-5(7)3-4-9-6(2)8/h5,7H,3-4H2,1-2H3

Upstream product

• 10150-87-5 1-acetoxybutan-3-one 
• 18826-95-4 1.3-butanediol 
• 108-24-7 acetic anhydride 
• 107-89-1 acetaldol 
• 75-07-0 acetaldehyde 
• 555-75-9 aluminum ethoxide 
• 766-20-1 2,4-dimethyl-[1,3]dioxane 
• 76397-53-0 3-acetylthiazolidine-2-thione 
• 75-36-5 acetyl chloride 
• 113406-49-8 4-methyl-2-methylene-1,3-dioxane 
• 108-22-5 Isopropenyl acetate 
• 2466-76-4 N-Acetylimidazole 
• 64-19-7 acetic acid 
• 35337-49-6 2-bromomethyl-4-methyl-1,3-dioxane 

Downstream Products

• 10150-87-5 1-acetoxybutan-3-one 
• 912816-43-4 acetic acid 3-(2-benzyl-4-ethyl-phenoxy)-butyl ester 
• 847344-52-9 acetic acid 3-(2-benzoyl-4-ethyl-phenoxy)-butyl ester 

Relevant academic research and scientific papers

DBN-Catalyzed Regioselective Acylation of Carbohydrates and Diols in Ethyl Acetate

The 1,5-diazabicyclo[4.3.0]non-5-ene (DBN)-catalyzed regioselective acylation of carbohydrates and diols in ethyl acetate has been developed. The hydroxyl groups can be selectively acylated by the corresponding anhydride in EtOAc in the presence of a catalytic amount (as low as 0.1 equiv.) of DBN at room temperature to 40 °C. This method avoids metal catalysts and toxic solvents, which makes it comparatively green and mild, and it uses less organic base compared with other selective acylation methods. Mechanism studies indicated that DBN could catalyze the selective acylation of hydroxyl moieties through a dual H-bonding interaction.

Sulfonic acid-functionalized periodic mesoporous organosilicas in esterification and selective acylation reactions

The application of sulfonic acid-functionalized periodic mesoporous organosilicas (PMOs) having either phenyl (1a) or ethyl (1b) bridging groups was investigated in the esterification of a variety of alcohols and fatty acids. It was found that 1b consistently exhibited higher catalytic performance than 1a in the described reaction. In particular, it was proposed that the superior catalytic activity of 1b in esterification of fatty acids with methanol is a result of adequate hydrophobic-hydrophilic surface balance in the ethyl PMO catalyst. In addition, the study of chemoselective acylation of 1,3-butanediol with dodecanoic acid with varied mesoporous silica-supported solid sulfonic acids including both 1a and 1b implies that there is a compromise between the reaction selectivity and the surface physicochemical properties of the employed catalyst. Our results clearly show that the catalyst having high surface hydrophilic nature gives high selectivity toward the formation of mono-acylated products whereas those with relatively high hydrophobic characteristics showed enhanced selectivity toward the formation of di-acylated products.

Simple and practical method for selective acylation of primary hydroxy group catalyzed by N-methyl-2-phenylimidazole (Ph-NMI) or 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT)

N-Methyl-2-phenylimidazole (Ph-NMI) and 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT) catalyzed selective acylation of primary alcohols using acid anhydrides. The Ph-NMI- or Ph-IBT-catalyzed reaction using (PhCO)2O as an acylating agent could particularly acylate the primary hydroxy group of 1,n-diols (n ≥ 3) with a high, synthetically useful selectivity.

Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water

A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups. This journal is

A highly selective, high-speed, and hydrolysis-free O-acylation in subcritical water in the absence of a catalyst

(Chemical Equation Presented) Fast and furious: A wide range of alcohols are acylated by acetic anhydride, in the absence of catalyst, in subcritical water in a flow-type microreaction system. The esters are selectively produced in high yields at temperatures of 200 to 250°C. Varying the amount of acetic anhydride added with respect to the alcohols allows the regioselective acylation of one or both hydroxy groups of various dihydroxy compounds (see picture).

Design and synthesis of dual peroxisome proliferator-activated receptors γ and δ agonists as novel euglycemic agents with a reduced weight gain profile

The design and synthesis of the dual peroxisome proliferator-activated receptor (PPAR) γ/δ agonist (R)-3-{4-[3-(4-chloro-2-phenoxy-phenoxy) -butoxy]-2-ethyl-phenyl}-propionic acid (20) for the treatment of type 2 diabetes and associated dyslipidemia is described. The compound possesses a potent dual hPPAR γ/δ agonist profile (IC50 = 19 nM/4 nM; EC50 = 102 nM/6 nM for hPPARγ and hPPARδ, respectively). In preclinical models, the compound improves insulin sensitivity and reverses diabetic hyperglycemia with less weight gain at a given level of glucose control relative to rosiglitazone.

Selective acylation of a sterically hindered hydroxyl group of unsymmetrical diols containing a primary hydroxyl group such as 1,5-hexanediol in the presence of silica gel with acetyl chloride

The selective acetylation of sterically hindered hydroxyl groups of 1,5-hexanediol preadsorbed on silica gel was reported. The relation between the adsorption of the diol on SiO2 and its reactivity for selective acetylation was studied. Results demonstrated that unsymmetrical diols get adsorbed on the surface of SiO2 preferentially via a primary OH group, leaving the non-adsorbed OH group available for reaction.

Lewis acid catalyzed acylation reactions: Scope and limitations

Acylation of alcohols, thiols, and sugars were studied with a variety of Lewis acids, and it was found that Cu- and Sn(OTf)2 are very efficient in catalyzing the reaction under mild conditions. Among these two catalysts, Cu(OTf)2 was preferred because of its lower cost and relatively higher yield of the acylated product. The reaction was studied in several solvents, but CH2Cl2 was preferred. It was also observed that the present method is suitable for acylation of tertiary alcohols. Sugars were also acylated without any epimerization at the anomeric center. It is further shown here that this method is also suitable for selective acylation of primary or secondary alcohols over tertiary ones.

Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis

Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary ones as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under the present reaction conditions. This method is highly practical since operation is quite simple. Esters and solvents can be used without purification and no inert atmosphere is necessary. The products can be isolated simply by column chromatography or distillation without aqueous workup.

Trimerization of aliphatic aldehydes to 1,3-diol monoesters catalyzed by Cp*2Sm(thf)2

Aliphatic aldehydes underwent trimerization in the presence of a catalytic amount of Cp*2Sm(thf)2 under ambient conditions to form 1,3- diol monoestcrs in good yields. For example, the reaction of acetoaldehyde catalyzed by Cp*2Sm(thf)2 gave 4-acetoxy-2-butanol (2a) and 3-acetoxy-1- butanol (3a) in 86% yield.