21963-26-8

Usage

Uses

Used in Food Industry:
5-pentylfuran-2(5H)-one is used as a flavor enhancer for its ability to impart a sugary, caramel flavor to a variety of foods, including baked goods, candy, and desserts. It enriches the taste experience by adding depth and sweetness without the need for additional sugar.
Used in Beverage Industry:
In the beverage sector, 5-pentylfuran-2(5H)-one is utilized as a flavoring agent to sweeten and enhance the taste of drinks, providing a pleasant caramel aroma and taste that can make beverages more appealing to consumers.
Used in Tobacco Products:
5-pentylfuran-2(5H)-one is used as an additive in tobacco products to improve the taste and aroma of the smoke, offering a caramel-like sweetness that can make the smoking experience more enjoyable for users.
Used in E-liquid Production for Electronic Cigarettes:
In the emerging market of electronic cigarettes, 5-pentylfuran-2(5H)-one is employed in the formulation of e-liquids to improve the taste and aroma of the vapor produced. This enhancement aims to simulate the sensory experience of traditional tobacco products while providing a potentially less harmful alternative for consumers.

InChI:InChI=1/C9H14O2/c1-2-3-4-5-8-6-7-9(10)11-8/h6-8H,2-5H2,1H3

Upstream product

• 14032-66-7 5-hydroxy-2-(5H)-furanone 
• 693-25-4 n-pentylmagnesium bromide 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 628-17-1 amyl iodide 
• 6064-52-4 4-oxononanoic acid 
• 128946-16-7 (Z)-methyl 4-hydroxy-2-nonenoate 
• 167902-86-5 5-Pentyl-4-(toluene-4-sulfonyl)-dihydro-furan-2-one 
• 145655-32-9 acrylic acid 1-vinyl-hexyl ester 
• 20497-95-4 methyl 3-nitropropionate 
• 66-25-1 hexanal 
• 28163-88-4 (E)-non-3-enoic acid 
• 111-71-7 heptanal 
• 84771-68-6 (E)-methyl 4-hydroxynon-2-enoate 
• 84477-20-3 5-Pentyl-4-phenylsulfanyl-dihydro-furan-2-one 

Downstream Products

• 4753-59-7 4-Bromobutyl acetate 
• 142685-41-4 C₁₁H₁₆O₃ 
• 1361199-98-5 C₁₃H₁₈O₄ 
• 1361200-08-9 dimethyl 1-(diphenoxyphosphoryloxy)-4-pentyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate 
• 1361200-02-3 5-pentylfuran-2-yl diphenyl phosphate 
• 1353637-85-0 (4S,5R)-4-dimethyl(phenyl)silyl-5-pentyl-4,5-dihydrofuran-2(3H)-one 
• 1436857-03-2 (4R,5S)-4-(dimethyl(phenyl)silyl)-5-pentyldihydrofuran-2(3H)-one 
• 63357-96-0 (R)-(+)-γ-nonalactone 
• 33673-62-0 trans-(4S,5R)-4,5-dihydro-4-methyl-5-pentyl-2(3H)-furanone 

Relevant academic research and scientific papers

One-pot synthesis of 5-Alkylfuran-2(5H)-ones

5-Alkylfuran-2(5H)-ones can be efficiently obtained using a one-pot approach, starting from methyl 3-nitropropanoate and aldehydes, in ethyl acetate, with Amberlyst A-21 as catalyst, in 60-90% overall yield. Copyright Taylor & Francis Group, LLC.

Convenient synthesis of 5-alkylfuran-2(5H)-ones

A convenient synthesis of 5-alkylfuran-2(5H)-ones are described starting from 3-nitropropanoate and aldehydes, promoted by neutral alumina, in 35-60% overall yields, via a condensation-lactonization-elimination pathway. Copyright

Synthetic method γ - nonene lactone

The invention relates to a synthesis method of γ - nonenolide, belongs to the technical field of perfume synthesis, first steps of adding malonic acid into a four-port flask containing a condensing tube and a water separator, adding piperidine, and then adding heptanal to the 95 - 105 °C condition to raise the temperature and react to obtain the intermediate 1. The second Acetic acid and hydrogen peroxide are mixed, the intermediate 1 is added dropwise, the control temperature is 40 °C, and the intermediate 2 is obtained. The third Intermediate 2, dichloromethane and triethylamine were mixed and acetyl chloride was added dropwise, and after the dropwise addition, γ - nonene lactone was obtained. No solvent is used in first steps of the invention, so that the reaction cost is reduced. The intermediate 1 is closed under the action of acetic acid and hydrogen peroxide, adopts hydrogen peroxide as an oxidant, and has the advantage of environmental friendliness. By replacing methane sulfonyl chloride with acetyl chloride, the use of methane sulfonyl chloride is reduced under the condition of ensuring the yield, the whole reaction process is simple, the route is short, and the raw materials are easily available.

Large-Scale Synthesis of a Niche Olefin Metathesis Catalyst Bearing an Unsymmetrical N-Heterocyclic Carbene (NHC) Ligand and its Application in a Green Pharmaceutical Context

A large-scale synthesis of known Ru olefin metathesis catalyst VII featuring an unsymmetrical N-heterocyclic carbene (NHC) ligand with one 2,5-diisopropylphenyl (DIPP) and one thiophenylmethylene N-substituent is reported. The optimised procedure does not require column chromatography in any step and allows for preparation of up to 0.5 kg batches of the catalyst from simple precursors. The application profile of the obtained catalyst was studied in environmentally friendly dimethyl carbonate (DMC). Although VII exhibited low efficiency in cross-metathesis (CM) with electron-deficient partners, good to excellent results were noted for substrates featuring easy to isomerise C?C double bonds. This includes polyfunctional substrates of medicinal chemistry interest, such as analogues of psychoactive 5F-PB-22 and NM-2201 and two PDE5 inhibitors—Sildenafil and Vardenafil. Finally, a larger scale ring-closing metathesis (RCM) of a Vardenafil derivative was conducted in DMC, allowing for straightforward isolation of the expected product (23 g) in high yield and with low Ru contamination level (7.7 ppm).

A facile synthesis of γ-butenolides via cyclization of 3-alkenoic acids with dimethyl sulfoxide and oxalyl bromide

The combination of dimethyl sulfoxide and oxalyl bromide was used to accomplish the cyclization of 3-alkenoic acids with the aid of a base to afford γ-butenolides, in which bromodimethylsulfonium salt generated in situ was proposed to serve as a Br+ source.

Highly efficient and time economical purification of olefin metathesis products from metal residues using an isocyanide scavenger

A sustainable protocol of olefin metathesis in non-degassed, undistilled ethyl acetate under air with commercially available self-scavenging ruthenium catalysts is described. Furthermore, a time economical, cost-effective and scalable method of removal of ruthenium residues is presented. Treatment of post-reaction mixtures with an isocyanide scavenger and then with acid followed by a simple filtration is shown to yield OM products with ruthenium contamination below 5 ppm even in highly challenging cases. Finally, a telescope RCM/Suzuki-Miyaura sequence with a rapid and efficient purification protocol for simultaneous removal of Ru and Pd residues from solution is described.

Preparation method of alpha, beta-unsaturated-gamma-lactone

The invention relates to a preparation method of alpha, beta-unsaturated-gamma-lactone shown as a structural formula below. The preparation method comprises the following steps: firstly dropwise adding a dichloromethane solution of dimethylsulfoxide (1.5 equiv) into a dichloromethane solution of oxaloyl bromide (1.5 equiv) at a temperature of 10 DEG C below zero, dropwise adding raw material (E) 3-alkenoic acid, then returning to a room temperature for reaction, adding a potassium carbonate aqueous solution and continuously reacting to obtain the corresponding alpha, beta-unsaturated-gamma-lactone; the yield is 85-90 percent.

A Novel Method for the Chlorolactonization of Alkenoic Acids Using Diphenyl Sulfoxide/Oxalyl Chloride

A facile chlorolactonization of alkenoic acids by treatment with diphenyl sulfoxide/oxalyl chloride has been developed. The reaction can generate various chlorolactones in moderate to good yields, wherein the chlorodiphenylsufonium salt derived from diphenyl sulfoxide/oxalyl chloride serves as the source of Cl +.

Method for preparing alpha,beta-unsaturated gamma-lactone

The invention relates to a method for preparing alpha,beta-unsaturated gamma-lactone represented by structural formula shown in the description. The method comprises the following steps: dropwise adding a dichloromethane solution of diphenyl sulfoxide (1.5 eq) to a dichloromethane solution of oxalyl chloride (1.5 eq) (or oxalyl bromide (1.5 eq)) at -78 DEG C, dropwise adding a raw material (E)-3-alkenoic acid, adding potassium carbonate and 18-crown-6 ether, and carrying out room temperature reaction to obtain the corresponding alpha,beta-unsaturated gamma-lactone with the yield of 80-85%.

Organocatalytic sequential α-aminoxylation and cis-Wittig olefination of aldehydes: Synthesis of enantiopure γ-butenolides

A short route to enantiopure γ-butenolides (up to 99% ee) has been developed from readily available starting materials. The strategy involves a sequential organocatalytic α-aminoxylation followed by cis-Wittig olefination of aldehydes. The utility of this protocol has been demonstrated in the asymmetric synthesis of trans-(+)-cognac lactone with high enantiomeric purity.