31323-51-0

Basic information

• Product Name: (S)-4-HEPTANOLIDE STANDARD FOR GC
• Synonyms: (S)-4-HEPTANOLIDE STANDARD FOR GC;(s)-γ-propyl-γ-butyrolactone;(S)-γ-Propyl-γ-butyrolactone, (S)-Dihydro-5-propyl-2(3H)-furanone;(S)-Dihydro-5-propyl-2(3H)-furanone
• CAS NO: 31323-51-0
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.16898
• EINECS: 203-279-9
• Mol File: 31323-51-0.mol

Chemical Properties

• Boiling Point: 226.3°Cat760mmHg
• Flash Point: 110 °C
• Appearance: /
• Density: 0.983g/cm³
• Vapor Pressure: 0.0827mmHg at 25°C
• Refractive Index: 1.436
• Storage Temp.: −20°C
• CAS DataBase Reference: (S)-4-HEPTANOLIDE STANDARD FOR GC(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-HEPTANOLIDE STANDARD FOR GC(31323-51-0)
• EPA Substance Registry System: (S)-4-HEPTANOLIDE STANDARD FOR GC(31323-51-0)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 36
• WGK Germany: 3
• Hazardous Substances Data: 31323-51-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Analysis Industry:
(S)-4-HEPTANOLIDE STANDARD FOR GC is used as a reference standard for the identification and quantification of similar compounds in various samples. It serves as a control substance for comparison and calibration in GC experiments, ensuring accurate and precise analysis of organic compounds.
Used in Research and Development:
(S)-4-HEPTANOLIDE STANDARD FOR GC is used as a benchmark in the development of new analytical methods and techniques for the detection and quantification of organic compounds. It aids researchers in validating the performance of their GC systems and refining their methodologies for better results.
Used in Quality Control:
(S)-4-HEPTANOLIDE STANDARD FOR GC is employed in quality control processes to ensure the reliability and consistency of GC analysis results. It helps in verifying the accuracy of the analytical instruments and maintaining the integrity of the data obtained from GC experiments.
Used in Environmental Monitoring:
(S)-4-HEPTANOLIDE STANDARD FOR GC is used in environmental monitoring to detect and quantify the presence of specific organic compounds in air, water, and soil samples. This helps in assessing the environmental impact of various pollutants and implementing appropriate measures for pollution control.
Used in Pharmaceutical Industry:
(S)-4-HEPTANOLIDE STANDARD FOR GC is utilized in the pharmaceutical industry for the analysis of drug substances and their metabolites. It aids in the development of new drugs, ensuring their safety and efficacy, and in the quality control of pharmaceutical products.
Used in Food and Beverage Industry:
(S)-4-HEPTANOLIDE STANDARD FOR GC is employed in the food and beverage industry for the analysis of flavor compounds, additives, and contaminants. It helps in ensuring the quality and safety of food products, as well as in the development of new and improved flavors for various beverages.

InChI:InChI=1/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3/t6-/m0/s1

Upstream product

• 44911-93-5 (S)-4-Hydroxy-heptanoic acid 
• 152723-40-5 5-allyl-dihydrofuran-2-one 
• 57753-49-8 4-Hydroxy-heptanoic acid amide 
• 40646-07-9 heptane-1,4-diol 
• 112607-22-4 (+)-(R)-5-(2-phenylethyl)dihydrofuran-2(3H)-one 
• 134627-14-8 (+)-1-Phenyl-hexan-3-ol 
• 13122-67-3 6-phenyl-4-oxohexanoic acid 
• 107736-28-7 2-Diazo-1-((2S,3R)-3-propyl-oxiranyl)-ethanone 
• 107736-37-8 (E)-(S)-4-Hydroxy-hept-2-enoic acid ethyl ester 
• 107796-99-6 Methyl (2S,3R)-(+)-3-propyloxirane-2-carboxylate 
• 92418-71-8 (2R,3R)-2,3-epoxy-1-hexanol 
• 1026217-79-7 4-Nitro-benzoic acid (S)-1-(2-carboxy-ethyl)-butyl ester 
• 154657-42-8 (4S)-4-<(p-Nitrobenzoyl)oxy>-1-heptene 
• 85520-72-5 (4S)-hept-1-en-4-ol 

Relevant articles and documents

Stereoselective reduction of 2-butenolides to chiral butanolides by reductases from cultured cells of Glycine max

The stereoselective reduction of 2-butenolides by two reductases, p51 and p83, from cultured plant cells of Glycine max was investigated. The reduction of 2-methyl-2-butenolide by p51 reductase produced (R)-2-methylbutanolide, whereas the reduction by p83 reductase gave (S)-2-methylbutanolide. Both reductases reduced 3-methyl-2-butenolide to (R)-3-methylbutanolide. The reduction of 2,3-dimethyl-2-butenolide by p51 reductase gave (2R,3R)-2,3-dimethylbutanolide, whereas the reduction by p83 reductase produced (2S,3R)-2,3-dimethylbutanolide. The reduction of 4-alkyl-2-butenolides with these reductases was accompanied by resolution of chiral centers affording (R)-4-alkylbutanolides.

Biocatalytic oxidation of 1,4-diols and γ-lactols into γ-lactones: Application to chemoenzymatic synthesis of drospirenone

Oxidation of 1-alkyl-1,4-butanediols with Acetobacter aceti MIM 2000/28 gave the corresponding γ-lactones in good yields. The biotransformation occurred with intermediate formation of γ-lactols, which are also substrates for oxidation with Acetobacter aceti MIM 2000/28, as validated by selective biotransformation of 6β,7β;15β,16β-dimethylene-3- oxo-17α-pregn-4-en-21,17-carbolactol to drospirenone.

Lactone synthesis via biotransformations of γ-hydroxyamides

An enzyme was expressed in E. coli from a cloned amidase gene. When characterized, it was more enantioselective than commercial amidases. Three pheromones were made. An enzyme was expressed in Escherichia coli from a cloned amidase gene. When characterized, it was more enantioselective than commercial amidases. Three pheromones were made using this biotransformation chemistry.

Convenient enantioselective synthesis of new 1,4-sulfanylalcohols from γ-lactones

A synthetic strategy based upon three basic reactions - enzymatic resolution, oxygen-sulfur exchange, reduction - allowed us to carry out an easy and useful synthesis of a series of new 1,4-sulfanylalcohols from aliphatic γ-lactones. Final products have been obtained in good yields with enantiomeric excesses in a 66-91% range.

A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B- allyldiisopinocampheylborane

Asymmetric allylboration of aldehydes containing an adjacent ester group with B-allyldiisopinocampheylborane, followed by hydrolysis and cyclization, provides the corresponding allyl substituted lactones in high yields and ≥92% enantiomeric excess. Hydrogenation of these lactones provides the corresponding propyl substituted lactones without any loss of optical purity.

Chiral synthesis via organoboranes. 39. A facile synthesis of γ- substituted-γ-butyrolactones in exceptionally high enantiomeric purity

Optically active homoallylic alcohols of exceptionally high enantiomeric purity (98-≥99% ee) readily available via asymmetric allylboration were converted into p-nitrobenzoate esters and subjected to hydroboration followed by oxidation with CrO3 in aqueous acetic acid (10% H2O) to obtain the corresponding carboxylic acids with the same number of carbon atoms. The protecting ester group was hydrolyzed and the product lactonized in situ to the γ-substituted γ-butyrolactones 5 (R = Me, Pr, i-Pr, t-Bu, Ph, (E)- CH=CHCH3) usually without racemization and in good yields. The method is convenient and potentially valuable for the synthesis of highly functionalized γ-butyrolactones in high optical purity.

Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

γ- and δ-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3, 4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid; the δ-lactones ware always obtained in an ee% higher than the γ-lactones and ranging from 70% to 100%.

ENZYMATIC RESOLUTION OF RACEMIC LACTONES

PPL, HLE or PLE enzymatic resolution of racemic γ, δ and ε-lactones gives optically active lactones (ee: 60 to 90percent).

Synthesis of the optical antipodes of 4-alkyl-γ-lactones

Optical antipodes of 4-alkyl-γ-lactones 3 have been prepared by photochemical rearrangement of optically active α,β-epoxy diazomethyl ketones 1 in ethanol to give 4-hydroxy-alkenoates 2, followed by reduction of the alkene bond and subsequent lactonization.The required epoxy diazomethyl ketones 1 were obtained via the following sequence of reactions: alkylation of 2-propyn-1-ol, subsequent reduction to the alkenols 6, Sharpless epoxidation to 2,3-epoxy alcohols 7, oxidation to glycidic esters 8 and finally conversion to diazo ketones 1.The enantiomeric purities range from 84 to 100percent.