74568-05-1

Basic information

• Product Name: (S)-4-UNDECANOLIDE STANDARD FOR GC
• Synonyms: (S)-4-UNDECANOLIDE STANDARD FOR GC;(S)-4-undecanolide
• CAS NO: 74568-05-1
• Molecular Formula: C₁₁H₂₀O₂
• Molecular Weight: 184.2753
• Mol File: 74568-05-1.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-4-UNDECANOLIDE STANDARD FOR GC(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-UNDECANOLIDE STANDARD FOR GC(74568-05-1)
• EPA Substance Registry System: (S)-4-UNDECANOLIDE STANDARD FOR GC(74568-05-1)

Safety Data

• Hazardous Substances Data: 74568-05-1(Hazardous Substances Data)

Usage

Description

(S)-4-Undecanolide, a chemical compound with the molecular formula C11H20O2, is a lactone or cyclic ester used as a standard for gas chromatography (GC). It is naturally found in various fruits and vegetables and serves as a flavoring agent in the food and beverage industry. In the laboratory, it acts as a reference compound for GC analysis, aiding in the identification and quantification of other compounds in a sample. Its unique chemical properties and stability make it a valuable tool for analytical chemistry and quality control across different industries.

Uses

Used in Analytical Chemistry:
(S)-4-Undecanolide is used as a reference compound for gas chromatography (GC) analysis. It helps in the identification and quantification of other compounds in a sample, ensuring accurate and reliable results.
Used in Flavoring Industry:
(S)-4-Undecanolide is used as a flavoring agent in the food and beverage industry, adding unique taste and aroma to various products.
Used in Quality Control:
(S)-4-Undecanolide is employed in quality control processes across various industries, ensuring the consistency and purity of products by serving as a standard for GC analysis.
Used in Pharmaceutical Industry:
(S)-4-Undecanolide may also be used in the pharmaceutical industry for the development and analysis of new drugs, as its properties can help in identifying and quantifying active ingredients in drug formulations.
Used in Environmental Science:
In environmental science, (S)-4-Undecanolide can be utilized as a standard for GC analysis to study the presence and concentration of various organic compounds in environmental samples, such as soil, water, and air. This helps in monitoring pollution levels and assessing the impact of human activities on the environment.

Upstream product

• 74568-03-9 (S)-4-Hydroxy-undecanoic acid 
• 57681-50-2 4-hydroxy-1-undecanoic acid sodium salt 
• 139126-66-2 4-Hydroxy-undecanoic acid propyl ester 
• 107736-72-1 (S)-4-Hydroxy-undecanoic acid ethyl ester 
• 107736-62-9 (S)-4-Acetoxy-undecanoic acid ethyl ester 
• 152241-73-1 ethyl (4S)-4-benzyloxy-2-undecynoate 
• 259675-64-4 Succinic acid mono-[(S)-1-(2-benzylcarbamoyl-ethyl)-octyl] ester 
• 104-67-6 5-heptyldihydro-2(3H)-furanone 
• 259675-59-7 4-hydroxy-undecanoic acid benzylamide 
• 99745-00-3 (2S,3S)-2,3-epoxydecan-1-ol 
• 74867-42-8 (-)-(S)-dec-1-yn-3-ol 
• 152241-68-4 [(2S,3S)]-2-(chloromethyl)-3-heptyloxirane 
• 152241-69-5 (3S)-3-benzyloxy-1-decyne 
• 107796-95-2 ((2R,3R)-3-heptyloxiran-2-yl)methanol 

Relevant articles and documents

Stereochemical elucidation of streptorubin B

Streptorubin B is a structurally remarkable mem-ber of the prodiginine group of antibiotics produced by several actinobacteria, including the model organism Streptomyces coelicolor A3(2). Transannular strain within the pyrrolophane structure of this molecule causes restricted rotation that gives rise to the possibility of (diastereomeric) atropisomers. Neither the relative nor the absolute stereochemistry of streptorubin B is known. NOESY NMR experiments were used to define the relative stereochemistry of the major atropisomer of streptorubin BHCl in solution as anti. We exploited this finding together with our knowledge of streptorubin B biosynthesis in S. coelicolor to determine the absolute stereochemistry of the anti atropisomer. 2-Undecylpyrrole stereoselectively labeled with deuterium at C-4′ was synthesized and fed to a mutant of S. coelicolor, which was unable to produce streptorubin B because it was blocked in 2-undecylpyrrole biosynthesis, and in which the genes responsible for the last two steps of streptorubin B biosynthesis were overexpressed. 1H and 2H NMR analysis of the stereoselectively deuterium-labeled streptorubin BHCl produced by this mutasynthesis strategy allowed us to assign the absolute stereochemistry of the major (anti) atropisomer as 7′S. HPLC analyses of streptorubin B isolated from S. coelicolor on a homochiral stationary phase and comparisons with streptorubin B derived from an enantioselective synthesis showed that the natural product consists of an approximately 88:7:5 mixture of the (7′S, anti), (7′S, syn), and (7′R, anti) stereoisomers.

Synthesis of (S)-γ- lactones with a combination of lipase-catalyzed resolution and mitsunobu reaction

Six kinds of (S) - lactones [e.g., (S) - decalactone, (S) - undecalactone, and (S) - jasmolactone] were synthesized with 71-88% yields and 97% optical purities by combining lipase-catalyzed resolution with the Mitsunobu reaction. Copyright Taylor & Francis Group, LLC.

Facile synthesis of optically active γ-lactones via lipase-catalyzed reaction of 4-substituted 4-hydroxybutyramides

Lipase-catalyzed transesterification of racemic 4-substituted 4- hydroxybutyramides with succinic anhydride proceeded enantioselectively to afford (S)-succinic acid monoester and unreacted (R)-4-hydroxybutyramide derivative, which were separated easily by