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

General Description

(S)-4-Undecanolide is a chemical compound used as a standard for gas chromatography (GC). It is a lactone, or cyclic ester, with a molecular formula of C11H20O2. It is found naturally in various fruits and vegetables and is also used as a flavoring agent in food and beverages. In the laboratory, it is used as a reference compound for GC analysis, where it helps to identify and quantify other compounds in a sample. Its unique chemical properties and stability make it a valuable tool for analytical chemistry and quality control in various industries.

Upstream product

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• 107736-53-8 (E)-(S)-4-Acetoxy-undec-2-enoic acid ethyl ester 
• 107736-32-3 2-Diazo-1-((2S,3R)-3-heptyl-oxiranyl)-ethanone 
• 107736-40-3 (E)-(S)-4-Hydroxy-undec-2-enoic acid ethyl ester 
• 107797-04-6 (2S,3R)-methyl-2,3-epoxydecanoate 

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