Description

(2S,3R)-2-((2Z,5Z)-Octa-2,5-Dienyl)-3-Undecyloxirane is a high-purity, stereochemically defined oxirane derivative of significant interest in advanced organic synthesis. This compound serves as a critical chiral building block for the construction of complex natural product analogs and bioactive molecules. It is primarily utilized by research institutions and pharmaceutical development companies engaged in the synthesis of novel therapeutic agents, fragrance components, and specialized chemical probes.

Application

• Pharmaceutical Intermediate: A key chiral synthon for the synthesis of prostaglandin analogs, leukotriene derivatives, and other bioactive lipid mediators.
• Agrochemical Research: Used in the development of novel insect pheromone analogs and plant growth regulators with specific stereochemical requirements.
• Fragrance & Flavor Chemistry: Serves as a precursor for the synthesis of specific, high-value odorants and flavorants where the precise stereochemistry defines the sensory profile.
• Material Science: Investigated as a monomer or cross-linking agent for creating polymers with unique optical or mechanical properties derived from its rigid oxirane and diene structure.
• Chemical Biology: Employed in the synthesis of activity-based probes and molecular tools for studying enzyme mechanisms, particularly those involving epoxide hydrolases.
• Academic & Process Chemistry: A valuable substrate for methodological development in asymmetric synthesis, catalysis, and studying stereoselective ring-opening reactions.

Basic Information

Product Name	(2S,3R)-2-((2Z,5Z)-Octa-2,5-Dienyl)-3-Undecyloxirane
CAS No.	81309-90-2
Molecular Formula	C₂₁H₃₈O
Molecular Weight	306.53 g/mol
Synonyms	(2S,3R)-2-[(2Z,5Z)-2,5-Octadienyl]-3-undecyloxirane; (2S,3R)-2-((2Z,5Z)-Octa-2,5-dien-1-yl)-3-undecyloxirane; (2S,3R)-2-[(2Z,5Z)-Octa-2,5-dienyl]oxiran-3-ylundecane; (2S,3R)-Epoxy-2-((2Z,5Z)-octadienyl)-3-undecyloxirane; Chiral C21 Epoxide; (Z,Z)-Diene-substituted Chiral Oxirane; Undecyl Oxirane Derivative
EINECS	Contact for details

Quality Control

Our (2S,3R)-2-((2Z,5Z)-Octa-2,5-Dienyl)-3-Undecyloxirane is produced under strict quality management protocols to ensure batch-to-batch consistency and high stereochemical purity. Each lot is supported by a comprehensive Certificate of Analysis (COA) detailing identity, purity, isomeric composition, and impurity profiles. We adhere to cGMP principles for advanced intermediates, and specifications can be aligned with client-specific pharmacopeial or internal standards.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry, and well-ventilated place at a controlled room temperature (15-25°C). This compound is light-sensitive and should be handled under an inert atmosphere for long-term stability. Keep away from strong oxidizing agents.

Specification

Item	Specification
Appearance	Colorless to pale yellow liquid
Identification (IR)	Conforms to structure
Purity (HPLC)	≥ 97.0%
Enantiomeric Excess (Chiral HPLC)	≥ 98.0%
Isomeric Purity (Z,Z)	≥ 95.0%
Water Content (KF)	≤ 0.5%

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.