162490-88-2

Basic information

• Product Name: sordidin
• Synonyms: sordidin;2,8-Dioxabicyclo[3.2.1]octane,1-ethyl-3,5,7-trimethyl-, (1S,3R,5R,7S)-;2,8-Dioxabicyclo[3.2.1]octane,1-ethyl-3,5,7-trimethyl-, [1S-(exo,exo)]-
• CAS NO: 162490-88-2
• Molecular Formula: C11H20O2
• Molecular Weight: 184.2753
• Product Categories: API
• Mol File: 162490-88-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: sordidin(CAS DataBase Reference)
• NIST Chemistry Reference: sordidin(162490-88-2)
• EPA Substance Registry System: sordidin(162490-88-2)

Safety Data

• Hazardous Substances Data: 162490-88-2(Hazardous Substances Data)

Usage

Uses

Used in Pest Control Industry:
Sordidin is used as a pheromone in pest control for the banana weevil. It serves as a lure to attract the weevils, enabling more effective pest removal when used in conjunction with pesticides. By targeting the weevils' aggregation behavior, sordidin helps to concentrate the pests, making it easier for pesticides to eliminate them and protect the banana crops from damage.

Upstream product

• 177989-44-5 2-[2-(2-Ethyl-[1,3]dioxolan-2-yl)-propyl]-pentane-1,4-diol 
• 16795-73-6 3-pentanone N,N-dimethylhydrazone 
• 96-22-0 pentan-3-one 
• 192118-52-8 (2S,6RS)-7,7-ethylenedioxy-4-methylene-6-methyl-2-nonanol 
• 192118-53-9 (2R,6RS)-7,7-ethylenedioxy-4-methylene-6-methyl-2-nonanol 
• 192118-56-2 tert-Butyl-[(R)-5-(2-ethyl-[1,3]dioxolan-2-yl)-1-methyl-3-methylene-hexyloxy]-dimethyl-silane 
• 177989-43-4 7,7-ethylenedioxy-4,6-dimethyl-2,4-nonanediol 
• 177989-42-3 tert-Butyl-(2-{2-[2-(2-ethyl-[1,3]dioxolan-2-yl)-propyl]-oxiranyl}-1-methyl-ethoxy)-dimethyl-silane 
• 177989-39-8 (RS)-6-bromo-4-methyl-6-hepten-3-one 
• 177989-40-1 (RS)-2-bromo-5,5-ethylenedioxy-4-methyl-1-heptene 
• 177989-46-7 tert-Butyl-[5-(2-ethyl-[1,3]dioxolan-2-yl)-1-methyl-3-methylene-hexyloxy]-dimethyl-silane 
• 177989-41-2 7,7-ethylenedioxy-4-methylene-6-methyl-2-nonanol 
• 433684-38-9 (2R,4S,6R)-2-Ethyl-2-methoxy-4,6-dimethyl-[1,3]dioxane 
• 24823-81-2 trimethoxypropane 

Relevant articles and documents

Synthesis and absolute configuration of sordidin, the male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus

The racemate as well as both the enantiomers of sordidin (1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1]octane, 1) were synthesized, and the natural pheromone was shown to be (1S,3R,5R,7S)-(+)-1.

Synthesis of (1S,3R,5R,7S)-sordidin, the main component of the aggregation pheromone of the banana weevil Cosmopolites sordidus

A synthesis of the banana weevil pheromone component (1S,3R,5R,7S)-sordidin starting from (S)-2-(2-ethyl-1,3-dioxolanyl) propan-1-ol and (R)-4-hydroxypentan-2-one is described. No epimerization was observed for the final, intramolecular, acid-catalyzed cy

Template-directed C-H activation: Development and application to the total synthesis of 7-episordidin

The development of a template-directed C-H activation strategy and its application to the diastereoselective synthesis of (±)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of t

Synthesis, analysis, and field activity of sordidin, a male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus

An efficient synthesis of the diastereoisomers of sordidin (1), a male-produced aggregation pheromone of Cosmopolites sordidus, has been developed from commercially available 4-methylpent-4-en-2-ol (2). Preparation of eχo-β-sordidin (1a) and endo-β-sordidin (1b) is via the anti epoxide, 4d, which is derived via iodocarbonation of 2. The endo-α-sordidin (1c) and eχo-α-sordidin (1d) are prepared from the corresponding syn epoxide, which is available via stereo controlled epoxidation of the triisopropylsilyloxy derivative, 3b. Silyloxy derivatives of the epoxides, 4 efficiently alkylate the anions of N-cyclohexyldiethylketimine (6a) and 3-pentanone N,N-dimethylhydrazone (6b). Acidic work-up of these alkylation reactions promotes cyclization to give 1. Gram quantities of 1a-1d, 1a + 1b and 1c + 1d have been prepared by this route. In field tests in a banana plantation in Costa Rica, compounds 1a-1d significantly increased capture rates of standard pseudostem traps. Comparable numbers of adults were attracted to pseudostem traps baited with the major naturally occurring isomers of sordidin 1c + 1d or 1a-1d. Although addition of the minor naturally occurring isomers of sordidin (la and lb) to pseudostem traps increased capture rates above controls, these compounds did not increase attraction of pseudostem traps to the same extent as 1a-1d. In comparison tests with conventional pseudostem traps, significantly more adults were trapped in water containing pitfall traps baited with 1a-1d.

Synthesis of (±)-7-episordidin

The stereoselective synthesis of (±)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of this work is a regioselective rhodium(II)-catalyzed diazocarbonyl C-H insertion reaction that simultaneously generates three of the natural product's four stereocenters. The work reported herein also represents a formal synthesis of sordidin.

Pheromone synthesis, CLXXXIV: Synthesis and absolute configuration of sordidin, the male-produced aggregation pheromone of the banana weevil, Cosmopolites sordidus

The racemate as well as both the enantiomers of sordidin (1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1]octane were synthesized, and the natural pheromone was shown to be (1S,3R,5R,7S)-(+)-1. VCH Verlagsgesellschaft mbH, 1997.

Stereoselective synthesis of (+)-sordidin, the male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus

Stereoselective synthesis of (1S,3R,5R,7S)-(+)-sordidin, the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar) starting from 5-benzyloxy-(2E)-pentene-1-ol is described. The key transformations employed in the synthesis are Sharpless asymmetric epoxidation, Ueno-Stork cyclization, and Jacobsen kinetic resolution.

First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, aggregation pheromones of the banana weevil cosmopolites sordidus

The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(-)-sordidin, both components of the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39%) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97%, ee ≥ 98%).

Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera)

As shown by synthesis and enantioselective gas chromatography, males and females of the caddisfly species Potamophylax latipennis and Potamophylax cingulatus produce (1R,3S,5S,7S)-1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo[3.2.1] octane, while Glyphotaelius

Absolute configuration of sordidin and 7-episordidin emitted by the Banana Weevil, Cosmopolites sordidus

Male-specific volatile components released by the banana weevil, Cosmopolites sordidus Germar, from Australia have been identified as (1S,3R,5R,7S)-1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo [3.2.1]octane and the 7R-epimer (as a minor component) by synthesis and enantioselective gas chromatography.