117415-46-0

Basic information

• Product Name: caudoxirene
• Synonyms: caudoxirene
• CAS NO: 117415-46-0
• Molecular Formula: C11H14O
• Molecular Weight: 162.22826
• Mol File: 117415-46-0.mol

Chemical Properties

• Boiling Point: 228.7°Cat760mmHg
• Flash Point: 87.7°C
• Appearance: /
• Density: 1.145g/cm³
• Vapor Pressure: 0.109mmHg at 25°C
• Refractive Index: 1.673
• CAS DataBase Reference: caudoxirene(CAS DataBase Reference)
• NIST Chemistry Reference: caudoxirene(117415-46-0)
• EPA Substance Registry System: caudoxirene(117415-46-0)

Safety Data

• Hazardous Substances Data: 117415-46-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14O/c1-3-8-6-5-7-9(8)11-10(4-2)12-11/h3-5,7-11H,1-2,6H2/t8-,9+,10-,11-/m0/s1

Upstream product

• 130517-66-7 cis-1-(5-vinylcyclopent-2-enyl)-2-(phenylthio)but-3-en-1-ol 
• 142428-33-9 (-)-(1S,2R,1'R,5'R)-2-(ethylthio)-1-(5'-vinylcyclopent-2'-enyl)but-3-en-1-ol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 84899-19-4 (1R,5R)-5-Vinyl-cyclopent-2-enecarbaldehyde 
• 142428-32-8 (+)-(2R,3R,1'S,5'S)-3-(5'vinylcyclopent-2'-enyl)oxirane-2-methanol 

Relevant articles and documents

Absolute Configuration and Synthesis of (+)-Caudoxirene, the Gamete-Releasing and Gamete-Attracting Pheromone of the Brown Alga Perithalia caudata (Phaeophyceae)

The absolute configuration of the gamete-releasing and -attracting pheromone 2-vinyl-3-(5'-vinylcyclopent-2'-enyl)oxirane ( = (+)-caudoxirene; (+)-1) of the marine brown alga Perithalia caudata is established as (2R,3R,1'S,5'S).Highly diastereoselective syntheses and the biological activities of three diastereoisomers of 1 are described.Compound (+)-(2R,3R,1'S,5'S)-1 is the first fully characterized epoxypheromone from marine brown algae (Phaeophyceae).

95. Structure and Synthesis of (+/-)-Caudoxirene, a New Spermatozoid-Releasing and -Attracting Pheromone from the Marine Brown Alga Perithalia caudata (Phaeophyceae, Sporochnales)

cis-3-(trans-1,2-Epoxybut-3-enyl)-4-vinylcyclopentene ((+/-)-4, caudoxirene) is a new gamete-releasing and gamete-attracting pheromone from the marine brown alga Perithalia caudata (Sporochnales).The key step of its synthesis is the diastereoselective alkylation of the aldehyde 8 with the titanium reagent 9 to yield the erythro-β-hydroxy sulfide 10 which affords 4 on sequential treatment with Me3O*BF4 and aq.NaOH.The lowest effective concentration of (+/-)-4 for gamete-release is found at 1.4 x 10-11 mol/l seawater.