4,5-epoxy-(E)-2-decenal

Base Information

• Chemical Name: 4,5-epoxy-(E)-2-decenal
• CAS No.: 134454-31-2
• Molecular Formula: C10H16O2
• Molecular Weight: 168.23
• European Community (EC) Number: 443-070-1,639-621-2
• DSSTox Substance ID: DTXSID50928629
• Nikkaji Number: J1.539.620B,J569.925H
• Wikipedia: Trans-4,5-Epoxy-(E)-2-decenal
• Wikidata: Q19904086
• Metabolomics Workbench ID: 42203
• Mol file: 134454-31-2.mol

Synonyms:4,5-epoxy-2-decenal

Chemical Property of 4,5-epoxy-(E)-2-decenal

Chemical Property:

• Boiling Point: 273.3±15.0 °C(Predicted)
• PSA: 29.60000
• Density: 1.022±0.06 g/cm3(Predicted)
• LogP: 2.08920
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 168.115029749
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

trans-4,5-epoxy-2(E)-Decenal ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1C(O1)C=CC=O
• Isomeric SMILES: CCCCCC1C(O1)/C=C/C=O
• Description: Polyunsaturated fatty acids such as arachidonate and linoeate, while essential to health maintenance, are subject to random peroxidation by ambient oxygen, resulting in fragmented and reactive decomposition products. One prominent autoxidation product of either trilinolein or arachidonic acid is trans-4,5-epoxy-2(E)-decenal. This aldehyde is responsible for a pungent metallic flavor of decomposed lipids, with a detection threshold of 1.5 pg/l in air. trans-4,5-epoxy-2(E)-Decenal also reacts with nucleophiles (lysine amino groups) on proteins, leading to loss of cell function and viability. This reactive aldehyde is therefore a useful tool in elucidating the effects of peroxidative damage in experimental models.

Technology Process of 4,5-epoxy-(E)-2-decenal

There total 26 articles about 4,5-epoxy-(E)-2-decenal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

(triphenylphosphoranylidene)acetaldehyde (2136-75-6) + trans-2,3-epoxyoctanal (113973-12-9) → (2E,4RS,5RS)-(±)-4,5-epoxy-(E)-2-decenal (134454-31-2)

Guidance literature:

In benzene; at 60 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.06.011

Reference yield: 86.0%

(2R,3S)-2,3-epoxyoctanal (89461-52-9,113973-12-9) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → trans-4,5-epoxy-(E)-2-decenal (89461-53-0,134454-31-2)

Guidance literature:

In benzene; at 60 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.06.011

Reference yield: 86.0%

(2S,3R)-3-pentyloxirane-2-carbaldehyde (110222-66-7,113973-12-9) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → trans-4,5-epoxy-(E)-2-decenal (134454-31-2)

Guidance literature:

In benzene; at 60 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2015.06.011

upstream raw materials:

(2R,3S)-2,3-epoxyoctanal

(triphenylphosphoranylidene)acetaldehyde

[(2S,3S)-3-pentyloxiran-2-yl]methanol

D-2-deoxyribose

Downstream raw materials:

14S,15S-epoxy-5Z,8Z,10E,12E-eicosatetraenoic acid

3-(2-Deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purine

Refernces

• 1、 Greger, Veronika,Schieberle, Peter. "Characterization of the key aroma compounds in apricots (Prunus armeniaca) by application of the molecular sensory science concept". . p. 5221 - 5228. Retrieved 2007.
• 2、 Mori, Kenji,Osada, Kazumi,Amaike, Masayasu. "Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal". . p. 861 - 867. Retrieved 2015/08/18.