152322-55-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S,3S)-3-[(1R)-1-hydroxyhexyl]oxirane-2-carbaldehyde is used as a key reagent for the production of pharmaceuticals and fine chemicals. Its unique stereochemistry and functional groups make it valuable in creating specific molecular structures with targeted properties, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (2S,3S)-3-[(1R)-1-hydroxyhexyl]oxirane-2-carbaldehyde serves as an important building block for synthesizing a diverse range of compounds. Its versatile structure allows for various chemical reactions and modifications, making it a useful component in the creation of complex organic molecules.
Used in Chemical Industry:
The chemical industry also benefits from the use of (2S,3S)-3-[(1R)-1-hydroxyhexyl]oxirane-2-carbaldehyde as a starting material or intermediate in the synthesis of various chemical products. Its unique structural features and reactivity make it a valuable asset in the development of new materials and compounds with specific applications in different sectors, such as materials science, coatings, and polymers.

InChI:InChI=1/C9H16O3/c1-2-3-4-5-7(11)9-8(6-10)12-9/h6-9,11H,2-5H2,1H3/t7-,8-,9+/m1/s1

Upstream product

• 850480-50-1 4-hydroxynon-2-enal 
• 1287249-04-0 (2S,3S,4S)-2,3-epoxy-4-triethylsilyloxynonan-1-al 
• 1287249-18-6 (2S,3S,4R)-2,3-epoxy-4-triethylsilyloxynonan-1-al 
• 1287249-06-2 (2R,3R,4S)-2,3-epoxy-4-triethylsilyloxynonan-1-al 
• 1287249-16-4 (2R,3R,4R)-2,3-epoxy-4-triethylsilyloxynonan-1-al 

Relevant academic research and scientific papers

Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine

2,3-Epoxy-4-hydroxynonanal (EHN) is a potential product of lipid peroxidation that gives rise to genotoxic etheno adducts. We have synthesized all four stereoisomers of EHN and individually reacted them with 2′-deoxyguanosine. In addition to 1,N2-etheno-2′- deoxyguanosine, 12 stereoisomeric products were isolated and characterized by 1H NMR and circular dichroism spectroscopy. The stereochemical assignments were consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations. Reversed-phase HPLC conditions were developed that could separate most of the adduct mixture.

Formation of a substituted 1,N6-etheno-2'-deoxyadenosine adduct by lipid hydroperoxide-mediated generation of 4-oxo-2-nonenal

Analysis of the reaction between 2'-deoxyadenosine and 13-hydroperoxylinoleic acid by liquid chromatography/constant neutral loss mass spectrometry revealed the presence of two major products (adducts A and B). Adduct A was shown to be a mixture of two isomers (A1 and A2) that each decomposed with the loss of water to form adduct B. The mass spectral characteristics of adduct B were consistent with the substituted 1,N6-etheno-2'-deoxyadensoine adduct 1'-[3-(2'-deoxy-β-D-erythro-pentafuranosyl)-3H-imidazo[2,1-i]purin-7-yl]hept an-2'-one. Adducts A1, A2, and B were formed when 2'-deoxyadenosine was treated with synthetic 4-oxo-2-nonenal, which suggested that it was formed by the breakdown of 13-hydroperoxylinoleic acid. A substantial increase in the rate of formation of adducts A1, A2, and B was observed when 13-hydroperoxylinoleic acid and 2'-deoxyadenosine were incubated in the presence of Fe(II). Thus, 4-oxo-2-nonenal was most likely formed by a homolytic process. Although adducts A1, A2, and B were formed in the reaction between 4-hydroxy-2-nonenal and 2'-deoxyadenosine, a number of additional products were observed. This suggested that 4-hydroxy-2-nonenal was not a precursor in the formation of 4-oxo-2-nonenal from 13-hydroperoxylinoleic acid. This study has provided additional evidence which shows that 4-oxo-2-nonenal is a major product of lipid peroxidation and that it reacts efficiently with DNA to form substituted etheno adducts.