29343-52-0

Basic information

• Product Name: 4-hydroxy-2-nonenal
• Synonyms: TRANS-4-HYDROXY-2-NONENAL;TRANS-4-HYDROXY-2,3-NONENAL;TRANS-4-HYDROXY-NONENAL;TRANS-4-OH-2-NONENAL;4-HYDROXY-2,3-TRANS-NONENAL;(E)-4-HYDROXY-2-NONENAL;(2E)-4-Hydroxy-2-nonenal;4-Hydroxy-trans-2-nonenal
• CAS NO: 29343-52-0
• Molecular Formula: C9H16O2
• Molecular Weight: 0
• Mol File: 29343-52-0.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 220.47°C (rough estimate)
• Flash Point: 115.2°C
• Appearance: /
• Density: 0.9188 (rough estimate)
• Vapor Pressure: 0.000633mmHg at 25°C
• Refractive Index: 1.4350 (estimate)
• CAS DataBase Reference: 4-hydroxy-2-nonenal(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-2-nonenal(29343-52-0)
• EPA Substance Registry System: 4-hydroxy-2-nonenal(29343-52-0)

Safety Data

• Hazardous Substances Data: 29343-52-0(Hazardous Substances Data)

Usage

Definition

ChEBI: An enal consisting of non-2-ene having an oxo group at the 1-position and a hydroxy group at the 4-position.

InChI:InChI=1/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3

Upstream product

• 112-63-0 Methyl linoleate 
• 60-33-3 linoleic acid 
• 1256782-46-3 (E)-4-[(tetrahydro-2H-pyran-2-yl)oxy]-2-nonenal 
• 130796-43-9 (E)-4-(tert-butyldimethylsilyloxy)-2-nonenal 
• 887496-40-4 C₂₆H₃₀O₄ 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 110222-66-7 (2S,3R)-3-pentyloxirane-2-carbaldehyde 
• 109296-10-8 4-hydroxy-trans-2-nonenal-dimethylacetal 
• 119009-01-7 (E)-(R)-1,1-Dimethoxy-non-2-en-4-ol 
• 119008-07-0 (E)-(S)-1,1-Dimethoxy-non-2-en-4-ol 
• 108-05-4 vinyl acetate 
• 10339-61-4 3-nonene-1-ol 
• 84771-68-6 (E)-methyl 4-hydroxynon-2-enoate 
• 14952-06-8 methyl (2E)-2-nonenoate 

Downstream Products

• 146764-24-1 N-acetyl-S-(tetrahydro-5-hydroxy-2-pentyl-3-furanyl)-L-cysteine 
• 62962-42-9 N²,3-ethenoguanine 
• 564-87-4 (11Z)-retinal 
• 29343-54-2 4-hydroxynon-2-enal 2,4-dinitrophenylhydrazone 
• 74567-98-9 4-hydroxynonanoic acid 
• 118354-84-0 2,3-epoxy-4-hydroxynonanal 
• 128860-91-3 (E)-(R)-1-((4S,5S)-1,3-Dimethyl-4,5-diphenyl-imidazolidin-2-yl)-oct-1-en-3-ol 

Relevant articles and documents

Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals

A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.

Isotopic labelling for the characterisation of HNE-sequestering agents in plant-based extracts and its application for the identification of anthocyanidins in black rice with giant embryo

Reactive carbonyl species (RCS) are cytotoxic molecules that originate from lipid peroxidation and sugar oxidation. Natural derivatives can be an attractive source of potential RCS scavenger. However, the lack of analytical methods to screen and identify bioactive compounds contained in complex matrices has hindered their identification. The sequestering actions of various rice extracts on RCS have been determined using ubiquitin and 4-hydroxy-2-nonenal (HNE) as a protein and RCS model, respectively. Black rice with giant embryo extract was found to be the most effective among various rice varieties. The identification of bioactive compounds was then carried out by an isotopic signature profile method using the characteristic isotopic ion cluster generated by the mixture of HNE: 2H5-HNE mixed at a 1:1 stoichiometric ratio. An in-house database was used to obtain the structures of the possible bioactive components. The identified compounds were further confirmed as HNE sequestering agents through HPLC-UV analysis.

NADP+-dependent dehydrogenase activity of carbonyl reductase on glutathionylhydroxynonanal as a new pathway for hydroxynonenal detoxification

An NADP+-dependent dehydrogenase activity on 3-glutathionyl-4-hydroxynonanal (GSHNE) was purified to electrophoretic homogeneity from a line of human astrocytoma cells (ADF). Proteomic analysis identified this enzymatic activity as associated with carbonyl reductase 1 (EC 1.1.1.184). The enzyme is highly efficient at catalyzing the oxidation of GSHNE (KM 33 μM, kcat 405 min-1), as it is practically inactive toward trans-4-hydroxy-2-nonenal (HNE) and other HNE-adducted thiol-containing amino acid derivatives. Combined mass spectrometry and nuclear magnetic resonance spectroscopy analysis of the reaction products revealed that carbonyl reductase oxidizes the hydroxyl group of GSHNE in its hemiacetal form, with the formation of the corresponding 3-glutathionylnonanoic-δ-lactone. The relevance of this new reaction catalyzed by carbonyl reductase 1 is discussed in terms of HNE detoxification and the recovery of reducing power.