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| CAS No.: | 75899-68-2 |
|---|---|
| Name: | HNE |
| Article Data: | 28 |
| Molecular Structure: | |
|
|
|
| Formula: | C9H16 O2 |
| Molecular Weight: | 156.225 |
| Synonyms: | (2E)-4-Hydroxy-2-nonenal;(E)-4-Hydroxy-2-nonenal; 4-Hydroxy-2(E)-nonenal; 4-Hydroxy-2-(E)-nonenal;4-Hydroxy-2-nonenal; 4-Hydroxy-2-trans-nonenal; 4-Hydroxynonenal |
| Density: | 0.941 g/cm3 |
| Boiling Point: | 275.6 °C at 760 mmHg |
| Flash Point: | 115.2 °C |
| Solubility: | Solubile in DMSO, Ethanol, Hexane |
| Appearance: | Colorless oil |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | R36/37/38 |
| PSA: | 37.30000 |
| LogP: | 1.68270 |
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- 97730-31-9(S)-4'-(2-Methylbutyl)Biphenyl-4-Carbonitrile
- 109296-10-8
4-hydroxy-2-trans-nonenal dimethylacetal
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| With sulfuric acid In tetrahydrofuran; water for 1h; Ambient temperature; | 97% |
| With sulfuric acid Yield given; | |
| With hydrogen cation In water Hydrolysis; | |
| With hydrogenchloride In water | |
| With hydrogenchloride In water at 20℃; for 1h; pH=3; Darkness; Inert atmosphere; |
A
- 1086461-21-3
1-hydroxy-2-propyl-9,10-anthraquinone-4-carboxylic acid
B
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| Stage #1: C27H29O6(1-)*K(1+) In water for 2.5h; pH=9; aq. buffer; Irradiation; Stage #2: With hydrogenchloride In water | A n/a B 97% |
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 3h; Reagent/catalyst; Solvent; Inert atmosphere; Reflux; stereoselective reaction; | 94% |
| With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 3h; Inert atmosphere; Reflux; stereoselective reaction; | 80% |
- 206050-60-4
2-{1-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-hexyloxy}-tetrahydro-pyran
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| With sodium periodate; acetic acid In water | 93% |
- 130796-43-9
(E)-4-(tert-butyldimethylsilyloxy)-2-nonenal
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| With hydrogen fluoride In acetonitrile for 1h; | 88% |
- 20763-19-3
(methoxymethylene)triphenylphosphorane
- 42134-50-9
2,3-epoxyoctanal
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at -78 - 20℃; | 83% |
- 66-25-1
hexanal
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| Stage #1: 3-(tert-butyldimethylsilyl)-2,3-epoxypropyl p-tolyl sulfone; hexanal With sodium hexamethyldisilazane In tetrahydrofuran at -80 - -60℃; for 0.333333h; Stage #2: With ethanol; tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran at -80℃; for 0.166667h; | 77% |
| Conditions | Yield |
|---|---|
| With Hoveyda-Grubbs catalyst 2nd generation In dichloromethane at 20℃; for 20h; | 75% |
- 1256782-46-3
(E)-4-[(tetrahydro-2H-pyran-2-yl)oxy]-2-nonenal
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In methanol at 0 - 20℃; for 2h; | 70% |
| With toluene-4-sulfonic acid In methanol | |
| With toluene-4-sulfonic acid |
A
- 75899-68-2
(E)-4-Hydroxy-2-nonenal
B
- 37423-49-7
4-acetyloxy-2-(E)-nonenal
| Conditions | Yield |
|---|---|
| With lipase In phosphate buffer at 37℃; for 0.25h; Product distribution; Further Variations:; reaction time; | A 43% B 57% |
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Chemistry
Chemical Name of HNE (CAS No.75899-68-2): HNE
Molecular Structure:
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Molecular Formula: C9H16O2
Molecular Weight: 156.2221
IUPAC Name: (E)-4-Hydroxynon-2-enal
Synonyms of HNE (CAS No.75899-68-2): 4-Hydroxy-2-nonenal ; 4-Hydroxynonenal ; CCRIS 1781 ; 2-Nonenal, 4-hydroxy-
CAS NO: 75899-68-2
Index of Refraction: 1.46
Molar Refractivity: 45.48 cm3
Molar Volume: 165.9 cm3
Surface Tension: 33.9 dyne/cm
Density: 0.941 g/cm3
Flash Point: 115.2 °C
Enthalpy of Vaporization: 59.68 kJ/mol
Boiling Point: 275.6 °C at 760 mmHg
Vapour Pressure of HNE (CAS No.75899-68-2): 0.000633 mmHg at 25°C
Production
The first characterization of HNE (CAS No.75899-68-2) was reported by Esterbauer, et al. in 1991,and since then the amount of research involving this chemical has been steadily increasing, with entire issues of relatively high-impact journals such as Molecular Aspects of Medicine and Free Radical Biology and Medicine devoting volumes to 4-HNE-centered publications.It is generated in the oxidation of lipids containing polyunsaturated omega-6 acyl groups, such as arachidonic or linoleic groups, and of the corresponding fatty acids. Although it is the most studied one, in the same process also other oxygenated α,β-unsaturated aldehydes (OαβUAs) are generated, which can also come from omega-3 fatty acids, such as 4-oxo-trans-2-nonenal, 4-hydroxy-trans-2-hexenal, 4-hydroperoxy-trans-2-nonenal and 4,5-epoxy-trans-2-decenal.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 69mg/kg (69mg/kg) | Personal Communication from H. Zollner, Institut fur Biochemie, Der Universitat, Gras, Oct. 23, 1975Vol. 23OCT1975, | |
| rat | LD50 | intraperitoneal | 35mg/kg (35mg/kg) | BEHAVIORAL: FLUID INTAKE BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) | Toxicologist. Vol. 4, Pg. 100, 1984. |
Specification
HNE (CAS No.75899-68-2) is an α,β-unsaturated hydroxyalkenal which is produced by lipid peroxidation in cells.It is the primary alpha,beta-unsaturated hydroxyalkenal formed in this process.It has 3 reactive groups: an aldehyde, a double-bond at carbon 2, and a hydroxy group at carbon 4.It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events.It has been hypothesized by several researchers to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion.