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HNE
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Name

HNE

 EINECS N/A
CAS No. 75899-68-2 Density 0.941 g/cm3
PSA 37.30000 LogP 1.68270
Solubility Solubile in DMSO, Ethanol, Hexane Melting Point N/A
Formula C9H16 O2 Boiling Point 275.6 °C at 760 mmHg
Molecular Weight 156.225 Flash Point 115.2 °C
Transport Information N/A Appearance Colorless oil
Safety Risk Codes R36/37/38
Molecular Structure Molecular Structure of 75899-68-2 (HNE) Hazard Symbols Xi
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

Article Data 28

HNE Synthetic route

109296-10-8

4-hydroxy-2-trans-nonenal dimethylacetal

75899-68-2

(E)-4-Hydroxy-2-nonenal

Conditions
ConditionsYield
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;

C27H29O6(1-)*K(1+)

A

1086461-21-3

1-hydroxy-2-propyl-9,10-anthraquinone-4-carboxylic acid

B

75899-68-2

(E)-4-Hydroxy-2-nonenal

Conditions
ConditionsYield
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%

(±)-anti-4-(2-hydroxyethyl)-5-pentyl-1,3-dioxolan-2-one

75899-68-2

(E)-4-Hydroxy-2-nonenal

Conditions
ConditionsYield
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
ConditionsYield
With sodium periodate; acetic acid In water93%
130796-43-9

(E)-4-(tert-butyldimethylsilyloxy)-2-nonenal

75899-68-2

(E)-4-Hydroxy-2-nonenal

Conditions
ConditionsYield
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
ConditionsYield
In tetrahydrofuran at -78 - 20℃;83%

3-(tert-butyldimethylsilyl)-2,3-epoxypropyl p-tolyl sulfone

66-25-1

hexanal

75899-68-2

(E)-4-Hydroxy-2-nonenal

Conditions
ConditionsYield
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%
3391-86-4

1-octen-3-ol

107-02-8

acrolein

75899-68-2

(E)-4-Hydroxy-2-nonenal

Conditions
ConditionsYield
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
ConditionsYield
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

1,1,4-tris(acetyloxy)-2-(E)-nonene

A

75899-68-2

(E)-4-Hydroxy-2-nonenal

B

37423-49-7

4-acetyloxy-2-(E)-nonenal

Conditions
ConditionsYield
With lipase In phosphate buffer at 37℃; for 0.25h; Product distribution; Further Variations:; reaction time;A 43%
B 57%

HNE Chemical Properties

Chemical Name of HNE (CAS No.75899-68-2): HNE
Molecular Structure:

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

HNE 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.

HNE 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.

HNE 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.

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