HNE supplier | CasNO.75899-68-2

Name
HNE
EINECS
CAS No. 75899-68-2
Article Data28
CAS DataBase
Density 0.941 g/cm³
Solubility Solubile in DMSO, Ethanol, Hexane
Melting Point
Formula C9H16 O2
Boiling Point 275.6 °C at 760 mmHg
Molecular Weight 156.225
Flash Point 115.2 °C
Transport Information
Appearance Colorless oil
Safety
Risk Codes R36/37/38
Molecular Structure
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
PSA 37.30000
LogP 1.68270

Synthetic route

: 109296-10-8
4-hydroxy-2-trans-nonenal dimethylacetal

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

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;

: 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

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%

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

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

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

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

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

Conditions	Yield
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

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%

: 3391-86-4
1-octen-3-ol

: 107-02-8
acrolein

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

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

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

: 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

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

: 110-53-2
1-Bromopentane

: 18778-96-6, 4093-49-6
(2E)-4,4-dimethoxybut-2-enal

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Stage #1: 1-Bromopentane With magnesium In diethyl ether Stage #2: (2E)-4,4-dimethoxybut-2-enal In diethyl ether at 0 - 20℃; for 1.5h;	44%

: 67-56-1
methanol

: 791615-15-1
1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone

A: 75899-68-2
(E)-4-Hydroxy-2-nonenal

B: 156334-29-1
1-Hydroxy-2-propyl-9,10-anthraquinone

C: 791808-24-7
2-(3-hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one

Conditions

Conditions	Yield
for 5h; Irradiation;	A 30% B 32% C 42%

...Expand

: 18287-01-9
1,1-dimethoxy-non-2t-ene

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
(i) NBS, AIBN, CCl4, (ii) Ag2O, H2O, acetone, (iii) aq. citric acid; Multistep reaction;

: 60-33-3
linoleic acid

A: 110-62-3
pentanal

B: 75899-68-2
(E)-4-Hydroxy-2-nonenal

C: 123-72-8
butyraldehyde

D: 66-25-1
hexanal

Conditions

Conditions	Yield
With air at 37℃; for 24h; Product distribution; other unsaturated fatty acids;

...Expand

: 5910-87-2
(E,E)-2,4-nonadienal

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
With triethylsilane; [5,10,15,20-tetra(2,6-dichlorophenyl)porphyrinato]cobalt(II); oxygen; phosphorous acid trimethyl ester 1.) 2-propanol, CH2Cl2, 28 deg C, 1.5 h, 1 atm, 2.) 2-propanol, CH2Cl2, 2 h, r.t.; Yield given. Multistep reaction;

: 13-[S-(Z,E)]-9,11-Hydroperoxyoctadecadienoic acid

A: 75899-68-2
(E)-4-Hydroxy-2-nonenal

B: 103560-62-9
(2E)-4-oxo-2-nonenal

C: 7439-43-2
(E)-4-Hydroperoxy-2-nonenal

Conditions

Conditions	Yield
With ammonium sulfate; potassium phosphate buffer; iron(II) sulfate at 37℃; for 0.5h; pH=7.0; Product distribution; Further Variations:; Reagents; reaction time;

...Expand

: 208119-82-8
3,4-epoxynonanol

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 20℃;	8.6 mg

: 194291-91-3
(E)-1,1-dimethoxy-2-nonen-4-one

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
With sodium tetrahydroborate

: 18445-69-7
4-hydroxy-trans-non-2-enal diethylacetal

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
With hydrogenchloride at 20℃; for 1h;

: 67-56-1
methanol

: 791615-15-1
1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone

A: 75899-68-2
(E)-4-Hydroxy-2-nonenal

B: 109296-10-8
4-hydroxy-2-trans-nonenal dimethylacetal

C: 156334-29-1
1-Hydroxy-2-propyl-9,10-anthraquinone

Conditions

Conditions	Yield
With oxygen In water for 3h; Product distribution; Further Variations:; Reagents; Solvents; Irradiation;

...Expand

: 791808-24-7
2-(3-hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one

A: 75899-68-2
(E)-4-Hydroxy-2-nonenal

B: 156334-29-1
1-Hydroxy-2-propyl-9,10-anthraquinone

Conditions

Conditions	Yield
In methanol Irradiation;

: 693-25-4
n-pentylmagnesium bromide

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 83 percent / tetrahydrofuran / 0.25 h / 0 °C 2: 64 percent / TBAF / tetrahydrofuran; dimethylformamide / 5 h / 20 °C 3: 42 percent / 5 h / Irradiation 4: methanol / Irradiation View Scheme
Multi-step reaction with 2 steps 1: 84 percent / tetrahydrofuran / 1.5 h / -40 - -15 °C 2: 97 percent / 2.5percent aq. H2SO4 / tetrahydrofuran; H2O / 1 h / Ambient temperature View Scheme

: 98262-71-6
1-bromo-4-hydroxy-(E)-2-nonene

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 64 percent / TBAF / tetrahydrofuran; dimethylformamide / 5 h / 20 °C 2: 42 percent / 5 h / Irradiation 3: methanol / Irradiation View Scheme

: 791615-15-1
1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 42 percent / 5 h / Irradiation 2: methanol / Irradiation View Scheme

: 693-25-4
n-pentylmagnesium bromide

tricyclohexyl germanium-bromide: tricyclohexyl germanium-bromide

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NH4Cl 2: H+ / H2O View Scheme

: 142-68-7
TETRAHYDROPYRANE

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: NaI, CaCO3 / tetrahydrofuran 2: 1.) Mg / 1.) Et2O, 1 h, 2.) Et2O, 30 min 3: 97 percent / PPTS / CH2Cl2 / Ambient temperature 4: 99 percent / n-Bu4NF / tetrahydrofuran / Ambient temperature 5: 91 percent / DMAP / CH2Cl2 / 18 h / 0 - 5 °C 6: 80 percent / NaBH4 / dimethylsulfoxide / 2 h / 85 °C 7: 93 percent / NaIO4, AcOH / H2O View Scheme

: 85514-45-0
tert-butyl((5-iodopentyl)oxy)dimethylsilane

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) Mg / 1.) Et2O, 1 h, 2.) Et2O, 30 min 2: 97 percent / PPTS / CH2Cl2 / Ambient temperature 3: 99 percent / n-Bu4NF / tetrahydrofuran / Ambient temperature 4: 91 percent / DMAP / CH2Cl2 / 18 h / 0 - 5 °C 5: 80 percent / NaBH4 / dimethylsulfoxide / 2 h / 85 °C 6: 93 percent / NaIO4, AcOH / H2O View Scheme

: (1E)-(3,3-dimethyl-2,4-dioxolanyl)oct-1-en-3-ol

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / PPTS / CH2Cl2 / Ambient temperature 2: 93 percent / NaIO4, AcOH / H2O View Scheme

: 206050-56-8
(E)-8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(tetrahydro-pyran-2-yloxy)-oct-7-en-1-ol

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / DMAP / CH2Cl2 / 18 h / 0 - 5 °C 2: 80 percent / NaBH4 / dimethylsulfoxide / 2 h / 85 °C 3: 93 percent / NaIO4, AcOH / H2O View Scheme

: 206050-53-5
(1E)-1-[3,3-dimethyl-(2,4-dioxolanyl)-8-(1,1,2,2-tetramethyl)-1-silapropoxy]oct-1-en-3-ol

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 97 percent / PPTS / CH2Cl2 / Ambient temperature 2: 99 percent / n-Bu4NF / tetrahydrofuran / Ambient temperature 3: 91 percent / DMAP / CH2Cl2 / 18 h / 0 - 5 °C 4: 80 percent / NaBH4 / dimethylsulfoxide / 2 h / 85 °C 5: 93 percent / NaIO4, AcOH / H2O View Scheme

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 673-49-4
N-acetylhistamine

: Nα-acetyl-Nτ-(2-hydroxy-5-pentyltetrahydrofuran-4-yl)histamine

Conditions

Conditions	Yield
With phosphate buffer In acetonitrile at 37℃; for 24h; Addition; cyclization;	86%

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 828-73-9
pentafluorophenyl hydrazine

: 1402134-69-3
(1E,2E)-1-[2-(perfluorophenyl)hydrazono]non-2-en-4-ol

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid at 20℃; Inert atmosphere;	85%

: 886-35-1
3,5-bis(trifluoromethyl)phenylhydrazine

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 1402134-67-1
(1E,2E)-1-{2-[3,5-bis(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid In ethanol at 20℃; Inert atmosphere;	80%

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 368-90-1
4-(trifluoromethyl)phenylhydrazine

: 1402134-66-0
(1E,2E)-1-{2-[4-(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid In acetonitrile at 20℃; for 0.25h; Inert atmosphere;	80%

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 365-34-4
2-(trifluoromethyl)phenylhydrazine

: 1402134-64-8
(1E,2E)-1-{2-[2-(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid In acetonitrile at 20℃; Inert atmosphere;	76%

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 109-73-9
N-butylamine

A: 3-(butylamino)-1,4-nonanediol

B: 1,3-bis(butylamino)-4-nonanol

Conditions

Conditions	Yield
Stage #1: (E)-4-Hydroxy-2-nonenal; N-butylamine With [2,2]bipyridinyl; sodium dihydrogenphosphate; copper(II) sulfate at 20℃; for 144h; pH=7.8; Condensation; Stage #2: With sodium tetrahydroborate Reduction;	A 69% B 6%

...Expand

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 368-90-1
4-(trifluoromethyl)phenylhydrazine

: 1402134-71-7
6-pentyl-1-[4-(trifluoromethyl)phenyl]-1,6-dihydropyridazine

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid In acetonitrile; tert-butyl alcohol at 70℃; for 5h;	64%

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 368-90-1
4-(trifluoromethyl)phenylhydrazine

A: 1402134-71-7
6-pentyl-1-[4-(trifluoromethyl)phenyl]-1,6-dihydropyridazine

: 6-pentyl-1-[4-(trifluoromethyl)phenyl]-5-{2-[4-(trifluoromethyl)-phenyl]hydrazinyl}-1,4,5,6-tetrahydropyridazine

: C23H26F6N4

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid In acetonitrile at 20 - 70℃; for 6h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	A 64% B n/a C n/a

...Expand

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 368-78-5
3-(trifluoromethyl)phenylhydrazine

: 1402134-65-9
(1E,2E)-1-{2-[3-(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid In ethanol at 20℃; Inert atmosphere;	63%

: 1402134-63-7
[2,4-bis(trifluoromethyl)phenyl]hydrazine

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 1402134-68-2
(1E,2E)-1-{2-[2,4-bis(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol

Conditions

Conditions	Yield
With magnesium sulphate; trifluoroacetic acid at 20℃; Inert atmosphere;	62%

: 75899-68-2
(E)-4-Hydroxy-2-nonenal

: 3777-69-3
2-pentylfuran

Conditions

Conditions	Yield
at 100 - 150℃;	43%

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.

Product Name

HNE

Synthetic route

HNE Chemical Properties

HNE Production

HNE Toxicity Data With Reference

HNE Specification

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