4-hydroxy-2-trans-nonenal dimethylacetal
(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
1-hydroxy-2-propyl-9,10-anthraquinone-4-carboxylic acid
B
(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% |
(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% |
2-{1-[(E)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-hexyloxy}-tetrahydro-pyran
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
With sodium periodate; acetic acid In water | 93% |
(E)-4-(tert-butyldimethylsilyloxy)-2-nonenal
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
With hydrogen fluoride In acetonitrile for 1h; | 88% |
(methoxymethylene)triphenylphosphorane
2,3-epoxyoctanal
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
In tetrahydrofuran at -78 - 20℃; | 83% |
hexanal
(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% |
(E)-4-[(tetrahydro-2H-pyran-2-yl)oxy]-2-nonenal
(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
(E)-4-Hydroxy-2-nonenal
B
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% |
1-Bromopentane
(2E)-4,4-dimethoxybut-2-enal
(E)-4-Hydroxy-2-nonenal
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% |
methanol
1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone
A
(E)-4-Hydroxy-2-nonenal
B
1-Hydroxy-2-propyl-9,10-anthraquinone
C
2-(3-hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one
Conditions | Yield |
---|---|
for 5h; Irradiation; | A 30% B 32% C 42% |
1,1-dimethoxy-non-2t-ene
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
(i) NBS, AIBN, CCl4, (ii) Ag2O, H2O, acetone, (iii) aq. citric acid; Multistep reaction; |
linoleic acid
A
pentanal
B
(E)-4-Hydroxy-2-nonenal
C
butyraldehyde
D
hexanal
Conditions | Yield |
---|---|
With air at 37℃; for 24h; Product distribution; other unsaturated fatty acids; |
(E,E)-2,4-nonadienal
(E)-4-Hydroxy-2-nonenal
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; |
A
(E)-4-Hydroxy-2-nonenal
B
(2E)-4-oxo-2-nonenal
C
(E)-4-Hydroperoxy-2-nonenal
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; |
3,4-epoxynonanol
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 20℃; | 8.6 mg |
(E)-1,1-dimethoxy-2-nonen-4-one
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
With sodium tetrahydroborate |
4-hydroxy-trans-non-2-enal diethylacetal
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; for 1h; |
methanol
1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone
A
(E)-4-Hydroxy-2-nonenal
B
4-hydroxy-2-trans-nonenal dimethylacetal
C
1-Hydroxy-2-propyl-9,10-anthraquinone
Conditions | Yield |
---|---|
With oxygen In water for 3h; Product distribution; Further Variations:; Reagents; Solvents; Irradiation; |
2-(3-hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one
A
(E)-4-Hydroxy-2-nonenal
B
1-Hydroxy-2-propyl-9,10-anthraquinone
Conditions | Yield |
---|---|
In methanol Irradiation; |
n-pentylmagnesium bromide
(E)-4-Hydroxy-2-nonenal
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 |
1-bromo-4-hydroxy-(E)-2-nonene
(E)-4-Hydroxy-2-nonenal
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 |
1-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 42 percent / 5 h / Irradiation 2: methanol / Irradiation View Scheme |
n-pentylmagnesium bromide
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NH4Cl 2: H+ / H2O View Scheme |
TETRAHYDROPYRANE
(E)-4-Hydroxy-2-nonenal
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 |
tert-butyl((5-iodopentyl)oxy)dimethylsilane
(E)-4-Hydroxy-2-nonenal
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 |
(E)-4-Hydroxy-2-nonenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97 percent / PPTS / CH2Cl2 / Ambient temperature 2: 93 percent / NaIO4, AcOH / H2O View Scheme |
(E)-8-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-(tetrahydro-pyran-2-yloxy)-oct-7-en-1-ol
(E)-4-Hydroxy-2-nonenal
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 |
(1E)-1-[3,3-dimethyl-(2,4-dioxolanyl)-8-(1,1,2,2-tetramethyl)-1-silapropoxy]oct-1-en-3-ol
(E)-4-Hydroxy-2-nonenal
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 |
(E)-4-Hydroxy-2-nonenal
N-acetylhistamine
Conditions | Yield |
---|---|
With phosphate buffer In acetonitrile at 37℃; for 24h; Addition; cyclization; | 86% |
(E)-4-Hydroxy-2-nonenal
pentafluorophenyl hydrazine
(1E,2E)-1-[2-(perfluorophenyl)hydrazono]non-2-en-4-ol
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid at 20℃; Inert atmosphere; | 85% |
3,5-bis(trifluoromethyl)phenylhydrazine
(E)-4-Hydroxy-2-nonenal
(1E,2E)-1-{2-[3,5-bis(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid In ethanol at 20℃; Inert atmosphere; | 80% |
(E)-4-Hydroxy-2-nonenal
4-(trifluoromethyl)phenylhydrazine
(1E,2E)-1-{2-[4-(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid In acetonitrile at 20℃; for 0.25h; Inert atmosphere; | 80% |
(E)-4-Hydroxy-2-nonenal
2-(trifluoromethyl)phenylhydrazine
(1E,2E)-1-{2-[2-(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid In acetonitrile at 20℃; Inert atmosphere; | 76% |
(E)-4-Hydroxy-2-nonenal
N-butylamine
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% |
(E)-4-Hydroxy-2-nonenal
4-(trifluoromethyl)phenylhydrazine
6-pentyl-1-[4-(trifluoromethyl)phenyl]-1,6-dihydropyridazine
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid In acetonitrile; tert-butyl alcohol at 70℃; for 5h; | 64% |
(E)-4-Hydroxy-2-nonenal
4-(trifluoromethyl)phenylhydrazine
A
6-pentyl-1-[4-(trifluoromethyl)phenyl]-1,6-dihydropyridazine
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 |
(E)-4-Hydroxy-2-nonenal
3-(trifluoromethyl)phenylhydrazine
(1E,2E)-1-{2-[3-(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid In ethanol at 20℃; Inert atmosphere; | 63% |
[2,4-bis(trifluoromethyl)phenyl]hydrazine
(E)-4-Hydroxy-2-nonenal
(1E,2E)-1-{2-[2,4-bis(trifluoromethyl)phenyl]hydrazono}non-2-en-4-ol
Conditions | Yield |
---|---|
With magnesium sulphate; trifluoroacetic acid at 20℃; Inert atmosphere; | 62% |
(E)-4-Hydroxy-2-nonenal
2-pentylfuran
Conditions | Yield |
---|---|
at 100 - 150℃; | 43% |
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
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.
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 (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.
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View