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539-82-2

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539-82-2 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 539-82-2 differently. You can refer to the following data:
1. clear colorless liquid
2. Ethyl valerate has a fruity odor suggestive of apple

Occurrence

Reported found in apples, bananas, guava, strawberry, cheeses, rum, whiskey, cider, sherry, grape wines, cocoa, coffee, honey and passion fruit, apricot, guava fruit and pineapple.

Uses

Different sources of media describe the Uses of 539-82-2 differently. You can refer to the following data:
1. Ethyl valerate has wide applications in the areas of food, pharmaceuticals and cosmetics industries.
2. Intermediate in perfumery.

Preparation

By refluxing valeric acid and ethyl alcohol in the presence of concentrated H2SO4.

Aroma threshold values

Detection: 1.5 to 5 ppb

Taste threshold values

Taste characteristics at 30 ppm: fruity, strawberry, sweet, estry, fruity, pineapple, and tropical fruit.

Synthesis Reference(s)

Canadian Journal of Chemistry, 58, p. 2271, 1980 DOI: 10.1139/v80-365The Journal of Organic Chemistry, 54, p. 4848, 1989 DOI: 10.1021/jo00281a029

General Description

Ethyl valerate is also known as the green apple flavor. Microwave spectrum of ethyl valerate, observed by molecular beam Fourier transform microwave spectroscopy, has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 539-82-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 9 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 539-82:
(5*5)+(4*3)+(3*9)+(2*8)+(1*2)=82
82 % 10 = 2
So 539-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H14O2/c1-3-5-6-7(8)9-4-2/h3-6H2,1-2H3

539-82-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A14854)  Ethyl valerate, 98%   

  • 539-82-2

  • 100ml

  • 161.0CNY

  • Detail
  • Alfa Aesar

  • (A14854)  Ethyl valerate, 98%   

  • 539-82-2

  • 500ml

  • 572.0CNY

  • Detail
  • Alfa Aesar

  • (A14854)  Ethyl valerate, 98%   

  • 539-82-2

  • 2500ml

  • 2615.0CNY

  • Detail
  • Sigma-Aldrich

  • (30784)  Ethylvalerate  analytical standard

  • 539-82-2

  • 30784-1ML

  • 238.68CNY

  • Detail

539-82-2Synthetic route

ethanol
64-17-5

ethanol

valeric acid
109-52-4

valeric acid

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 3h;99%
With sulfuric acid at 100℃; for 3h;99%
With Rhizomucor miehei lipase In n-heptane at 40℃; for 24h; Enzymatic reaction;63.1%
valeric acid
109-52-4

valeric acid

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With 0.08%-SO3H functionalized-benzylated Al-SBA-15 nanoporous catalyst at 79.84℃; for 2h;95%
2-propyl-malonic acid monoethyl ester
2985-35-5

2-propyl-malonic acid monoethyl ester

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With 1H-imidazole In neat (no solvent) at 125℃; for 0.0666667h; Temperature; Wavelength; Microwave irradiation;86%
boron trifluoride diethyl etherate
109-63-7

boron trifluoride diethyl etherate

valeric acid
109-52-4

valeric acid

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
at 120℃; for 4h;86%
ethanol
64-17-5

ethanol

hexan-1-amine
111-26-2

hexan-1-amine

carbon monoxide
201230-82-2

carbon monoxide

A

Ethyl hexanoate
123-66-0

Ethyl hexanoate

B

ethyl n-valerate
539-82-2

ethyl n-valerate

C

ethyl heptanoate
106-30-9

ethyl heptanoate

D

N-hexylcarbamic acid ethyl ester
7451-47-0

N-hexylcarbamic acid ethyl ester

Conditions
ConditionsYield
With oxygen; Sulfate; zirconium(IV) oxide; palladium dichloride at 170℃; under 45003.6 Torr; for 3h; Further byproducts given. Title compound not separated from byproducts;A n/a
B n/a
C n/a
D 81%
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

N-butylamine
109-73-9

N-butylamine

A

N-butylformamide
871-71-6

N-butylformamide

B

ethyl n-valerate
539-82-2

ethyl n-valerate

C

N-(ethoxycarbonyl)butylamine
591-62-8

N-(ethoxycarbonyl)butylamine

D

butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

Conditions
ConditionsYield
With oxygen; Sulfate; zirconium(IV) oxide; palladium dichloride at 170℃; under 45003.6 Torr; for 3h; Title compound not separated from byproducts;A n/a
B n/a
C 80%
D n/a
ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
In hexane; ethyl acetate; mineral oil80%
4-oxopentanoic acid ethyl ester
539-88-8

4-oxopentanoic acid ethyl ester

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

C

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With hydrogen; 10 wtpercent nickel/0.1 wtpercent platinum on silica Product distribution / selectivity;A n/a
B 77%
C n/a
With hydrogen; 10 wtpercent rhenium/0.1 wtpercent platinum on silica Product distribution / selectivity;A n/a
B 68%
C n/a
With hydrogen; 1 wtpercent ruthenium on silica Product distribution / selectivity;A n/a
B 54%
C n/a
Ethyl diphenylphosphinite
719-80-2

Ethyl diphenylphosphinite

valeric acid
109-52-4

valeric acid

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With 2,6-dimethyl-1,4-benzoquinone In dichloromethane at 20℃; for 0.5h;76%
ethanol
64-17-5

ethanol

levulinic acid
123-76-2

levulinic acid

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With hydrogen at 240℃; under 22502.3 Torr; for 3h; Reagent/catalyst; Autoclave;A 74%
B 23%
5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With 3Pd-10Nb-500AC; hydrogen In ethanol at 250℃; under 15001.5 Torr; for 10h; Autoclave;70%
ethanol
64-17-5

ethanol

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With hydrogen at 240℃; under 22502.3 Torr; for 3h; Autoclave;A 69%
B 22%
10 wt% nickel/0.1 wt% platinum on silica and zeolite β Product distribution / selectivity; Heating / reflux;
1 wt% platinum on silica and zeolite β Product distribution / selectivity;
nickel on silica Product distribution / selectivity;
With hydrogen at 250℃; under 760.051 Torr; for 50h; Catalytic behavior; Reagent/catalyst; Temperature; Flow reactor;
ethanol
64-17-5

ethanol

levulinic acid
123-76-2

levulinic acid

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With hydrogen at 210℃; under 22502.3 Torr; for 3h; Autoclave;A 13%
B 68%
ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

carbon dioxide
124-38-9

carbon dioxide

potassium carbonate
584-08-7

potassium carbonate

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; 2.9-dimethyl-1,10-phenanthroline; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C60H36N2 In N,N-dimethyl-formamide at 20℃; for 24h; Molecular sieve; Irradiation;A 25 %Spectr.
B 66%
rac-ethyl 2-[dimethyl(phenyl)silyl]pentanoate

rac-ethyl 2-[dimethyl(phenyl)silyl]pentanoate

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With mercury(II) diacetate; tetrabutyl ammonium fluoride In tetrahydrofuran; methanol at 0℃; for 0.583333h;62%
pentanal
110-62-3

pentanal

ethanol
64-17-5

ethanol

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide at 60℃; for 4h;60%
diethyl propylmalonate
2163-48-6

diethyl propylmalonate

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether In ethanol; benzene 1.) room temperature, 9 h, 2.) reflux, 13 h;59%
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 72 h / 20 °C
2: 1H-imidazole / neat (no solvent) / 0.07 h / 125 °C / Microwave irradiation
View Scheme
1-iodo-butane
542-69-8

1-iodo-butane

ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; polymer-anchored palladium(II) chloride at 80℃; under 1551.4 Torr; for 8h;56%
ethyl iodide
75-03-6

ethyl iodide

valeric acid
109-52-4

valeric acid

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With tetrabutylammomium bromide; potassium carbonate In water; benzene for 6h; Ambient temperature;23%
C8H18BrCuMg

C8H18BrCuMg

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
In tetrahydrofuran at 25℃; Inert atmosphere;17%
ethanol
64-17-5

ethanol

pentanonitrile
110-59-8

pentanonitrile

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With sulfuric acid
1,1-diethoxy-pent-1-ene
682802-51-3

1,1-diethoxy-pent-1-ene

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With water
bis-(5-ethoxycarbonyl-valeryl)-peroxide
42367-85-1

bis-(5-ethoxycarbonyl-valeryl)-peroxide

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

ethyl 4-pentenoate
1968-40-7

ethyl 4-pentenoate

C

diethyl adipate
141-28-6

diethyl adipate

D

diethyl sebacate
110-40-7

diethyl sebacate

Conditions
ConditionsYield
bei der explosiven Zersetzung;
O1-benzoyl-monoperoxyadipic acid-6-ethyl ester
855597-17-0

O1-benzoyl-monoperoxyadipic acid-6-ethyl ester

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
Pyrolysis;
4-oxopentanoic acid ethyl ester
539-88-8

4-oxopentanoic acid ethyl ester

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc; ethanol at 20℃;
With hydrogen
Multi-step reaction with 2 steps
1: hydrogen; 3Pd-10Nb-500AC / water / 5 h / 100 °C / 3750.38 Torr
2: 10Nb-500-AC; water / 5 h / 100 °C / 3750.38 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 3Pd-10Nb-500AC / water / 5 h / 100 °C / 3750.38 Torr
2: hydrogen; 3Pd-10Nb-500AC / ethanol / 10 h / 250 °C / 15001.5 Torr / Autoclave
View Scheme
Multi-step reaction with 3 steps
1: hydrogen; 3Pd-10Nb-500AC / water / 5 h / 100 °C / 3750.38 Torr
2: hydrogen; 3Pd-10Nb-500AC / water / 5 h / 100 °C / 3750.38 Torr
3: hydrogen; 3Pd-10Nb-500AC / ethanol / 10 h / 250 °C / 15001.5 Torr / Autoclave
View Scheme
propionyl chloride
79-03-8

propionyl chloride

ethyl acetoacetate
141-97-9

ethyl acetoacetate

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With magnesium In benzene
ethanol
64-17-5

ethanol

n-valeryl chloride
638-29-9

n-valeryl chloride

ethyl n-valerate
539-82-2

ethyl n-valerate

n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With water 1.) diethyl ether, room temp., 2 h, 2.) 1N HCl; Yield given. Multistep reaction;
Ethyl thiophene-2-carboxylate
2810-04-0

Ethyl thiophene-2-carboxylate

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With NaH-t-AmONa-Ni(OAc)2-bpy In tetrahydrofuran at 63℃; for 1h; Product distribution; Mechanism; other thiophenecarboxylates; other reagents, and solvents, var. reaction times;
ethanol
64-17-5

ethanol

pentamide
626-97-1

pentamide

ethyl n-valerate
539-82-2

ethyl n-valerate

Conditions
ConditionsYield
With hydrogenchloride; titanium tetrachloride for 25h; Heating; Yield given;
ethyl n-valerate
539-82-2

ethyl n-valerate

valeric acid hydrazide
38291-82-6

valeric acid hydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol for 12h; Reflux;99%
With hydrazine hydrate In ethanol at 100℃; for 12h;99%
ethyl n-valerate
539-82-2

ethyl n-valerate

5-aminoimidazole-4-carboxamide hydrochloride
72-40-2

5-aminoimidazole-4-carboxamide hydrochloride

2-butyl-6-hydroxypurine

2-butyl-6-hydroxypurine

Conditions
ConditionsYield
With ethanol; sodium for 20h; Heating / reflux;98%
ethyl n-valerate
539-82-2

ethyl n-valerate

monoethyl phthalate
2306-33-4

monoethyl phthalate

2-[(2-ethoxycarbonyl)pentanoyl]benzoic acid

2-[(2-ethoxycarbonyl)pentanoyl]benzoic acid

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 100℃;93.8%
chlorobromomethane
74-97-5

chlorobromomethane

ethyl n-valerate
539-82-2

ethyl n-valerate

1-bromo-1-chlorohexan-2-one
497933-08-1

1-bromo-1-chlorohexan-2-one

Conditions
ConditionsYield
Stage #1: chlorobromomethane With lithium diisopropyl amide In tetrahydrofuran at -95℃; for 0.25h;
Stage #2: ethyl n-valerate In tetrahydrofuran at -95 - -60℃; for 2.5h;
92%
ethyl n-valerate
539-82-2

ethyl n-valerate

n-hexyldiphenylphosphine oxide
19259-70-2

n-hexyldiphenylphosphine oxide

6-Diphenylphosphinoylundecan-5-one
201872-03-9

6-Diphenylphosphinoylundecan-5-one

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane 1.) -30 deg C, 1 h, 2.) -78 deg C, 2 h;90%
ethyl n-valerate
539-82-2

ethyl n-valerate

5-amino-1-(phenylmethyl)-1H-imidazole-4-carboxamide
3815-69-8

5-amino-1-(phenylmethyl)-1H-imidazole-4-carboxamide

9-benzyl-2-butylhypoxanthine
640274-67-5

9-benzyl-2-butylhypoxanthine

Conditions
ConditionsYield
With ethanol; sodium for 10h; Heating;89%
ethyl n-valerate
539-82-2

ethyl n-valerate

[1,1-2H2]-1-pentanol
35658-10-7

[1,1-2H2]-1-pentanol

Conditions
ConditionsYield
With lithium aluminium deuteride In diethyl ether at 20℃;88%
With lithium aluminium deuteride
ethyl n-valerate
539-82-2

ethyl n-valerate

1-(iodomethyl)-3,5-dimethoxybenzene
66769-61-7

1-(iodomethyl)-3,5-dimethoxybenzene

2-(3,5-Dimethoxy-benzyl)-pentanoic acid ethyl ester
196926-60-0

2-(3,5-Dimethoxy-benzyl)-pentanoic acid ethyl ester

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane for 2h; Ambient temperature;88%
2,2,6,6-Tetramethyl-1-piperidinyloxy free radical
2564-83-2, 45842-10-2

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical

ethyl n-valerate
539-82-2

ethyl n-valerate

A

ethyl 2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pentanoate
1377149-79-5

ethyl 2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pentanoate

B

methyl 2-methyl-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)butyrate
1357253-56-5

methyl 2-methyl-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)butyrate

Conditions
ConditionsYield
Stage #1: ethyl n-valerate With n-butyllithium; diisopropylamine; lithium chloride In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere;
Stage #2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical With ferrocenium hexafluorophosphate In tetrahydrofuran; hexane at -78℃; Inert atmosphere;
A 87%
B 4%
ethyl n-valerate
539-82-2

ethyl n-valerate

1-benzyloxy-3-phenylpropane
70770-06-8

1-benzyloxy-3-phenylpropane

3-phenyl-1-propyl pentanoate
5451-88-7

3-phenyl-1-propyl pentanoate

Conditions
ConditionsYield
With Bromotrichloromethane; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dichloromethane at 20℃; for 12h; Inert atmosphere; Irradiation;87%
ethyl n-valerate
539-82-2

ethyl n-valerate

1-{4-[3-(dibutylamino)propyl]phenyl}ethanone
1356411-42-1

1-{4-[3-(dibutylamino)propyl]phenyl}ethanone

1-{4-[3-(dibutylamino)propyl]phenyl}heptane-1,3-dione
1356411-41-0

1-{4-[3-(dibutylamino)propyl]phenyl}heptane-1,3-dione

Conditions
ConditionsYield
With sodium methylate In 1-methyl-pyrrolidin-2-one at 5 - 20℃;82%
ethyl n-valerate
539-82-2

ethyl n-valerate

acetonitrile
75-05-8

acetonitrile

3-oxo-heptanenitrile
70102-84-0

3-oxo-heptanenitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 70℃;81%
With sodium hydride In tetrahydrofuran
ethyl n-valerate
539-82-2

ethyl n-valerate

Homophthalic acid
89-51-0

Homophthalic acid

3-butylisochromen-1-one
30531-69-2

3-butylisochromen-1-one

Conditions
ConditionsYield
for 0.166667h; microwave irradiation;81%
1-phenylimidazole
7164-98-9

1-phenylimidazole

ethyl n-valerate
539-82-2

ethyl n-valerate

C14H16N2O

C14H16N2O

Conditions
ConditionsYield
Stage #1: 1-phenylimidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: ethyl n-valerate In tetrahydrofuran; hexane at -78 - 20℃; for 8h; Inert atmosphere;
81%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

ethyl n-valerate
539-82-2

ethyl n-valerate

C9H14N2O

C9H14N2O

Conditions
ConditionsYield
Stage #1: 1-methyl-1H-imidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: ethyl n-valerate In tetrahydrofuran; hexane at -78 - 20℃; for 8h; Inert atmosphere;
81%
ethyl n-valerate
539-82-2

ethyl n-valerate

Diethyl methylphosphonate
683-08-9

Diethyl methylphosphonate

2-oxohexylphosphonate de diethyle
3450-63-3

2-oxohexylphosphonate de diethyle

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃;80.5%
ethyl n-valerate
539-82-2

ethyl n-valerate

Phenylselenyl bromide
34837-55-3

Phenylselenyl bromide

ethyl 2-phenylselanylpentanoate
308335-49-1

ethyl 2-phenylselanylpentanoate

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.25h; selenenylation;78%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

ethyl n-valerate
539-82-2

ethyl n-valerate

A

tri-n-butyl-carbinol
597-93-3

tri-n-butyl-carbinol

B

5-Nonanone
502-56-7

5-Nonanone

Conditions
ConditionsYield
With chloro-trimethyl-silane In tetrahydrofuran 1.) -100 deg C, 10 min, 2.) -78 deg C, 10 min;A n/a
B 77%
With hydrogenchloride; chloro-trimethyl-silane multistep reaction, acylation of organolithium reagents by esters;
ethyl n-valerate
539-82-2

ethyl n-valerate

butyldiphenylphosphine oxide
4233-13-0

butyldiphenylphosphine oxide

4-Diphenylphosphinoylnonan-5-one

4-Diphenylphosphinoylnonan-5-one

Conditions
ConditionsYield
With n-butyllithium; tetramethylpiperidine 1.) -30 deg C, 1 h; 2.) -78 deg C, 2 h;77%
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane 1.) -30 deg C, 1 h, 2.) -78 deg C, 2 h;77%
ethyl n-valerate
539-82-2

ethyl n-valerate

1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole
111198-02-8

1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole

1-Benzotriazol-1-yl-1-phenoxy-hexan-2-one
189343-52-0

1-Benzotriazol-1-yl-1-phenoxy-hexan-2-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h;75%
ethyl n-valerate
539-82-2

ethyl n-valerate

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water; ethyl acetate74%

539-82-2Relevant articles and documents

Carlson,Helquist

, p. 173 (1969)

Thermoalkalophilic lipase from an extremely halophilic bacterial strain Bacillus atrophaeus FSHM2: Purification, biochemical characterization and application

Ameri, Atefeh,Shakibaie, Mojtaba,Faramarzi, Mohammad Ali,Ameri, Alieh,Amirpour-Rostami, Sahar,Rahimi, Hamid Reza,Forootanfar, Hamid

, p. 151 - 160 (2017)

The present study was designed to isolate and identify an extremely halophilic lipase-producing bacterial strain, purify and characterize the related enzyme and evaluate its application for ethyl and methyl valerate synthesis. Among four halophilic isolates, the lipolytic ability of one isolate (identified as Bacillus atrophaeus FSHM2) was confirmed. The enzyme (designated as BaL) was purified using three sequential steps of ethanol precipitation and dialysis, Q-Sepharose XL anion-exchange chromatography and SP Sepharose cation-exchange chromatography with a final yield of 9.9% and a purification factor of 31.8. The purified BaL (Mw~85 kDa) was most active at 70 °C and pH 9 in the presence of 4?M NaCl and retained 58.7% of its initial activity after 150 min of incubation at 80 °C. The enzyme was inhibited by Cd2+ (35.6 ± 1.7%) but activated by Ca2+ (132.4 ± 2.2%). Evaluation of BaL's stability in the presence of organic solvents showed that xylene (25%) enhanced the relative activity of the enzyme to 334.2 ± 0.6% after 1 h of incubation. The results of esterification studies using the purified BaL revealed that maximum ethyl valerate (88.5%) and methyl valerate (67.5%) synthesis occurred in the organic solvent medium (xylene) after 48 h of incubation at 50 °C.

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

Bai, Hangyu,Jiang, Weiqi,Li, Qi,Li, Tian,Ma, Shichuang,Shi, Baojun,Wu, Wenjun

, p. 11572 - 11581 (2021/10/12)

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

The relevance of Lewis acid sites on the gas phase reaction of levulinic acid into ethyl valerate using CoSBA-xAl bifunctional catalysts

Cecilia, J. A.,Dumesic, J. A.,Jiménez-Gómez, C. P.,López Granados, M.,Maireles-Torres, P.,Mariscal, R.,Mu?oz-Olasagasti, M.

, p. 4280 - 4293 (2021/06/30)

A series of Co supported on Al-modified SBA-15 catalysts has been studied in the gas phase direct transformation of levulinic acid (LA) into ethyl valerate (EV) using a continuous fixed-bed reactor and ethanol as solvent. It was observed that once the intermediate product gamma-valerolactone (GVL) has been formed, the presence of aluminum is required for the selective transformation to EV. Three Lewis acid sites (LAS) are identified (from highest to lowest acid strength): aluminum ions in tetrahedral and octahedral coordination and Co2+sites. The intrinsic activity of these LAS for the key reaction, the GVL ring opening, decreases with the strength of these acid sites, but so does the undesirable formation of coke, also catalyzed by these centers. The best catalyst was that with the highest Al content, CoSBA-2.5Al, that reached an EV yield of up to 70%. This result is associated with the presence of LAS attributed to the presence of Co2+surface species that, although having low intrinsic activity in the selective GVL ring-opening reaction, are highly concentrated in this sample and also possess less activity in the undesirable and deactivating formation of coke. These Co2+LAS have been stabilized by incorporation of aluminum into the support, modifying the reducibility and dispersion of cobalt species. Additionally, the lower proportion of metallic Co species decreases the hydrogenating capacity of this catalyst. This decrease is a positive result because it prevents GVL hydrogenation to undesired products. This catalyst also showed promising stability in a 140 h on-stream run.

Catalytic transfer hydrogenation of ethyl levulinate to γ-valerolactone over supported MoS2catalysts

Diao, Xinyong,Ji, Na,Jiang, Sinan,Liu, Caixia,Liu, Qingling,Liu, Zhenyu,Lu, Xuebin,Ma, Degang,Song, Chunfeng,Yu, Zhihao

, p. 5062 - 5076 (2021/08/16)

The hydrogenation of levulinate esters to γ-valerolactone (GVL) is an important step in the transformation of biomass into biofuels. It is attractive to develop new efficient systems for the catalytic transfer hydrogenation (CTH) of levulinate esters to value-added GVL. In this work, a series of MoS2-based supported catalysts were prepared via an impregnation method for the CTH of biomass-derived ethyl levulinate (EL) to GVL. By comprehensive characterization and catalytic measurements, we found that the CTH activity of EL to GVL is closely related to the MoS2 morphology and acid distribution on the support. Among the catalysts with different supports, the AC support with abundant Lewis acid sites and large surface area facilitated the high dispersion of low stacked MoS2 slabs, and the MoS2-acid synergistic catalysis contributed to the superior activity and selectivity. The conversion of EL and the selectivity of GVL reached 97.2% and 91.2% under optimized conditions over the MoS2/AC catalyst (230 °C, 1 MPa H2, 1.5 h), respectively. We also conducted reaction kinetic experiments to reveal the relationship between the active site of the MoS2/AC catalyst and its catalytic performance, and the plausible reaction pathway and mechanism over MoS2/AC was proposed. The catalytic performance gradually declined during recycling tests due to the oxidation of MoS2 and can be easily recovered by resulfuration.

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