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124-07-2

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124-07-2 Usage

Description

Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. It is found naturally in the milk of various mammals, and it is a minor constituent of coconut oil and palm kernel oil. It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste. Two other acids are named after goats: caproic (C6) and capric (C10). Along with caprylic acid these total 15 % in goat milk fat.

Chemical Properties

Octanoic acid has a mildly unpleasant odor and a burning, rancid taste. Octanoic acid is also reported as having a faint, fruity–acid odor and slightly sour taste. Caprylic acid is the common name for octanoic acid, CH3(CH2)6COOH, a saturated fatty acid. As an eight-carbon compound, it is among the fatty acids considered to be of short or medium chain length.

Physical properties

Caprylic acid, CH3(CH2)6COOH, also known as hexylacetic acid,n-octanoic acid, octylie acid, and octic acid, is a colorless, oily liquid having a mildly unpleasant odor and a burning, rancid taste. It is only slightly soluble in water (68 mg per 100 mL at 20°C). It is a natural component of coconut and palm nut oils and butter fat. Caprylic acid has also been identified in trace amounts in beer, brandy distillate, the essential oil of fermented Russian black tea leaves, and raw soybeans.It is used in manufacturing drugs and dyes.

Occurrence

Octanoic acid is found naturally in the milk of various mammals and is a natural component of coconut and palm nut oils and butter fat. Caprylic acid has also been identified in trace amounts in beer, brandy distillate, the essential oil of fermented Russian black tea leaves and raw soybeans. Reported as occurring naturally in the essential oils of Cupressus torulosa, Cryptomeria japonica, Andropogon iwarancusa, Cymbopogon javanensis, camphor, nutmeg, lemongrass, lime, tobacco (flowers), Artemisia herba-alba, chamomile, hops and others; also reported in apple aroma, coconut oil as glyceride, and wine as an ester; it has been identified (free and esterified) among the constituents of petitgrain lemon oil.

Uses

Octanoic acid is a flavoring agent considered to be a short or medium chain fatty acid. It occurs normally in various foods and is commercially prepared by oxidation of n-octanol or by fermentation and fractional distillation of the volatile fatty acids present. It is used in maximum levels, as served, of 0.13% for baked goods; 0.04% for cheeses; 0.005% for fats and oils, frozen dairy desserts, gelatins and puddings, meat products, and soft candy; 0.016% for snack foods; and 0.001% or less for all other food categories.

Definition

ChEBI: Octanoic acid is a straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid. It has a role as an antibacterial agent, a human metabolite and an Escherichia coli metabolite. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of an octanoate.

Application

Octanoic acid is widely applied in various fields, It is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. In addition, caprylic acid is used as an algaecide, bactericide, and fungicide in nurseries, greenhouses, garden centers, and interiorscapes on ornamentals. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.Caprylic acid is also used in the treatment of some bacterial infections. Due to its relatively short chain length it has no difficulty in penetrating fatty cell wall membranes, hence its effectiveness in combating certain lipid-coated bacteria, such as Staphylococcus aureus and various species of Streptococcus.Octanoic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes.Some studies have shown that Caprylic acid is effective to excess calorie burning taken as a dietary supplement, resulting in weigh loss.

Preparation

Octanoic acid is produced by fermentation and fractional distillation of the volatile fatty acids present in coconut oil.

Aroma threshold values

Detection: 910 ppb to 19 ppm. Aroma characteristics at 1.0%: waxy, dirty, sweaty and cheesy fatty, with dirty oily and creamy dairy nuances.

Taste threshold values

Taste characteristics at 10 ppm: creamy, waxy, dirty, sweaty, dairy cheeselike.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 5395, 1989 DOI: 10.1021/jo00283a044Synthetic Communications, 19, p. 2151, 1989 DOI: 10.1080/00397918908052610

General Description

Octanoic acid appears as a colorless to light yellow liquid with a mild odor. Burns, but may be difficult to ignite. Corrosive to metals and tissue.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by intravenous route. Mildly toxic by ingestion. Mutation data reported. A skin irritant. Yields irritating vapors that can cause coughmg. When heated to decomposition it emits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 124-07-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 4 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 124-07:
(5*1)+(4*2)+(3*4)+(2*0)+(1*7)=32
32 % 10 = 2
So 124-07-2 is a valid CAS Registry Number.
InChI:InChI=1/2C8H16O2.Sn/c2*1-2-3-4-5-6-7-8(9)10;/h2*2-7H2,1H3,(H,9,10);/q;;+2/p-2

124-07-2 Well-known Company Product Price

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

  • (A11149)  Octanoic acid, 98+%   

  • 124-07-2

  • 25ml

  • 159.0CNY

  • Detail
  • Alfa Aesar

  • (A11149)  Octanoic acid, 98+%   

  • 124-07-2

  • 500ml

  • 224.0CNY

  • Detail
  • Alfa Aesar

  • (A11149)  Octanoic acid, 98+%   

  • 124-07-2

  • 2500ml

  • 572.0CNY

  • Detail
  • Alfa Aesar

  • (A11149)  Octanoic acid, 98+%   

  • 124-07-2

  • 10000ml

  • 2137.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1202)  Caprylic Acid (Octanoic Acid)  pharmaceutical secondary standard; traceable to USP and PhEur

  • 124-07-2

  • PHR1202-1G

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (C0426000)  Caprylicacid  European Pharmacopoeia (EP) Reference Standard

  • 124-07-2

  • C0426000

  • 1,880.19CNY

  • Detail
  • USP

  • (1091040)  Caprylicacid  United States Pharmacopeia (USP) Reference Standard

  • 124-07-2

  • 1091040-300MG

  • 4,662.45CNY

  • Detail
  • Sigma-Aldrich

  • (21639)  Octanoicacid  analytical standard

  • 124-07-2

  • 21639-5ML

  • 827.19CNY

  • Detail

124-07-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name octanoic acid

1.2 Other means of identification

Product number -
Other names Octylic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Surfactants
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:124-07-2 SDS

124-07-2Synthetic route

2-bromoheptane
1974-04-5

2-bromoheptane

carbon dioxide
124-38-9

carbon dioxide

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 20h; regioselective reaction;92%
With rubidium carbonate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 10℃; under 750.075 Torr; for 20h; Schlenk technique; Sealed tube; Irradiation;48%
Stage #1: 2-bromoheptane; carbon dioxide With nickel(II) bromide dimethoxyethane; C32H32N2; C42H34F10IrN4(1+)*F6P(1-); N-ethyl-N,N-diisopropylamine; lithium tert-butoxide In N,N-dimethyl-formamide at 30℃; for 24h; Microwave irradiation; Schlenk technique;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide Reagent/catalyst;
25%
Stage #1: carbon dioxide With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; Schlenk technique;
Stage #2: 2-bromoheptane In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 20h; Schlenk technique;
Stage #3: With hydrogenchloride In water; N,N-dimethyl-formamide Reagent/catalyst;
76 %Spectr.
octanol
111-87-5

octanol

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nitric acid for 0.333333h; Ambient temperature; sonication;100%
With nitric acid for 0.333333h; Ambient temperature; sonication;100%
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 16h;100%
Octanal
124-13-0

Octanal

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With tris[2-(4,6-difluorophenyl)pyridinato-C2,N]-iridium(III); oxygen In acetonitrile at 20℃; Irradiation; Sealed tube; Green chemistry; chemoselective reaction;99%
With diphenyl diselenide; dihydrogen peroxide In water at 20℃; for 3h; Green chemistry;99%
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;99%
carbon dioxide
124-38-9

carbon dioxide

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 20h; regioselective reaction;81%
2-bromoheptane
1974-04-5

2-bromoheptane

carbon dioxide
124-38-9

carbon dioxide

A

2-methylheptanoic acid
116454-37-6, 128441-06-5, 1188-02-9

2-methylheptanoic acid

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
Stage #1: 2-bromoheptane; carbon dioxide With nickel(II) iodide; manganese; 2,9-diethyl-4,7-diphenyl-1,10-phenanthroline In N,N-dimethyl-formamide at 30℃; under 760.051 Torr; for 17h; Schlenk technique;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide Reagent/catalyst; Temperature; Solvent;
A n/a
B 72%
With rubidium carbonate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide at 10℃; under 750.075 Torr; for 20h; Reagent/catalyst; Schlenk technique; Sealed tube; Irradiation; Overall yield = 48 %; Overall yield = 17.3 mg;
4-bromoheptane
998-93-6

4-bromoheptane

carbon dioxide
124-38-9

carbon dioxide

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 20h; regioselective reaction;72%
6-propyl-tetrahydro-pyran-2-one
698-76-0

6-propyl-tetrahydro-pyran-2-one

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With palladium on activated carbon; W(OTf)6; hydrogen In neat (no solvent) at 135℃; under 760.051 Torr; for 12h;98%
With palladium 10% on activated carbon; W(OTf)6; hydrogen at 135℃; under 760.051 Torr; for 12h;92%
carbon dioxide
124-38-9

carbon dioxide

A

2-methylheptanoic acid
116454-37-6, 128441-06-5, 1188-02-9

2-methylheptanoic acid

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
Stage #1: 3-bromoheptane; carbon dioxide With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 17h; Schlenk technique;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide
A n/a
B 81%
carbon dioxide
124-38-9

carbon dioxide

2-(p-toluenesulfonyl)heptane
5011-57-4

2-(p-toluenesulfonyl)heptane

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 20h; regioselective reaction;56%
dimethyl 2-((5-(hydroxymethyl)furan-2-yl)methylene)malonate

dimethyl 2-((5-(hydroxymethyl)furan-2-yl)methylene)malonate

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; W(OTf)6; hydrogen; acetic acid at 180℃; under 22502.3 Torr; for 10h; Autoclave;80%
With palladium on activated charcoal; W(OTf)6; hydrogen; acetic acid at 180℃; under 22502.3 Torr; for 10h; Autoclave;80%
4-bromoheptane
998-93-6

4-bromoheptane

carbon dioxide
124-38-9

carbon dioxide

A

2-methylheptanoic acid
116454-37-6, 128441-06-5, 1188-02-9

2-methylheptanoic acid

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
Stage #1: 4-bromoheptane; carbon dioxide With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 17h; Schlenk technique;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide
A n/a
B 72%
oxone

oxone

Os(VIII)

Os(VIII)

non-1-ene
124-11-8

non-1-ene

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium sulfate; OsO4 In ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol90%
(E)-oct-2-enoic acid
1871-67-6

(E)-oct-2-enoic acid

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With carbon monoxide; hydrogen; triethylamine; acetylacetonatodicarbonylrhodium(l); triphenylphosphine In dichloromethane at 25℃; under 7500.75 Torr; for 24h;42%
carbon dioxide
124-38-9

carbon dioxide

4-heptyltoluene-p-sulphonate
4883-86-7

4-heptyltoluene-p-sulphonate

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; C36H40N2 In N,N-dimethyl-formamide at 25℃; under 760.051 Torr; for 20h; regioselective reaction;50%
3-(5-methylfuran-2-yl) acrylic acid
14779-25-0

3-(5-methylfuran-2-yl) acrylic acid

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With palladium on activated charcoal; W(OTf)6; hydrogen; acetic acid at 180℃; under 22502.3 Torr; for 10h; Autoclave;86%
octanol
111-87-5

octanol

A

oct-1-ene
111-66-0

oct-1-ene

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With 1,10-Phenanthroline; oxygen; cobalt(II) nitrate In dimethyl sulfoxide at 100℃; under 9000.9 Torr; for 12h;A 36%
B 53%
non-1-ene
124-11-8

non-1-ene

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
Stage #1: non-1-ene With oxygen; ozone In tetrahydrofuran at 0℃;
Stage #2: With semicarbazide hydrochloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
95%
Stage #1: non-1-ene With ozone In dichloromethane; acetic acid at 0℃;
Stage #2: With semicarbazide hydrochloride In dichloromethane; acetic acid at 0 - 20℃;
95%
With Oxone; osmium(VIII) oxide In N,N-dimethyl-formamide; tert-butyl alcohol at 20℃; for 3h;90%
1-Heptene
592-76-7

1-Heptene

carbon dioxide
124-38-9

carbon dioxide

A

2-methylheptanoic acid
116454-37-6, 128441-06-5, 1188-02-9

2-methylheptanoic acid

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; Bathocuproine; water In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 40h;A n/a
B 49%
oct-2-ynoic acid
5663-96-7

oct-2-ynoic acid

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With ethanol; lithium; nickel dichloride; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 20℃; for 12h;93%
With sodium hydroxide; Triethoxysilane; water; palladium diacetate for 4h; Ambient temperature;92%
With sodium tetrahydroborate; sodium hydroxide In water at 20 - 60℃;92%
With ethanol; sodium
methyl octanate
111-11-5

methyl octanate

A

caprylohydroxamic acid
7377-03-9

caprylohydroxamic acid

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With hydroxylamine nitrate; sodium hydroxide In methanol at 0 - 50℃; for 3h;A 84%
B 3 g
non-1-ene
124-11-8

non-1-ene

decanoic acid hydrazide
20478-70-0

decanoic acid hydrazide

A

Octanoic acid
124-07-2

Octanoic acid

B

N'-[(1E)-octylidene]decanohydrazide

N'-[(1E)-octylidene]decanohydrazide

Conditions
ConditionsYield
Stage #1: non-1-ene With oxygen; ozone In tetrahydrofuran at 0℃;
Stage #2: decanoic acid hydrazide In tetrahydrofuran at 0 - 20℃; for 72h;
A 12%
B 78%
octanol
111-87-5

octanol

A

Octanal
124-13-0

Octanal

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium nitrite In dichloromethane; water at 20℃; under 760.051 Torr; for 12h; in air;A 92%
B 5.2%
With Succinimide; sodium hypochlorite solution; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate In ethyl acetate at 0 - 10℃; for 2h;A 86%
B 7%
With potassium chromate; copolyesteramide (from N,N'-bis(4-methoxycarbonylbenzoyl)hexamethylenediamine, 1,6-hexanediol, poly(ethylene glycol)); sulfuric acid In dichloromethane at -5℃; for 0.25h;A 83%
B 2.1%
(E)-oct-2-enoic acid
1871-67-6

(E)-oct-2-enoic acid

carbon monoxide
201230-82-2

carbon monoxide

A

Octanal
124-13-0

Octanal

B

Octanoic acid
124-07-2

Octanoic acid

C

C9H16O3
1039763-53-5

C9H16O3

Conditions
ConditionsYield
With tris(2,4-di-tert-butylphenyl)phosphite; hydrogen; acetylacetonatodicarbonylrhodium(l) In dichloromethane at 25℃; under 7500.75 Torr; for 24h;A 23%
B 33%
C 12%
hept-2-ene
592-77-8

hept-2-ene

carbon dioxide
124-38-9

carbon dioxide

A

2-methylheptanoic acid
116454-37-6, 128441-06-5, 1188-02-9

2-methylheptanoic acid

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With nickel(II) iodide; manganese; Bathocuproine; water In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 40h;A n/a
B 15%
methyl ester of 5-methyl-3-(2-furyl)propanoic acid
1456-12-8

methyl ester of 5-methyl-3-(2-furyl)propanoic acid

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With hydrogen; trifluoroacetic acid In n-heptane at 190℃; under 22502.3 Torr; for 10h; Reagent/catalyst; Temperature; Pressure; Autoclave; High pressure;91 %Chromat.
(E)-oct-2-enoic acid
1871-67-6

(E)-oct-2-enoic acid

carbon monoxide
201230-82-2

carbon monoxide

A

Octanal
124-13-0

Octanal

B

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With hydrogen; acetylacetonatodicarbonylrhodium(l) In dichloromethane at 25℃; under 7500.75 Torr; for 24h;
With hydrogen; acetylacetonatodicarbonylrhodium(l) In dichloromethane at 25℃; under 7500.75 Torr; for 20.5h;A 91 % Chromat.
B 4.5 % Spectr.
octanol
111-87-5

octanol

A

Octanoic acid
124-07-2

Octanoic acid

B

octyl octylate
2306-88-9

octyl octylate

Conditions
ConditionsYield
With sodium bromate; sodium hydrogensulfite for 2h; Ambient temperature;A 3%
B 94%
Stage #1: octanol With gold on titanium oxide In water at 90℃; for 0.166667h; Inert atmosphere;
Stage #2: With dihydrogen peroxide In water at 90℃; for 1.08333h; Inert atmosphere; chemoselective reaction;
A 90%
B n/a
With sodium tungstate; dihydrogen peroxide In water at 90℃; for 4h;A 87%
B 2%
non-1-ene
124-11-8

non-1-ene

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

A

Octanoic acid
124-07-2

Octanoic acid

B

4-methyl-N'-octylidenebenzene-1-sulfonohydrazide

4-methyl-N'-octylidenebenzene-1-sulfonohydrazide

Conditions
ConditionsYield
Stage #1: non-1-ene With oxygen; ozone In dichloromethane; acetic acid at 0℃;
Stage #2: toluene-4-sulfonic acid hydrazide In dichloromethane; acetic acid at 20℃; Inert atmosphere;
A 19%
B 42%
ethanol
64-17-5

ethanol

Octanal
124-13-0

Octanal

Octanoic acid
124-07-2

Octanoic acid

Conditions
ConditionsYield
With oxygen at 100℃; under 3750.38 Torr; for 5h; Autoclave;11 %Chromat.
ethanol
64-17-5

ethanol

Octanal
124-13-0

Octanal

A

1,1-diethoxy-octane
54889-48-4

1,1-diethoxy-octane

B

Octanoic acid
124-07-2

Octanoic acid

C

octanoic acid ethyl ester
106-32-1

octanoic acid ethyl ester

Conditions
ConditionsYield
With oxygen at 100℃; under 3750.38 Torr; for 5h; Autoclave;A 27 %Chromat.
B 8 %Chromat.
C 7 %Chromat.
With oxygen at 100℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Autoclave;A 8 %Chromat.
B 13 %Chromat.
C 58 %Chromat.
With oxygen at 100℃; under 3750.38 Torr; for 5h; Reagent/catalyst; Autoclave;A 63 %Chromat.
B 6 %Chromat.
C 12 %Chromat.
Octanoic acid
124-07-2

Octanoic acid

3-(2-vinyloxyethoxy)-1,2-propylene carbonate
54107-24-3

3-(2-vinyloxyethoxy)-1,2-propylene carbonate

Octanoic acid 1-[2-(2-oxo-[1,3]dioxolan-4-ylmethoxy)-ethoxy]-ethyl ester
127827-87-6

Octanoic acid 1-[2-(2-oxo-[1,3]dioxolan-4-ylmethoxy)-ethoxy]-ethyl ester

Conditions
ConditionsYield
With heptafluorobutyric Acid at 75℃; for 3h;100%
Octanoic acid
124-07-2

Octanoic acid

2-(vinyloxy)ethyl isothiocyanate
59565-09-2

2-(vinyloxy)ethyl isothiocyanate

Octanoic acid (2-vinyloxy-ethyl)-amide

Octanoic acid (2-vinyloxy-ethyl)-amide

Conditions
ConditionsYield
With triethylamine at 45 - 50℃; for 1h;100%
Octanoic acid
124-07-2

Octanoic acid

2-(Trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-3-O-<(3R)-3-hydroxytetradecanoyl>-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside
125034-39-1

2-(Trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-3-O-<(3R)-3-hydroxytetradecanoyl>-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

2-(Trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-3-O-<(3R)-3-octanoyloxytetradecanoyl>-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside
125056-34-0

2-(Trimethylsilyl)ethyl 6-O-tert-butyldimethylsilyl-2-deoxy-4-O-diphenoxyphosphinyl-3-O-<(3R)-3-octanoyloxytetradecanoyl>-2-<(3R)-3-<(2-trimethylsilylethoxy)methoxy>tetradecanamido>-β-D-glucopyranoside

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane Ambient temperature;100%
Octanoic acid
124-07-2

Octanoic acid

n-heptane
142-82-5

n-heptane

Conditions
ConditionsYield
With palladium on silica gel; hydrogen at 300℃; under 760.051 Torr; for 4h; Temperature; Flow reactor;100%
With hydrogen; silica gel; palladium at 330℃; Ni/Al2O3, 180 deg C;97%
With Au0012O19676(00)Pd042(98)Si038; hydrogen at 260℃; under 760.051 Torr; Catalytic behavior; Reagent/catalyst;
Octanoic acid
124-07-2

Octanoic acid

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride
3945-69-5

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

octanoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester

octanoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 0℃; for 3h; Condensation;100%
Octanoic acid
124-07-2

Octanoic acid

C8H16O2*C19H21NO

C8H16O2*C19H21NO

Conditions
ConditionsYield
In tetrahydrofuran at 40 - 50℃; for 5h;100%
Octanoic acid
124-07-2

Octanoic acid

benzydamine
642-72-8

benzydamine

C19H23N3O*C8H16O2

C19H23N3O*C8H16O2

Conditions
ConditionsYield
In tetrahydrofuran at 40 - 50℃; for 5h;100%
Octanoic acid
124-07-2

Octanoic acid

palladium diacetate
3375-31-3

palladium diacetate

palladium dioctanoate

palladium dioctanoate

Conditions
ConditionsYield
In cyclohexane at 40℃; Solvent;100%
lauric acid
143-07-7

lauric acid

trichlorovinylsilane
75-94-5

trichlorovinylsilane

Octanoic acid
124-07-2

Octanoic acid

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C36H68O6Si
1330066-17-5

C36H68O6Si

Conditions
ConditionsYield
In toluene at 60 - 150℃; for 4h;99.82%
Octanoic acid
124-07-2

Octanoic acid

1-Hexadecanol
36653-82-4

1-Hexadecanol

Octanoic acid, hexadecyl ester
29710-31-4

Octanoic acid, hexadecyl ester

Conditions
ConditionsYield
With choline chloride; zinc(II) chloride at 110℃; for 6h;99%
With immobilized lipase Novozym 435 from Candida antarctica B supported on a macroporous acrylic resin In carbon dioxide at 63.7℃; under 76657.7 Torr; for 0.333333h; Supercritical conditions; Enzymatic reaction; liquid CO2;99.5%
rhodium(III) hydroxide

rhodium(III) hydroxide

Octanoic acid
124-07-2

Octanoic acid

dirhodium(II) tetraoctanoate

dirhodium(II) tetraoctanoate

Conditions
ConditionsYield
at 105℃; for 6h; Temperature; Concentration;99.24%
Octanoic acid
124-07-2

Octanoic acid

glycerol
56-81-5

glycerol

tricaprilin
538-23-8

tricaprilin

Conditions
ConditionsYield
With acetic acid at 275℃; for 0.5h;99.2%
With tungsten(VI) oxide at 175℃; under 1 Torr; for 22h; Reagent/catalyst;93%
at 100℃; Beim Erhitzen in Gegenwart von aus Naphthalin,Oelsaeure und konz.Schwefelsaeure in Petrolaether dargestelltem Twitchells Reagens;
methanol
67-56-1

methanol

Octanoic acid
124-07-2

Octanoic acid

methyl octanate
111-11-5

methyl octanate

Conditions
ConditionsYield
polyaniline sulfate at 70℃; for 24h;99%
With N-Bromosuccinimide at 70℃; for 2h; Time;97%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 2h;97%
Octanoic acid
124-07-2

Octanoic acid

octanol
111-87-5

octanol

Conditions
ConditionsYield
With samarium diiodide; heptanal; samarium(III) trifluoromethanesulfonate In tetrahydrofuran; methanol; potassium hydroxide at 20℃; for 0.075h; Reduction;99%
With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate) In toluene at 80℃; for 16h; sealed tube;91%
With hydrogen In neat (no solvent) at 180℃; under 37503.8 Torr; for 12h;91%
Octanoic acid
124-07-2

Octanoic acid

caprylohydroxamic acid
7377-03-9

caprylohydroxamic acid

Conditions
ConditionsYield
With Novozym 435 (Candida antarctica lipase B on Lewatit E); hydroxylamine In water at 40℃; for 20h; Condensation; Enzymatic reaction;99%
Stage #1: Octanoic acid With acetic anhydride for 0.166667h;
Stage #2: With hydroxylamine hydrochloride for 0.666667h;
95.81%
With liverextract; hydroxylamine
With hydroxylamine; 1,1'-carbonyldiimidazole
With hydroxylamine; adenosine monophosphate ligase SfaB from Streptomyces thioluteus; ATP; magnesium chloride; Cleland's reagent In aq. buffer at 30℃; for 6h; pH=8; Enzymatic reaction;
Octanoic acid
124-07-2

Octanoic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl caprylate
10276-85-4

benzyl caprylate

Conditions
ConditionsYield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 10h;99%
With pyrographite; toluene-4-sulfonic acid for 0.00777778h; Esterification; Microwave irradiation (675 W);90%
With tris(2-methoxyphenyl)bismuthine In benzene for 12h; Heating;86%
Octanoic acid
124-07-2

Octanoic acid

4-(1,1-dimethylethyl)-cyclohexanol
98-52-2

4-(1,1-dimethylethyl)-cyclohexanol

octanoic acid 4-tert-butyl-cyclohexyl ester

octanoic acid 4-tert-butyl-cyclohexyl ester

Conditions
ConditionsYield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;99%
Octanoic acid
124-07-2

Octanoic acid

cyclohexanol
108-93-0

cyclohexanol

octanoic acid cyclohexyl ester
1551-42-4

octanoic acid cyclohexyl ester

Conditions
ConditionsYield
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride In dichloromethane at 20℃; for 6h;99%

124-07-2Related news

Kinetic study of Octanoic acid (cas 124-07-2) enhanced crystal growth of boehmite under sub- and supercritical hydrothermal conditions09/29/2019

This paper describes the kinetics of particle growth of boehmite under hydrothermal conditions in the presence of octanoic acid. The size of the boehmite particles formed after hydrothermal treatment between 200 and 400 °C in a batch reactor was measured after various treatment times (several m...detailed

Octanoic acid (cas 124-07-2) potentiates glucose-stimulated insulin secretion and expression of glucokinase through the olfactory receptor in pancreatic β-cells09/28/2019

Olfactory receptors (ORs) are G protein-coupled receptors that mediate olfactory chemosensation, leading to the perception of smell. ORs are expressed in many tissues, but their functions are largely unknown. Here, we show that the olfactory receptor Olfr15 is highly and selectively expressed in...detailed

Esterification of guaiacol with Octanoic acid (cas 124-07-2) over functionalized mesoporous silica10/01/2019

Ester products, obtaining from guaiacol and octanoic acid which were the degeneration products of lignin, were tested over sulfonic acid-functionalized SiO2 materials. The results showed that the functionalized mesoporous SiO2 had a high activity and stability, resulting in ester yield of 62%. T...detailed

Differences in crystal growth behaviors of boehmite particles with Octanoic acid (cas 124-07-2) and sodium octanoate under supercritical hydrothermal conditions09/27/2019

Crystal growth behaviors of boehmite particles with octanoic acid and sodium octanoate under supercritical hydrothermal condition were investigated. It was confirmed that adding carboxylic acid is effective in synthesizing hexagonal plate particles with high aspect ratios, while rhombic plate pa...detailed

Deoxygenation of Octanoic acid (cas 124-07-2) catalyzed by hollow spherical Ni/ZrO209/25/2019

A series of Ni located on hollow spherical ZrO2 catalysts was prepared, and their catalytic performances for octanoic acid deoxygenation were investigated. The ZrO2 hollow spheres saturated by the water phase served as a nanoreactor that captured octanoic acid to react with Ni located inside a h...detailed

Antimicrobial action of Octanoic acid (cas 124-07-2) against Escherichia coli O157:H7 during washing of baby spinach and grape tomatoes09/10/2019

We investigated the antimicrobial efficacy of octanoic acid (OA) against Escherichia coli O157:H7 inoculated on the surface of baby spinach and grape tomatoes during simulated washing processes. 3 mM OA at 45 °C achieved >6 log CFU/g reduction from the surface of tomatoes within 2 min. However,...detailed

The response of the central and peripheral tremor component to Octanoic acid (cas 124-07-2) in patients with essential tremor09/09/2019

ObjectiveTo investigate the effect of octanoic acid (OA) on the peripheral component of tremor, as well as OA’s differential effects on the central and peripheral tremor component in essential tremor (ET) patients.detailed

Short communicationProduction of ω-hydroxy Octanoic acid (cas 124-07-2) with Escherichia coli09/08/2019

The present proof-of-concept study reports the construction of a whole-cell biocatalyst for the de novo production of ω-hydroxy octanoic acid. This was achieved by hijacking the natural fatty acid cycle and subsequent hydroxylation using a specific monooxygenase without the need for the additio...detailed

124-07-2Relevant articles and documents

-

Raistrick,Robinson,Todd

, p. 80,83 (1937)

-

Reaction of octyl ether with nitric acid and its mixtures

Svetlakov,Nikitin,Ruziev

, p. 290 - 291 (2002)

-

A green and efficient oxidation of alcohols by amphiphilic resin-supported gold nanoparticles in aqueous H2O2

Xie, Ting,Lu, Min,Zhang, Wenwen,Li, Jun

, p. 397 - 399 (2011)

A green and highly efficient oxidation of alcohols in aqueous H 2O2 using amphiphilic resin (PS-PEG-NH2)-supported gold nanoparticles is described. The reaction proceeded with excellent yields and selectivities, in particular, for nonactivated alcohols without base. The catalyst, in addition, could be readily recovered by simple work-up and reused several times without significant loss of its catalytic activity.

Synthesis of α,β-unsaturated aldehydes as potential substrates for bacterial luciferases

Brodl, Eveline,Ivkovic, Jakov,Tabib, Chaitanya R.,Breinbauer, Rolf,Macheroux, Peter

, p. 1487 - 1495 (2017)

Bacterial luciferase catalyzes the monooxygenation of long-chain aldehydes such as tetradecanal to the corresponding acid accompanied by light emission with a maximum at 490?nm. In this study even numbered aldehydes with eight, ten, twelve and fourteen carbon atoms were compared with analogs having a double bond at the α,β-position. These α,β-unsaturated aldehydes were synthesized in three steps and were examined as potential substrates in vitro. The luciferase of Photobacterium leiognathi was found to convert these analogs and showed a reduced but significant bioluminescence activity compared to tetradecanal. This study showed the trend that aldehydes, both saturated and unsaturated, with longer chain lengths had higher activity in terms of bioluminescence than shorter chain lengths. The maximal light intensity of (E)-tetradec-2-enal was approximately half with luciferase of P. leiognathi, compared to tetradecanal. Luciferases of Vibrio harveyi and Aliivibrio fisheri accepted these newly synthesized substrates but light emission dropped drastically compared to saturated aldehydes. The onset and the decay rate of bioluminescence were much slower, when using unsaturated substrates, indicating a kinetic effect. As a result the duration of the light emission is doubled. These results suggest that the substrate scope of bacterial luciferases is broader than previously reported.

Hydration of nitriles to amides in water by SiO2-supported Ag catalysts promoted by adsorbed oxygen atoms

Shimizu, Ken-Ichi,Imaiida, Naomichi,Sawabe, Kyoichi,Satsuma, Atsushi

, p. 114 - 120 (2012)

A series of silica-supported silver catalysts with similar Ag loading (5 or 7 wt%) but with different preparation methods (calcination in air and reduction by H2 or NaBH4) were prepared, and their structure was characterized by microscopy (STEM), X-ray absorption fine structure (XAFS), and CO-titration of surface oxygen atom. Ag is present as metal nanoparticle with a size range of 17-30 nm. Their surface was partially covered with oxygen atoms, and the surface coverage of the oxygen depends on the preparation condition. For hydration of 2-cyanopyridine as a test reaction, turnover frequency (TOF) per surface Ag species is estimated. TOF does not show a good correlation with Ag particle size, but it linearly increases with the coverage of the surface oxygen atoms on Ag particles. The Ag/SiO2 catalyst prepared by H 2 reduction at 700 °C shows the highest TOF and it acts as effective and recyclable heterogeneous catalyst for selective hydration of various nitriles to the corresponding amides. Kinetic and Raman spectroscopic studies suggest that the surface oxygen atom adjacent to Ag0 sites plays an important role in the dissociation of H2O.

Identification of novel fatty acid glucosides from the tropical fruit Morinda citrifolia L.

Kim, Hye-Kyeong,Kwon, Min-Kyong,Kim, Jin-Nam,Kim, Chang-Kwon,Lee, Yeon-Ju,Shin, Hee Jae,Lee, Joongku,Lee, Hyi-Seung

, p. 238 - 241 (2010)

Two new fatty acid glucosides, 1,6-di-O-octanoyl-β-D-glucopyranose (1) and 6-O-(β-D-glucopyranosyl)-1-O-decanoyl-β-D-glucopyranose (2), were isolated from a methanol extract of the fruit of Morinda citrifolia L. along with five known saccharide fatty acid esters. The structures of these compounds were determined by combination of spectral and chemical analyses. These fatty acid glucosides exhibited inhibitory effect against copper-induced low-density lipoprotein oxidation. Compound 2 had the strongest effect, which was almost comparable to that of butylated hydroxytoluene.

Molecular characterization, expression analysis, and role of ALDH3B1 in the cellular protection against oxidative stress

Marchitti, Satori A.,Brocker, Chad,Orlicky, David J.,Vasiliou, Vasilis

, p. 1432 - 1443 (2010)

Aldehyde dehydrogenase (ALDH) enzymes are critical in the detoxification of aldehydes. The human genome contains 19 ALDH genes, mutations in which are the basis of several diseases. The expression, subcellular localization, enzyme kinetics, and role of ALDH3B1 in aldehyde- and oxidant-induced cytotoxicity were investigated. ALDH3B1 was purified from Sf9 cells using chromatographic methods, and enzyme kinetics were determined spectrophotometrically. ALDH3B1 demonstrated high affinity for hexanal (Km=62μM), octanal (Km=8μM), 4-hydroxy-2-nonenal (4HNE; Km=52μM), and benzaldehyde (Km=46μM). Low affinity was seen toward acetaldehyde (Km=23.3mM), malondialdehyde (Km=152mM), and the ester p-nitrophenyl acetate (Km=3.6mM). ALDH3B1 mRNA was abundant in testis, lung, kidney, and ovary. ALDH3B1 protein was highly expressed in these tissues and the liver. Immunofluorescence microscopy of ALDH3B1-transfected human embryonic kidney (HEK293) cells and subcellular fractionation of mouse kidney and liver revealed a cytosolic protein localization. ALDH3B1-transfected HEK293 cells were significantly protected from the lipid peroxidation-derived aldehydes trans-2-octenal, 4HNE, and hexanal and the oxidants H2O2 and menadione. In addition, ALDH3B1 protein expression was up-regulated by 4HNE in ARPE-19 cells. The results detailed in this study support a pathophysiological role for ALDH3B1 in protecting cells from the damaging effects of oxidative stress.

Micellar Catalysis of Organic Reactions. 25. Orientational Effects in Hydroxy-Functionalized Micelles

Broxton, Trevor J.,Christie, John R.,Sango, Xenia

, p. 1919 - 1922 (1989)

The basic hydrolysis of a number of aspirin derivatives in the presence of the hydroxy-functionalized micelles cetyl(2-hydroxyethyl)dimethylammonium bromide (CHEDAB), cetyl(2-hydroxypropyl)dimethylammonium bromide (CHPDAB), and (2-hydroxycetyl)trimethylammonium bromide (2-OH CTAB) and in the presence of cetyltrimethylammonium bromide (CTAB) has been compared.It has been found that of the hydroxy-functionalized micelles CHEDAB best discriminates between substrates with reaction centers at the micelle-water interface and those with reaction centers that are more deeplyburied in the micellar interior.This discrimination is shown in differences in the ratios of the optimum rates of hydrolysis in the hydroxy-functionalized micelles and in CTAB.It is also shown in the ratios of the calculated rates of reaction in the micellar pseudophase for the hydroxy-functionalized micelles and for CTAB.Thus the orientation of substrates within micellar aggregates is important in determining the magnitude of micellar catalysis.

Ester Ammoniolysis: a New Enzymatic Reaction

Zoete, Marian C. de,Kock-van Dalen, Alida C.,Rantwijk, Fred van,Sheldon, Roger A.

, p. 1831 - 1832 (1993)

A new enzymatic reaction of carboxylic esters and ammonia (ammoniolysis) provides a synthetically useful and mild procedure for the enantioselective synthesis of amides.

Kharasch et al.

, p. 435 (1967)

-

Parker et al.

, p. 4037,4038 (1955)

-

Manganese-catalyzed direct oxidation of methyl ethers to ketones

Kamijo, Shin,Amaoka, Yuuki,Inoue, Masayuki

, p. 486 - 489 (2010)

Direct C-H oxidation of alkyl ethers into ketones was achieved using 0.1 mol % of MnCl2 and 4, 4′, 4″-tri(tert-butyl)-2, 2′:6′, 2″-terpyridine (tBu-terpy) in the presence of mCPBA. Conversion of methyl ethers into ketones was particularly efficient and chemoselective. Electron-deficient oxygen functionalities survived under the reaction conditions. The present method broadens the utility of methyl ethers as stable protective groups for hydroxy functionalities and as precursors to carbonyl compounds. (Chemical equation presented).

Resin glycosides. XVI. Marubajalapins I-VII, new ether-soluble resin glycosides from Pharbitis purpurea

Ono,Ueguchi,Murata,Kawasaki,Miyahar

, p. 3169 - 3173 (1992)

Fifteen new resin glycosides, marubajalapins I-XV, were isolated from the jalapin fraction of the aerial part (leaves and stems) of Pharbitis purpurea. Among them, the structures of marubajalapins I-VII have been determined on the basis of chemical and spectral data. They are the first examples of jalapins with operculinic acid E obtained previously as a minor glycosidic acid of the crude jalapin from Jalapae Braziliensis.

Pt-Catalyzed selective oxidation of alcohols to aldehydes with hydrogen peroxide using continuous flow reactors

Kon, Yoshihiro,Nakashima, Takuya,Yada, Akira,Fujitani, Tadahiro,Onozawa, Shun-Ya,Kobayashi, Shū,Sato, Kazuhiko

, p. 1115 - 1121 (2021)

The oxidation of alcohols to aldehydes is a powerful reaction pathway for obtaining valuable fine chemicals used in pharmaceuticals and biologically active compounds. Although many oxidants can oxidize alcohols, only a few hydrogen peroxide oxidations can be employed to continuously synthesize aldehydes in high yields using a liquid-liquid two-phase flow reactor, despite the possibility of the application toward a safe and rapid multi-step synthesis. We herein report the continuous flow synthesis of (E)-cinnamaldehyde from (E)-cinnamyl alcohol in 95%-98% yields with 99% selectivity for over 5 days by the selective oxidation of hydrogen peroxide using a catalyst column in which Pt is dispersed in SiO2. The active species for the developed selective oxidation is found to be zero-valent Pt(0) from the X-ray photoelectron spectroscopy measurements of the Pt surface before and after the oxidation. Using Pt black diluted with SiO2as a catalyst to retain the Pt(0) species with the optimal substrate and H2O2introduction rate not only enhances the catalytic activity but also maintains the activity during the flow reaction. Optimizing the contact time of the substrate with Pt and H2O2using a flow reactor is important to proceed with the selective oxidation to prevent the catalytic H2O2decomposition.

Positional assembly of enzymes in polymersome nanoreactors for cascade reactions

Vriezema, Dennis M.,Garcia, Paula M. L.,Sancho Oltra, Nuria,Hatzakis, Nikos S.,Kuiper, Suzanne M.,Nolte, Roeland J. M.,Rowan, Alan E.,Van Hest, Jan C. M.

, p. 7378 - 7382 (2007)

In a good position: Nanoreactors can be constructed by the controlled positioning of glucose oxidase (GOX) and horseradish peroxidase (HRP) within the central water pool and block-copolymer membrane of polymersomes. A one-pot multistep reaction sequence is performed with the nanoreactor in combination with free Candida antarctica lipase B (CALB) in the bulk solution (see picture; ABTS: 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)). (Chemical Equation Presented)

Study on the performance and mechanism of aerobic oxidative desulfurization based on a dual-functional material possessing catalytic and adsorptive properties

Dou, Shuai-yong,Wang, Rui

, p. 3226 - 3235 (2019)

Herein, three polyoxometalates, namely K3PW12O40·10H2O, K6[α-P2W18O62]·14H2O, and K8H[P2W15V3O62]·9H2O, were successfully prepared and used in the air/n-octanaloxidative desulfurization (ODS) system. Among the compounds, the Dawson-type polyoxometalate K6[α-P2W18O62]·14H2O exhibited the best performance, with a 99.63% desulfurization ratio. Then, K6[α-P2W18O62]·14H2O was supported on graphene oxide (GO) to obtain K6P2W18O62/GO. The prepared catalysts were characterized by Fourier transform infrared spectroscopy (FTIR), 31P nuclear magnetic resonance (31P NMR) spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray (EDX) spectroscopy, transmission electron microscopy (TEM), and Boehm titration. Using K6P2W18O62/GO as a catalyst, a final sulfur removal ratio of 96.10% was achieved without extraction post-treatment due to the inherent adsorption capacity of the catalyst. In addition, the factors influencing the desulfurization process were investigated. The recovery experiment showed that the supported catalyst could be reused 5 times with slight catalyst deactivation. Finally, the reaction mechanism was proposed with the aid of gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS) and contrast tests.

Spontaneous product segregation from reactions in ionic liquids: Application in Pd-catalyzed aliphatic alcohol oxidation

Van Doorslaer, Charlie,Schellekens, Yves,Mertens, Pascal,Binnemans, Koen,De Vos, Dirk

, p. 1741 - 1749 (2010)

A methodology is introduced to separate polar reaction products from ionic liquids without the need for organic solvent extraction or distillation. We investigated product isolation after an alcohol oxidation performed in ionic liquids. Suitable ionic liquids were selected based on their mixing or demixing with a range of alcohols and the derived ketones. The aim was to obtain complete miscibility with the alcohol substrate at reaction temperature and a clear phase separation of the derived ketone product at room temperature. Six imidazolium based ionic liquids displayed this desired behaviour and were sufficiently stable to oxidation. These ionic liquids were then employed in the oxidation of non-activated aliphatic alcohols with molecular oxygen in the presence of palladium(ii) acetate. In 1-butyl-3-methylimidazolium tetrafluoroborate, 2-ketone yields of 79 and 86% were obtained for, respectively, 2-octanol and 2-decanol. After cooling to room temperature the ionic liquid expels the immiscible ketone and the product phase can be isolated by decantation. In addition, the ionic liquid acts as an immobilization medium for the palladium catalyst, allowing efficient catalyst recycling.

Anionic N,O-ligated Pd(ii) complexes: Highly active catalysts for alcohol oxidation

Bailie, David S.,Clendenning, Grainne M. A.,McNamee, Laura,Muldoon, Mark J.

, p. 7238 - 7240 (2010)

There is a need to develop effective catalytic methods for alcohol oxidation. Pd(ii) complexes have shown great promise as catalysts, however a comparatively small number of ligands have been reported so far. Herein we report the use of commercially available anionic N,O-ligands to produce highly active catalysts.

Insights in the aerobic oxidation of aldehydes

Vanoye, Laurent,Favre-Reguillon, Alain,Aloui, Asma,Philippe, Regis,De Bellefon, Claude

, p. 18931 - 18937 (2013)

The hydroformylation of olefins (oxo synthesis) is the most important process for the production of higher aldehydes (>C4). The liquid phase oxidation of the latter to carboxylic acids by molecular oxygen or air has been known for more than 150 years and is an industrially important process. However, in the recent literature, several different oxidizing reagents and catalytic processes have been reported for this oxidation but most of them have limitations as they use environmentally unacceptable reagents or unnecessarily sophisticated conditions. Herein, we re-evaluated the air oxidation of aldehydes. We show that under mild conditions (air or oxygen and non-optimized stirring), reactions are transfer limited and thus catalyst has no effect on reaction rate. Using efficient stirring (self-suction turbine), uncatalysed air oxidation of 0.8 M aldehyde is possible in 50 min at room temperature whereas less than 10 min was necessary with 10 ppm Mn(ii). Thus, recommendations for avoiding common pitfalls that may rise during the evaluation of new catalysts are made. The Royal Society of Chemistry 2013.

Dendritic phosphonates and the in situ assembly of polyperoxophosphotungstates: Synthesis and catalytic epoxidation of alkenes with hydrogen peroxide

Vasylyev, Maxym V.,Astruc, Didier,Neumann, Ronny

, p. 39 - 44 (2005)

First and second-generation rigid dendrimers based on polyphenylated tetrahedral adamantane cores with four or sixteen peripheral phosphonate moieties, PD1 and PD2, respectively, were synthesized and characterized. Further reaction of the dendritic phosphonates with tungstic acid in the presence of hydrogen peroxide led to the stepwise in situ formation of mono- and dinuclear phosphoperoxotungstates. These assemblies were effective catalysts for the epoxidation of alkenes in an aqueous acetonitrile solvent.

Crystal structures of two Bacillus carboxylesterases with different enantioselectivities

Rozeboom, Henriette J.,Godinho, Luis F.,Nardini, Marco,Quax, Wim J.,Dijkstra, Bauke W.

, p. 567 - 575 (2014)

Naproxen esterase (NP) from Bacillus subtilis Thai I-8 is a carboxylesterase that catalyzes the enantioselective hydrolysis of naproxenmethylester to produce S-naproxen (E > 200). It is a homolog of CesA (98% sequence identity) and CesB (64% identity), both produced by B. subtilis strain 168. CesB can be used for the enantioselective hydrolysis of 1,2-O-isopropylideneglycerol (solketal) esters (E > 200 for IPG-caprylate). Crystal structures of NP and CesB, determined to a resolution of 1.75 A and 2.04 A, respectively, showed that both proteins have a canonical α/β hydrolase fold with an extra N-terminal helix stabilizing the cap subdomain. The active site in both enzymes is located in a deep hydrophobic groove and includes the catalytic triad residues Ser130, His274, and Glu245. A product analog, presumably 2-(2-hydroxyethoxy)acetic acid, was bound in the NP active site. The enzymes have different enantioselectivities, which previously were shown to result from only a few amino acid substitutions in the cap domain. Modeling of a substrate in the active site of NP allowed explaining the different enantioselectivities. In addition, Ala156 may be a determinant of enantioselectivity as well, since its side chain appears to interfere with the binding of certain R-enantiomers in the active site of NP. However, the exchange route for substrate and product between the active site and the solvent is not obvious from the structures. Flexibility of the cap domain might facilitate such exchange. Interestingly, both carboxylesterases show higher structural similarity to meta-cleavage compound (MCP) hydrolases than to other α/β hydrolase fold esterases.

Bimetallic Co-Pd alloy nanoparticles as magnetically recoverable catalysts for the aerobic oxidation of alcohols in water

Ito, Yoshikazu,Ohta, Hidetoshi,Yamada, Yoichi M.A.,Enoki, Toshiaki,Uozumi, Yasuhiro

, p. 6146 - 6149 (2014)

Co-Pd bimetallic alloy nanoparticle catalysts were prepared from CoCl2, Pd(OAc)2and several capping agents with Li(C2H5)3BH. The nanoparticle catalysts were applied to the aerobic oxidation of a variety of alcohols in water to give the corresponding carbonyl products. The catalyst was magnetically recovered and reused for further oxidation. The nanoparticle catalysts were characterized with TEM, ICP, and XPS analyses.

Acylguanidine derivatives of zanamivir and oseltamivir: Potential orally available prodrugs against influenza viruses

Hsu, Peng-Hao,Chiu, Din-Chi,Wu, Kuan-Lin,Lee, Pei-Shan,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Tsai, Keng-Chang,Cheng, Ting-Jen,Fang, Jim-Min

, p. 314 - 323 (2018)

Zanamivir (ZA) and guanidino-oseltamivir carboxylic acid (GOC) are very potent inhibitors against influenza neuraminidase (NA). The guanidinium moiety plays an important role in NA binding; however, its polar cationic nature also hinders the use of ZA and GOC from oral administration. In this study, we investigated the use of ZA and GOC acylguanidine derivatives as possible orally available prodrugs. The acylguanidine derivatives were prepared by coupling with either n-octanoic acid or (S)-naproxen. The lipophilic acyl substituents were verified to improve cell permeability, and may also improve the bioavailability of acylguanidine compounds. In comparison, the acylguanidines bearing linear octanoyl chain showed better NA inhibitory activity and higher hydrolysis rate than the corresponding derivatives having bulky branched naproxen moiety. Our molecular docking experiments revealed that the straight octanoyl chain could extend to the 150-cavity and 430-cavity of NA to gain extra hydrophobic interactions. Mice receiving the ZA octanoylguanidine derivative survived from influenza infection better than those treated with ZA, whereas the GOC octanoylguanidine derivative could be orally administrated to treat mice with efficacy equal to oseltamivir. Our present study demonstrates that incorporation of appropriate lipophilic acyl substituents to the polar guanidine group of ZA and GOC is a feasible approach to develop oral drugs for influenza therapy.

Nucleophilically Assisted Deacylation in Sodium Dodecanoate and Dodecyl Sulfate Micelles. Quantitative Evidence on Premicellar Complexes

Marconi, Dilma M. O.,Frescura, Vera L. A.,Zanette, Dino,Nome, Faruk,Bunton, Clifford A.

, p. 12415 - 12419 (1994)

Hydrolyses of 2,4-dinitrophenyl acetate and octanoate (DNPA and DNPO, respectively) and benzoic anhydride (Bz2O) in the pH range 8.9-10.2 are inhibited by anionic micelles of sodium dodecyl sulfate (SDS), and reactions of fully micellar-bound substrates are very slow.The effect of micellized sodium dodecanoate, SDOD, depends on pH.At high pH reactions of DNPA and Bz2O involve OH- and are inhibited by SDOD, but there are significant rates at high .At low-pH reactions of DNPA and Bz2O are inhibited at low and assisted at high .The inhibition is due to formation of kinetically ineffective premicellar complexes and rate-surfactant profiles can be fitted quantitatively in terms of this model.When the substrates are fully micellar-bound rate constants in mixtures of SDOD and SDS follow the mole fraction of SDOD and second-order rate constants of nucleophilic attack by the dodecanoate ion at micellar surfaces are similar to those for the reactions of OAc- in water.

Dehydrogenative alcohol coupling and one-pot cross metathesis/dehydrogenative coupling reactions of alcohols using Hoveyda-Grubbs catalysts

?zer, Halenur,Arslan, Dilan,?ztürk, Bengi ?zgün

supporting information, p. 5992 - 6000 (2021/04/12)

In this study,in situformed ruthenium hydride species that were generated from Grubbs type catalysts are used as efficient catalysts for dehydrogenative alcohol coupling and sequential cross-metathesis/dehydrogenative coupling reactions. The selectivity of Grubbs first generation catalysts (G1) in dehydrogenative alcohol coupling reactions can be tuned for the ester formation in the presence of weak bases, while the selectivity can be switched to the β-alkylated alcohol formation using strong bases. The performance of Hoveyda-Grubbs 2nd generation catalyst (HG2) was improved in the presence of tricyclohexylphosphine for the selective synthesis of ester derivatives with weak and strong bases in quantitative yields. Allyl alcohol was used as self and cross-metathesis substrate for the HG2 catalyzed sequential cross-metathesis/dehydrogenative alcohol coupling reactions to obtain γ-butyrolactone and long-chain ester derivatives in quantitative yields.

Ruthenium(ii)-supported phosphovanadomolybdates [Ru(dmso)3PMo6V3O32]6-and [Ru(PMo6V3O32)2]14-, and their use as heterogeneous catalysts for oxidation of alcohols

Shi, Hao-Yu,Zhou, Wen-Yan,Song, Xiao-Ming,Jia, Ai-Quan,Shi, Hua-Tian,Zhang, Qian-Feng

, p. 1551 - 1555 (2021/02/06)

Self-assembly of cis-[RuCl2(dmso)4], NaVO3, Na2MoO4 and NaH2PO4 in a molar ratio of 1?:?3?:?6?:?1 in HOAc-NaOAc buffer (pH = 4-5) in the presence of CsCl gave a ruthenium(ii)-supported phosphovanadomolybdate [RuII(dmso)3PMoVI6VV3O32]6- (1). While a similar reaction with the reactants in a molar ratio of 1?:?6?:?12?:?2 afforded a ruthenium substituted "sandwich"type polyoxometalate [RuII(PMoVI6VV3O32)2]14- (2). Clusters 1 and 2 were well characterized by single-crystal X-ray diffraction. Their use as heterogeneous catalysts for oxidation of alcohols in the presence of molecular oxygen was also investigated.

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