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111-64-8

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111-64-8 Usage

Chemical Properties

clear liquid

Uses

Different sources of media describe the Uses of 111-64-8 differently. You can refer to the following data:
1. Octanoyl chloride is used to produce adhesives. It is used as an acylating agent for a variety of compounds such as sugars (e.g. Sucrose, aromatic compounds (e.g. Anisole and monoglycerides.
2. Applications of octanoyl chloride include:Synthesis of (R)-2-propyloctanoic acid, a therapeutic agent for Alzheimer′s disease.Synthesis of a variety of N-n-octyl-D-gluconamide based organogels.Building 2-heptylbenzo[d]thiazole moiety to synthesize conjugated copolymer with fluorine, as cathode interlayer in inverted polymer solar cells (PSCs).Octanoyl chloride is one of the essential precursors in the total synthesis of (?)-mandelalide L, a marine macrolide that display significant cytotoxicity against human cancer cell lines.

Preparation

Diphosgene (108.8 g) was added to a mixture of octanoic acid (144.2 g) and DMF (1.5 L) at 70 C°. The mixture was left to stand for 1 h, and then nitrogen was bubbled through it for 30 min at 100 C° to give 96.9% of octanoyl chloride (purity 99.99%). Benzoyl chloride and terephthaloyl chloride were similarly prepared.

General Description

Clear colorless to straw-colored liquid with a pungent odor.

Air & Water Reactions

Reacts vigorously with water to form HCl and caprylic acid. Insoluble in water.

Reactivity Profile

Octanoyl chloride is incompatible with bases (including amines), water, alcohols, and with oxidizing agents . May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Fire Hazard

Octanoyl chloride is combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 111-64-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 111-64:
(5*1)+(4*1)+(3*1)+(2*6)+(1*4)=28
28 % 10 = 8
So 111-64-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H17Cl/c1-2-3-4-5-6-7-8-9/h2-8H2,1H3

111-64-8 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L03526)  Octanoyl chloride, 99%   

  • 111-64-8

  • 100ml

  • 149.0CNY

  • Detail
  • Alfa Aesar

  • (L03526)  Octanoyl chloride, 99%   

  • 111-64-8

  • 500ml

  • 458.0CNY

  • Detail
  • Aldrich

  • (O4733)  Octanoylchloride  99%

  • 111-64-8

  • O4733-5ML

  • 271.44CNY

  • Detail
  • Aldrich

  • (O4733)  Octanoylchloride  99%

  • 111-64-8

  • O4733-100ML

  • 348.66CNY

  • Detail
  • Aldrich

  • (O4733)  Octanoylchloride  99%

  • 111-64-8

  • O4733-500ML

  • 1,091.61CNY

  • Detail

111-64-8SDS

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 Octanoyl chloride

1.2 Other means of identification

Product number -
Other names caprylic chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:111-64-8 SDS

111-64-8Synthetic route

Octanoic acid
124-07-2

Octanoic acid

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Conditions
ConditionsYield
With thionyl chloride for 10h; Reflux;95.6%
With phosgene; propionyl chloride at 50℃; for 12h; Reagent/catalyst; Temperature;93.2%
With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃; Substitution;92%
1,1-dichloroethyl ethyl ether
50966-31-9

1,1-dichloroethyl ethyl ether

Octanoic acid
124-07-2

Octanoic acid

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

caprylic hydrazide
6304-39-8

caprylic hydrazide

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Conditions
ConditionsYield
With thionyl chloride In chloroform Heating;
oxalyl dichloride
79-37-8

oxalyl dichloride

n-caprylic acid

n-caprylic acid

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

oxalyl dichloride
79-37-8

oxalyl dichloride

Octanoic acid
124-07-2

Octanoic acid

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Conditions
ConditionsYield
With N,N-dimethyl-formamide In dichloromethane for 3h; Heating;
In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 2.33333h; Inert atmosphere;
In dichloromethane at 20℃; for 3h; Inert atmosphere;
C3Cl2(C3H7)2
69151-13-9

C3Cl2(C3H7)2

Octanoic acid
124-07-2

Octanoic acid

A

2,3-diisopropylcyclopropenone
877675-72-4

2,3-diisopropylcyclopropenone

B

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;A 70.7 mg
B n/a
sodium caprylate
1984-06-1

sodium caprylate

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Conditions
ConditionsYield
With thionyl chloride at 50℃; for 1.5h;
thiophene
188290-36-0

thiophene

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

1-(thiophen-2-yl)octan-1-one
30711-41-2

1-(thiophen-2-yl)octan-1-one

Conditions
ConditionsYield
With aluminium trichloride In benzene at 0 - 20℃; Acylation;100%
With tin(IV) chloride; benzene
With carbon disulfide; aluminium trichloride
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Octanal
124-13-0

Octanal

Conditions
ConditionsYield
With methanesulfonic acid; tributylphosphine; copper; zinc In acetonitrile for 1h; Product distribution; Ambient temperature; reactions of other acid chlorides; solvent-effect; effect of var. metals;100%
With tri-n-butyl-tin hydride In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;96%
With pumice stone; platinum at 195℃; under 80 - 90 Torr; Hydrogenation;
2-ethoxycarbonyethylzinc iodide
104089-16-9

2-ethoxycarbonyethylzinc iodide

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

4-Oxoundecansaeure-ethylester
22769-72-8

4-Oxoundecansaeure-ethylester

Conditions
ConditionsYield
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide; benzene at 60℃; for 0.5h; various co-solvents;100%
tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl acetamide; benzene at 60℃; for 0.5h;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

(2R)-bornane-10,2-sultam
94594-90-8

(2R)-bornane-10,2-sultam

N-octanoyl-(1S)-(-)-10,2-camphorsultam
141341-55-1

N-octanoyl-(1S)-(-)-10,2-camphorsultam

Conditions
ConditionsYield
Stage #1: (2R)-bornane-10,2-sultam With sodium hydride In toluene; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: n-octanoic acid chloride In toluene; mineral oil at 0 - 20℃; for 27h; Inert atmosphere;
100%
With dmap; triethylamine In tetrahydrofuran at -5 - 0℃; for 0.5h; Large scale;100%
With dmap; triethylamine In tetrahydrofuran at 0℃; for 1h; Acylation;98.6%
With sodium hydride 1) toluene, rt, 2 h, 2) toluene, rt, 2 h; Yield given. Multistep reaction;
With dmap; triethylamine In tert-butyl methyl ether at 20℃; for 1h;99.7 %Chromat.
2-Mercaptopyridine
2637-34-5

2-Mercaptopyridine

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

S-(pyridin-2-yl)octanethioate
89397-99-9

S-(pyridin-2-yl)octanethioate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; Cooling with ice bath;100%
With TEA In dichloromethane at 0℃;
Stage #1: 2-Sulfanylpyridine With triethylamine In dichloromethane at 0℃;
Stage #2: n-octanoic acid chloride at 20℃; for 1.5h;
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

7,11,15,28-tetrakis(4-aminophenyl)-1,21,23,25-tetraundecyl 2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxin

7,11,15,28-tetrakis(4-aminophenyl)-1,21,23,25-tetraundecyl 2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxin

7,11,15,28-tetrakis(4-n-octanoylamidophenyl)-1,21,23,25-tetraundecyl 2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxin

7,11,15,28-tetrakis(4-n-octanoylamidophenyl)-1,21,23,25-tetraundecyl 2,20:3,19-dimetheno-1H,21H,23H,25H-bis[1,3]dioxocino[5,4-i:5',4'-i']benzo[1,2-d:5,4-d']bis[1,3]benzodioxin

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate for 2h; Ambient temperature;100%
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

n-octanophenone
1674-37-9

n-octanophenone

Conditions
ConditionsYield
With palladium diacetate; sodium carbonate In acetone at 20℃; for 0.0833333h;100%
With sodium carbonate; palladium diacetate In acetone at 20℃; for 0.0833333h; Suzuki reaction;98%
2-octylthiophene
880-36-4

2-octylthiophene

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

2-octanoyl-5-octylthiophene
241806-30-4

2-octanoyl-5-octylthiophene

Conditions
ConditionsYield
With aluminium trichloride In benzene at 0 - 20℃; Acylation;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

(2-amino-4-methyl-benzyl)-phosphonic acid diethyl ester
503856-46-0

(2-amino-4-methyl-benzyl)-phosphonic acid diethyl ester

(4-methyl-2-octanoylamino-benzyl)-phosphonic acid diethyl ester
303040-42-8

(4-methyl-2-octanoylamino-benzyl)-phosphonic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

(6-amino-benzo[1,3]dioxol-5-ylmethyl)-phosphonic acid diethyl ester
503856-53-9

(6-amino-benzo[1,3]dioxol-5-ylmethyl)-phosphonic acid diethyl ester

(6-octanoylamino-benzo[1,3]dioxol-5-ylmethyl)-phosphonic acid diethyl ester
303040-44-0

(6-octanoylamino-benzo[1,3]dioxol-5-ylmethyl)-phosphonic acid diethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

(R)-2-Amino-2-(3-methoxy-phenyl)-ethanol; hydrochloride

(R)-2-Amino-2-(3-methoxy-phenyl)-ethanol; hydrochloride

N-[(1R)-2-hydroxy-1-(3-methoxyphenyl)ethyl]octanamide
532987-05-6

N-[(1R)-2-hydroxy-1-(3-methoxyphenyl)ethyl]octanamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane at 0℃; for 2h;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

(1S,2S)-1-amino-1-(3-methoxyphenyl)propan-2-ol hydrochloride

(1S,2S)-1-amino-1-(3-methoxyphenyl)propan-2-ol hydrochloride

N-[(1S,2S)-2-hydroxy-1-(3-methoxyphenyl)propyl]octanamide
526217-28-7

N-[(1S,2S)-2-hydroxy-1-(3-methoxyphenyl)propyl]octanamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; 1,4-dioxane at 0℃; for 4h;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

Propargylamine
2450-71-7

Propargylamine

N-(prop-2-yn-1-yl)octanamide
422284-34-2

N-(prop-2-yn-1-yl)octanamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2h;99%
With pyridine In diethyl ether68%
With dmap; triethylamine In dichloromethane at 0 - 20℃;66%
With triethylamine In dichloromethane at 0℃; for 1h;
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

4-hydroxy-2H-1,4-benzoxazin-3-one
771-26-6

4-hydroxy-2H-1,4-benzoxazin-3-one

4-octanoyloxy-(2H)-1,4-benzoxazin-3(4H)-one

4-octanoyloxy-(2H)-1,4-benzoxazin-3(4H)-one

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;100%
With pyridine for 12h;99%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

4-hydroxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one
69884-06-6

4-hydroxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

4-octanoyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

4-octanoyloxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one

Conditions
ConditionsYield
With pyridine at 20℃; for 12h;100%
(1S)-(-)-2,10-camphorsultam
94594-90-8

(1S)-(-)-2,10-camphorsultam

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-octanoyl-(1S)-(-)-2,10-camphorsultam

N-octanoyl-(1S)-(-)-2,10-camphorsultam

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 0℃; for 1h;100%
methylamine hydrochloride
593-51-1

methylamine hydrochloride

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-methyloctanoylamide
1119-57-9

N-methyloctanoylamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 5℃; for 2.5h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;100%
With triethylamine In dichloromethane at 0 - 20℃; for 3h;100%
homoalylic alcohol
627-27-0

homoalylic alcohol

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

but-3-enyl octanoate
1070316-20-9

but-3-enyl octanoate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

1-(1H-pyrrol-3-yl)octan-1-one
114900-83-3

1-(1H-pyrrol-3-yl)octan-1-one

1-(5-octanoyl-1H-pyrrol-3-yl)octan-1-one
1314253-27-4

1-(5-octanoyl-1H-pyrrol-3-yl)octan-1-one

Conditions
ConditionsYield
Stage #1: n-octanoic acid chloride With aluminum (III) chloride In 1,2-dichloro-ethane at 25℃; for 0.166667h; Inert atmosphere;
Stage #2: 1-(1H-pyrrol-3-yl)octan-1-one In 1,2-dichloro-ethane at 25℃; for 2h; Inert atmosphere; regioselective reaction;
100%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-benzyl-N-methyloctanamide
1315320-39-8

N-benzyl-N-methyloctanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;100%
C41H52O13

C41H52O13

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

C49H66O14

C49H66O14

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 20h;100%
O-methyl-N-(4-nitrobenzyl)hydroxylamine
54615-17-7

O-methyl-N-(4-nitrobenzyl)hydroxylamine

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-methoxy-N-(4-nitrobenzyl)octanamide

N-methoxy-N-(4-nitrobenzyl)octanamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;100%
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;100%
2,3:4,5-di-O-isopropylidene-1-methoxymethyl-d-galactitol-6-yl 4,6-O-benzylidene-3-O-benzyl-β-D-mannopyranoside

2,3:4,5-di-O-isopropylidene-1-methoxymethyl-d-galactitol-6-yl 4,6-O-benzylidene-3-O-benzyl-β-D-mannopyranoside

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

2,3:4,5-di-O-isopropylidene-1-methoxymethyl-D-galactitol-6-yl 4,6-O-benzylidene-3-O-benzyl-2-O-octanoyl-β-D-mannopyranoside

2,3:4,5-di-O-isopropylidene-1-methoxymethyl-D-galactitol-6-yl 4,6-O-benzylidene-3-O-benzyl-2-O-octanoyl-β-D-mannopyranoside

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 20h;100%
4-bromo-n-butan-1-amine hydrobromide
24566-81-2

4-bromo-n-butan-1-amine hydrobromide

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-(4-bromobutyl)octanamide
1619235-29-8

N-(4-bromobutyl)octanamide

Conditions
ConditionsYield
Stage #1: 4-bromo-n-butan-1-amine hydrobromide With sodium carbonate In dichloromethane; water at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: n-octanoic acid chloride In dichloromethane; water at 0 - 20℃; for 4h; Inert atmosphere;
100%
6-bromo-1-aminohexane hydrobromide
14502-76-2

6-bromo-1-aminohexane hydrobromide

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-(6-bromohexyl)octanamide
1619235-33-4

N-(6-bromohexyl)octanamide

Conditions
ConditionsYield
Stage #1: 6-bromo-1-aminohexane hydrobromide With sodium carbonate In dichloromethane; water at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: n-octanoic acid chloride In dichloromethane; water at 0 - 20℃; for 4h; Inert atmosphere;
100%
3-bromopropylamine hydrochloride
5003-71-4

3-bromopropylamine hydrochloride

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-(3-bromopropyl)octanamide
1152510-70-7

N-(3-bromopropyl)octanamide

Conditions
ConditionsYield
Stage #1: 3-bromopropylamine hydrochloride With sodium carbonate In dichloromethane; water at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: n-octanoic acid chloride In dichloromethane; water at 0 - 20℃; for 4h; Inert atmosphere;
100%
4-((methoxyamino)methyl)benzonitrile
543731-34-6

4-((methoxyamino)methyl)benzonitrile

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

N-(4-cyanobenzyl)-N-methoxyoctanamide

N-(4-cyanobenzyl)-N-methoxyoctanamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;100%
1,2:3,4-di-O-isopropylidene-D-arabinitol-5-yl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

1,2:3,4-di-O-isopropylidene-D-arabinitol-5-yl 3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranoside

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

1,2:3,4-di-O-isopropylidene-D-arabinitol-5-yl 3-O-benzyl-4,6-O-benzylidene-2-O-octanoyl-β-D-mannopyranoside

1,2:3,4-di-O-isopropylidene-D-arabinitol-5-yl 3-O-benzyl-4,6-O-benzylidene-2-O-octanoyl-β-D-mannopyranoside

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 20℃; for 7h;100%
16-hydroxyhexadecanoic acid
506-13-8

16-hydroxyhexadecanoic acid

n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

16-(octanoyloxy)hexadecanoic acid

16-(octanoyloxy)hexadecanoic acid

Conditions
ConditionsYield
In chloroform for 4h; Reflux;100%
In chloroform at 70℃; for 4h;100%
n-octanoic acid chloride
111-64-8

n-octanoic acid chloride

[3-(3-hydroxypropylamino)propyl]carbamic acid tert-butyl ester
845821-10-5

[3-(3-hydroxypropylamino)propyl]carbamic acid tert-butyl ester

tert-butyl (3-(N-(3-hydroxypropyl)octanamido)propyl)carbamate

tert-butyl (3-(N-(3-hydroxypropyl)octanamido)propyl)carbamate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 5 - 20℃; for 3.58333h;100%

111-64-8Relevant articles and documents

Chili pepper fruits: Presumed precursors of fatty acids characteristic for capsaicinoids

Thiele, Roland,Mueller-Seitz, Erika,Petz, Michael

, p. 4219 - 4224 (2008)

Capsaicin is a molecule unique to fruits from the genus Capsicum. It is responsible for the pungent sensation and displays valuable pharmacological properties. Despite the fruits' economic importance and decades of research, the regulation of the content of capsaicinoids in individual fruits is not completely elucidated, and no agricultural cultivation of chili of defined pungency is assured. Precursor candidates of the fatty acid moiety of the capsaicinoids, especially for the unique 8-methyl-trans-6-nonenoic acid, were examined. Thioesters, acyl-ACP and acyl-CoA, were isolated from the placenta of Capsicum fruits by means of DEAE-Sepharose chromatography, selectively converted to the corresponding N-butylamides, and analyzed by GC-MS. Fatty acid moieties characteristic for capsaicinoids were identified. In two different varieties (Capsicum chinense var. Habanero orange and Capsicum annuum var. Jalapeno) it was shown that the fatty acid pattern corresponds to the distribution pattern of the capsaicinoids formed up to this time. The acyl-thioester fractions contained already the 8-methyl-trans-6-nonenoic acid.

Synthesis, Physicochemical Properties, and Thermo-Oxidative Stability of Diesters of 5,7-Dimethyl-1,3-Adamantanediol and 5,7-Dimethyl-1,3-bis(Hydroxymethyl)adamantane

Ivleva,Baimuratov,Demidov,Lukashenko,Malinovskaya, Yu. A.,Klimochkin, Yu. N.,Tyshchenko,Kulikova,Pozdnyakov,Ovchinnikov,Rudyak

, p. 687 - 693 (2018)

A series of diesters on the basis of 5,7-dimethyl-1,3-adamantanediol and 5,7-dimethyl-1,3- bis(hydroxymethyl)adamantane and C3–C10 aliphatic acids have been synthesized and their physicochemical and thermo-oxidative properties have been studied. The properties of the esters obtained have been compared to those of trimethylolpropane and neopentyl glycol esters.

Synthesis, modelling and kinetic assays of potent inhibitors of purple acid phosphatase

Mohd-Pahmi, Siti Hajar,Hussein, Waleed M.,Schenk, Gerhard,McGeary, Ross P.

, p. 3092 - 3094 (2011)

Purple acid phosphatases (PAPs) are binuclear metallohydrolases that have been isolated from various mammals, plants, fungi and bacteria. In mammals PAP activity is associated with bone resorption and can lead to bone metabolic disorders such as osteoporosis; thus human PAP is an attractive target to develop anti-osteoporotic drugs. Based on a previous lead compound and rational drug design, acyl derivatives of α-aminonaphthylmethylphosphonic acid were synthesised and tested as PAP inhibitors. Kinetic analysis showed that they are good PAP inhibitors whose potencies improve with increasing acyl chain length. Maximum potency is reached when the number of carbons in the acyl chain is between 12 and 14. The most potent inhibitor of red kidney bean PAP is the dodecyl-derivative with Kic = 5 μM, while the most potent pig PAP inhibitor is the tetradecyl-derivative with Kic = 8 μM, the most potent inhibitor of a mammalian PAP yet reported.

Potent anticonvulsant urea derivatives of constitutional isomers of valproic acid

Shimshoni, Jakob Avi,Bialer, Meir,Wlodarczyk, Bogdan,Finnell, Richard H.,Yagen, Boris

, p. 6419 - 6427 (2007)

Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential candidates to become new, potent AEDs.

Assessment of intermolecular N-H.F and N-H.Cl hydrogen bonding in stabilising hetero- and homodimers in solution

Liu, Yan-Hua,Xu, Xiao-Na,Zhao, Xin,Li, Zhan-Ting

, p. 310 - 320 (2015)

This paper describes the first assessment of intermolecular weak N-H.F and N-H.Cl hydrogen bonding in stabilising hetero- and homodimers in solution. Aromatic amide and urea monomers have been designed and synthesised. The association constants of the heterodimers formed by two complementary monomers and the homodimers formed by self-complementary monomers have been determined by using 1H titration and dilution experiments. The results show that both N-H.F and N-H.Cl hydrogen bonds are able to stabilise the corresponding dimers to a measurable extent, even though the stability of the dimers is generally low.

Copper-Catalyzed Bromination of C(sp3)?H Bonds Distal to Functional Groups

Liu, Tao,Myers, Michael C.,Yu, Jin-Quan

, p. 306 - 309 (2017)

Selective bromination of γ-methylene C(sp3)?H bonds of aliphatic amides and δ-methylene C(sp3)?H bonds of nosyl-protected alkyl amines are developed using NBS as the brominating reagent and catalytic amount of CuII/phenanthroline complexes as the catalyst. Aryl and benzylic C?H bonds at other locations remain intact during this directed radical abstraction reaction.

Pyrene-derived novel one- and two-component organogelators

Babu,Sangeetha,Vijaykumar,Maitra, Uday,Rissanen, Kari,Raju

, p. 1922 - 1932 (2003)

A new class of alkyl-chainappended pyrene derivatives 4 - 14 were synthesized and evaluated for their gelation abilities. Depending on the nature of the linking group, these compounds gelated a number of organic solvents, either in the presence or in the absence of the acceptor molecule 2,4,7-trinitrofluorenone (TNF). Compounds with ester, ether, or alkyl linkages gelated a number of hydroxylic and hydrocarbon solvents by means of a charge-transfer interaction with TNF, while compounds with amide, urethane and urea linkers formed gels on their own in a variety of solvents by means of π-π stacking and hydrogen-bonding interactions. The X-ray crystal structure of urethane (S)-12 showed hydrogen-bonding and stacking features, as suggested by the model. The gels obtained were investigated by spectroscopic and electron microscopic techniques which provided structural insights.

3-Aminobenzenesulfonamides incorporating acylthiourea moieties selectively inhibit the tumor-associated carbonic anhydrase isoform IX over the off-target isoforms I, II and IV

Fattah, Tanzeela Abdul,Bua, Silvia,Saeed, Aamer,Shabir, Ghulam,Supuran, Claudiu T.

, p. 123 - 128 (2019)

We describe the synthesis of a series of novel 1-aroyl/acyl-3-(3-aminosulfonylphenyl) thioureas (4a–k) acting as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. Reaction of alkyl/aryl isothiocyanates with 3-aminobenzenesulfonamide afforded a series of the title compounds incorporating a variety of short as well as highly lipophilic long tails. The newly synthesized sulfonamides were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IV, and IX). Several compounds showed interesting inhibitory activity. The tumor-associated hCA IX was the most sensitive isoform to inhibition with these compounds, with KIs in the range of 21.5–44.0 nM and selectivity ratios over the major cytosolic isoform hCA II in the range of 3.35–37.3. The sulfonamides incorporating the phenylacetylthioureido and pentadecanoylthioureido moieties were the most hCA IX-selective inhibitors detected in this work, making them of interest for further investigations.

Structure, supramolecular organization and phase behavior of N-acyl-β-alanines: Structural homologues of mammalian brain constituents N-acylglycine and N-acyl-GABA

Sivaramakrishna,Swamy, Musti J.

, p. 1 - 10 (2016)

N-Acyl-β-alanines (NABAs) are structural homologues of N-acylglycines (NAGs) and N-acyl-γ-aminobutyric acids (NAGABAs), and achiral isomers of N-acylalanines, which are all present in mammalian brain and other tissues and modulate activity of biological receptors with various functions. In the present study, we synthesized and characterized a homologous series of NABAs bearing saturated acyl chains (n = 8-20) and investigated their supramolecular organization and thermotropic phase behavior. In differential scanning calorimetric (DSC) studies, most of the NABAs gave one or two minor transitions before the main chain-melting phase transition in the dry state as well as upon hydration with water, but gave only a single transition when hydrated with buffer (pH 7.6). Transition enthalpies (ΔHt) and entropies (ΔSt), obtained from the DSC studies showed linear dependence on the chain length in the dry state and upon hydration with buffer, whereas odd-even alteration was observed when hydrated with water. The crystal structures of N-lauroyl-β-alanine (NLBA) and N-myristoyl-β-alanine (NMBA) were solved in monoclinic system in the P21/c space group. Both NLBA and NMBA were packed in tilted bilayers with head-to-head (and tail-to-tail) arrangement with tilt angles of 33.28° and 34.42°, respectively. Strong hydrogen bonding interactions between [sbnd]COOH groups of the molecules from opposite leaflets as well as N[sbnd]H?O hydrogen bonds between the amide groups from adjacent molecules in the same leaflet as well as dispersion interactions between the acyl chains stabilize the bilayer structure. The d-spacings calculated from powder X-ray diffraction studies showed odd-even alteration with odd-chain length compounds exhibiting higher values as compared to the even-chain length ones and the tilt angles calculated from the PXRD data are higher for the even chain NABAs. These observations are relevant to developing structure-activity relationships for these amphiphiles and understand how NABAs differ from their homologues and isomers, namely NAGs, NAGABAs, and N-acylalanines.

Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine

Li, Ying-Hong,Li, Yi,Yang, Peng,Kong, Wei-Jia,You, Xue-Fu,Ren, Gang,Deng, Hong-Bin,Wang, Yue-Ming,Wang, Yan-Xiang,Jiang, Jian-Dong,Song, Dan-Qing

, p. 6422 - 6428 (2010)

In order to enhance oral bioavailability of berberine (BBR) for its cholesterol-lowering efficacy in vivo, a series of ester or ether prodrugs of berberrubine (M1), which is an active metabolite of BBR after first-pass metabolism, were designed, semi-synthesized, and evaluated. Among these M1 prodrugs, compound 5g possessing palmitate at the 9-position showed a moderate Log P value and esterase hydrolysis rate for releasing M1 in blood. Its cholesterol-lowering efficacy in vivo was evaluated in hyperlipidemic SD rats. Compound 5g (100 mg/kg/d) reduced blood CHO and LDL-c by 35.8% and 45.5%, respectively, similar to that by BBR. It also exhibited a good safety in rats with no side-effect on liver and kidney function. Therefore, the design of M1 prodrug appears to be an effective strategy to improve pharmacokinetic feature of BBR for its lipid-lowering efficacy in vivo.

Premating behavior of Bombus confusus males and analysis of their labial gland secretion

Hovorka, Oldrich,Urbanova, Klara,Valterova, Irena

, p. 183 - 193 (1998)

Premating behavior in the bumblebee Bombus confusus was studied. Visual searching for females is not the only premating strategy of this species, as was believed earlier. Males of B. confusus have a normally developed labial gland and its secretion is used to mark a perch from which they visually search for females. The labial gland secretion contains geranylcitronellol and (Z)-9-octadecenyl acetate as the main components.

Lipophilic quinolone derivatives: Synthesis and in vitro antibacterial evaluation

Sadowski, Elodie,Bercot, Beatrice,Chauffour, Aurélie,Gomez, Catherine,Varon, Emmanuelle,Mainardis, Mary,Sougakoff, Wladimir,Mayer, Claudine,Sachon, Emmanuelle,Anquetin, Guillaume,Aubry, Alexandra

, (2021/11/22)

This paper reports on the design of a series of 10 novel lipophilic piperazinyl derivatives of the 1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, their synthesis, their characterisation by 1H, 13C and 19F NMR, IR spectroscopy and HRMS, as well as their biological activity against bacteria of medical interest. Among these derivatives, 2 were as potent as the parent quinolone against Neisseria gonorrhoeae whereas all the compounds displayed lower activity than the parent quinolone against other bacteria of medical interest. Our results showing that the increased lipophilicity was deleterious for antibacterial activity may help to design new quinolone derivatives in the future, especially lipophilic quinolones which have been poorly investigated previously.

Carbon dots as photocatalysts for organic synthesis: Metal-free methylene-oxygen-bond photocleavage

Cailotto, Simone,Negrato, Matteo,Daniele, Salvatore,Luque, Rafael,Selva, Maurizio,Amadio, Emanuele,Perosa, Alvise

supporting information, p. 1145 - 1149 (2020/03/11)

We report for the first time that irradiation of four different citric acid-derived carbon dots (CDs), in the absence of any other redox mediators, promotes an organic reaction. In this proof-of-concept study methylene-oxygen bond reductive photocleavage in N-methyl-4-picolinium esters is demonstrated. Cyclic voltammetry and UV-Vis spectra of the CDs and of the esters indicate that photocleavage reactivity correlates with the redox properties and the relative energies expressed in the Fermi scale. A photo-fragmentation mechanism is proposed. This study offers a new possibility to employ inexpensive and readily available CDs to promote photo-organic reactions.

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