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Palmitoyl chloride is a clear colorless to light yellow liquid with a pungent odor. It has a freezing point of 11-12°C and is known to irritate skin, eyes, and mucous membranes. It may be toxic by ingestion, inhalation, and skin absorption.

112-67-4

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112-67-4 Usage

Uses

Used in Biotechnology Industry:
Palmitoyl chloride is used as a polymeric carrier for plasmid DNA (pDNA) delivery to 293T cells. This application is significant in the field of biotechnology, as it aids in the efficient transfer of genetic material for various research and therapeutic purposes.
Used in Pharmaceutical Industry:
As a polymeric carrier, palmitoyl chloride is utilized for plasmid DNA delivery to 293T cells. This is important in the pharmaceutical industry for the development of new drugs and therapies, as it enables the efficient transfer of genetic material for research and clinical applications.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 6101, 1989 DOI: 10.1021/jo00287a023

Air & Water Reactions

Decomposes rather slowly in water to form hydrochloric acid and palmitic acid, a fatty acid that is not soluble in water.

Reactivity Profile

HEXADECANOYL CHLORIDE is incompatible with bases (including amines), with strong oxidizing agents, and with alcohols. 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].

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 112-67-4 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 2 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 112-67:
(5*1)+(4*1)+(3*2)+(2*6)+(1*7)=34
34 % 10 = 4
So 112-67-4 is a valid CAS Registry Number.

112-67-4 Well-known Company Product Price

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  • Alfa Aesar

  • (A13812)  Palmitoyl chloride, 98%   

  • 112-67-4

  • 100g

  • 444.0CNY

  • Detail
  • Alfa Aesar

  • (A13812)  Palmitoyl chloride, 98%   

  • 112-67-4

  • 500g

  • 1590.0CNY

  • Detail
  • Aldrich

  • (P78)  Palmitoylchloride  98%

  • 112-67-4

  • P78-5ML

  • 372.06CNY

  • Detail
  • Aldrich

  • (P78)  Palmitoylchloride  98%

  • 112-67-4

  • P78-100ML

  • 1,242.54CNY

  • Detail
  • Aldrich

  • (P78)  Palmitoylchloride  98%

  • 112-67-4

  • P78-500ML

  • 4,347.72CNY

  • Detail
  • Aldrich

  • (P78)  Palmitoylchloride  98%

  • 112-67-4

  • P78-1L

  • 7,452.90CNY

  • Detail

112-67-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Palmitoyl chloride

1.2 Other means of identification

Product number -
Other names HEXADECANOYL CHLORIDE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Pigments,Solids separation agents
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:112-67-4 SDS

112-67-4Synthetic route

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Conditions
ConditionsYield
With thionyl chloride Reflux;100%
With thionyl chloride In N,N-dimethyl-formamide for 3h; Reflux;97%
With thionyl chloride; N,N-dimethyl-formamide for 3h; Reflux;97%
hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

A

methylene chloride
74-87-3

methylene chloride

B

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

C

WOCl4

WOCl4

Conditions
ConditionsYield
With tungsten(VI) chloride In benzene at 20℃; for 90h; Product distribution;
sodium palmitate
408-35-5

sodium palmitate

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Conditions
ConditionsYield
With thionyl chloride at 20℃;
oxalyl dichloride
79-37-8

oxalyl dichloride

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Conditions
ConditionsYield
With N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h;
In dichloromethane for 12h; Inert atmosphere;
DL-3,4,5,6-Tetra-O-benzyl-3,5/4,6-tetrahydroxycyclohex-1-ene-1-methanol
130277-53-1, 130324-58-2

DL-3,4,5,6-Tetra-O-benzyl-3,5/4,6-tetrahydroxycyclohex-1-ene-1-methanol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

methyl Hexadecanoate
130277-54-2, 130324-59-3

methyl Hexadecanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane for 2h; Ambient temperature;100%
9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-2-{[(4-methoxyphenyl)diphenylmethyl]amino}-6,9-dihydro-1H-purin-6-one
88110-81-0

9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-2-{[(4-methoxyphenyl)diphenylmethyl]amino}-6,9-dihydro-1H-purin-6-one

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Hexadecanoic acid 3-hexadecanoyloxy-2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-propyl ester
88110-83-2

Hexadecanoic acid 3-hexadecanoyloxy-2-(2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-propyl ester

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane for 20h; Ambient temperature;100%
1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxymethyl-3-propanol
190505-04-5

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxymethyl-3-propanol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Hexadecanoic acid 2-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester
190505-07-8

Hexadecanoic acid 2-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester

Conditions
ConditionsYield
With dmap In pyridine for 2h; Heating;100%
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

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

7,11,15,28-tetrakis(4-palmitoylamidophenyl)-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-palmitoylamidophenyl)-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%
N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
177898-40-7

N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Hexadecanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide
218924-27-7

Hexadecanoic acid octyl-((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide

Conditions
ConditionsYield
In pyridine for 1h; Ambient temperature;100%
pyrrolidine
123-75-1

pyrrolidine

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

1-(pyrrolidin-1-yl)hexadecan-1-one
70974-48-0

1-(pyrrolidin-1-yl)hexadecan-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With pyridine at 20℃; for 3h; Acylation;4.5 g
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;
(+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-3-O-(4-methoxybenzyl)-sn-glycerol
345287-87-8

(+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-3-O-(4-methoxybenzyl)-sn-glycerol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

(+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-2-O-hexadecanoyl-3-O-(4-methoxybenzyl)-sn-glycerol
345287-88-9

(+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-2-O-hexadecanoyl-3-O-(4-methoxybenzyl)-sn-glycerol

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃;100%
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere;100%
With pyridine; dmap In dichloromethane90%
Stage #1: (+)-1-O-[12-N-(benzyloxycarbonyl)aminododecanoyl]-3-O-(4-methoxybenzyl)-sn-glycerol With pyridine; dmap In dichloromethane at 0℃; for 0.5h;
Stage #2: n-hexadecanoyl chloride In dichloromethane at 20℃; Further stages.;
70%
1-O-hexanoyl-3-pmethoxybenzyl-sn-glycerol

1-O-hexanoyl-3-pmethoxybenzyl-sn-glycerol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

1-O-hexanoyl-2-O-palmitoyl-3-O-p-methoxybenzyl-sn-glycerol

1-O-hexanoyl-2-O-palmitoyl-3-O-p-methoxybenzyl-sn-glycerol

Conditions
ConditionsYield
With dmap In pyridine at 20℃; for 20h;100%
3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene

3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

3-palmitoylnortropine

3-palmitoylnortropine

Conditions
ConditionsYield
Stage #1: 3-[4-(3α-hydroxynortropanylazo)phenoxy]propyloxymethylpolystyrene; n-hexadecanoyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 12h;
Stage #2: With trifluoroacetic acid In dichloromethane at 0℃; Further stages.;
100%
3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene

3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

4-palmitoyloxypiperidine

4-palmitoyloxypiperidine

Conditions
ConditionsYield
Stage #1: 3-[3-(4-hydroxypiperidinylazo)phenoxy]propyloxymethylpolystyrene; n-hexadecanoyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 12h;
Stage #2: With trifluoroacetic acid In dichloromethane at 0℃; Further stages.;
100%
diethylaminopropylamine
104-78-9

diethylaminopropylamine

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N,N-diethyl-N'-hexadecanoyl-1,3-propanediamine

N,N-diethyl-N'-hexadecanoyl-1,3-propanediamine

Conditions
ConditionsYield
In methanol; sodium hydroxide; dichloromethane; chloroform100%
2-(2-Aminoethoxy)ethanol
929-06-6

2-(2-Aminoethoxy)ethanol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N-(ω-hydroxyethoxyethyl)hexadecanamide
20138-27-6

N-(ω-hydroxyethoxyethyl)hexadecanamide

Conditions
ConditionsYield
Stage #1: 2-(2-Aminoethoxy)ethanol With magnesium oxide In tetrahydrofuran; water at 5℃; for 0.5h;
Stage #2: n-hexadecanoyl chloride In tetrahydrofuran; water at 5 - 10℃; for 2h;
100%
With triethylamine In dichloromethane at 0℃; for 4h;92%
With magnesium oxide In tetrahydrofuran; water
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

palmitic acid N-succinimide ester
14464-31-4

palmitic acid N-succinimide ester

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 8h; Cooling with ice;100%
With triethylamine In chloroform at 20℃; for 8h; Cooling with ice;100%
2-amino-5,10,15,20-tetraphenylporphyrin
82945-59-3

2-amino-5,10,15,20-tetraphenylporphyrin

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

C60H61N5O

C60H61N5O

Conditions
ConditionsYield
Stage #1: 2-amino-5,10,15,20-tetraphenylporphyrin With triethylamine In dichloromethane at 20℃; for 0.25h;
Stage #2: n-hexadecanoyl chloride In dichloromethane at 20℃; for 3h;
100%
(3R)-3-hydroxytetradecanoic acid phenacyl ester
87357-65-1

(3R)-3-hydroxytetradecanoic acid phenacyl ester

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Hexadecanoic acid (R)-1-(2-oxo-2-phenyl-ethoxycarbonylmethyl)-dodecyl ester
339316-64-2

Hexadecanoic acid (R)-1-(2-oxo-2-phenyl-ethoxycarbonylmethyl)-dodecyl ester

Conditions
ConditionsYield
With dmap In pyridine; dichloromethane Ambient temperature;99.4%
methylamine
74-89-5

methylamine

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N-methylhexadecanamide
7388-58-1

N-methylhexadecanamide

Conditions
ConditionsYield
In dichloromethane; water at 20℃; for 12h;99%
In dichloromethane; water at 20℃; for 24h;92%
With water
n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

pentadecanyl isocyanate
39633-51-7

pentadecanyl isocyanate

Conditions
ConditionsYield
With sodium azide In para-xylene for 2h; Heating;99%
With sodium azide; benzene
With sodium azide In toluene for 5h; Reflux; Inert atmosphere;
thiazolidine-2-thione
134469-06-0

thiazolidine-2-thione

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one
74058-64-3

1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 50℃; for 0.5h;99%
With triethylamine In dichloromethane at 0 - 5℃; for 3h;75%
N-hydroxy-N-methylbenzenecarbothioamide
89861-45-0

N-hydroxy-N-methylbenzenecarbothioamide

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N-methyl-N-palmitoyloxythiobenzamide
89861-46-1

N-methyl-N-palmitoyloxythiobenzamide

Conditions
ConditionsYield
With pyridine In diethyl ether for 0.5h; Ambient temperature;99%
DL-(1,2,4/3,5,6)-2,5,6-Tri-O-benzyl-2,3,4,5,6-pentahydroxy-3,4-bis-O-(4-methoxybenzyl)cyclohexane-1-methanol, DL-(1,2,3,5/4,6)-2,3,6-Tri-O-benzyl-2,3,4,5,6-pentahydroxy-4,5-bis-O-(4-methoxybenzyl)cyclohexane-1-methanol
130277-63-3, 130324-67-3

DL-(1,2,4/3,5,6)-2,5,6-Tri-O-benzyl-2,3,4,5,6-pentahydroxy-3,4-bis-O-(4-methoxybenzyl)cyclohexane-1-methanol, DL-(1,2,3,5/4,6)-2,3,6-Tri-O-benzyl-2,3,4,5,6-pentahydroxy-4,5-bis-O-(4-methoxybenzyl)cyclohexane-1-methanol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

methyl Hexadecanoate, methyl Hexadecanoate
130277-66-6, 130324-68-4

methyl Hexadecanoate, methyl Hexadecanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 25℃; for 1h;99%
rac-1-O-hexadecyl-3-O-benzylglycerol
103475-80-5

rac-1-O-hexadecyl-3-O-benzylglycerol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Hexadecanoic acid 2-benzyloxy-1-hexadecyloxymethyl-ethyl ester
95895-49-1

Hexadecanoic acid 2-benzyloxy-1-hexadecyloxymethyl-ethyl ester

Conditions
ConditionsYield
With pyridine In benzene at 70℃;99%
RETINOL
68-26-8

RETINOL

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
In toluene at 35℃; for 1h;99%
With pyridine In 1,2-dichloro-ethane
6,7dihydroxy-3methyl-4-thiaheptanoic acid t-butyl ester
167768-03-8

6,7dihydroxy-3methyl-4-thiaheptanoic acid t-butyl ester

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

6,7-bis(palmitoyloxy)-3-methyl-4-thiaheptanoic acid t-butyl ester
167768-04-9

6,7-bis(palmitoyloxy)-3-methyl-4-thiaheptanoic acid t-butyl ester

Conditions
ConditionsYield
With dmap In dichloromethane for 1h; Ambient temperature;99%
With 2-(Dimethylamino)pyridine; sodium bicarbonate; triethylamine; citric acid In chloroform; water99%
(S)-2-(4-{[3-(3-Hexadecanoylamino-2-hydroxy-propylsulfanyl)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester
204583-04-0

(S)-2-(4-{[3-(3-Hexadecanoylamino-2-hydroxy-propylsulfanyl)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

(S)-2-(4-{[3-(3-Hexadecanoylamino-2-hexadecanoyloxy-propylsulfanyl)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester
204583-05-1

(S)-2-(4-{[3-(3-Hexadecanoylamino-2-hexadecanoyloxy-propylsulfanyl)-propionylamino]-methyl}-benzoylamino)-pentanedioic acid di-tert-butyl ester

Conditions
ConditionsYield
With dmap In dichloromethane for 0.5h; Ambient temperature;99%
methyl furan-2-ylacetate
4915-22-4

methyl furan-2-ylacetate

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

(5-hexadecanoylfuran-2-yl)acetic acid methyl ester
852152-07-9

(5-hexadecanoylfuran-2-yl)acetic acid methyl ester

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -5℃; for 1h;99%
With tin(IV) chloride In dichloromethane at -5℃; for 1h; Friedel-Crafts acylation;98%
With tin(IV) chloride In dichloromethane at -5℃; for 1h; Substitution; Friedel-Crafts reaction;
With tin(IV) chloride In dichloromethane at -5℃; Friedel-Crafts acylation;
3-O-Benzyl-1-O-octadecanoyl-sn-glycerin
4145-51-1, 6236-22-2, 116947-35-4, 988-76-1

3-O-Benzyl-1-O-octadecanoyl-sn-glycerin

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

3-O-benzyl-2-O-hexadecanoyl-1-O-octadecanoyl-sn-glycerol
282532-76-7

3-O-benzyl-2-O-hexadecanoyl-1-O-octadecanoyl-sn-glycerol

Conditions
ConditionsYield
With dmap In pyridine; dichloromethane at 0 - 20℃; Acylation;99%
(S)-3-Hydroxy-2-(2-tetradecanoylamino-acetylamino)-propionic acid benzyl ester
260785-43-1

(S)-3-Hydroxy-2-(2-tetradecanoylamino-acetylamino)-propionic acid benzyl ester

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

Hexadecanoic acid (S)-2-benzyloxycarbonyl-2-(2-tetradecanoylamino-acetylamino)-ethyl ester

Hexadecanoic acid (S)-2-benzyloxycarbonyl-2-(2-tetradecanoylamino-acetylamino)-ethyl ester

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 6h; Acylation;99%
O-(5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol
94458-63-6

O-(5-Acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl)-(1->4)-O-β-D-glucopyranosyl)-(1->1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-hexadecanamino-4-octadecene-1,3-diol

(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-hexadecanamino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 2h;99%
With sodium acetate In tetrahydrofuran; water Acylation;
glycine ethyl ester hydrochloride
5680-79-5

glycine ethyl ester hydrochloride

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

N-hexadecanoyl glycine methyl ester
214706-34-0

N-hexadecanoyl glycine methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;99%
With sodium hydrogencarbonate In chloroform; water at 20℃; for 2h;
Stage #1: glycine ethyl ester hydrochloride With potassium carbonate In dichloromethane; water at 0℃; for 0.0833333h;
Stage #2: n-hexadecanoyl chloride In dichloromethane; water at 20℃; for 16h;
1.48 g

112-67-4Relevant articles and documents

Analysis of Intact Cholesteryl Esters of Furan Fatty Acids in Cod Liver

Hammann, Simon,Wendlinger, Christine,Vetter, Walter

, p. 611 - 620 (2015)

Furan fatty acids (F-acids) are a class of natural antioxidants with a furan moiety in the acyl chain. These minor fatty acids have been reported to occur with high proportions in the cholesteryl ester fraction of fish livers. Here we present a method for the direct analysis of intact cholesteryl esters with F-acids and other fatty acids in cod liver lipids. For this purpose, the cholesteryl ester fraction was isolated by solid phase extraction (SPE) and subsequently analyzed by gas chromatography with mass spectrometry (GC/MS) using a cool-on-column inlet. Pentadecanoic acid esterified with cholesterol was used as an internal standard. GC/MS spectra of F-acid cholesteryl esters featured the molecular ion along with characteristic fragment ions for both the cholesterol and the F-acid moiety. All investigated cod liver samples (n = 8) showed cholesteryl esters of F-acids and, to a lower degree, of conventional fatty acids. By means of GC/MS-SIM up to ten F-acid cholesteryl esters could be determined in the samples. The concentrations of cholesteryl esters with conventional fatty acids amounted to 78-140 mg/100 g lipids (mean 97 mg/100 g lipids), while F-acid cholesteryl esters were present at 47-270 mg/100 g lipids (mean 130 mg/100 g lipids).

Amphiphilic hyperbranched copolymers bearing a hyperbranched core and dendritic shell: Synthesis, characterization and guest encapsulation performance

Liu, Yi,Fan, You,Liu, Xun-Yong,Jiang, Song-Zi,Yuan, Yuan,Chen, Yu,Cheng, Fa,Jiang, Shi-Chun

, p. 8361 - 8369 (2012)

The 2,2-bis(hydroxymethyl)propionic acid (BHP)-based generation 1 dendron with two palmitate tails (D1-C16) and the generation 2 dendron with four palmitate tails (D2-C16) were synthesized. The coupling of D1-C16 or D2-C16 with hyperbranched polyethylenimine (PEI) through the amidation reaction resulted in amphiphilic hyperbranched copolymers bearing a hyperbranched PEI core and a dendritic D1-C16 shell or dendritic D2-C16 shell. The structure of the obtained copolymers was verified through Fourier transform infrared (FTIR) and 1H nuclear magnetic resonance (NMR) characterization. Differential scanning calorimetry (DSC) measurement demonstrated that the existence of the branching units in the shell pronouncedly reduced the crystallinity of the hyperbranched copolymers, and the copolymers with less branched shells had a higher melting temperature and melting enthalpy. These novel amphiphilic hyperbranched copolymers could be used as nanocarriers to efficiently accommodate the hydrophilic guests, including Methyl Orange (MO), Congo Red (CR) and Direct Blue 15 (DB), into the hydrophilic amidated PEI core. Each nanocarrier with a branched shell could accommodate a much higher number of guests than the corresponding nanocarriers with linear shells, which indicated that the dendritic structure of the shell played a key role in significantly enhancing the encapsulation capacity of the nanocarriers. As far as the weight ratio of the encapsulated guests to the nanocarriers was concerned, the nanocarriers with branched shells could be modulated to have a similar encapsulation capacity for the small MO with a mono-sulfonate group, but a much superior encapsulation capacity for the large CR and DB guests with multi-sulfonate groups to the nanocarriers with linear shells.

Antitumor liposomes bearing a prodrug of combretastatin A-4 and a tetrasaccharide ligand of selectins

Sitnikov,Boldyrev,Moiseeva,Shavyrin,Beletskaya,Combes,Bovin,Fedorov,Vodovozova

, p. 2290 - 2296 (2010)

Therapeutic liposomes with an average diameter of 100 nm based on natural phospholipids (phosphatidylcholine and phosphatidylinositol) containing palmitoyl or oleoyl derivatives of the antimitotic agent combretastatin A-4 were constructed. The cytotoxicity of liposomes with the oleoyl derivative in the human breast cancer cell culture turned out to be only three times lower than that of combretastatin A-4, thus indicating the probability of facile intracellular hydrolysis of the prodrug. To achieve selective drug delivery to the tumor tissue in vivo, the diglyceride conjugate of the tetrasaccharide ligand of selectins, viz., Sialyl-Lewis X (SiaLeX, 2 mol.%) was incorporated into the liposomes. The SiaLeX-equipped liposomes loaded with the lipophilic prodrug showed a reliable inhibition of tumor growth on the model of spontaneous breast cancer in mice.

Association of adhesive spheres formed by hydrophobically end-capped PEO. 1. Influence of the presence of single end-capped PEO

Lafleche, Fabrice,Durand, Dominique,Nicolai, Taco

, p. 1331 - 1340 (2003)

Mixtures of poly(ethylene oxide) (PEO) end-capped on one or both ends with hexadecyl, but with the same hydrophilic-lypophilic balance, were studied using static and dynamic light scattering and dynamic mechanical measurements. In aqueous solution the mixtures form polymeric micelles with aggregation numbers that are independent of the fraction of difunctionalized PEO. Difunctionalized PEO bridges between two micelles, which leads to reversible association of the micelles. The phase behavior and the association of the micelles can be described by modeling the micelles as adhesive spheres with an adhesion parameter that depends on the fraction of difunctionalized PEO and the temperature. Above a given concentration the micelles percolate, leading to a strong increase of the viscosity and the high-frequency shear modulus. The viscosity has an Arrhenius temperature dependence with an activation energy close to that of the relaxation time that characterizes the decay of the shear modulus. At even higher concentrations an abrupt transition is observed that is characterized by the appearance of a second relaxation process with a very long relaxation time. The transition can be induced by small increases of the temperature or the concentration. The slow relaxation is attributed to restructuring of a solution of close packed micelles (e.g., hopping of micelles) while the fast relaxation, which is still visible at high concentrations, is attributed to the breakup of elastic bridges by the escape of end groups from the micelles.

Odd-even effect in a thiazole based organogelator: Understanding the interplay of non-covalent interactions on property and applications

Yadav, Priyanka,Ballabh, Amar

, p. 721 - 730 (2015)

New series of thiazole based amides, namely, 1e [N-(thiazol-2-yl)pentadecamide] to 1h [N-(thiazol-2-yl)stearamide], 2e [N-(4-methylthiazol-yl)pentadecamide] to 2h [N-(4-methylthiazol-yl)stearamide], 3e [N-(5-methylthiazol-yl)pentadecamide] to 3h [N-(5-methylthiazol-yl)stearamide] were synthesized, characterized and investigated for their gelation properties. Interestingly, out of three series of thiazole amides synthesized, two (1e-1h and 3e-3h) had displayed odd-even effect on gelation property with an increase in the methylene functional group of alkyl chain attached with thiazole moiety. The gelation-non-gelation of solvents was found to be more significant for the series of compounds 1e-1h, whereas a subtle effect was observed in the series of compounds 3e-3h. A single crystal study of non-gelator (2d) highlighted the crucial role of the methyl group and its position on the thiazole moiety in bringing about a change in supramolecular synthon from a robust cyclic N-H...N interaction to the combination of N-H...N and N-H...O interactions. Self-assembly of four molecules of 2d led to the formation of a zero-dimensional (0-D) hydrogen bonded network instead of a one-dimensional hydrogen bonded network observed in gelling compounds mediated by (methyl)C-H...N, C-H...O and van der Waals interaction. Various gelling agents (3e-3h) were used for the synthesis of nearly spherical silver and ZnO nanoparticles using a sol-gel method, through encapsulation and stabilization of nanoparticles in the gel network. Interestingly, the alkyl chain lengths of thiazole amides were found to affect the size of synthesized Ag and ZnO nanoparticles.

Sonication-Induced Halogenative Decarboxylation of Thiohydroxamic Esters

Dauben, William G.,Bridon, Dominique P.,Kowalczyk, Bruce A.

, p. 6101 - 6106 (1989)

The sonication of primary, secondary, and tertiary thiohydroxamic esters in CCl4 has led to their synthetic transformation to alkyl chlorides, bromides, or iodides.The high yields were comparable to the previous thermal-or photoinduced version of this same reaction.This radical reaction calls attention to the utility of ultrasound in production of trichloromethyl radical, which was concluded to initiate decomposition of the thiohydroxamic esters.

Tryptamine-derived alkaloids from Annonaceae exerting neurotrophin-like properties on primary dopaminergic neurons

Schmidt, Fanny,Douaron, Gael Le,Champy, Pierre,Amar, Majid,Seon-Meniel, Blandine,Raisman-Vozari, Rita,Figadere, Bruno

, p. 5103 - 5113 (2010)

N-fatty acyl tryptamines constitute a scarce group of natural compounds mainly encountered in Annonaceous plants. No biological activity was reported so far for these rare molecules. This study investigated the neurotrophic properties of these natural tryptaminic derivatives on dopaminergic (DA) neurons in primary mesencephalic cultures. A structure-activity relationships study led us to precise the role of a nitrogen atom into the aliphatic chain conferring to the compounds a combined neuroprotective and neuritogenic activity in the nanomolar range. The potent antioxidant activity of these natural products seems to be involved in part of their mechanism of action. This study provides the first description of natural neurotrophin mimetics present in Annonaceae extracts, and led to the biological characterization of compounds, which present a potential interest in neurodegenerative diseases such as Parkinson's disease.

Reducing the cost, smell, and toxicity of the Barton reductive decarboxylation: Chloroform as the hydrogen atom source

Ko, Eun Jung,Williams, Craig M.,Savage, G. Paul,Tsanaktsidis, John

, p. 1944 - 1947 (2011)

When used as solvent, chloroform was found to act as a hydrogen atom donor in Barton reductive decarboxylation reactions. Chloroform offers a substantial practical advantage over pre-existing hydrogen atom donors.

Quadruple helix formation of a photoresponsive peptide amphiphile and its light-triggered dissociation into single fibers

Muraoka, Takahiro,Cui, Honggang,Stupp, Samuel I.

, p. 2946 - 2947 (2008)

Using a peptide amphiphile having a bulky photolabile 2-nitrobenzyl group between the alkyl chain and the peptide segment, we demonstrated quadruple helical fiber formation and its dissociation into single fibrils in response to light. Putting the bulky g

Synthesis and characterization of allyl fatty acid derivatives as reactive coalescing agents for latexes

Barbosa, Joana V.,Oliveira, Fernanda,Moniz, Jorge,Magalhaes, Fernao D.,Bastos, Margarida M. S. M.

, p. 2215 - 2226 (2012)

This work evaluated the use of allyl fatty acid esters derived from vegetable oil (palmitic acid, soybean and sunflower oils) as reactive coalescing agents in a waterborne latex system. Allyl fatty acid derivatives (AFAD) from vegetable oils were synthesized by two different processes. The synthesis was monitored by IR-spectroscopy and the final product characterized by FT-IR, GC-MS, 1H and 13C NMR. The presence of conjugated double bonds in the aliphatic chain was confirmed, which is a determinant for the proposed autoxidative latexes drying mechanism. Each of the AFAD were subsequently added to a standard acrylic emulsion, in order to study its potential as reactive coalescing agent. The minimum film-forming temperature (MFT), glass transition temperature (Tg), drying time and rubbing resistance to solvents were evaluated. The results showed that, when added to water-borne acrylic resins, an AFAD acts as a non-volatile plasticizer capable of autoxidative crosslinking with itself. AOCS 2012.

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