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557-59-5

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557-59-5 Usage

Description

Lignoceric acid is a 24-carbon saturated (24:0) fatty acid. In mammals, it is synthesized during brain development and is found in cerebrosides. The deficient peroxisomal oxidation of very-long-chain fatty acids, including lignoceric acid, contributes to certain syndromes, including Zellweger cerebro-hepato-renal syndrome and X chromosome-linked adrenoleukodystrophy. Lignoceric acid is also a by-product of lignin production.

Uses

Tetracosanoic Acid is a chemical component of a dried mushroom powder exhibiting antioxidant properties. It is a long chain fatty acid present in peanut oil.

Definition

ChEBI: A C24 straight-chain saturated fatty acid.

Purification Methods

Crystallise the acid from acetic acid, Me2CO, toluene, pet ether/Me2CO or*C6H6/Me2CO. [Beilstein 2 IV 1301.]

Check Digit Verification of cas no

The CAS Registry Mumber 557-59-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 557-59:
(5*5)+(4*5)+(3*7)+(2*5)+(1*9)=85
85 % 10 = 5
So 557-59-5 is a valid CAS Registry Number.
InChI:InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)

557-59-5SDS

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 lignoceric acid

1.2 Other means of identification

Product number -
Other names Tetracosanoic acid

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:557-59-5 SDS

557-59-5Synthetic route

Sodium; 7-oxo-tetracosanoate
78386-99-9

Sodium; 7-oxo-tetracosanoate

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In ethylene glycol 1.) reflux, 1 h, 2.) reflux, 1 h;81.53%
tetracosyl alcohol
506-51-4

tetracosyl alcohol

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; 3C7H18N(1+)*O24PW4(3-) In water at 90℃; for 8h;78.1%
Nervonic acid
506-37-6

Nervonic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
With diethyl ether; palladium Hydrogenation;
2-hydroxytetracosanoic acid
544-57-0

2-hydroxytetracosanoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With phosphorus; hydrogen iodide; acetic acid at 120 - 125℃;
n-triacontane
638-68-6

n-triacontane

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
at 95℃; beim Durchleiten von Luft;
7-oxo-tetracosanoic acid
77850-94-3

7-oxo-tetracosanoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate; diethylene glycol at 195℃;
10-oxo-tetracosanoic acid
95746-75-1

10-oxo-tetracosanoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc; acetic acid
tetracosa-4,8,12,15,18,21-hexaenoic acid

tetracosa-4,8,12,15,18,21-hexaenoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
Hydrogenation;
docosyl-malonic acid
4431-35-0

docosyl-malonic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
at 140 - 150℃; im Hochvakuum;
at 160 - 180℃;
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With methanol; sebacic acid mono methyl ester; sodium Electrolysis.Behandlung des Reaktionsprodukts mit methanol.Natronlauge;
3-β-O-<β-D-2-tetracosylxylopyranosyl>-stigmasterol
131870-90-1

3-β-O-<β-D-2-tetracosylxylopyranosyl>-stigmasterol

A

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

B

(2S,3R,4S,5R)-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-3,4,5-triol
132014-42-7

(2S,3R,4S,5R)-2-[(3S,8S,9S,10R,13R,14S,17R)-17-((E)-(1R,4S)-4-Ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy]-tetrahydro-pyran-3,4,5-triol

Conditions
ConditionsYield
With potassium hydroxide In methanol for 6h; Heating;A n/a
B 26 mg
7-oxotriacontanoic acid
72106-49-1

7-oxotriacontanoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
usual Wolf-Kishner reduction;
(9E,11E,13E)-Tetracosa-9,11,13-trienoic acid
74473-92-0

(9E,11E,13E)-Tetracosa-9,11,13-trienoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide0.086 g
10-oxo-tetracosanoic acid (1)

10-oxo-tetracosanoic acid (1)

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc
13-oxo-tetracosanoic acid (1)

13-oxo-tetracosanoic acid (1)

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With hydrogenchloride; amalgamated zinc
6-oxo-tetracosanoic acid (1)

6-oxo-tetracosanoic acid (1)

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With sodium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol zulezt bei 200grad nach teilweisen Abdestillieren des Loesungsmittels;
bovine spleen

bovine spleen

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
Hydrolysis;
cis-Δ15-tetracosenoic acid

cis-Δ15-tetracosenoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With platinum(IV) oxide; ethanol under 2280 Torr; Hydrogenation;
With nickel at 180℃; under 1140 Torr; Hydrogenation;
methanol
67-56-1

methanol

kerasin

kerasin

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With sulfuric acid Hydrolysis.das Methylester ist entstanden;
ethanol
64-17-5

ethanol

kerasin

kerasin

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With sulfuric acid Hydrolysis.das Aethylester ist entstanden;
lignocerylsphingosine

lignocerylsphingosine

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
Hydrolysis;
n-tricosyl cyanide

n-tricosyl cyanide

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With sodium hydroxide
diethyl ether
60-29-7

diethyl ether

Nervonic acid
506-37-6

Nervonic acid

palladium charcoal

palladium charcoal

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
Hydrogenation;
paraffin-wax

paraffin-wax

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
durch Oxidation;
ethanol
64-17-5

ethanol

Nervonic acid
506-37-6

Nervonic acid

platinum black

platinum black

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
Hydrogenation;
ethanol
64-17-5

ethanol

tetracos-15t-enoic acid
115863-91-7

tetracos-15t-enoic acid

platinum oxide

platinum oxide

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
Hydrogenation;
trans-Δ15-tetracosenoic acid

trans-Δ15-tetracosenoic acid

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

Conditions
ConditionsYield
With platinum(IV) oxide; ethanol under 2280 Torr; Hydrogenation;
With nickel at 180℃; under 1140 Torr; Hydrogenation;
lup-20(29)-ene-7β,15α-diol-3β-fatty acid ester mixture (III)

lup-20(29)-ene-7β,15α-diol-3β-fatty acid ester mixture (III)

A

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

B

lup-20(29)-ene-3β,7β,15α-triol
115498-81-2

lup-20(29)-ene-3β,7β,15α-triol

C

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

D

stearic acid
57-11-4

stearic acid

Conditions
ConditionsYield
With hydrogenchloride; potassium hydroxide; ethanol for 2h; Heating; Further byproducts given;A 7 % Chromat.
B 36 mg
C 17 % Chromat.
D 6 % Chromat.
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2R,3S,4E)-1,3-di-O-(1-ethoxyethyl)-2-amino-4-octadecene-1,3-diol
102842-95-5

(2R,3S,4E)-1,3-di-O-(1-ethoxyethyl)-2-amino-4-octadecene-1,3-diol

(2R,3S,4E)-1,3-di-O-(1-ethoxyethyl)-N-tetracosanyl-2-amino-4-octadecene-1,3-diol
102842-97-7

(2R,3S,4E)-1,3-di-O-(1-ethoxyethyl)-N-tetracosanyl-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 1h; Heating;99.5%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

tetracosanoic acid N-hydroxysuccinimide ester
39782-75-7

tetracosanoic acid N-hydroxysuccinimide ester

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;99%
With dicyclohexyl-carbodiimide
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2R,3S,4Z)-1,3-di-O-(1-ethoxyethyl)-2-amino-4-octadecene-1,3-diol
102842-95-5

(2R,3S,4Z)-1,3-di-O-(1-ethoxyethyl)-2-amino-4-octadecene-1,3-diol

(2R,3S,4Z)-1,3-di-O-(1-ethoxyethyl)-N-tetracosanyl-2-amino-4-octadecene-1,3-diol
102842-97-7

(2R,3S,4Z)-1,3-di-O-(1-ethoxyethyl)-N-tetracosanyl-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 1h; Heating;98%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2S,3R,4E,6R)-2-amino-1,3,6-tris(tert-butyldimethylsilyloxy)-4-octadecene
651718-24-0

(2S,3R,4E,6R)-2-amino-1,3,6-tris(tert-butyldimethylsilyloxy)-4-octadecene

Tetracosanoic acid [(E)-(1S,2R,5R)-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-heptadec-3-enyl]-amide
873802-50-7

Tetracosanoic acid [(E)-(1S,2R,5R)-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-heptadec-3-enyl]-amide

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h;96%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

N-[3-(dimethylamino)propyl] tetracosanamide

N-[3-(dimethylamino)propyl] tetracosanamide

Conditions
ConditionsYield
With aluminum oxide; sodium fluoride at 165℃; for 12h; Inert atmosphere;95%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2S,3S)-1,3-di-O-(1-ethoxyethyl)-2-amino-4-octadecene-1,3-diol
102842-95-5

(2S,3S)-1,3-di-O-(1-ethoxyethyl)-2-amino-4-octadecene-1,3-diol

(2S,3S)-1,3-di-O-(1-ethoxyethyl)-N-tetracosanoyl-2-amino-4-octadecene-1,3-diol
102842-97-7

(2S,3S)-1,3-di-O-(1-ethoxyethyl)-N-tetracosanoyl-2-amino-4-octadecene-1,3-diol

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 1h; Heating;94.5%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(S)-2-hydroxy-1-tetradecyloxycarbonylethylammonium chloride

(S)-2-hydroxy-1-tetradecyloxycarbonylethylammonium chloride

(S)-2-tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester

(S)-2-tetracosanoylamino-3-hydroxypropionic acid tetradecyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 20h;92%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine
155021-56-0

tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine

N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]eicosanamide
1042940-12-4

N-[tris(3-(N-tert-butoxycarbonylamino)propyl)methyl]eicosanamide

Conditions
ConditionsYield
Stage #1: n-tetracosanoic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine With dmap In dichloromethane for 2h;
91%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2S,3S,4R)-2-amino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol
745041-72-9

(2S,3S,4R)-2-amino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol

(2S,3S,4R)-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol
745041-79-6

(2S,3S,4R)-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-2-tetracosanoylamino-1,3,4-nonanetriol

Conditions
ConditionsYield
Stage #1: n-tetracosanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: (2S,3S,4R)-2-amino-3,4-O-isopropylidene-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1,3,4-nonanetriol With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 30℃; for 16h;
89%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0 - 30℃;89%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

C121H167N3O52Si

C121H167N3O52Si

C145H213N3O53Si

C145H213N3O53Si

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In 1,2-dichloro-ethane for 1h; Ambient temperature;88%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

tetracosanoic acid-d47

tetracosanoic acid-d47

Conditions
ConditionsYield
With palladium 10% on activated carbon; water-d2; potassium hydroxide at 195℃; under 11251.1 Torr; for 100h; Inert atmosphere;83%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

tetracosyl alcohol
506-51-4

tetracosyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; Inert atmosphere;82%
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In tetrahydrofuran
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

2-amino-1,3-bis(1-ethoxyethoxy)-4-Z-D-erythro-octadec-4-ene
97818-15-0

2-amino-1,3-bis(1-ethoxyethoxy)-4-Z-D-erythro-octadec-4-ene

1,3-bis(1-ethoxyethoxy)-2-tetracosanamido-4-Z-D-erythro-octadec-4-ene
97818-16-1

1,3-bis(1-ethoxyethoxy)-2-tetracosanamido-4-Z-D-erythro-octadec-4-ene

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 1h; Heating;78%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(+/-)-2-bromotetracosanoic acid
102809-35-8

(+/-)-2-bromotetracosanoic acid

Conditions
ConditionsYield
With phosphorus; bromine at 95℃; for 6h;77%
With anhydrous phosphorus trichloride; bromine In water
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2S,3S,4R)-1,3,4-tri-O-benzyl-2-amino-1,3,4-octadecanetriol
129779-77-7

(2S,3S,4R)-1,3,4-tri-O-benzyl-2-amino-1,3,4-octadecanetriol

(2S,3S,4R)-1,3,4-tri-O-benzyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol
129779-78-8

(2S,3S,4R)-1,3,4-tri-O-benzyl-N-tetracosanoyl-2-amino-1,3,4-octadecanetriol

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 1h; Heating;75%
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane for 2h; Heating; Yield given;
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane
1082745-96-7

(2S,3S,4R)-2-amino-1,3,4-tris(tert-butyldimethylsilyloxy)nonane

(2S,3S,4R)-1,3,4-tris(tert-butyldimethylsilanyloxy)-2-tetracosanoylaminononane
872356-91-7

(2S,3S,4R)-1,3,4-tris(tert-butyldimethylsilanyloxy)-2-tetracosanoylaminononane

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 15h;75%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-amine
102522-47-4

6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-amine

N-[tris(tert-butyldimethylsilyloxymethyl)methyl]tetraeicosanamide
1279697-37-8

N-[tris(tert-butyldimethylsilyloxymethyl)methyl]tetraeicosanamide

Conditions
ConditionsYield
Stage #1: n-tetracosanoic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h;
Stage #2: 6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-amine With dmap In dichloromethane for 2h;
72%
Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 5h; Inert atmosphere;71%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

rotigotine
99755-59-6

rotigotine

rotigotine lignocerate

rotigotine lignocerate

Conditions
ConditionsYield
Stage #1: n-tetracosanoic acid With oxalyl dichloride In dichloromethane at 20℃; Inert atmosphere;
Stage #2: rotigotine With triethylamine In dichloromethane
70%
L-threo-dihydrosphingosine
15639-50-6

L-threo-dihydrosphingosine

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

N-((2S,3S)-1,3-dihydroxyoctadecan-2-yl)-tetracosanamide
121470-51-7

N-((2S,3S)-1,3-dihydroxyoctadecan-2-yl)-tetracosanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;68%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

tert-butyl-(S)-4-((1R,4R,E)-1,4-dihydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

tert-butyl-(S)-4-((1R,4R,E)-1,4-dihydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

N-((2S,3R,6R,E)-1,3,6-trihydroxyoctadec-4-en-2-yl)tetracosanamide

N-((2S,3R,6R,E)-1,3,6-trihydroxyoctadec-4-en-2-yl)tetracosanamide

Conditions
ConditionsYield
Stage #1: tert-butyl-(S)-4-((1R,4R,E)-1,4-dihydroxyhexadec-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate With trifluoroacetic acid In water at 20℃; for 24h; Inert atmosphere;
Stage #2: n-tetracosanoic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran; dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;
65%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(2S,3S,4E)-L-threo sphingosine
25695-95-8

(2S,3S,4E)-L-threo sphingosine

N-((2S,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl)tetracosanamide
121470-52-8

N-((2S,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl)tetracosanamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;62%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

C32H57NO12

C32H57NO12

(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-tetracosanoylamino-3,4-octadecanediol

(2S,3S,4R)-1-(α-D-galactopyranosyloxy)-2-tetracosanoylamino-3,4-octadecanediol

Conditions
ConditionsYield
Stage #1: n-tetracosanoic acid With triethylamine; isobutyl chloroformate In dichloromethane at 20℃; for 0.833333h;
Stage #2: C32H57NO12 In dichloromethane; N,N-dimethyl-formamide at 0℃; Inert atmosphere;
58%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

1-(((R,E)-1-((2S,3S)-3-isobutylaziridin-2-yl)pentadec-1-en-3-yl)oxy)pyrrolidine

1-(((R,E)-1-((2S,3S)-3-isobutylaziridin-2-yl)pentadec-1-en-3-yl)oxy)pyrrolidine

N-((4S,5R,8R,E)-5-hydroxy-2-methyl-8-(pyrrolidin-1-yloxy)icos-6-en-4-yl)tetracosanamide

N-((4S,5R,8R,E)-5-hydroxy-2-methyl-8-(pyrrolidin-1-yloxy)icos-6-en-4-yl)tetracosanamide

Conditions
ConditionsYield
With triethylamine; scandium tris(trifluoromethanesulfonate) In acetonitrile at 65℃; for 72h; Sealed tube; regioselective reaction;51%
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

C81H117NO33Si

C81H117NO33Si

O-(2,3,4,6-tetra-O-acetyl-α-D-manp)-(1->3)-O-<(2,3,4-tri-O-acetyl-β-D-xylp)-(1->2)>-O-(4,6-di-O-acetyl-β-D-manp)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->1)-3-O-(tert-butyldiphenylsilyl)-2-N-tetracosanoyl-(4E)-sphingenine
128377-28-6

O-(2,3,4,6-tetra-O-acetyl-α-D-manp)-(1->3)-O-<(2,3,4-tri-O-acetyl-β-D-xylp)-(1->2)>-O-(4,6-di-O-acetyl-β-D-manp)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->1)-3-O-(tert-butyldiphenylsilyl)-2-N-tetracosanoyl-(4E)-sphingenine

Conditions
ConditionsYield
With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide In dichloromethane at 30℃; for 3h;49%
(S)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propylamine

(S)-1-((4S,5R)-2,2-Dimethyl-5-pentyl-[1,3]dioxolan-4-yl)-3-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propylamine

n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol
862718-92-1

(3S,4S,5R)-4,5-O-isopropylidene-1-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-3-tetracosanoylamino-4,5-decanediol

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;48%
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃;
n-tetracosanoic acid
557-59-5

n-tetracosanoic acid

1-(((R,E)-1-((2S,3S)-3-isobutylaziridin-2-yl)pentadec-1-en-3-yl)oxy)piperidine

1-(((R,E)-1-((2S,3S)-3-isobutylaziridin-2-yl)pentadec-1-en-3-yl)oxy)piperidine

N-((4S,5R,8R,E)-5-hydroxy-2-methyl-8-(piperidin-1-yloxy)icos-6-en-4-yl)tetracosanamide

N-((4S,5R,8R,E)-5-hydroxy-2-methyl-8-(piperidin-1-yloxy)icos-6-en-4-yl)tetracosanamide

Conditions
ConditionsYield
With triethylamine; scandium tris(trifluoromethanesulfonate) In acetonitrile at 60℃; for 72h; Sealed tube; regioselective reaction;47%

557-59-5Relevant articles and documents

De Lederkremer et al.

, p. 263,265 (1977)

Sydykov et al.

, (1978)

METHOD FOR THE PRODUCTION OF LIGNOCERIC ACID

-

Page/Page column 3-4, (2012/06/01)

The invention is related to a process for production of lignoceric acid from mixtures of long-chain aliphatic alcohols that contain lignoceric alcohol, wherein the process consists in oxidizing the mixture in a biphasic catalytic system using quaternary ammonium peroxotungstophosphate as a catalyst and hydrogen peroxide as an oxidant, followed by several physical or chemical unitary steps to separate and purify the lignoceric acid.

Structure of a novel diterpenoid ester, fritillahupehin from bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia

Ruan, Hanli,Zhang, Yonghui,Wu, Jizhou,Deng, Shukai,Sun, Handong,Fujita, Tetsuro

, p. 288 - 291 (2007/10/03)

A new diterpenoid ester, fritillahupehin (1) together with three known fatty acids: palmitic acid (2), lignoceric acid (3) and azelaic acid (4) were isolated from the bulbs of Fritillaria hupehensis Hsiao and K.C. Hsia. The structure of fritillahupehin has been established to be ent-kauran-16β-yl lignocerate by means of spectroscopic and chemical evidence. Compounds 2-4 were isolated from Fritillaria sp. for the first time.

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