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506-37-6

Basic Information
CAS No.: 506-37-6
Name: Nervonic acid
Article Data: 9
Molecular Structure:
Molecular Structure of 506-37-6 (Nervonic acid)
Formula: C24H46 O2
Molecular Weight: 366.628
Synonyms: 15-Tetracosenoicacid, (Z)- (8CI); 15-Tetracosenoic acid, cis- (5CI); (15Z)-Tetracosenoic acid;(Z)-15-Tetracosenoic acid; Nervonic acid; Nevonic acid; Selacholeic acid;cis-15-Tetracosenoic acid
EINECS: 610-549-3
Density: 0.887g/cm3
Melting Point: 42 - 44 C
Boiling Point: 479.2ºC
Flash Point: >110 ºC
Solubility: Insoluble clear to yellowish crystalline powder
Hazard Symbols:
Risk Codes: R36/37/38   
Safety: 1728551
Transport Information: OTH
PSA: 37.30000
LogP: 8.44910
Synthetic route
50995-29-4

1-hydroxy-cis-15-tetracosene

506-37-6

Nervonic acid

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In water; acetonitrile at 20℃; for 7h;70%
111924-39-1

(Z)-22-bromo-9-docosene

996-82-7

sodium diethylmalonate

A

506-37-6

Nervonic acid

B

115863-91-7

tetracos-15t-enoic acid

Conditions
ConditionsYield
With ethanol Verseifen des Reaktionsprodukts mit siedender alkoh.KOH und Erhitzen der erhaltenen Dicarbonsaeure auf 175-210grad; die Trennung der beiden Stereoisomeren erfolgt durch fraktionierte Krystallysation aus Aethanol oder Aceton;
With i-Amyl alcohol Verseifen des Reaktionsprodukts mit siedender alkoh.KOH und Erhitzen der erhaltenen Dicarbonsaeure auf 175-210grad; die Trennung der beiden Stereoisomeren erfolgt durch fraktionierte Krystallysation aus Aethanol oder Aceton;

docos-13c-enyl-malonic acid

506-37-6

Nervonic acid

Conditions
ConditionsYield
at 175℃;
112-80-1

cis-Octadecenoic acid

suberic acid monomethyl ester

suberic acid monomethyl ester

506-37-6

Nervonic acid

Conditions
ConditionsYield
With methanol; sodium methylate Electrolysis.Hydrolyse des gebildeten Tetracos-15c-ensaeure-methylesters durch Erwaermen mit wss.-methanol.Natronlauge;
629-98-1

erucyl alcohol

506-37-6

Nervonic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene; phosphorus (III)-bromide / 0 - 5 °C
2: sodium ethylate; ethanol / beim Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge
3: 175 °C
View Scheme
Multi-step reaction with 3 steps
1.1: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 0 - 20 °C
1.2: 60 °C
2.1: magnesium; iodine / 1 h / Reflux
2.2: 4 h / -40 °C / Inert atmosphere
3.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 7 h / 20 °C
View Scheme
111924-39-1

(Z)-22-bromo-9-docosene

506-37-6

Nervonic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium ethylate; ethanol / beim Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge
2: 175 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium; iodine / 1 h / Reflux
1.2: 4 h / -40 °C / Inert atmosphere
2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 7 h / 20 °C
View Scheme
1120-34-9

methyl cis-13-docosenoate

506-37-6

Nervonic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium alanate; diethyl ether
2: toluene; phosphorus (III)-bromide / 0 - 5 °C
3: sodium ethylate; ethanol / beim Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge
4: 175 °C
View Scheme
124-19-6

nonan-1-al

856055-61-3

C26H50O2

506-37-6

Nervonic acid

Conditions
ConditionsYield
Stage #1: C26H50O2 With potassium hydroxide; water In methanol at 60℃; for 0.333333h;
Stage #2: nonan-1-al With hydrogenchloride In tetrahydrofuran; water
112-86-7

cis-13-docosenoic acid

506-37-6

Nervonic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sulfuric acid / Reflux
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
3.1: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 0 - 20 °C
3.2: 60 °C
4.1: magnesium; iodine / 1 h / Reflux
4.2: 4 h / -40 °C / Inert atmosphere
5.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 7 h / 20 °C
View Scheme
37910-77-3

ethyl (13Z)-13-docosenoate

506-37-6

Nervonic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: dmap; triethylamine; methanesulfonyl chloride / dichloromethane / 0 - 20 °C
2.2: 60 °C
3.1: magnesium; iodine / 1 h / Reflux
3.2: 4 h / -40 °C / Inert atmosphere
4.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile; water / 7 h / 20 °C
View Scheme
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Chemistry

Molecular Structure:

Molecular Formula: C24H46O2
Molecular Weight: 366.6208
IUPAC Name: (Z)-Tetracos-15-enoic acid
Synonyms of Nervonic acid (CAS NO.506-37-6): 15-Tetracosenoic acid ; cis-15-Tetracosenoic acid; Selacholeic acid
CAS NO: 506-37-6
Product Categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives ; Biochemistry ; Higher Fatty Acids & Higher Alcohols ; Unsaturated Higher Fatty Acids ; Functional Products
Melting point: 42-43 °C
Index of Refraction: 1.468
Molar Refractivity: 114.85 cm3
Molar Volume: 412.9 cm3
Surface Tension: 33.8 dyne/cm
Density: 0.887 g/cm3
Flash Point: 375.8 °C
Enthalpy of Vaporization: 81.44 kJ/mol
Boiling Point: 479.2 °C at 760 mmHg
Vapour Pressure: 1.68E-10 mmHg at 25°C

Uses

  Nervonic acid (CAS NO.506-37-6) is used in the treatment of disorders involving demyelination.

Safety Profile

Hazard Codes of Nervonic acid (CAS NO.506-37-6): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 3
F: 8-10