Nervonic acid supplier | CasNO.506-37-6

Name
Nervonic acid
EINECS 610-549-3
CAS No. 506-37-6
Article Data9
CAS DataBase
Density 0.887g/cm³
Solubility Insoluble
Hazard Symbols
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
PSA 37.30000
LogP 8.44910

Synthetic route

: 50995-29-4
1-hydroxy-cis-15-tetracosene

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: docos-13c-enyl-malonic acid

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
at 175℃;

: 112-80-1
cis-Octadecenoic acid

suberic acid monomethyl ester: suberic acid monomethyl ester

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

: 112-62-9
Methyl oleate

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride 2: dibromotriphenylphosphorane / dichloromethane 3: (1,2-dimethoxyethane)dichloronickel(II); 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; manganese / N,N-dimethyl-formamide / 4 h / 40 °C 4: sodium hydroxide / ethanol / 1 h / 60 °C / Inert atmosphere View Scheme

: 143-28-2
oleyl alcohol

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dibromotriphenylphosphorane / dichloromethane 2: (1,2-dimethoxyethane)dichloronickel(II); 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; manganese / N,N-dimethyl-formamide / 4 h / 40 °C 3: sodium hydroxide / ethanol / 1 h / 60 °C / Inert atmosphere View Scheme

: 13044-38-7, 62871-05-0, 6110-53-8
(Z)-1-bromo-9-octadecene

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (1,2-dimethoxyethane)dichloronickel(II); 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; manganese / N,N-dimethyl-formamide / 4 h / 40 °C 2: sodium hydroxide / ethanol / 1 h / 60 °C / Inert atmosphere View Scheme

: 2733-88-2
methyl cis-tetracos-15-enate

: 506-37-6
Nervonic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 60℃; for 1h; Inert atmosphere;

: 506-37-6
Nervonic acid

: 145411-43-4
(Z)-tetracos-15-enoyl chloride

Conditions

Conditions	Yield
With thionyl chloride for 2h; Reflux; Inert atmosphere;	99%
With oxalyl dichloride for 3h;
With phosphorus pentachloride In diethyl ether at 20℃; for 3h;

: 506-37-6
Nervonic acid

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 460740-61-8
(Z)-Tetracos-15-enoic acid methoxy-methyl-amide

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25℃; for 1h;	94%

: 506-37-6
Nervonic acid

: 100-46-9
benzylamine

: (Z)-N-benzyltetracos-15-enamide

Conditions

Conditions	Yield
Stage #1: Nervonic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Stage #2: benzylamine With dmap In dichloromethane at 20℃; for 18h;	94%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h;

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 506-37-6
Nervonic acid

: 191354-88-8
nervonic acid N-hydroxysuccinimide ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate	76%

: 506-37-6
Nervonic acid

: 2238-90-6, 52050-17-6, 56453-02-2, 95119-84-9, 95975-32-9, 106565-70-2
psychosine

: 17283-91-9
(2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h; Heating;	64%

: (2S,3R,4E)-2-azido-3-benzoyloxy-1-[6-O-(tert-butyldiphenylsilyl)-2-O-levulinyl-3-O-(4-methoxybenzyl)-4-O-{[β-(trimethylsilyl)ethoxy]methyl}-β-D-galactopyranosyloxy]-octadec-4-ene

: 506-37-6
Nervonic acid

: 910898-19-0
(2S,3R,4E)-3-benzoyloxy-1-[6-O-(tert-butyldiphenylsilyl)-2-O-levulinyl-3-O-(4-methoxybenzyl)-4-O-{[β-(trimethylsilyl)ethoxy]methyl}-β-D-galactopyranosyloxy]-2-((Z)-tetracos-15-enoylamino)-octadec-4-ene

Conditions

Conditions	Yield
With tributylphosphine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Staudinger reaction;	60%

: 506-37-6
Nervonic acid

: (2S,3R,4E)-2-amino-1-(6-O-methoxycarbonylmethyl-α-D-galactopyranosyloxy)octadec-4-en-3-ol

: (2S,3R,4E)-1-(6-O-methoxycarbonylmethyl-α-D-galactopyranosyloxy)-2-[15(Z)-tetracosenoylamino]octadec-4-en-3-ol

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 4h; Heating;	57%

: 506-37-6
Nervonic acid

: C24H46O3

Conditions

Conditions	Yield
Stage #1: Nervonic acid With n-butyllithium; isopropylamine In tetrahydrofuran at -55℃; for 0.5h; Stage #2: With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 0 - 20℃; for 16h; Stage #3: With oxygen In tetrahydrofuran at 0℃; for 1h;	56%

: 506-37-6
Nervonic acid

: methoxy PEG2000-4-(4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoate

: methoxy PEG2000-4-(2-methoxy-5-nitro-4-(1-(tetracos-15-enoyloxy)ethyl)phenoxy)butanoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane	50%

: 506-37-6
Nervonic acid

: 1460-18-0
pentadecanedioic acid

Conditions

Conditions	Yield
With chloroform; ozone Beim Spalten des Ozonids mit Wasser auf dem Wasserbad und Oxydieren mit Kaliumpermanganat;

: 506-37-6
Nervonic acid

: 557-59-5
n-tetracosanoic acid

Conditions

Conditions	Yield
With ethanol; platinum Hydrogenation;
With diethyl ether; palladium Hydrogenation;

: 506-37-6
Nervonic acid

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

Conditions

Conditions	Yield
With nitros gas
With nitros gas; acetone

: 506-37-6
Nervonic acid

: 13756-62-2
(+/-)-threo-15,16-dihydroxy-tetracosanoic acid

Conditions

Conditions	Yield
With formic acid; dihydrogen peroxide beim anschliessenden Erhitzen mit wss. Natronlauge;

: 506-37-6
Nervonic acid

: 13756-62-2
(+/-)-erythro-15,16-dihydroxy-tetracosanoic acid

Conditions

Conditions	Yield
With potassium hydroxide; potassium permanganate

: 506-37-6
Nervonic acid

: 112-05-0
nonanoic acid

Conditions

Conditions	Yield
With chloroform bei der Ozonspaltung;

: 506-37-6
Nervonic acid

: 15,16-Dibromo-tetracosanoic acid

Conditions

Conditions	Yield
With bromine In chloroform

: 506-37-6
Nervonic acid

: 15,16-Diiodo-tetracosanoic acid

Conditions

Conditions	Yield
With iodine In chloroform

: 506-37-6
Nervonic acid

: 4617-33-8
15-hydroxylpentadecanoic acid

Conditions

Conditions	Yield
With sodium hydroxide; potassium borohydride; ozone 1.) EtOH, hexane; Yield given. Multistep reaction;

: 60-29-7
diethyl ether

: 506-37-6
Nervonic acid

palladium charcoal: palladium charcoal

: 557-59-5
n-tetracosanoic acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 64-17-5
ethanol

: 506-37-6
Nervonic acid

platinum black: platinum black

: 557-59-5
n-tetracosanoic acid

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 506-37-6
Nervonic acid

nitros gas: nitros gas

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

: 506-37-6
Nervonic acid

: 67-66-3
chloroform

: 7726-95-6
bromine

2.15.16-tribromo-tetracosanoic acid (1): 2.15.16-tribromo-tetracosanoic acid (1)

Conditions

Conditions	Yield
Kochen des Reaktionsprodukts mit Brom und rotem Phosphor und Verseifen mit Wasser;

...Expand

: 506-37-6
Nervonic acid

: 67-66-3
chloroform

A: 124-19-6
nonan-1-al

B: 112-05-0
nonanoic acid

C 15-oxo-pentadecanoic acid-(1): 15-oxo-pentadecanoic acid-(1)

D tridecane-dicarboxylic acid-(1.13): tridecane-dicarboxylic acid-(1.13)

Conditions

Conditions	Yield
Ozonisierung;

...Expand

Nervonic acid Chemical Properties

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

Nervonic acid Uses

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

Nervonic acid Safety Profile

Hazard Codes of Nervonic acid (CAS NO.506-37-6): Irritant Xi
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

Product Name

Nervonic acid

Synthetic route

Nervonic acid Chemical Properties

Nervonic acid Uses

Nervonic acid Safety Profile

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