Product Name

  • Name

    Oleamide

  • EINECS 206-103-9
  • CAS No. 301-02-0
  • Article Data41
  • CAS DataBase
  • Density 0.879 g/cm3
  • Solubility Insoluble in water.
  • Melting Point 70 °C
  • Formula C18H35NO
  • Boiling Point 433.3 °C at 760 mmHg
  • Molecular Weight 281.482
  • Flash Point 215.9 °C
  • Transport Information
  • Appearance White powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 301-02-0 (Oleamide)
  • Hazard Symbols IrritantXi
  • Synonyms 9-Octadecenamide,(Z)-;Oleamide (6CI,8CI);(Z)-9-Octadecenamide;9-cis-Oleamide;Alflow 10E;Alflow E 10;Amide O;Armoslip CP;Armoslip CP-P;Atmer SA 1758FD;Oleamide (Oleic acid amide);Oleamide;Atmer SA 1759FD;Crodamide OR;Crodamide VRX;Denon SL 1;Diamid M 309;Diamid O;Diamid O 200;Fatty Amide O-N;Finawax O;Kemamide O;Kemamide U;Kemamide VO;Neutron P;Oleic acid amide;PP 5926;Slip-eze;Unislip 1757;Unislip 1758;Unislip 1759;Unislip4407;cis-9-10-Octadecenoamide;cis-Stearyl amido-9-ene;Oleic Acidamide;
  • PSA 43.09000
  • LogP 6.20950

Synthetic route

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ammonia; zircornium(IV) n-propoxide at 165℃; for 9h; Reagent/catalyst;98.6%
With Candida antarctica lipase B; ammonium carbamate In various solvent(s) at 35℃; for 96h; Substitution;95%
With Candida antarctica lipase B; ammonium carbamate In various solvent(s) at 35℃; for 72h; Substitution;94%
linoleamide
3999-01-7

linoleamide

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ammonia In dichloromethane for 1h; Ambient temperature;95%
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;86%
With ammonium hydroxide In tetrahydrofuran at 0 - 20℃; for 3h;86%
With ammonia In dichloromethane; water at 0℃; for 0.5h;79%
octadec-9(Z)-enoyl azide
77165-66-3

octadec-9(Z)-enoyl azide

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane at 0 - 5℃; for 1.5h;84%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

acetylurea
591-07-1

acetylurea

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
at 230℃;
at 230℃;
at 230℃;
Methyl oleate
112-62-9

Methyl oleate

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ammonia at 165℃;
With ammonia at 165 - 180℃;
With lithium aluminium tetrahydride; ammonia In tetrahydrofuran
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

formamide
77287-34-4, 77287-35-5, 60100-09-6

formamide

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
at 230℃;
at 160℃;
at 200℃;
at 230℃;
at 230℃;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

urea
57-13-6

urea

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
at 230℃;
at 230℃;
at 230℃;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

B

Methyl oleate
112-62-9

Methyl oleate

C

tetradecanamide
638-58-4

tetradecanamide

D

pentadecanoic acid[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide
3843-51-4

pentadecanoic acid[2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-piperidin-4-yl]-amide

Conditions
ConditionsYield
With Bacillus megaterium NRRL B-3437; ammonium chloride In water at 28℃; for 96h; Product distribution;A 1 % Chromat.
B n/a
C n/a
D n/a
...Expand
almond oil

almond oil

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ethanol; ammonia
hazel-nut oil

hazel-nut oil

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ethanol; ammonia
oleic acid nitrile

oleic acid nitrile

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With water; zinc(II) oxide at 240℃;
olive oil

olive oil

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
With ammonia at 110℃;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

petroleum ether

petroleum ether

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: oxalyl chloride
2: ammonia
View Scheme
Multi-step reaction with 2 steps
1: (COCl)2 / CH2Cl2 / 4 h / 20 °C
2: aq. NH4 / 0.08 h / 0 °C
View Scheme
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

(+)-camphor-β-sulfonic acid

(+)-camphor-β-sulfonic acid

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (COCl)2 / CH2Cl2 / 4 h / 25 °C
2: aq, NH4OH / 0.08 h / 0 °C
View Scheme
linoleic acid
60-33-3

linoleic acid

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (COCl)2, DMF / benzene / 3 h / Ambient temperature
2: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature
3: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature
View Scheme
linoleyl chloride
7459-33-8

linoleyl chloride

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature
2: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature
View Scheme
EtOAc-hexanes

EtOAc-hexanes

oxalyl dichloride
79-37-8

oxalyl dichloride

aqueous NH4OH

aqueous NH4OH

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
In dichloromethane
...Expand
EtOAc-hexanes

EtOAc-hexanes

oxalyl dichloride
79-37-8

oxalyl dichloride

aqueous NH4 OH

aqueous NH4 OH

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Conditions
ConditionsYield
In dichloromethane
...Expand
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

A

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

B

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

Conditions
ConditionsYield
With ammonia In dichloromethane at 0 - 20℃;
dimethyl amine
124-40-3

dimethyl amine

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate
2733-91-7

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate

A

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

B

N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide
1323108-64-0

N,N-dimethyl-(12S,13R)-epoxy-cis-9-octadecenyl amide

C

Palmitamide
629-54-9

Palmitamide

D

stearamide
124-26-5

stearamide

Conditions
ConditionsYield
Stage #1: dimethyl amine; methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate With sodium methylate In methanol for 2h; Reflux;
Stage #2: In methanol at 0℃; for 24.25h;
...Expand
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

8-[(2S*3R*)-3-octyloxirane-2-yl]octanamide

8-[(2S*3R*)-3-octyloxirane-2-yl]octanamide

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3h;96%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

cis-9-octadecenenitrile
112-91-4

cis-9-octadecenenitrile

Conditions
ConditionsYield
With phosphorus pentoxide at 150℃; for 8h;95%
With thionyl chloride at 80℃; for 4h;60%
With Ketene at 420℃; ueber Glasringe;
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

(Z)-9-octadecen-1-amine
112-90-3

(Z)-9-octadecen-1-amine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran Reflux;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;95%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;95%
Stage #1: cis-9-octadecenoamide With lithium aluminium tetrahydride In tetrahydrofuran at 50 - 60℃; for 3.5 - 6.75h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran at 40℃; for 1 - 2h; Product distribution / selectivity;
EtOAc-hexanes

EtOAc-hexanes

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

9-T-butyldiphenylsilyloxy-nonanal

9-T-butyldiphenylsilyloxy-nonanal

Conditions
ConditionsYield
With diisobutylaluminium hydride In methanol; toluene94.9%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

benzylamine
100-46-9

benzylamine

(9Z)-N-benzyl-9-octadecenamide
101762-87-2

(9Z)-N-benzyl-9-octadecenamide

Conditions
ConditionsYield
With Ce(III) immobilised on an aminated epichlorohydrin-activated agarose matrix at 140℃; for 25h; Green chemistry;90%
oxalyl dichloride
79-37-8

oxalyl dichloride

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

C37H68N2O3

C37H68N2O3

Conditions
ConditionsYield
for 3h; Inert atmosphere; Schlenk technique; Reflux;84%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

(Z)-octadec-9-enethioamide

(Z)-octadec-9-enethioamide

Conditions
ConditionsYield
With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; for 2h;81%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate
108869-64-3

3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate

1-N-oleanoly-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-gulcopyranosyl)amine

1-N-oleanoly-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-gulcopyranosyl)amine

Conditions
ConditionsYield
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;76%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl trichloroacetimidate
136738-80-2

2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl trichloroacetimidate

1-N-oleanoly-2,3,5-tri-O-benzoyl-β-D-ribofuranosylamine

1-N-oleanoly-2,3,5-tri-O-benzoyl-β-D-ribofuranosylamine

Conditions
ConditionsYield
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;74%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

3,4,6-tri-O-benzyl-D-galactal
80040-79-5

3,4,6-tri-O-benzyl-D-galactal

1-N-oleanoly-(2-deoxyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-amine

1-N-oleanoly-(2-deoxyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-amine

Conditions
ConditionsYield
With 2-chloro-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In toluene at 30℃; for 48h; Reagent/catalyst; Concentration; Molecular sieve; Inert atmosphere;74%
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Ser(tBu)-OH
71989-33-8

Fmoc-Ser(tBu)-OH

Fmoc-Lys(tert-butoxycarbonyl)
71989-26-9

Fmoc-Lys(tert-butoxycarbonyl)

Fmoc-Arg(Pbf)-OH
119831-72-0

Fmoc-Arg(Pbf)-OH

C56H105N9O6

C56H105N9O6

Conditions
ConditionsYield
Stage #1: cis-9-octadecenoamide With sodium cyanoborohydride; acetic acid In methanol; N,N-dimethyl-formamide at 80℃; for 2.5h; solid phase reaction;
Stage #2: Fmoc-Arg(Pbf)-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 2h; solid phase reaction;
Stage #3: Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl) Further stages;		70.8%
...Expand
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate
108869-64-3

3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate

A

3,4,6-tri-O-benzyl-1,2-O-[1-oleamidoethylidene]-α-D-glucopyranose

3,4,6-tri-O-benzyl-1,2-O-[1-oleamidoethylidene]-α-D-glucopyranose

B

1-N-oleanoly-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-gulcopyranosyl)amine

1-N-oleanoly-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-gulcopyranosyl)amine

Conditions
ConditionsYield
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 3-dodecyl-2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;A 62%
B 16%
...Expand
diiodomethane
75-11-6

diiodomethane

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

N,N'-bis<9(Z)-octadecenoylamino>methane
10436-16-5

N,N'-bis<9(Z)-octadecenoylamino>methane

Conditions
ConditionsYield
With iodine; copper In toluene for 48h; Heating;35%
methanol
67-56-1

methanol

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

carbon monoxide
201230-82-2

carbon monoxide

C20H39NO3

C20H39NO3

Conditions
ConditionsYield
With pyridine; [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)](OTf) at 90℃; under 15001.5 Torr; for 90h; Schlenk technique; Autoclave;27%
...Expand
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl trichloroacetimidate
136738-80-2

2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl trichloroacetimidate

A

3,5-di-O-benzoyl-1,2-O-(1-oleamidobenzylidene)-α-D-ribofuranose

3,5-di-O-benzoyl-1,2-O-(1-oleamidobenzylidene)-α-D-ribofuranose

B

1-N-oleanoly-2,3,5-tri-O-benzoyl-β-D-ribofuranosylamine

1-N-oleanoly-2,3,5-tri-O-benzoyl-β-D-ribofuranosylamine

Conditions
ConditionsYield
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 3-dodecyl-2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;A 14.8%
B 19%
...Expand
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

5-(dimethylamino)naphth-1-ylsulfonyl chloride
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

N-(5-(dimethylamino)naphth-1-yl)sulfonyloleamide

N-(5-(dimethylamino)naphth-1-yl)sulfonyloleamide

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 3h;18%
sodium formaldehyde bisulfite
870-72-4

sodium formaldehyde bisulfite

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

oleoylamino-methanesulfonic acid ; sodium-salt
17736-09-3

oleoylamino-methanesulfonic acid ; sodium-salt

Conditions
ConditionsYield
at 185℃;
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

(Z)-9,10-epoxyoctadecamide
15498-10-9

(Z)-9,10-epoxyoctadecamide

Conditions
ConditionsYield
With peracetic acid; acetic acid
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

n-Nonylamin
112-20-9

n-Nonylamin

Conditions
ConditionsYield
With copper-chromite-catalyst; ammonia; Petroleum ether unter Druck;
cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

acetic anhydride
108-24-7

acetic anhydride

acetyl-oleoyl-amine
782480-58-4

acetyl-oleoyl-amine

cis-9-octadecenoamide
301-02-0

cis-9-octadecenoamide

triethylentetramine
112-24-3

triethylentetramine

N-{2-[2-(2-amino-ethylamino)-ethylamino]-ethyl}-oleamide
88658-04-2

N-{2-[2-(2-amino-ethylamino)-ethylamino]-ethyl}-oleamide

Conditions
ConditionsYield
at 130℃; unter vermindertem Druck;
at 130℃; unter vermindertem Druck;

Oleamide Chemical Properties

Empirical Formula: C18H35NO
Molecular Weight: 281.4766
Nominal Mass: 281 Da
Average Mass: 281.4766 Da
Monoisotopic Mass: 281.271865 Da 
EINECS: 206-103-9 
Index of Refraction: 1.468
Molar Refractivity: 89.06 cm3
Molar Volume: 320 cm3
Surface Tension: 33.4 dyne/cm
Density: 0.879 g/cm3
Flash Point: 215.9 °C
Enthalpy of Vaporization: 68.93 kJ/mol
Boiling Point: 433.3 °C at 760 mmHg
Vapour Pressure: 1.03E-07 mmHg at 25 °C
Melting Point: 70 °C
Storage temp.: -20 °C
Appearance: White powder
Structure of Oleamide (CAS NO.301-02-0):
                          

                                    
IUPAC Name: (Z)-Octadec-9-enamide
Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)N
Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)N
InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
InChIKey: FATBGEAMYMYZAF-KTKRTIGZSA-N
Product Category of Oleamide (CAS NO.301-02-0): Mixed Fatty Acids;Color Former & Related Compounds;Functional Materials;Sensitizer;Fatty Acid Derivatives & Lipids;Cannabinoid receptor

Oleamide History

 Oleamide (CAS NO.301-02-0) was originally characterized as an endogenous bioactive substance, isolated from the cerebrospinal fluid of sleep deprived cats. It was characterised in 1995 by Benjamin Cravatt III and Richard Lerner at The Scripps Research Institute in La Jolla, CA .

Oleamide Uses

 Oleamide (CAS NO.301-02-0) is a brain lipid, which may represent a new class of biological signaling molecules, that induces physiological sleep at nanomolar quantities when injected into rats.

Oleamide Safety Profile

Hazard Codes: 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: 1

Oleamide Specification

 Oleamide , its cas register number is 301-02-0. It also can be called cis-9-Octadecenoamide ; cis-9,10-Octadecenoamide ; and 9-Octadecenamide,(z)- . It occurs naturally in the body of animals, and accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression. Oleamide was found by researchers to be leaking out of polypropylene plastics used in laboratory experiments, affecting experimental results.

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