Oleamide

Base Information

• Chemical Name: Oleamide
• CAS No.: 301-02-0
• Deprecated CAS: 181057-55-6,65862-65-9,69899-60-1,94554-98-0,1905405-76-6,65862-65-9,69899-60-1,94554-98-0
• Molecular Formula: C18H35NO
• Molecular Weight: 281.482
• Hs Code.: 29241990
• European Community (EC) Number: 206-103-9
• NSC Number: 26987
• UNII: 7L25QK8BWO
• DSSTox Substance ID: DTXSID6027137
• Nikkaji Number: J36.613G
• Wikipedia: Oleamide
• Wikidata: Q4370
• Pharos Ligand ID: 4Q2SWQ2U8N74
• Metabolomics Workbench ID: 4494
• ChEMBL ID: CHEMBL15927
• Mol file: 301-02-0.mol

Synonyms:9,10-octadecenamide;9-octadecenamide;cis-9,10-octadecenoamide;oleamide;oleic acid amide;oleylamide;oleylamide, (E)-isomer;trans-9,10-octadecenoamide

Chemical Property of Oleamide

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.03E-07mmHg at 25°C
• Melting Point: 70 °C
• Refractive Index: 1.468
• Boiling Point: 433.3 °C at 760 mmHg
• PKA: 16.61±0.40(Predicted)
• Flash Point: 215.9 °C
• PSA: 43.09000
• Density: 0.879 g/cm³
• LogP: 6.20950
• Storage Temp.: −20°C
• Solubility.: Soluble in chloroform (50 mg/ml), ethanol (100 mM), DMSO (~14 mg/ml), and DMF (~14 mg/ml)
• Water Solubility.: Insoluble in water.
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 15
• Exact Mass: 281.271864740
• Heavy Atom Count: 20
• Complexity: 236

Purity/Quality:

98%, ^*data from raw suppliers

Oleamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-36-37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)N
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)N
• Uses: The purpose is as following: 1, it is the chemical additives which must been added to the low-density polyethylene (LDPE) film material. 2, it is also the modifying agent of the plastic ink. 3, it can also be used as the lubricants such as polypropylene (PP), polystyrene (GPPS), phenol (PF) resin, antistatic agents and anti-caking additives. 4, it can also be used as polyethylene, polypropylene, synthetic fibers and other color concentrates and cables (insulation) material lubricant and release agent. 5, it can also be used as the additive for polypropylene (seal) tabletting, efficient heat sheet and sealed material. 6, metal protective agent; stabilizer of the melamine tableware products; lubricants, antifreeze additives of the brake; lubricants of the coatings and dispersion stabilizer of the aluminum coating as well as oil drilling auxiliaries. A brain lipid that induces physiological sleep at nanomolar quantities when injected into rats. This lipid may represent a new class of biological signaling molecules A brain lipid that induces physiological sleep at nanomolar quantities when injected into rats. This lipid may represent a new class of biological signaling molecules. Oleamide has been used as a supplement in glucose and galactose media to prevent the rescue of galactose-induced Leigh syndrome (LS).
• Description: OOleamide (301-02-0) was originally identified in the cerebrospinal fluid of sleep-deprived cats acting as an inducer of physiological sleep in animals.1 Displays agonist activity at cannabinoid CB1 receptors (Ki=8.13 μM).2 Activates PPARγ.3 Produces vasodilator effects in rats.4 Displays neuroprotective effects5 and attenuates sepsis-induced intestinal injury6.

Technology Process of Oleamide

There total 23 articles about Oleamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.6%

cis-Octadecenoic acid (112-80-1,2027-47-6) → cis-9-octadecenoamide (301-02-0,3322-62-1,94554-98-0)

Guidance literature:

With ammonia; zircornium(IV) n-propoxide; at 165 ℃; for 9h; Reagent/catalyst;

Reference yield: 97.0%

(Z)-9-octadecen-1-amine (112-90-3) → cis-9-octadecenoamide (301-02-0,3322-62-1,94554-98-0)

Guidance literature:

With C₃₁H₂₉Br₂N₃Ru; potassium tert-butylate; In tert-butyl alcohol; at 70 ℃; for 24h; regioselective reaction;

DOI:10.1039/d1cy01541a

Reference yield: 95.0%

linoleamide (3999-01-7,3072-13-7) → cis-9-octadecenoamide (301-02-0,3322-62-1,94554-98-0)

Guidance literature:

With ammonia; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88524-0

upstream raw materials:

cis-Octadecenoic acid

acetylurea

Methyl oleate

(Z)-9-octadecenoyl chloride

Downstream raw materials:

cis-9-octadecenenitrile

(Z)-9,10-epoxyoctadecamide

n-Nonylamin

(Z)-9-octadecen-1-amine

Refernces

• 1、 Roe et al.. "-". . p. 18. Retrieved 1952.
• 2、 Yadav, Suman,Reshi, Noor U Din,Pal, Saikat,Bera, Jitendra K.. "Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex". . p. 7018 - 7028. Retrieved 2021/11/17.
• 3、 Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.. "A Convenient Protocol for the Synthesis of Fatty Acid Amides". supporting information. p. 213 - 217. Retrieved 2019/01/14.