301-02-0 Usage
Description
Oleamide, also known as cis-9-octadecenamide, is a fatty amide derived from oleic acid. It is a white powder that is originally obtained from the cerebrospinal fluid of sleep-deprived cats and acts as an inducer of physiological sleep in animals. Oleamide displays agonist activity at cannabinoid CB1 receptors, activates PPARγ, produces vasodilator effects in rats, exhibits neuroprotective effects, and attenuates sepsis-induced intestinal injury.
Uses
Used in Chemical Industry:
Oleamide is used as a chemical additive for low-density polyethylene (LDPE) film material, enhancing the properties and performance of the material.
Used in Plastics and Coatings Industry:
Oleamide is used as a modifying agent for plastic ink, improving its characteristics and application in various coatings.
Used in Lubricants and Additives:
Oleamide is used as a lubricant for materials such as polypropylene (PP), polystyrene (GPPS), phenol (PF) resin, and as an antistatic agent and anti-caking additive, providing improved performance and functionality.
Used in Color Concentrates and Cable Materials:
Oleamide is used as a lubricant and release agent for polyethylene, polypropylene, synthetic fibers, and other color concentrates, as well as for cable (insulation) materials, enhancing their processing and performance.
Used in Pharmaceutical Industry:
Oleamide has been used as a supplement in glucose and galactose media to prevent the rescue of galactose-induced Leigh syndrome (LS), indicating its potential therapeutic applications.
Used in Metal Protection and Stabilization:
Oleamide is used as a metal protective agent, stabilizer for melamine tableware products, and as a lubricant for coatings and dispersion stabilizer for aluminum coating, as well as an oil drilling auxiliary, showcasing its versatility in various industrial applications.
Used in the Automotive Industry:
Oleamide is used as a lubricant and antifreeze additive for brake systems, contributing to improved performance and longevity of automotive components.
Used in Neurobiology and Sleep Research:
Oleamide is a brain lipid that induces physiological sleep at nanomolar quantities when injected into rats, representing a new class of biological signaling molecules with potential implications in sleep regulation and related research.
Nonionic surfactant
Oleamide is a non-ionic surfactant and is white powder-like or flake-like at room temperature. It is nontoxic, insoluble in water and soluble in hot ethanol, ether other organic solvents. It is obtained by refinement of vegetable oil. It has special internal and external lubrication effect and is relative stable to heat, oxygen, and ultraviolet. It has various kinds of properties including anti-adhesive, slipping, leveling, waterproof, moisture-proof, anti-settling, anti-fouling, anti-static electricity and dispersion. Its effects of anti-sticking, anti-static and dispersion are very strong with no hydroscopic property. It is mainly used for high-pressure polyethylene (LDPE) film and composite film, multi-layer co-extruded film, gas-bag, super-thin film, and the slipping agent, anti-block and anti-static agent for polyvinyl chloride (PVC) calendaring film, polypropylene (PP) and curtain-coating polypropylene (CPP); it can also be used as the slipping agent and release agent of resins such as ethylene-vinyl acetate copolymer (EVA), poly-formaldehyde (POM), polycarbonate (PC), polyethylene terephthalate (PET) and polyamide (PA); it can also be used as the slipping agent and antistatic agent of PU surface treatment agent and fiber masterbatch; caking inhibiter, flatting agent, slipping brightening agent of plastic table printing (compound) inks and thermoplastic PE powder; the lubricant and dispersant of pigments, colorants and masterbatch; a indispensable excellent aids for functional opening, slipping masterbatch: it can also be used as metal protecting agent and the lubricants of polyolefin material.
Erucamide
Erucamide is a higher fatty acid amide and is an important derivative of erucic acid and is refined from vegetable oils. It is as waxy solid with no smell and is insoluble in water. It has certain solubility in organic solvents such as ketones, esters, alcohols, ether and benzene. Since the molecular structure contains long chain and unsaturated C22 chain polar amide group, it has excellent surface polarity effect with high melting point and good thermal stability. It can be as substitutes of other similar additive for being widely applied to other plastic, rubber, printing, machinery and other industries. As the processing aid for polyethylene and polypropylene plastics, it can not only make the products be not bonded and increase lubricity, but also can reinforce the thermoplastic and heat resistance of plastics and the product is also non-toxic. Foreign country has allowed it for being applied to foreign food packaging materials. Add the erucic acid amide into the rubber can increase the gloss of the rubber products, tensile strength and elongation rate and enhance the vulcanization accelerator and abrasion resistance with particularly efficacy in preventing the effect of the sun cracks. Adding it to the ink can increase the adhesion, scratch resistance, offset resistance and dye solubility. In addition, erucic acid amide can also be used as the surface lacquer of the calendared paper, protective films of metal and the foam stabilizer of detergent.
The above information is edited by the lookchem of Dai Xiongfeng.
Slippery agent
At present time, common domestic varieties include amides (oleamide and erucamide), soaps (calcium stearate) and organic silicon (silicone). Organic silicon is liquid-like and is expensive as well as being inconvenient for adding usage. There is no domestic professional manufacturer and is difficult for application. Soap products, although is cheap, but has an unsatisfactory effect. It also demands a large adding amount and generally can’t be used in moderate-grade or high-grade products. The slippery agent, oleamide and erucamide has many advantages such as affordable price and significant effect, extremely small addition amount (0.05% to 0.3%), no toxicity (certified by the FDA), wide application range and broad application prospect.
Addition of 0.05%~0.3% oleamide to the low-density polyethylene film can not only improve the antistatic property and lubricating properties, but also improve the anti-moisture performance and can significantly reduce the coefficient of friction and adhesion resistance, significantly increase the efficacy of the membrane blowing (extrusion molding) and can effectively prevent the caking between the film and the agglomeration between the pellets. It may also increase the smoothness of the film surface and prevent the dust accumulation in the surface of the product, leading to very smooth plastic products.
In the polyolefin cable material and wholly plastic communication cable material, addition of oleamide (0.05%) can reduce the friction factor from 0.7 to 0.16 while changing its coloring as well as carbon black dispersion and achieve high-speed extrusion of cable aggregate material and improve the smoothness of the inner wall in the cable jacket pipe.
Adding 2-5 oleamide to the polyamide plastic ink can improve the printing performance and lubricity of ink, enhance the water resistance and scratch resistance and anti-offset characteristic (the fouling caused due to that the ink hasn’t become dry yet) and abrasion resistance. In addition, it can also improve the malleability and adhesiveness of the ink on the printed surface, so that the imprinting is clear and has bright color.
Biological Activity
Endogenous sleep-inducing lipid. Acts as an agonist at the CB 1 cannabinoid receptor (EC 50 = 1.64 μ M). Also appears to potentiate the actions of 5-HT on 5-HT 2A and 2C receptors, and act via an allosteric regulatory site on 5-HT 7 receptors.
Biochem/physiol Actions
Sleep-inducing brain lipid, which allosterically modulates GABAA receptors and potentiates 5-HT7 serotonin receptor responses. Selective endogenous agonist of rat and human CB1 cannabinoid receptor.
Synthesis
Oleamide can be synthesized by ammonolysis of fatty acid or esters with ammonia gas at high pressure.
References
Boger et al. (1998), Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules; Curr. Pharm. Des., 4 303
Leggett et al. (2004), Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors; Br. J. Pharmacol., 141 253
Dionisi et al. (2012), Oleamide activates peroxisome proliferator-activated receptor gamma (PPARγ) in vitro; Lipids Health Dis., 11 51
Hernandez-Diaz et al. (2020), Effects of Oleamide on the Vasomotor Responses in the Rat; Cannabis Cannabinoid Res. 5 42
Maya-Lopez et al. (2020), A Cannabinoid Receptor-Mediated Mechanism Participates in the Neuroprotective Effects of Oleamide Against Excitotoxic Damage in Rat Brain Synaptosomes and Cortical Slices; Neurotox. Res., 37 126
Zou et al. (2019), Cx43 Inhibition Attenuates Sepsis-Induced Intestinal Injury via Downregulating ROS Transfer and the Activation of the JNK1/Sirt1/FoxO3a Signaling Pathway; Mediators Inflamm., 2019 7854389
Check Digit Verification of cas no
The CAS Registry Mumber 301-02-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,0 and 1 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 301-02:
(5*3)+(4*0)+(3*1)+(2*0)+(1*2)=20
20 % 10 = 0
So 301-02-0 is a valid CAS Registry Number.
InChI:InChI=1/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+
301-02-0Relevant articles and documents
Synthesis of primary amides by lipase-catalyzed amidation of carboxylic acids with ammonium salts in an organic solvent
Litjens, Mike J. J.,Straathof, Adrie J. J.,Jongejan, Jaap A.,Heijnen, Joseph J.
, p. 1255 - 1256 (1999)
The synthesis of butyramide and oleamide, by Candida antarctica lipase B-catalyzed amidation of the carboxylic acids, in an organic solvent with ammonium bicarbonate or ammonium carbamate as a source of ammonia results in good yields, making prior activation of the acids unnecessary.
Design, synthesis and gelation of low molecular weight organo-gelators derived from oleic acid via, amidation
Gupta, Gaurav R.,Joshi, Narendra S.,Phalak, Raju P.,Waghulde, Govinda P.
, p. 1109 - 1116 (2021/11/17)
In recent decades, gels have been widely considered for various medicinal purposes and, in particular, wound healing applications. In this regard, amides of oleic acids and 9, 10-dihydroxyoctadecanoic acid are synthesized and characterized with the help of modern analytical tools. Among the mentioned amide frameworks, N-(2-aminoethyl)-oleamide exhibits high order of gelation not only with different organic solvents such as n-hexane and DMSO but also with different edible oils such as sesame oil, mustard oil, coconut oil and citriodora oil. Here, we briefly discuss the optimization of gelation conditions for the synthesized amides as organo-gelator, in addition to that the minimum gelation concentration and gelation temperature have also been studied.
CHEMICAL UNCOUPLERS OF RESPIRATION AND METHODS OF USE THEREOF
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Paragraph 0248, (2020/11/27)
Uncoupling of respiration is a well-recognized process that increases respiration and heat production in cells. Provided herein are chemical uncouplers of respiration that are compounds of Formula (I). Also provided are methods for preventing or treating metabolic disorders and modulating metabolic processes using compound of Formula (I).
A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides
Dalu, Francesca,Scorciapino, Mariano A.,Cara, Claudio,Luridiana, Alberto,Musinu, Anna,Casu, Mariano,Secci, Francesco,Cannas, Carla
supporting information, p. 375 - 381 (2018/02/07)
A green, one-pot approach based on the solvothermal amidation of carboxylic acids with amines has been developed for the synthesis of diverse aliphatic and aromatic amides. It does not require the use of catalysts or coupling reagents and it occurs in the presence of ethanol that has been proved to have a key role in the process. The proposed strategy is also extendable to biologically active amides and could represent a low-cost and waste-less alternative to the common synthetic pathways.