20545-92-0

Basic information

• Product Name: N-(2-hydroxyethyl)undec-10-enamide
• Synonyms: N-(2-hydroxyethyl)undec-10-enamide;UNDECYLENAMIDE MEA;10-Undecenamide, N-(2-hydroxyethyl)-;10-Undecylenic acid monoethanolamide;N-(2-Hydroxyethyl)-10-undecenamide;Undecylenic monoethanolamide;Fungicid UMA;Mayfung
• CAS NO: 20545-92-0
• Molecular Formula: C₁₃H₂₅NO₂
• Molecular Weight: 227.3431
• EINECS: 243-870-9
• Mol File: 20545-92-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 56-58℃
• Boiling Point: 409.4°Cat760mmHg
• Flash Point: 201.4°C
• Appearance: /
• Density: 0.940
• Vapor Pressure: 2.06E-08mmHg at 25°C
• Refractive Index: 1.467
• PKA: 14.49±0.10(Predicted)
• CAS DataBase Reference: N-(2-hydroxyethyl)undec-10-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyethyl)undec-10-enamide(20545-92-0)
• EPA Substance Registry System: N-(2-hydroxyethyl)undec-10-enamide(20545-92-0)

Safety Data

• Hazardous Substances Data: 20545-92-0(Hazardous Substances Data)

Usage

Description

N-(2-hydroxyethyl)undec-10-enamide, commonly known as oleamide, is a fatty acid primary amide that is naturally found in the human body. It is synthesized from oleic acid and is structurally similar to the endogenous neurotransmitter, anandamide. This similarity allows oleamide to interact with various proteins and receptors, such as cannabinoid, GABA, and serotonin receptors, and is associated with sleep induction, mood regulation, and other neurological functions. Furthermore, its plasticizing and stabilizing properties make it a valuable component in the production of polymeric materials.

Uses

Used in Pharmaceutical Applications:
N-(2-hydroxyethyl)undec-10-enamide is used as a neurological agent for its sleep-inducing and mood-regulating properties. Its interaction with cannabinoid, GABA, and serotonin receptors contributes to its therapeutic effects on the central nervous system.
Used in Polymer Manufacturing:
N-(2-hydroxyethyl)undec-10-enamide is used as a plasticizer and stabilizer in the production of polymeric materials. Its ability to enhance the flexibility and stability of polymers makes it an essential component in the manufacturing process.
Used in Cosmetics Industry:
N-(2-hydroxyethyl)undec-10-enamide is used as an ingredient in cosmetic formulations for its potential skin conditioning and moisturizing effects, which can be attributed to its interaction with skin proteins and lipids, improving the overall texture and appearance of the skin.

InChI:InChI=1/C13H25NO2/c1-2-3-4-5-6-7-8-9-10-13(16)14-11-12-15/h2,15H,1,3-12H2,(H,14,16)

Upstream product

• 112-38-9 10-undecenoic acid 
• 141-43-5 ethanolamine 
• 692-86-4 ethyl 10-undecenenoate 

Relevant articles and documents

Poly-2-oxazoline-derived polyurethanes: A versatile synthetic approach to renewable polyurethane thermosets

2-Nonyl-2-oxazoline and 2-(9-decenyl)-2-oxazoline have been copolymerized in different proportions by cationic ring-opening polymerization to obtain a series of random linear copolymers with tailored molecular weight and double bond functionality in the side chains. Thiol-ene addition of 2-mercaptoethanol has been used to produce a set of polyoxazoline-polyols under mild conditions and with quantitative double bond transformation. The polyols obtained in this way were reacted with methylene-bis(phenylisocyanate) to yield a series of amorphous and semicrystalline polyurethane networks. The thermal stability and the thermomechanical properties of these thermosets have been studied and related with the structure of the parent polyols.

ANTIMICROBIAL PRESERVATIVE COMPOSITIONS FOR PERSONAL CARE PRODUCTS

A personal product antimicrobial preservative composition for preservation of topical personal care formulations is provided comprising [A] one or more undecylenic acid derivatives depicted by Formula (I), [B] one or more octanoic acid derivatives depicted by Formula (II), and [C] 2-phenoxy ethanol or 2-ethyl hexyl glyceryl ether or mixture of these two ‘liquid alcohol ethers’; wherein, each of the two components [A] and [B] is present in the range of 5 to 20% by weight and together [A] and [B] constitute 10 to 30% by weight and the ‘liquid alcohol ether’, component [C], is present 70 to 90% by weight of the total preservative composition. A method for preserving personal care product from microbial attack is provided containing an aqueous phase comprising three component composition from about 0.5 to 2.5% by weight of the total personal care formulation.

Synthesis and anticonvulsant activity of N-(2-hydroxyethyl)amide derivatives

A series novel of N-(2-hydroxyethyl)amide derivatives was synthesized and screened for their anticonvulsant activities by the maximal electroshock (MES) test, and their neurotoxicity was evaluated by the rotarod test (Tox). The maximal electroshock test showed that N-(2-hydroxyethyl)decanamide 1g, N-(2-hydroxyethyl)palmitamide 1l, and N-(2-hydroxyeth-yl)stearamide 1n were found to show a better anticonvulsant activity and also had lower toxicity than the marked anti-epileptic drug valproate. In the anti-MES potency test, these compounds exhibited median effective doses (ED50) of 22.0, 23.3, 20.5 mg/kg, respectively, and median toxicity doses (TD50) of 599.8, >1000, >1000 mg/kg, respectively, resulting in a protective index (PI) of 27.5, >42.9, >48.8, respectively. This is a much better protective index than that of the marked anti-epileptic drug valproate (PI = 1.6). To further investigate the effects of the anticonvulsant activity in several different models, compounds 1g, 1l, and 1n were tested having evoked convulsions with chemical substances, including pentylenetetrazloe, isoniazide, 3-mercaptopropionic acid, bicuculline, thiosemicarbazide, and strychnine.