9,12-octadecadienamide, (9Z,12Z)-
None found
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(9Z,12Z)-octadeca-9,12-dienamide (Click)
CAS Number: 3999-01-7Picture of molecule
ECHA EINECS - REACH Pre-Reg: 223-644-6
Nikkaji Web: 42693.4
XlogP3-AA: 5.90 (est)
Molecular Weight: 279.46721000
Formula: C18 H33 N O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 437.60 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.000000 mm/Hg @ 25.00 °C. (est)
Flash Point: 425.00 °F. TCC ( 218.40 °C. ) (est)
logP (o/w): 6.231 (est)
Soluble in:
 water, 0.07195 mg/L @ 25 °C (est)
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Organoleptic Properties:
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antistatic agents
hair conditioning
opacifying agents
viscosity controlling agents
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 None found
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Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: cosmetic agents
Recommendation for linoleamide usage levels up to:
 not for fragrance use.
Recommendation for linoleamide flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 3999-01-7
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 6435901
National Institute of Allergy and Infectious Diseases: Data
Chemidplus: 0003999017
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NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 6435901
Pubchem (sid): 135020464
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
ChemSpider: View
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Potential Blenders and core components note
None Found
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Potential Uses:
 antistatic agents 
 opacifying agents 
 viscosity controlling agents 
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Occurrence (nature, food, other): note
 not found in nature
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 linoleic acid amide
(9Z,12Z)-octadeca-9,12-dienoic acid amide
9,12-octadecadienamide, (9Z,12Z)-
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PubMed: [Potential cytostatic effect of the maleimide derivative 1-(4-Cl-benzyl)-3-Cl-4-(CF3-phenylamino)-1-H-pyrrol-2,5-dione].
PubMed: The macamide N-3-methoxybenzyl-linoleamide is a time-dependent fatty acid amide hydrolase (FAAH) inhibitor.
PubMed: Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells.
PubMed: Anti-inflammatory effects of fatty acids isolated from Chromolaena odorata.
PubMed: Hypolipidemic and antioxidant activity of the novel acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor KY-455 in rabbits and hamsters.
PubMed: The biohydrogenation of linoleamide in vitro and its effects on linoleic acid concentration in duodenal contents of sheep.
PubMed: Effect of oleamide on Ca(2+) signaling in human bladder cancer cells.
PubMed: Linoleamide, a brain lipid that induces sleep, increases cytosolic Ca2+ levels in MDCK renal tubular cells.
PubMed: [Effect of presynaptic dopaminergic agonism on the immobility of mice in the forced swimming test].
PubMed: Mass spectrometric identification of N-phenyllinoleamide metabolites in mouse peritoneal macrophages.
PubMed: Effects of NB-598, a potent squalene epoxidase inhibitor, on the apical membrane uptake of cholesterol and basolateral membrane secretion of lipids in Caco-2 cells.
PubMed: [Effect of some GABA, glycine, or glutamic acid derivatives on the forced swimming test in mice].
PubMed: [Are there glutamatergic, anti-GABAergic or antiglycinergic components in the action mechanism of adamantamines? Study of convulsions induced by amantadine or 1-adamantylcyclopentanamine in mice].
PubMed: [Effect of glutamic acid palmitamide or linoleamide on convulsions induced by pentetrazole].
PubMed: [Oral dyskinesia in rats after a single administration of haloperidol combined with GABA-linoleamide. A model of dyskinesia in man].
PubMed: Cholesterol-lowering effect of N-(alpha-methylbenzyl)linoleamide (melinamide) in cholesterol-fed diabetic rats.
PubMed: Determination of oxidation products of N-phenyllinoleamide: Spanish toxic oil syndrome studies.
PubMed: [Effect of glycine-steatamide or glutamic acid palmitamide on oral dyskinesia, obtained by a single administration of haloperidol combined with GABA-linoleamide in rats].
PubMed: [Synthesis and pharmacological study of glutamic acid palmitamide and linoleamide].
PubMed: Chain-shortening of a xenobiotic acyl compound by the peroxisomal beta-oxidation system in rat liver.
PubMed: Mechanism of the inhibition of cholesterol absorption by DL-melinamide: inhibition of cholesterol esterification.
PubMed: [Vacuous chewing after haloperidol and GABA-linoleamide administration in the rat].
PubMed: [Effect of GABA-linoleamide and glycine-linoleamide on catalepsy in the rat after chronic administration of reserpine].
PubMed: Inhibitory effect of melinamide on cholesterol solubility in mixed micellar solution of sodium taurocholate.
PubMed: [Effects of GABA-ergic and glycinergic agents on pentamethylenetetrazole-induced convulsions in rats submitted to repeated injections of reserpine].
PubMed: [Effect of GABA-linoleamide and glycine linoleamide on pentamethylenetetrazole convulsions].
PubMed: [Effect of glycine linoleamide on haloperidol and reserpine catalepsy in the rat].
PubMed: [Effect of glycine linoleamide on thermoregulation in mice and rats].
PubMed: [Synthesis and pharmacological study of glycine linoleamide].
PubMed: [The effect of various new GABAergics on motor and oral stereotypes with apomorphine in the rat].
PubMed: [2 new GABA-ergics (GABA-linoleamide and GABA-steatamide). On 2 experimental models of depression].
PubMed: [Effect of GABA linoleamide on thermoregulation in mice exposed to low temperatures].
PubMed: [Action of GABA-linoleamide on blood cholesterol in rats].
PubMed: [Effect of GABA linoleamide on internal temperature regulation in the mouse].
PubMed: [Psychopharmacologic profile of a new product: GABA linoleamide (Gabalid)].
PubMed: 14C-labelling of a hypocholesterolemic agents, N-(alpha-methylbenzyl) linoleamide.
PubMed: Linoleic acid amides: effect on cholesteremia and atherosclerosis.
PubMed: Metabolism of linoleamides. II. Absorption, distribution, excretion and metabolism of N-[alpha-phenyl-beta-(p-tolyl)ethyl]linoleamide.
PubMed: Metabolism of linoleamides. I. Absorption, excretion and metabolism of N-(alpha-methylbenzyl)linoleamide in rat and man.
PubMed: Effect of (-)N-[alpha-phenyl-beta-(p-tolyl)ethyl] linoleamide on lipid levels in serum and liver in cholesterol-fed rats.
PubMed: Inhibition of cholesterol absorption by (-)N-[alpha-phenyl-beta-(p-tolyl)ethyl] linoleamide in rats.
PubMed: Influence of N( -methylbenzyl)linoleamide upon cholesterol metabolism in rats.
PubMed: Enzymatic hydrolysis of N-(alpha-methylbenzyl)linoleamide.
PubMed: Cholesterol esterification in vitro with DL-N-(alpha-methylbenzyl)-(1-14C)linoleamide.
PubMed: The effect of (--)N-(alpha-phenyl-beta-(p-tolyl)ethyl) linoleamide on experimental atherosclerosis in rabbits.
PubMed: The effect of N-(alpha-methylbenzyl) linoleamide on cholesterol metabolism in rats.
PubMed: Cholesterol-lowering effects of DL-N-(alpha-methylbenzyl)-linoleamide and its optically active isomers in cholesterol-fed animals.
PubMed: The effect of N-(alpha-methylbenzyl) linoleamide on experimental atherosclerosis in rabbits.
PubMed: Agents affecting lipid metabolism. XXXVI. Effect of N-cyclohexyl linoleamide on hepatic cholesterogenesis in vitro.
PubMed: Influence of N-cyclohexyl linoleamide on cholesterol synthesis by rat liver slices.
PubMed: Effect of N-cyclohexyl linoleamide on cholesterol metabolism in rats.
PubMed: Linolexamide (N-cyclohexyl linoleamide) in experimental atherosclerosis in rabbits.
PubMed: The effect of N-cyclohexyl linoleamide on experimental atherosclerosis in rabbits.
PubMed: N-cyclohexyl linoleamide: metabolism and cholesterol-lowering effect in rats.
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