linoleamide MEA
9,12-octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)-
 
Notes:
Linoleoyl ethanolamide inhibits arachidonoylethanolamide amidohydrolase. [HMDB]
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(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide (Click)
CAS Number: 68171-52-8Picture of molecule
ECHA EINECS - REACH Pre-Reg: 269-029-6
FDA UNII: 889DYX0816
MDL: MFCD00674434
XlogP3-AA: 5.60 (est)
Molecular Weight: 323.52029000
Formula: C20 H37 N O2
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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PubMed: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 499.06 °C. @ 760.00 mm Hg (est)
Flash Point: 492.00 °F. TCC ( 255.60 °C. ) (est)
logP (o/w): 6.003 (est)
Soluble in:
 water, 0.108 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antistatic agents
foam boosting agents
hair conditioning
viscosity controlling agents
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Suppliers:
Santa Cruz Biotechnology
For experimental / research use only.
Linoleylethanolamide
Sigma-Aldrich: Sigma
For experimental / research use only.
Linoleyl ethanolamide ≥98%, ethanol solution
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Safety Information:
Preferred SDS: View
 
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
 
Pictogram
 
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 MEA usage levels up to:
 not for fragrance use.
 
Recommendation for linoleamide MEA 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): 68171-52-8
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5283446
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide
Chemidplus: 0068171528
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References:
 (9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5283446
Pubchem (sid): 135065874
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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
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB12252
FooDB: FDB028893
Household Products: Search
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 antistatic agents 
 viscosity controlling agents 
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
monoethanolamine linoleic acid amide
9-(Z),12-(Z)-N-(2-hydroxyethyl) octadeca-9,12-dien-1-amide
N-(2-hydroxyethyl)-linoleamide
N-(2-hydroxyethyl)linoleamide
(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide
 linoleic ethanolamide
 linoleoyl ethanolamide
 linoleoyl monoethanolamide
 linoleoylethanolamide
(9Z,12Z)-octadeca-9,12-dienoic acid (2-hydroxy-ethyl)-amide
9,12-octadecadienamide, N-(2-hydroxyethyl)-, (9Z,12Z)-
N-(9Z,12Z-octadecadienoyl)-ethanolamine
N-cis-9-cis-12-octadecadienoylethanolamine
(9Z,12Z)-N-(2-xhydroxyethyl)octadeca-9,12-dien-1-amide
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Articles:
PubMed: Dietary non-esterified oleic Acid decreases the jejunal levels of anorectic N-acylethanolamines.
PubMed: Simultaneous ultra-high performance liquid chromathograpy-electrospray ionization-quadrupole-time of flight mass spectrometry quantification of endogenous anandamide and related N-acylethanolamides in bio-matrices.
PubMed: Role of anorectic N-acylethanolamines in intestinal physiology and satiety control with respect to dietary fat.
PubMed: Classical endocannabinoid-like compounds and their regulation by nutrients.
PubMed: Troubleshooting in LC-MS/MS method for determining endocannabinoid and endocannabinoid-like molecules in rat brain structures applied to assessing the brain endocannabinoid/endovanilloid system significance.
PubMed: Effect of diet on tissue levels of palmitoylethanolamide.
PubMed: Quantitative analysis of multiple fatty acid ethanolamides using ultra-performance liquid chromatography-tandem mass spectrometry.
PubMed: Lauroylethanolamide and linoleoylethanolamide improve functional outcome in a rodent model for stroke.
PubMed: Dietary fat decreases intestinal levels of the anorectic lipids through a fat sensor.
PubMed: N-acylethanolamines, anandamide and food intake.
PubMed: Influence of dietary fatty acids on endocannabinoid and N-acylethanolamine levels in rat brain, liver and small intestine.
PubMed: Food intake regulates oleoylethanolamide formation and degradation in the proximal small intestine.
PubMed: Intestinal levels of anandamide and oleoylethanolamide in food-deprived rats are regulated through their precursors.
PubMed: Anandamide and 2-arachidonoylglycerol inhibit fatty acid amide hydrolase by activating the lipoxygenase pathway of the arachidonate cascade.
PubMed: Anandamide induces apoptosis in human cells via vanilloid receptors. Evidence for a protective role of cannabinoid receptors.
PubMed: Cannabinoid mimics in chocolate utilized as an argument in court.
PubMed: Anandamide activates human platelets through a pathway independent of the arachidonate cascade.
PubMed: Anandamide hydrolysis by human cells in culture and brain.
PubMed: Dioxygenation of N-linoleoyl amides by soybean lipoxygenase-1.
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