oleamide MEA
9-octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
ceramidase inhibitor. N-Oleoylethanolamine (NOE or OEA) is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337, 12056855, 12560208, 11997249). N-oleoyl ethanolamine is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis and degradation to anandamide, NOE cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to NOE can be attributed to activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of NOE inhibits body weight gain in rats. In adipocytes and hepatocytes, NOE inhibits mitogenic and metabolic signaling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. NOE is permanently elevated in diabetic obese patients. NOE also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181). NOE has been shown to be an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, NOE has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536). [HMDB]
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(Z)-N-(2-hydroxyethyl)octadec-9-enamide (Click)
CAS Number: 111-58-0Picture of molecule
ECHA EINECS - REACH Pre-Reg: 203-884-8
Nikkaji Web: J193.596H
MDL: MFCD00045972
XlogP3-AA: 6.30 (est)
Molecular Weight: 325.53623000
Formula: C20 H39 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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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 496.35 °C. @ 760.00 mm Hg (est)
Flash Point: 489.00 °F. TCC ( 254.00 °C. ) (est)
logP (o/w): 6.406 (est)
Soluble in:
 water, 0.06886 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
viscosity controlling agents
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Matrix Scientific
For experimental / research use only.
N-(2-Hydroxyethyl)oleamide, 95%
Santa Cruz Biotechnology
For experimental / research use only.
Oleylethanolamide 98%
Sigma-Aldrich: Sigma
For experimental / research use only.
N-Oleoylethanolamine ∼98% (TLC)
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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
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 oleamide MEA usage levels up to:
 not for fragrance use.
Recommendation for oleamide 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): 111-58-0
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5283454
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
Chemidplus: 0000111580
RTECS: RG2241000 for cas# 111-58-0
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NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 111-58-0
Pubchem (cid): 5283454
Pubchem (sid): 135025785
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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
KEGG (GenomeNet): C20792
HMDB (The Human Metabolome Database): HMDB02088
FooDB: FDB022839
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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N-(2-hydroxyethyl) oleamide
(Z)-octadec-9-enoic acid (2-hydroxy-ethyl)-amide
9-octadecenamide, N-(2-hydroxyethyl)-, (9Z)-
9-octadecenamide, N-(2-hydroxyethyl)-, (Z)-
N-(cis-9-octadecenoyl) ethanolamine
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