Home Other Building Blocks 301-02-0
301-02-0,MFCD00053638
Catalog No.:AA0037BY

301-02-0 | (9Z)-octadec-9-enamide

Pack Size
Purity
Availability
Price(USD)
Quantity
  
100g
65%
in stock  
$12.00   $8.00
- +
500g
65%
in stock  
$32.00   $22.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0037BY
Chemical Name:
(9Z)-octadec-9-enamide
CAS Number:
301-02-0
Molecular Formula:
C18H35NO
Molecular Weight:
281.4766
MDL Number:
MFCD00053638
SMILES:
CCCCCCCC/C=C\CCCCCCCC(=O)N
NSC Number:
26987
Properties
Properties
 
BP:
433.3°C at 760 mmHg  
Form:
Solid  
MP:
70 °C  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
236  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
15  
XLogP3:
6.6  

Downstream Synthesis Route

[1],1957,vol.6,p.83    Chem.Abstr.,1961,p.4992

[1]Barton;Jaszberenyi;Theodorakis[Tetrahedron,1992,vol.48,#13,p.2613-2626]

[2]Witt,Timo;Stempfle,Florian;Roesle,Philipp;Häussler,Manuel;Mecking,Stefan[ACSCatalysis,2015,vol.5,#8,p.4519-4529]

[3]CurrentPatentAssignee:EASTMANKODAKCO-US2458373,1945,A

[4]CurrentPatentAssignee:AKZONOBELNV-US2206351,1937,A

[5]CurrentPatentAssignee:AKZONOBELNV-US2206351,1937,A

[6]CurrentPatentAssignee:AKZONOBELNV-US2206351,1937,A

[1]Roe;Scanlan;Swern[JournaloftheAmericanChemicalSociety,1949,vol.71,p.2219]

[1]CurrentPatentAssignee:MARTINDENNIS-US2294442,1939,A

[1]Roe;Scanlan;Swern[JournaloftheAmericanChemicalSociety,1949,vol.71,p.2217]

[2]Roe;Scanlan;Swern[JournaloftheAmericanChemicalSociety,1949,vol.71,p.2217]

[3]CurrentPatentAssignee:RESINOUSPRODCHEMICAL-US1989968,1934,A

Literature

Title: Neuroprotective activity of macamides on manganese-induced mitochondrial disruption in U-87 MG glioblastoma cells.

Journal: Toxicology and applied pharmacology 20180201

Title: Screening of endocrine activity of compounds migrating from plastic baby bottles using a multi-receptor panel of in vitro bioassays.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20161201

Title: Role of heteromeric gap junctions in the cytotoxicity of cisplatin.

Journal: Toxicology 20130809

Title: The endocannabinoid system modulates the valence of the emotion associated to food ingestion.

Journal: Addiction biology 20120701

Title: Lipopolysaccharide effects on the proliferation of NRK52E cells via alternations in gap-junction function.

Journal: The journal of trauma and acute care surgery 20120701

Title: Enhanced vasorelaxant effects of the endocannabinoid-like mediator, oleamide, in hypertension.

Journal: European journal of pharmacology 20120605

Title: Primary fatty acid amide metabolism: conversion of fatty acids and an ethanolamine in N18TG2 and SCP cells.

Journal: Journal of lipid research 20120201

Title: Oleamide activates peroxisome proliferator-activated receptor gamma (PPARγ) in vitro.

Journal: Lipids in health and disease 20120101

Title: Trilysinoyl oleylamide-based cationic liposomes for systemic co-delivery of siRNA and an anticancer drug.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20111010

Title: A novel hypothesis about mechanisms affecting conduction velocity of central myelinated fibers.

Journal: Neurochemical research 20111001

Title: Identification of oleamide in Guatteria recurvisepala by LC/MS-based Plasmodium falciparum thioredoxin reductase ligand binding method.

Journal: Planta medica 20111001

Title: Gap junctions favor normal rat kidney epithelial cell adaptation to chronic hypertonicity.

Journal: American journal of physiology. Cell physiology 20110901

Title: Therapeutic effects of connexin inhibitors on detrusor overactivity induced by bladder outlet obstruction in rats.

Journal: Urology 20110801

Title: Low concentrations of alendronate increase the local invasive potential of osteoblastic sarcoma cell lines via connexin 43 activation.

Journal: Pathology, research and practice 20110715

Title: The endogenous cannabinoid anandamide shares discriminative stimulus effects with ∆(9)-tetrahydrocannabinol in fatty acid amide hydrolase knockout mice.

Journal: European journal of pharmacology 20110410

Title: Berberine potentizes apoptosis induced by X-rays irradiation probably through modulation of gap junctions.

Journal: Chinese medical journal 20110401

Title: Connexin 32 and its derived homotypic gap junctional intercellular communication inhibit the migration and invasion of transfected HeLa cells via enhancement of intercellular adhesion.

Journal: Molecular medicine reports 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Oleamide administered into the nucleus accumbens shell regulates feeding behaviour via CB1 and 5-HT2C receptors.

Journal: The international journal of neuropsychopharmacology 20101001

Title: Oleamide suppresses lipopolysaccharide-induced expression of iNOS and COX-2 through inhibition of NF-kappaB activation in BV2 murine microglial cells.

Journal: Neuroscience letters 20100503

Title: Acute and subchronic administration of anandamide or oleamide increases REM sleep in rats.

Journal: Pharmacology, biochemistry, and behavior 20100301

Title: Chemical synthesis of 9(Z)-octadecenamide and its hypolipidemic effect: a bioactive agent found in the essential oil of mountain celery seeds.

Journal: Journal of agricultural and food chemistry 20100210

Title: The structure of oleamide films at the aluminum/oil interface and aluminum/air interface studied by Sum Frequency Generation (SFG) vibrational spectroscopy and Reflection Absorption Infrared Spectroscopy (RAIRS).

Journal: ACS applied materials & interfaces 20090801

Title: Insights into the mechanism and inhibition of fatty acid amide hydrolase from quantum mechanics/molecular mechanics (QM/MM) modelling.

Journal: Biochemical Society transactions 20090401

Title: Mechanisms involved in oleamide-induced vasorelaxation in rat mesenteric resistance arteries.

Journal: European journal of pharmacology 20090401

Title: One-step formation of straight nanostripes from a mammal lipid-oleamide directly on highly oriented pyrolytic graphite.

Journal: Langmuir : the ACS journal of surfaces and colloids 20090217

Title: The role of gap junctions in megakaryocyte-mediated osteoblast proliferation and differentiation.

Journal: Bone 20090101

Title: Selective blockade of 2-arachidonoylglycerol hydrolysis produces cannabinoid behavioral effects.

Journal: Nature chemical biology 20090101

Title: Biosynthesis of oleamide.

Journal: Vitamins and hormones 20090101

Title: Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors.

Journal: Journal of medicinal chemistry 20081211

Title: Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation.

Journal: Bioorganic & medicinal chemistry 20081115

Title: Bioactive contaminants leach from disposable laboratory plasticware.

Journal: Science (New York, N.Y.) 20081107

Title: Biosynthesis, degradation and pharmacological importance of the fatty acid amides.

Journal: Drug discovery today 20080701

Title: Effect of oleamide on pentylenetetrazole-induced seizures in rats.

Journal: Bulletin of experimental biology and medicine 20080201

Title: Evaluation of fatty acid amides in the carrageenan-induced paw edema model.

Journal: Neuropharmacology 20080101

Title: Oleamide derivatives are prototypical anti-metastasis drugs that act by inhibiting Connexin 26.

Journal: Current drug safety 20070901

Title: Neuropharmacological effects of oleamide in male and female mice.

Journal: Behavioural brain research 20070822

Title: Anxiolytic-like effects of oleamide in group-housed and socially isolated mice.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20070815

Title: Oleamide synthesizing activity from rat kidney: identification as cytochrome c.

Journal: The Journal of biological chemistry 20070803

Title: Oleamide derivatives suppress the spontaneous metastasis by inhibiting connexin 26.

Journal: International journal of cancer 20070701

Title: Does rat granulation tissue maturation involve gap junction communications?

Journal: Plastic and reconstructive surgery 20070701

Title: The functional interrelationship between gap junctions and fenestrae in endothelial cells of the liver organoid.

Journal: The Journal of membrane biology 20070601

Title: Interferon-gamma inhibits intestinal restitution by preventing gap junction communication between enterocytes.

Journal: Gastroenterology 20070601

Title: Comparison of three gas chromatography methods for the determination of slip agents in polyethylene films.

Journal: Journal of chromatography. A 20070525

Title: Potent and selective alpha-ketoheterocycle-based inhibitors of the anandamide and oleamide catabolizing enzyme, fatty acid amide hydrolase.

Journal: Journal of medicinal chemistry 20070308

Title: Identification of fatty acids and fatty acid amides in human meibomian gland secretions.

Journal: Investigative ophthalmology & visual science 20070101

Title: Oleamide: a fatty acid amide signaling molecule in the cardiovascular system?

Journal: Cardiovascular drug reviews 20070101

Title: Elucidation of hydrolysis mechanisms for fatty acid amide hydrolase and its Lys142Ala variant via QM/MM simulations.

Journal: Journal of the American Chemical Society 20061227

Title: A second fatty acid amide hydrolase with variable distribution among placental mammals.

Journal: The Journal of biological chemistry 20061201

Title: In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide.

Journal: Prostaglandins & other lipid mediators 20061201

Title: Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N-oleoylethanolamine analogues.

Journal: Chemistry and physics of lipids 20061001

Title: Determination of oleamide and erucamide in polyethylene films by pressurised fluid extraction and gas chromatography.

Journal: Journal of chromatography. A 20060818

Title: Gap junction communications influence upon fibroblast synthesis of Type I collagen and fibronectin.

Journal: Journal of cellular biochemistry 20060701

Title: Possible involvement of gap junctions in the barrier function of tight junctions of brain and lung endothelial cells.

Journal: Journal of cellular physiology 20060701

Title: Fatty acid amide hydrolase (-/-) mice exhibit an increased sensitivity to the disruptive effects of anandamide or oleamide in a working memory water maze task.

Journal: The Journal of pharmacology and experimental therapeutics 20060401

Title: Enhanced radiosensitization of p53 mutant cells by oleamide.

Journal: International journal of radiation oncology, biology, physics 20060401

Title: Vasorelaxant effects of oleamide in rat small mesenteric artery indicate action at a novel cannabinoid receptor.

Journal: British journal of pharmacology 20060301

Title: [The role of gap junction communication in metastatic B16 melanoma in C57BL mice].

Journal: Voprosy onkologii 20060101

Title: Pharmacological enhancement of cannabinoid CB1 receptor activity elicits an antidepressant-like response in the rat forced swim test.

Journal: European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20051201

Title: The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

Journal: Journal of medicinal chemistry 20050811

Title: A spectrophotometric assay for fatty acid amide hydrolase suitable for high-throughput screening.

Journal: Biochemical pharmacology 20050415

Title: Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells.

Journal: Biochemistry 20041005

Title: A derivative of oleamide potently inhibits the spontaneous metastasis of mouse melanoma BL6 cells.

Journal: Carcinogenesis 20041001

Title: Acyl-CoA: cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas.

Journal: Bioorganic & medicinal chemistry letters 20040816

Title: Characterization of the sleep-wake patterns in mice lacking fatty acid amide hydrolase.

Journal: Sleep 20040801

Title: Oleamide and anandamide effects on food intake and sexual behavior of rats.

Journal: Neuroscience letters 20040624

Title: Bilateral organization of unilaterally generated activity in lumbar spinal motoneurons of the rat.

Journal: Brain research 20040529

Title: The sleep lipid oleamide may represent an endogenous anticonvulsant: an in vitro comparative study in the 4-aminopyridine rat brain-slice model.

Journal: Neuropharmacology 20040301

Title: Differential effects of the sleep-inducing lipid oleamide and cannabinoids on the induction of long-term potentiation in the CA1 neurons of the rat hippocampus in vitro.

Journal: Brain research 20040130

Title: The sleep inducing brain lipid cis-oleamide (cOA) does not modulate serotonergic transmission in the CA1 pyramidal neurons of the hippocampus in vitro.

Journal: Neuropharmacology 20040101

Title: Oleamide: a member of the endocannabinoid family?

Journal: British journal of pharmacology 20040101

Title: Oleamide is a selective endogenous agonist of rat and human CB1 cannabinoid receptors.

Journal: British journal of pharmacology 20040101

Title: The serotonergic system may be involved in the sleep-inducing action of oleamide in rats.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20031201

Title: Carbenoxolone inhibits DNA synthesis and collagen gene expression in rat hepatic stellate cells in culture.

Journal: Journal of hepatology 20031101

Title: Selective effect of oleamide, an endogenous sleep-inducing lipid amide, on pentylenetetrazole-induced seizures in mice.

Journal: The Journal of pharmacy and pharmacology 20030801

Title: Economically pertinent continuous amide formation by direct lipase-catalyzed amidation with ammonia.

Journal: Biotechnology and bioengineering 20030620

Title: Effects of oleamide on choline acetyltransferase and cognitive activities.

Journal: Bioscience, biotechnology, and biochemistry 20030601

Title: Expression of connexin 43 mRNA in microisolated murine osteoclasts and regulation of bone resorption in vitro by gap junction inhibitors.

Journal: Biochemical and biophysical research communications 20030418

Title: Patterns of dye coupling in lumbar motor nuclei of the rat.

Journal: The Journal of comparative neurology 20021202

Title: Membrane protein crystallization in meso: lipid type-tailoring of the cubic phase.

Journal: Biophysical journal 20021201

Title: Induction of Oct-3/4 expression in somatic cells by gap junction-mediated cAMP signaling from blastomeres.

Journal: European journal of cell biology 20021101

Title: Oleamide attenuates apoptotic death in cultured rat cerebellar granule neurons.

Journal: Neuroscience letters 20020809

Title: Pharmacological activity of fatty acid amides is regulated, but not mediated, by fatty acid amide hydrolase in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 20020701

Title: The sleep hormone oleamide modulates inhibitory ionotropic receptors in mammalian CNS in vitro.

Journal: British journal of pharmacology 20020401

Title: Gap junction intercellular communication propagates cell death in cancerous cells.

Journal: Oncogene 20020327

Title: Fatty acid amide hydrolase, an enzyme with many bioactive substrates. Possible therapeutic implications.

Journal: Current pharmaceutical design 20020101

Title: Deletion of the GABA(A) receptor beta 3 subunit eliminates the hypnotic actions of oleamide in mice.

Journal: Neuroreport 20011221

Title: Allosteric modulation of the human 5-HT(7A) receptor by lipidic amphipathic compounds.

Journal: Molecular pharmacology 20011201

Title: Effect of oleamide on Ca(2+) signaling in human bladder cancer cells.

Journal: Biochemical pharmacology 20011115

Title: Oleamide modulates memory in rats.

Journal: Neuroscience letters 20011102

Title: Effect of oleamide on sleep and its relationship to blood pressure, body temperature, and locomotor activity in rats.

Journal: Experimental neurology 20011101

Title: The hypnotic actions of the fatty acid amide, oleamide.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20011101

Title: Behavioral evidence for the interaction of oleamide with multiple neurotransmitter systems.

Journal: The Journal of pharmacology and experimental therapeutics 20011001

Title: Fatty acid amides are putative endogenous ligands for anaesthetic recognition sites in mammalian CNS.

Journal: British journal of anaesthesia 20010901

Title: Fatty acid amide hydrolase: biochemistry, pharmacology, and therapeutic possibilities for an enzyme hydrolyzing anandamide, 2-arachidonoylglycerol, palmitoylethanolamide, and oleamide.

Journal: Biochemical pharmacology 20010901

Title: Effective reduction of neuronal death by inhibiting gap junctional intercellular communication in a rodent model of global transient cerebral ischemia.

Journal: Experimental neurology 20010801

Title: Gap junctions modulate survival-promoting effects of fibroblast growth factor-2 on cultured midbrain dopaminergic neurons.

Journal: Molecular and cellular neurosciences 20010701

Title: alpha-Keto heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group modification and alpha-substitution.

Journal: Bioorganic & medicinal chemistry letters 20010618

Title: Direct methylation procedure for converting fatty amides to fatty acid methyl esters in feed and digesta samples.

Journal: Journal of agricultural and food chemistry 20010501

Title: Inhibition of gap-junctional communication induces the trans-differentiation of osteoblasts to an adipocytic phenotype in vitro.

Journal: The Journal of biological chemistry 20010427

Title: Linoleamide, a brain lipid that induces sleep, increases cytosolic Ca2+ levels in MDCK renal tubular cells.

Journal: Life sciences 20010119

Title: Anesthetic-like interaction of the sleep-inducing lipid oleamide with voltage-gated sodium channels in mammalian brain.

Journal: Anesthesiology 20010101

Title: How to close a gap junction channel. Efficacies and potencies of uncoupling agents.

Journal: Methods in molecular biology (Clifton, N.J.) 20010101

Title: Allosteric regulation by oleamide of the binding properties of 5-hydroxytryptamine7 receptors.

Journal: Biochemical pharmacology 19991201

Title: Mendelson WB, et al. The hypnotic actions of the fatty acid amide, oleamide. Neuropsychopharmacology. 2001 Nov;25(5 Suppl):S36-9.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:301-02-0 Molecular Formula|301-02-0 MDL|301-02-0 SMILES|301-02-0 (9Z)-octadec-9-enamide