Home Other Building Blocks (5Z,8Z,11Z,14Z)-1,3-Dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate

(5Z,8Z,11Z,14Z)-1,3-Dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate

CAS No.:
53847-30-6
Catalog Number:
AG003GKF
Molecular Formula:
C23H40O3
Molecular Weight:
364.5619
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95% (as a 9:1 mixture of the 2-<wbr/>AG and 1-<wbr/>AG)
1 week
United States
$91
- +
5mg
≥95% (as a 9:1 mixture of the 2-<wbr/>AG and 1-<wbr/>AG)
1 week
United States
$196
- +
10mg
≥95% (as a 9:1 mixture of the 2-<wbr/>AG and 1-<wbr/>AG)
1 week
United States
$265
- +
25mg
≥95% (as a 9:1 mixture of the 2-<wbr/>AG and 1-<wbr/>AG)
1 week
United States
$447
- +
Product Description
Catalog Number:
AG003GKF
Chemical Name:
(5Z,8Z,11Z,14Z)-1,3-Dihydroxypropan-2-yl icosa-5,8,11,14-tetraenoate
CAS Number:
53847-30-6
Molecular Formula:
C23H40O3
Molecular Weight:
364.5619
MDL Number:
MFCD01862600
IUPAC Name:
1,3-dihydroxypropan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
InChI:
InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-22(20-24)21-25/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/b7-6-,10-9-,13-12-,16-15-
InChI Key:
RCRCTBLIHCHWDZ-DOFZRALJSA-N
SMILES:
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCOC(CO)CO
UNII:
8D239QDW64
Properties
Complexity:
445  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
4  
Exact Mass:
378.277g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
378.553g/mol
Monoisotopic Mass:
378.277g/mol
Rotatable Bond Count:
18  
Topological Polar Surface Area:
66.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
5.3  
Literature
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A synthetic cannabinoid, CP55940, inhibits lipopolysaccharide-induced cytokine mRNA expression in a cannabinoid receptor-independent mechanism in rat cerebellar granule cells. The Journal of pharmacy and pharmacology 20110501
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The endocannabinoid 2-arachidonoyl-glycerol activates human neutrophils: critical role of its hydrolysis and de novo leukotriene B4 biosynthesis. Journal of immunology (Baltimore, Md. : 1950) 20110301
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Tonic modulation of spinal hyperexcitability by the endocannabinoid receptor system in a rat model of osteoarthritis pain. Arthritis and rheumatism 20101201
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Hydrolysis of 2-arachidonoylglycerol in Tetrahymena thermophila. Identification and partial characterization of a Monoacylglycerol Lipase-like enzyme. European journal of protistology 20101101
Localization of an endocannabinoid system in the hypophysial pars tuberalis and pars distalis of man. Cell and tissue research 20101101
Differential subcellular recruitment of monoacylglycerol lipase generates spatial specificity of 2-arachidonoyl glycerol signaling during axonal pathfinding. The Journal of neuroscience : the official journal of the Society for Neuroscience 20101020
Circulating endocannabinoids and N-acyl-ethanolamides in patients with sleep apnea--specific role of oleoylethanolamide. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association 20101001
Pitfalls in the sample preparation and analysis of N-acylethanolamines. Journal of lipid research 20101001
Inhibitors of monoacylglycerol lipase, fatty-acid amide hydrolase and endocannabinoid transport differentially suppress capsaicin-induced behavioral sensitization through peripheral endocannabinoid mechanisms. Pharmacological research 20100901
Possible inhibitory roles of endogenous 2-arachidonoylglycerol during corticotropin-releasing factor-induced activation of central sympatho-adrenomedullary outflow in anesthetized rats. European journal of pharmacology 20100901
Endocannabinoid-mediated synaptically evoked suppression of GABAergic transmission in the cerebellar cortex. Neuroscience 20100901
Distinct coincidence detectors govern the corticostriatal spike timing-dependent plasticity. The Journal of physiology 20100815
Activation of TRPC6 channels promotes endocannabinoid biosynthesis in neuronal CAD cells. Neurochemistry international 20100801
Endocannabinoid system in the adult rat circumventricular areas: an immunohistochemical study. The Journal of comparative neurology 20100801
2-arachidonyl glycerol activates platelets via conversion to arachidonic acid and not by direct activation of cannabinoid receptors. British journal of clinical pharmacology 20100801
The serine hydrolase ABHD6 controls the accumulation and efficacy of 2-AG at cannabinoid receptors. Nature neuroscience 20100801
Regulation of plasticity of glutamate synapses by endocannabinoids and the cyclic-AMP/protein kinase A pathway in midbrain dopamine neurons. The Journal of physiology 20100715
Circulating and hepatic endocannabinoids and endocannabinoid-related molecules in patients with cirrhosis. Liver international : official journal of the International Association for the Study of the Liver 20100701
Endocannabinoids and non-endocannabinoid fatty acid amides in cirrhosis. Liver international : official journal of the International Association for the Study of the Liver 20100701
Effects of 2-AG on the reinforcing properties of wheel activity in obese and lean Zucker rats. Behavioural pharmacology 20100701
The endocannabinoid 2-arachidonoyl-glycerol controls odor sensitivity in larvae of Xenopus laevis. The Journal of neuroscience : the official journal of the Society for Neuroscience 20100630
Chronic constriction injury reduces cannabinoid receptor 1 activity in the rostral anterior cingulate cortex of mice. Brain research 20100621
Transcriptional regulation of cannabinoid receptor-1 expression in the liver by retinoic acid acting via retinoic acid receptor-gamma. The Journal of biological chemistry 20100618
A lipid pathway for ligand binding is necessary for a cannabinoid G protein-coupled receptor. The Journal of biological chemistry 20100604
F2-isoprostanes and 2-arachidonylglycerol as biomarkers of lipid peroxidation in pigs with hepatic ischemia/reperfusion injury. The Journal of surgical research 20100601
Substantially altered expression pattern of cannabinoid receptor 2 and activated endocannabinoid system in patients with severe heart failure. Journal of molecular and cellular cardiology 20100601
Endocannabinoid biosynthesis and inactivation, from simple to complex. Drug discovery today 20100601
Abnormal mGlu 5 receptor/endocannabinoid coupling in mice lacking FMRP and BC1 RNA. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20100601
CB1 cannabinoid receptors promote oxidative/nitrosative stress, inflammation and cell death in a murine nephropathy model. British journal of pharmacology 20100601
Endocannabinoid modulation of hyperaemia evoked by physiologically relevant stimuli in the rat primary somatosensory cortex. British journal of pharmacology 20100601
Involvement of 2-arachidonoyl glycerol in the increased consumption of and preference for ethanol of mice treated with neurotoxic doses of methamphetamine. British journal of pharmacology 20100601
Transient receptor potential vanilloid 1 channels control acetylcholine/2-arachidonoylglicerol coupling in the striatum. Neuroscience 20100519
Opposing actions of endocannabinoids on cholangiocarcinoma growth is via the differential activation of Notch signaling. Experimental cell research 20100515
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