870817P

Avanti

N-palmitoylglycine

powder

Empirical Formula (Hill Notation):
C18H35NO3
CAS Number:
Molecular Weight:
313.48
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (870817P-10mg)

manufacturer/tradename

Avanti Polar Lipids 870817P

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(CCCCCCCCCCCCCCC)NCC(O)=O

InChI

1S/C18H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(21)22/h2-16H2,1H3,(H,19,20)(H,21,22)

InChI key

KVTFEOAKFFQCCX-UHFFFAOYSA-N

General description

N-palmitoylglycine belongs to the family of acyl amides, which are endogenous lipids with a potential to modulate pain and inflammation. Structurally, N-palmitoylglycine (PalGly) comprises 16-carbon saturated fatty acid attached to glycine through amide linkage. It is a structural analog of phospholipid-derived N-acyl ethanolamine. N-palmitoylglycine, a saturated lipid is endogenously produced at high levels in rat skin and spinal cord.

Application

N-palmitoylglycine has been used as an intact polar lipid (IPL) standard for determination of δ 15N values of nitrogen containing headgroups of IPLs using gas chromatography/combustion/isotope-ratio mass spectrometry.

Biochem/physiol Actions

N-palmitoylglycine stimulates calcium influx and nitric oxide (NO) production through calcium-sensitive nitric-oxide synthase in sensory neurons. It acts as a lipid activator of G-protein-coupled receptor GPR132.

Packaging

5 mL Amber Glass Screw Cap Vial (870817P-10mg)

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Elisabeth Svensson et al.
Rapid communications in mass spectrometry : RCM, 29(23), 2263-2271 (2015-11-03)
Compound-specific isotope analysis (CSIA) of nitrogen in amino acids has proven a valuable tool in many fields (e.g. ecology). Several intact polar lipids (IPLs) also contain nitrogen, and their nitrogen isotope ratios have the potential to elucidate food-web interactions or...
Neta Rimmerman et al.
Molecular pharmacology, 74(1), 213-224 (2008-04-22)
N-arachidonoyl glycine is an endogenous arachidonoyl amide that activates the orphan G protein-coupled receptor (GPCR) GPR18 in a pertussis toxin (PTX)-sensitive manner and produces antinociceptive and antiinflammatory effects. It is produced by direct conjugation of arachidonic acid to glycine and...
Cyrine Ezzili et al.
Bioorganic & medicinal chemistry letters, 20(20), 5959-5968 (2010-09-08)
Key studies leading to the discovery and definition of the role of endogenous fatty acid amide signaling molecules are summarized.
Shalini Chaturvedi et al.
Prostaglandins & other lipid mediators, 81(3-4), 136-149 (2006-11-07)
Oleamide (cis-9-octadecenamide) is a member of an emerging class of lipid-signaling molecules, the primary fatty acid amides. A growing body of evidence indicates that oleamide mediates fundamental neurochemical processes including sleep, thermoregulation, and nociception. Nevertheless, the mechanism for oleamide biosynthesis...
James R Foster et al.
Pharmacology research & perspectives, 7(6), e00542-e00542 (2019-11-27)
The G-protein-coupled receptor GPR132, also known as G2A, is activated by 9-hydroxyoctadecadienoic acid (9-HODE) and other oxidized fatty acids. Other suggested GPR132 agonists including lysophosphatidylcholine (LPC) have not been readily reproduced. Here, we identify N-acylamides in particular N-acylglycines, as lipid...

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