870817 | N-palmitoylglycine

N-palmitoylglycine


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N-palmitoylglycine

N-palmitoylglycine

N-palmitoylglycine

The acyl amides are a family of endogenous lipids that act as potent modulators of pain and inflammation. The best characterized members of this family are the arachidonoyl amides, which includes N-arachidonoyl ethanolamide (AEA; anandamide). N-palmitoylglycine (PalGly) contains a 16-carbon saturated fatty acid that is amide-linked to glycine and is structurally similar to the phospholipid-derived N-acyl ethanolamines. Endogenously produced in rat skin and spinal cord, PalGly is present in 100-fold greater amounts in skin and 3-fold greater in brain compared to AEA.1
1 Rimmerman, N., Bradshaw, H.B., Hughes, H.V., Chen, J.S., Hu, S.S., McHugh, D., Vefring, E., Jahnsen, J.A., Thompson, E.L., Masuda, K., Cravatt, B.F., Burstein, S., Vasko, M.R., Prieto, A.L., O'Dell, D.K., Walker, J.M.  (2008) N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons. Mol Pharmacol 74:213-224.
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C18H35NO3
Percent Composition
C 68.97%, H 11.25%, N 4.47%, O 15.31%
Purity
>99%
Stability
1 Years
Storage Temperature
-20°C
CAS Number
2441-41-0
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
313.475
Exact Mass
313.262
Synonyms
PalGly

Bradshaw HB, Rimmerman N, Hu SS, Burstein S, Walker JM. Novel endogenous N-acyl glycines identification and characterization. Vitam Horm. 2009;81:191-205. doi: 10.1016/S0083-6729(09)81008-X. PMID: 19647113.

PubMed ID: 19647113

Rimmerman N, Bradshaw HB, Hughes HV, Chen JS, Hu SS, McHugh D, Vefring E, Jahnsen JA, Thompson EL, Masuda K, Cravatt BF, Burstein S, Vasko MR, Prieto AL, O'Dell DK, Walker JM. N-palmitoyl glycine, a novel endogenous lipid that acts as a modulator of calcium influx and nitric oxide production in sensory neurons. Mol Pharmacol. 2008 Jul;74(1):213-24. doi: 10.1124/mol.108.045997. Epub 2008 Apr 18. PMID: 18424551.

PubMed ID: 18424551

Chaturvedi S, Driscoll WJ, Elliot BM, Faraday MM, Grunberg NE, Mueller GP. In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide. Prostaglandins Other Lipid Mediat. 2006 Dec;81(3-4):136-49. doi: 10.1016/j.prostaglandins.2006.09.001. Epub 2006 Oct 5. PMID: 17085322; PMCID: PMC1712674.

PubMed ID: 17085322

Merkler DJ, Merkler KA, Stern W, Fleming FF. Fatty acid amide biosynthesis: a possible new role for peptidylglycine alpha-amidating enzyme and acyl-coenzyme A: glycine N-acyltransferase. Arch Biochem Biophys. 1996 Jun 15;330(2):430-4. doi: 10.1006/abbi.1996.0272. PMID: 8660675.

PubMed ID: 8660675