O9762

Sigma-Aldrich

N-Oleoylglycine

≥98%

Synonym(s):
N-(1-Oxo-9-octadecenyl)-(Z)-glycine
Empirical Formula (Hill Notation):
C20H37NO3
CAS Number:
Molecular Weight:
339.51
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98%

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCCCCC/C=C\CCCCCCCC(NCC(O)=O)=O

InChI

1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-

InChI key

HPFXACZRFJDURI-KTKRTIGZSA-N

Biochem/physiol Actions

N-Oleoylglycine is equally efficient as oleamide in reducing locomotion and hypothermia.
Enzymatically produced in mammals. Substrate for peptidylglycine α-amidating enzyme.

Preparation Note

Prepare stock solutions (10 mg/mL) by dissolving the crystalline solid in an organic solvent such as ethanol, methanol, acetone, acetonitrile, or DMSO. Working dilutions may be made in aqueous buffers.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. O9762.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide
Chaturvedi S, et al.
Prostaglandins & other lipid mediators, 81(3-4), 136-149 (2006)
Zhanru Yu et al.
Talanta, 165, 685-691 (2017-02-06)
Two-dimensional gas chromatography mass spectrometry (GCxGC-MS) is utilized to an increasing extent in biomedical metabolomics. Here, we established and adapted metabolite extraction and derivatization protocols for cell/tissue biopsy, serum and urine samples according to their individual properties. GCxGC-MS analysis revealed...
Sarah Nicolai et al.
Science immunology, 5(43) (2020-01-05)
During industrialization, humans have been exposed to increasing numbers of foreign chemicals. Failure of the immune system to tolerate drugs, cosmetics, and other skin products causes allergic contact dermatitis, a T cell-mediated disease with rising prevalence. Models of αβ T...

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