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O9762

Sigma-Aldrich

N-Oleoylglycine

≥98%

Synonym(s):

N-(1-Oxo-9-octadecenyl)-(Z)-glycine

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About This Item

Empirical Formula (Hill Notation):
C20H37NO3
CAS Number:
2601-90-3
Molecular Weight:
339.51
EC Number:
220-009-5
MDL number:
MFCD01320532
UNSPSC Code:
12352211
PubChem Substance ID:
329818944
NACRES:
NA.77

Quality Level

200

assay

≥98%

form

solid

lipid type

neutral glycerides

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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