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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

O9762-VAR:
O9762-BULK:
O9762-10MG:
O9762-10MG-PW:

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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