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O8382

Sigma-Aldrich

17-Octadecynoic acid

≥95% (GC)

Synonym(s):

17-ODYA, Alkynyl Stearic Acid, Octadec-17-ynoic acid

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About This Item

Empirical Formula (Hill Notation):
C18H32O2
CAS Number:
34450-18-5
Molecular Weight:
280.45
MDL number:
MFCD00077382
UNSPSC Code:
12352106
PubChem Substance ID:
24898058
NACRES:
NA.77

Quality Level

200

Assay

≥95% (GC)

form

powder

solubility

chloroform: 10 mg/mL to clear, colorless to faintly yellow

SMILES string

OC(=O)CCCCCCCCCCCCCCCC#C

InChI

1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h1H,3-17H2,(H,19,20)

InChI key

DZIILFGADWDKMF-UHFFFAOYSA-N

Application

17-Octadecynoic acid has been used in lipid synthesis.

Biochem/physiol Actions

17-Octadecynoic acid (7-ODYA) is an irreversible inhibitor of cytochrome P450 isozymes, that participates in long-chain fatty acid metabolism.
Suicide substrate inhibitor that selectively and irreversibly inhibits cytochrome P450 epoxygenases and ω-hydrolases.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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H Dong et al.
British journal of pharmacology, 120(4), 695-701 (1997-02-01)
1. The nature and cellular mechanisms that are responsible for endothelium-dependent relaxations resistant to indomethacin and NG-nitro-L-arginine methyl ester (L-NAME) were investigated in phenylephrine (PE) precontracted isolated carotid arteries from the rabbit. 2. In the presence of the cyclo-oxygenase inhibitor
Jacob S Yount et al.
Current protocols in chemical biology, 3(2), 65-79 (2011-05-01)
Protein fatty-acylation is the covalent addition of a lipid chain at specific amino acids. This modification changes the inherent hydrophobicity of a protein, often targeting it to cellular membrane compartments. Acylation may also regulate protein activity, stability, and protein-protein interactions.
Ossama A Hatoum et al.
American journal of physiology. Heart and circulatory physiology, 288(1), H48-H54 (2004-09-04)
The endothelium plays an important role in maintaining vascular homeostasis by synthesizing and releasing several mediators of vasodilation, which include prostacyclin (PGI(2)), nitric oxide, and endothelium-derived hyperpolarizing factor (EDHF). We have recently defined the role of nitric oxide and PGI(2)
Sphingosine-1-phosphate lyase deficient cells as a tool to study protein lipid interactions
Gerl M J, et al.
Testing, 11(4), e0153009-e0153009 (2016)
M H Wang et al.
The Journal of pharmacology and experimental therapeutics, 284(3), 966-973 (1998-03-13)
We characterized the inhibitory activity of several acetylenic and olefinic compounds on cytochrome P450 (CYP)-derived arachidonic acid omega-hydroxylation and epoxidation using rat renal cortical microsomes and recombinant CYP proteins. Among the acetylenic compounds, 6-(2-propargyloxyphenyl)hexanoic acid (PPOH) and N-methylsulfonyl-6-(2-propargyloxyphenyl)hexanamide were found
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