O8382
17-Octadecynoic acid
≥95% (GC), Cytochrome P450 epoxygenase inhibitor, powder
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:
Molecular Weight:
280.45
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
17-Octadecynoic acid, ≥95% (GC)
SMILES string
C#CCCCCCCCCCCCCCCCC(O)=O
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
assay
≥95% (GC)
form
powder
solubility
chloroform: 10 mg/mL to clear, colorless to faintly yellow
Quality Level
Related Categories
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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)
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
Effects of intrarenal infusion of 17-octadecynoic acid on renal antihypertensive mechanisms in anesthetized rabbits
Evans R G, et al.
American Journal of Hypertension, 11(7), 803-812 (1998)
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)
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.
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