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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

Assay

≥95% (GC)

form

powder

solubility

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

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

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

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

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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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)
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)
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
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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