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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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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
Kristina Hofmann et al.
Scientific reports, 7(1), 10779-10779 (2017-09-09)
The grey and white matter regions of the mammalian brain consist of both neurons and neuroglial cells. Among the neuroglia, the two macroglia oligodendrocytes and astrocytes are the most abundant cell types. While the major function of oligodendrocytes is the
Lu Wei et al.
Nature methods, 11(4), 410-412 (2014-03-04)
Sensitive and specific visualization of small biomolecules in living systems is highly challenging. We report stimulated Raman-scattering imaging of alkyne tags as a general strategy for studying a broad spectrum of small biomolecules in live cells and animals. We demonstrate
Mamta Fuloria et al.
American journal of physiology. Lung cellular and molecular physiology, 283(2), L383-L389 (2002-07-13)
We examined the responses of newborn piglet pulmonary resistance arteries (PRAs) to 5,6-epoxyeicosatrienoic acid (5,6-EET), a cytochrome P-450 metabolite of arachidonic acid. In PRAs preconstricted with a thromboxane A(2) mimetic, 5,6-EET caused a concentration-dependent dilation. This dilation was partially inhibited
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