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Sigma-Aldrich

10-Undecynoic acid

95%

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About This Item

Linear Formula:
HC≡C(CH2)8CO2H
CAS Number:
Molecular Weight:
182.26
Beilstein:
1704918
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

95%

bp

180 °C/15 mmHg (lit.)

mp

40-42 °C (lit.)

SMILES string

OC(=O)CCCCCCCCC#C

InChI

1S/C11H18O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h1H,3-10H2,(H,12,13)

InChI key

OAOUTNMJEFWJPO-UHFFFAOYSA-N

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General description

10-Undecynoic acid (10- UDYA, UDY) is an acetylenic fatty acid. It is reported as highly selective irreversible inhibitor of hepatic ω- and ω-1-lauric acid hydroxylases. Enzyme catalyzed esterification of 10-undecynoic acid has been reported. UDY has been reported to be synthesized by the dehydrobromination of 10-undecenoic acid.

Application

10-Undecynoic acid was employed as model compound to investigate the microwave assisted surface click reactions catalyzed with Cu(II)/sodium L-ascorbate.†
It may be used:
  • As a biochemical probe in an assay for the microsomal hydroxylation of lauric acid (LA), based on HPLC with flow-through radiochemical detection.
  • To form molecular layers by adsorbing on the fluorite surface.
  • In the supercritical hydrothermal synthesis of iron oxide nanoparticles.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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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Anna Goc et al.
PloS one, 14(4), e0214763-e0214763 (2019-04-19)
In the search for novel agents against oral pathogens in their planktonic and biofilm form, we have focused our attention on 10-undecynoic acid as the representative of the acetylenic fatty acids. Using macro-broth susceptibility testing method we first established MIC
Fabrizio Cattaruzza et al.
Nucleic acids research, 34(4), e32-e32 (2006-03-02)
Unoxidized crystalline silicon, characterized by high purity, high homogeneity, sturdiness and an atomically flat surface, offers many advantages for the construction of electronic miniaturized biosensor arrays upon attachment of biomolecules (DNA, proteins or small organic compounds). This allows to study
Fengyun Xu et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 283(3), R710-R720 (2002-08-20)
The cytochrome P-450 eicosanoid 20-hydroxyeicosatetraenoic acid (20-HETE) is a potent vasoconstrictor that is implicated in the regulation of blood pressure. The identification of selective inhibitors of renal 20-HETE formation for use in vivo would facilitate studies to determine the systemic
N O Reich et al.
Biochemical pharmacology, 35(8), 1227-1233 (1986-04-15)
Clofibrate, an antilipidemic drug that acts by a still obscure mechanism, is known to specifically increase up to 30-fold the activity of the hepatic cytochrome P-450 isozyme that omega-hydroxlates lauric acid. The thesis that accelerated catabolism of medium-length fatty acids
P R Ortiz de Montellano et al.
The Journal of biological chemistry, 259(7), 4136-4141 (1984-04-10)
The terminal acetylenic analogue of lauric acid, 11-dodecynoic acid (11-DDYA), specifically inactivates hepatic cytochrome P-450 enzymes that catalyze omega- and omega-1-hydroxylation of lauric acid. The inactivation, as required for a suicidal process, is NADPH- and time-dependent and follows pseudo-first order

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