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Dokumente

406546

Sigma-Aldrich

10-Undecinsäure

95%

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About This Item

Lineare Formel:
HC≡C(CH2)8CO2H
CAS-Nummer:
2777-65-3
Molekulargewicht:
182.26
Beilstein:
1704918
EG-Nummer:
220-471-8
MDL-Nummer:
MFCD00014389
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24865385
NACRES:
NA.22

Assay

95%

bp

180 °C/15 mmHg (lit.)

mp (Schmelzpunkt)

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)

InChIKey

OAOUTNMJEFWJPO-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

235.4 °F - closed cup

Flammpunkt (°C)

113 °C - closed cup

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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Formation and wetting characteristics of adsorbed layers of unsaturated carboxylic acids at a fluorite surface.
Drelich J, et al.
Journal of Colloid and Interface Science, 178(2), 720-732 (1996)
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
Studies of lipase-catalyzed esterification reactions of some acetylenic fatty acids.
Jie MSFLK and Xun F.
Lipids, 33(1), 71-75 (1998)
R C Zangar et al.
Archives of biochemistry and biophysics, 337(2), 217-224 (1997-01-15)
CYP2B, CYP4A, and CYP2E1 mRNA levels are elevated in response to pathophysiological conditions, such as diabetes, high-fat diet, and fasting, in which lipids and ketone bodies are increased. In order to avoid confounding hormonal effects, we utilized primary rat hepatocytes
M C Romano et al.
Analytical biochemistry, 170(1), 83-93 (1988-04-01)
An assay for the microsomal hydroxylation of lauric acid (LA), based on HPLC with flow-through radiochemical detection, has been developed. Conditions were optimized for resolution and quantitation of three microsomal metabolites of LA, one of which has not been reported
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