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Sigma-Aldrich

10-Undecynoic acid

95%

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About This Item

Formula condensata:
HC≡C(CH2)8CO2H
Numero CAS:
Peso molecolare:
182.26
Beilstein:
1704918
Numero CE:
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22

Saggio

95%

P. eboll.

180 °C/15 mmHg (lit.)

Punto di fusione

40-42 °C (lit.)

Stringa SMILE

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)
OAOUTNMJEFWJPO-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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.

Pittogrammi

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Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

235.4 °F - closed cup

Punto d’infiammabilità (°C)

113 °C - closed cup

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


Certificati d'analisi (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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