406546
10-Undecynoic acid
95%
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About This Item
Linear Formula:
HC≡C(CH2)8CO2H
CAS Number:
Molecular Weight:
182.26
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
220-471-8
Beilstein/REAXYS Number:
1704918
MDL number:
Product Name
10-Undecynoic acid, 95%
InChI key
OAOUTNMJEFWJPO-UHFFFAOYSA-N
InChI
1S/C11H18O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h1H,3-10H2,(H,12,13)
SMILES string
OC(=O)CCCCCCCCC#C
assay
95%
bp
180 °C/15 mmHg (lit.)
mp
40-42 °C (lit.)
functional group
carboxylic acid
Quality Level
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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:
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.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
Studies of lipase-catalyzed esterification reactions of some acetylenic fatty acids.
Jie MSFLK and Xun F.
Lipids, 33(1), 71-75 (1998)
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
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)
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
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