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406546

Sigma-Aldrich

10-Undecynoic acid

95%

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About This Item

Linear Formula:
HC≡C(CH2)8CO2H
CAS Number:
2777-65-3
Molecular Weight:
182.26
Beilstein/REAXYS Number:
1704918
EC Number:
220-471-8
MDL number:
MFCD00014389
UNSPSC Code:
12352100
PubChem Substance ID:
24865385
NACRES:
NA.22

Quality Level

200

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

235.4 °F

flash_point_c

113 °C

ppe

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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C A CaJacob et al.
Biochemistry, 25(16), 4705-4711 (1986-08-12)
The hepatic cytochrome P-450 isozymes that catalyze omega- and (omega - 1)-hydroxylation of lauric acid are specifically inactivated in vitro but not in vivo by 10-undecynoic acid. The lack of in vivo activity may result from rapid degradation of the
Gerard Lligadas et al.
Biomacromolecules, 8(6), 1858-1864 (2007-05-03)
Novel biobased aromatic triols (1,3,5-(9-hydroxynonyl)benzene and 1,3,5-(8-hydroxyoctyl)-2,4,6-octylbenzene) were synthesized through the transition-metal-catalyzed cyclotrimerization of two alkyne fatty acid methyl esters (methyl 10-undecynoate and methyl 9-octadecynoate) followed by the reduction of the ester groups to give terminal primary hydroxyl groups. A
Thiol-yne reaction of alkyne-derivatized fatty acids: biobased polyols and cytocompatibility of derived polyurethanes.
Gonzalez-Paz RJ, et al.
Polym. Chem., 3(9), 2471-2478 (2012)
Continuous hydrothermal synthesis of in situ functionalized iron oxide nanoparticles: a general strategy to produce metal oxide nanoparticles with clickable anchors.
de Tercero MD, et al.
Particle & Particle Systems Characterization, 30(3), 229-234 (2013)
C A CaJacob et al.
The Journal of biological chemistry, 263(35), 18640-18649 (1988-12-15)
Cytochrome P-450LA omega purified from clofibrate-induced rat liver oxidizes lauric acid to 11- and 12-hydroxydodecanoic acid in approximately a 1:17 ratio at a rate of 20 nmol/nmol P-450/min. In contrast, cytochrome P-450b oxidizes lauric acid much more slowly (0.5 nmol/nmol
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