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Sigma-Aldrich

10-Undecenoic acid

98%

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Synonym(s):
Undecylenic acid
Linear Formula:
CH2=CH(CH2)8COOH
CAS Number:
112-38-9
Molecular Weight:
184.28
Colour Index Number:
42650
Beilstein:
1762631
EC Number:
203-965-8
MDL number:
MFCD00004442
PubChem Substance ID:
24847622
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

refractive index

n20/D 1.449 (lit.)

bp

137 °C/2 mmHg (lit.)

mp

23-25 °C (lit.)

solubility

H2O: insoluble
alcohol: soluble
chloroform: soluble
diethyl ether: soluble

density

0.912 g/mL at 25 °C (lit.)

SMILES string

OC(=O)CCCCCCCCC=C

InChI

1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)

InChI key

FRPZMMHWLSIFAZ-UHFFFAOYSA-N

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General description

10-Undecenoic acid undergoes copolymerisation with ethylene using the metallocene catalyst system Cp2ZrCl2 / methylaluminoxane.

Application

10-Undecenoic acid has been used to study the methods and mechanisms for the formation of molecular monolayers on silicon surface. It was used as starting reagent in the syntheses of pheromone (11Z)-hexadecenal and agriculturally important insect pheromones.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H412

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

300.2 °F

Flash Point(C)

149 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Metallocene-Catalysed Copolymerisation of Ethylene with 10-Undecenoic Acid: The Effect of Experimental Conditions.
Santos JM, et al.
Macromolecular Chemistry and Physics, 202(11), 2195-2201 (2001)
10-Undecenoic acid, an inexpensive source for the synthesis of the pheromones of cotton pests, peach tree borer and cherry tree borer.
Pawar AS and Chattopadhyay S.
Molecules (Basel), 2(6), 87-90 (1997)
Molecular monolayers on silicon surfaces.
Lopinski GP and Wayner DDM.
Material Matters, 3(2), 38-38 (2008)
Xing-Cong Li et al.
Antimicrobial agents and chemotherapy, 52(7), 2442-2448 (2008-05-07)
Our continuing effort in antifungal natural product discovery has led to the identification of five 6-acetylenic acids with chain lengths from C(16) to C(20): 6-hexadecynoic acid (compound 1), 6-heptadecynoic acid (compound 2), 6-octadecynoic acid (compound 3), 6-nonadecynoic acid (compound 4)
Terence Tieu et al.
Biomaterials science, 9(1), 133-147 (2020-11-03)
Targeted delivery of chemotherapeutics to cancer cells has the potential to yield high drug concentrations in cancer cells while minimizing any unwanted side effects. However, the development of multidrug resistance in cancer cells may impede the accumulation of chemotherapy drugs
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Articles

Molecular Monolayers on Silicon Surfaces

Molecular monolayers made via reactions of alkenes with H-Si(111) are often referred to as “self-assembled” monolayers on silicon surfaces by analogy with thiol monolayers on gold. These monolayers are chemically robust.

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