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27817

Sigma-Aldrich

10-Undecenoic acid

puriss., meets analytical specification of Ph. Eur., BP, USP, 98-100.5%

Synonym(s):

Undecylenic acid

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About This Item

Linear Formula:
CH2=CH(CH2)8COOH
CAS Number:
112-38-9
Molecular Weight:
184.28
Colour Index Number:
42650
Beilstein/REAXYS Number:
1762631
EC Number:
203-965-8
MDL number:
MFCD00004442
UNSPSC Code:
12352100
PubChem Substance ID:
329752899

description

peroxide value <= 10

grade

puriss.

assay

98-100.5%

form

powder

quality

meets analytical specification of Ph. Eur., BP, USP

impurities

fats, mineral oils, complies
 in water soluble matter, complies
 residual solvents, complies
≤0.001% heavy metals (as Pb)

ign. residue

≤0.1% (as SO4)

refractive index

n25/D 1.447-1.448
n20/D 1.449 (lit.)

bp

137 °C/2 mmHg (lit.)

mp

23-25 °C (lit.)

iodine value

131‑138

transition temp

solidification point ≥21 °C

solubility

water: insoluble

density

0.912 g/mL at 25 °C (lit.)

suitability

corresponds for degree of unsaturation

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 selective hydroxylation with a light-activated hybrid P450 BM3 enzyme[1]. It participates in Passerini reaction with an unsaturated isocyanide to afford dendrimers[2].

Application

10-Undecenoic acid has been used in total synthesis of clavaminol-G and 1-aminoundecan-2-ol[3].

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

300.2 °F - closed cup

flash_point_c

149 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SZB71650V
71650
SZB71650
52500
31180

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T Vijai Kumar Reddy et al.
European journal of medicinal chemistry, 67, 384-389 (2013-08-06)
The first total synthesis of clavaminol-G (1) and 1-aminoundecan-2-ol (2) has been achieved from 10-undecenoic acid using epoxidation, regioselective azidolysis and in situ detosylation and reduction reactions as key steps. The methodology is extended for the synthesis of 1-aminoundecan-2-ol derivatives;
Mallory Kato et al.
Bioorganic & medicinal chemistry, 22(20), 5687-5691 (2014-06-19)
We report herein the selective hydroxylation of 10-undecenoic acid with a light-activated hybrid P450 BM3 enzyme. Under previously developed photocatalytic reaction conditions, only a monohydroxylated product is detected by gas chromatography. Hydroxylation occurs exclusively at the allylic position as confirmed
Oliver Kreye et al.
Macromolecular rapid communications, 35(3), 317-322 (2013-12-21)
The combination of the Passerini reaction and olefin cross-metathesis is shown to be a very useful approach for the divergent synthesis of dendrimers. Castor oil-derived platform chemicals, such as 10-undecenoic acid and 10-undecenal, are reacted in a Passerini reaction with
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)
Bin Guan et al.
Scientific reports, 5, 12641-12641 (2015-08-01)
This Report presents a nitrogen-doping method by chemically forming self-assembled monolayers on silicon. Van der Pauw technique, secondary-ion mass spectroscopy and low temperature Hall effect measurements are employed to characterize the nitrogen dopants. The experimental data show that the diffusion
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