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406546

10-Undecynoic acid

Name: 10-Undecynoic acid
Brand: ALDRICH

95%

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About This Item

Linear Formula:

HC≡C(CH₂)₈CO₂H

CAS Number:

2777-65-3

Molecular Weight:

182.26

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24865385

EC Number:

220-471-8

Beilstein/REAXYS Number:

1704918

MDL number:

MFCD00014389

Assay:

95%

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Properties

Quality Level

200

assay

95%

bp

180 °C/15 mmHg (lit.)

mp

40-42 °C (lit.)

functional group

carboxylic acid

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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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Effects of fatty acids and ketone bodies on cytochromes P450 2B, 4A, and 2E1 expression in primary cultured rat hepatocytes.

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

Specific inactivation of hepatic fatty acid hydroxylases by acetylenic fatty acids.

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)

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Global Trade Item Number

SKU	GTIN
406546-5G	04061831987768