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Merck

O1008

Sigma-Aldrich

Oleic acid

≥99% (GC)

Synonim(y):

9Z-Octadecenoic acid, cis-Oleic acid, cis-9-Octadecenoic acid, Elainic acid

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About This Item

Wzór liniowy:
CH3(CH2)7CH=CH(CH2)7COOH
Numer CAS:
Masa cząsteczkowa:
282.46
Beilstein:
1726542
Numer WE:
Numer MDL:
Kod UNSPSC:
12352211
Identyfikator substancji w PubChem:
NACRES:
NA.25

pochodzenie biologiczne

plant (Sunflower)

Poziom jakości

ciśnienie pary

1 mmHg ( 176 °C)

Próba

≥99% (GC)

Postać

viscous liquid

kolor

colorless to very faintly yellow

współczynnik refrakcji

n20/D 1.459 (lit.)

tw

194-195 °C/1.2 mmHg (lit.)

mp

13-14 °C (lit.)

rozpuszczalność

H2O: insoluble (practically)
alcohol: soluble
benzene: soluble
chloroform: soluble
oil: soluble (fixed and volatile)

gęstość

0.89 g/mL at 25 °C (lit.)

Zastosowanie

life science and biopharma
lipidomics

grupa funkcyjna

oleic acid

typ lipidu

unsaturated FAs

Warunki transportu

ambient

temp. przechowywania

−20°C

ciąg SMILES

CCCCCCCC\C=C/CCCCCCCC(O)=O

InChI

1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

Klucz InChI

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

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Opis ogólny

Oleic acid (OA), a non-essential fatty acid, is classified as monounsaturated fatty acid (MUFA) richly present in olive oil. Its quantitative removal from the mixtures of triglyceride and partial glycerides has been reported. OA is widely used as a surfactant for the stabilization of magnetic nanoparticles. Monodisperse magnetite nanoparticles (7 and 19nm) coated with OA have been prepared.

Zastosowanie

Oleic acid has been used:
  • to study the effects of fatty acids on gastric cancer (GC)
  • to induce lipid droplet formation in cell culture
  • as an additive in the magnetorheological fluid preparation.
Oleic acid may be used in the preparation of 10-hydroxy octadecanoic acid and methyl ester of the 10-hydroxy octadecanoic acid.

Działania biochem./fizjol.

Oleic acid is known to improve immune function and health. Dietary supplement of this fatty acid contributes to the reduction in cholesterol levels, atherogenesis risk, blood pressure, and host versus graft response. Oleic acid has been proven to benefit autoimmune diseases by exhibiting anti-inflammatory action. It also ameliorates the condition of breast cancer. Oleic acid produces physiological effects such as protein kinase C activation in hepatocytes, uncoupling oxidative phosphorylation, and 2,4-dinitrophenol−stimulated ATPase inhibition. This action can be reversed by adding serum albumin.

Inne uwagi

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Kod klasy składowania

10 - Combustible liquids

Klasa zagrożenia wodnego (WGK)

WGK 1

Środki ochrony indywidualnej

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Oleic acid coating on the monodisperse magnetite nanoparticles.
Zhang L, et al.
Applied Surface Science, 253(5), 2611-2617 (2006)
THE STEREOSPECIFIC CONVERSION OF STEARIC ACID TO OLEIC ACID.
G J SCHROEPFER et al.
The Journal of biological chemistry, 240, 54-63 (1965-01-01)
P Belfrage et al.
Journal of lipid research, 10(3), 341-344 (1969-05-01)
Oleic acid has a partition coefficient, upper phase/lower phase, of 1.9 (22 degrees C) in the liquid-liquid partition system described herein. Tri-, di-, and monoolein are found almost exclusively in the lower (organic) phase. Oleic acid can be quantitatively removed
Yasutaka Kuwahara et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(2), 380-389 (2016-11-26)
One-pot reaction involving Pd-catalyzed H
Qingwen Qian et al.
Cellular and molecular gastroenterology and hepatology, 8(1), 95-110 (2019-03-31)
The lysosome is an acidic organelle that is important for maintaining cellular and metabolic homeostasis in hepatocytes. Lysosomal dysfunction and chronic inflammation coexist, and both contribute to obesity-associated hepatic insulin resistance. However, in the context of obesity, the interplay between

Produkty

Fatty acids of the n-3, n-6 and n-9 families are important supplements for cell culture systems. They are important in cell culture systems used to biomanufacture heterologous proteins, such as monoclonal antibodies.

How the unsaturated fatty acid, oleic acid and other cell culture components affect the performance of serum-free, protein-free cell culture systems used for biomanufacturing heterologous proteins including monoclonal antibodies.

Protokoły

Syntetyczna membrana Strat-M® naśladuje ludzką skórę do testów przenikania in vitro (IVPT) preparatów do stosowania miejscowego i transdermalnego.

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