Oleic acid Chemische Eigenschaften,Einsatz,Produktion Methoden
ERSCHEINUNGSBILD
FARBLOSE FLüSSIGKEIT, VERFäRBT SICH GELB BIS BRAUN BEI KONTAKT MIT LUFT.
CHEMISCHE GEFAHREN
Schwache Säure.
ARBEITSPLATZGRENZWERTE
TLV nicht festgelegt.
MAK: Krebserzeugend Kategorie 3A; (DFG 2008).
INHALATIONSGEFAHREN
Verdampfen bei 20°C vernachlässigbar; eine belästigende Partikelkonzentration in der Luft kann jedoch beim Versprühen schnell erreicht werden.
WIRKUNGEN BEI KURZZEITEXPOSITION
WIRKUNGEN BEI KURZZEITEXPOSITION: Die Substanz reizt leicht die Augen und die Haut.
LECKAGE
Ausgelaufene Flüssigkeit in abgedeckten Behältern sammeln. Verschüttete Flüssigkeit mit viel Wasser wegspülen.
R-Sätze Betriebsanweisung:
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R34:Verursacht Verätzungen.
R40:Verdacht auf krebserzeugende Wirkung.
R43:Sensibilisierung durch Hautkontakt möglich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R38:Reizt die Haut.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Oleic acid, C17H33COOH, also known as red oil, elaine oil, and octadecenoic acid, is a yellowish unsaturated fatty acid with an aroma similar to lard. Oleic acid consists chiefly of (Ζ)-9-octadecenoic acid together with varying amounts of saturated and other unsaturated acids. It is insoluble in water, but soluble in most organic solvents. Oleic acid is the main component in cooking and olive oils.It is used for making aluminum oleate, which thickens lubricating oil, and in the preparation of soaps and cosmetics.
Occurrence
Reported found in apple, banana, cranberry, guava, grapes, melon, papaya, ginger, hop oil, ginger, beef fat,
beer, rum, whiskies, cider, sherry, tea, goat milk, butterfat, celery, cheese, blue cheese, munster cheese, other cheeses, cognac, country
cured ham, pork fat, potato, raspberry oil, tomato, peanut oil, coconut meat, avocado, mushroom, fenugreek, tamarind, kelp,
cardamom, rice, dill seed, sake, buckwheat, malt, wort, roasted chicory root and cape gooseberry.
Verwenden
Oleic acid is a monounsaturated omega-9 fatty acid. Oleic Acid is obtained by the hydrolysis of various animal and vegetable fats and oils. Oleic Acid is used as an emulsifying or solubilizing agent i
n aerosol products.
Vorbereitung Methode
Oleic acid is obtained by the hydrolysis of various animal and
vegetable fats or oils, such as olive oil, followed by separation of the
liquid acids. It consists chiefly of (Ζ)-9-octadecenoic acid. Oleic acid
that is to be used systemically should be prepared from edible
sources.
Definition
ChEBI: Oleic acid is an octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry. It has a role as an EC 3.1.1.1 (carboxylesterase) inhibitor, an Escherichia coli metabolite, a plant metabolite, a Daphnia galeata metabolite, a solvent, an antioxidant and a mouse metabolite. It is a conjugate acid of an oleate. It derives from a hydride of a cis-octadec-9-ene.
Allgemeine Beschreibung
Colorless to pale yellow liquid with a mild odor. Floats on water.
Air & Water Reaktionen
Keep cis-9-Octadecenoic acid well closed; protect cis-9-Octadecenoic acid from air and light. . May form peroxides upon exposure to air. This is taken to account for an explosion that occurred, by the mixing of the acid with aluminum, [J. Chem. Educ., 1956, 36, 308]. Water Insoluble.
Health Hazard
Industrial use of compound involves no known hazards. Ingestion causes mild irritation of mouth and stomach. Contact with eyes or skin causes mild irritation.
Brandgefahr
cis-9-Octadecenoic acid is combustible.
Pharmazeutische Anwendungen
Oleic acid is used as an emulsifying agent in foods and topical
pharmaceutical formulations. It has also been used as a penetration enhancer in transdermal formulations,to improve the bioavailability
of poorly water-soluble drugs in tablet formulations,
and as part of a vehicle in soft gelatin capsules, in topical
microemulsion formulations,in oral self-emulsifying drug
delivery systems,in oral mucoadhesive patches,and in a
metered dose inhaler.Oleic acid was shown to be an important
factor in the hypoglycemic effect produced by multiple emulsions
containing insulin intended for intestinal delivery of insulin.
The phase behavior of sonicated dispersions of oleic acid has
been described,and mechanisms for the topical penetrationenhancing
actions of oleic acid have been presented.
Oleic acid has been reported to act as an ileal ‘brake’ that slows
down the transit of luminal contents through the distal portion of
the small bowel.
Oleic acid labeled with 131I and 3H is used in medical imaging.
Sicherheitsprofil
Poison by intravenous route. Mildly toxic by ingestion. Mutation data reported. A human skin and eye irritant. Questionable carcinogen with experimental tumorigenic data. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical. The peroxidzed acid explodes on contact with aluminum. Potentially dangerous reaction with perchloric acid + heat. When heated to decomposition it emits acrid smoke and irritating fumes.
Sicherheit(Safety)
Oleic acid is used in oral and topical pharmaceutical formulations.
In vitro tests have shown that oleic acid causes rupture of red
blood cells (hemolysis), and intravenous injection or ingestion of a
large quantity of oleic acid can therefore be harmful. The effects of
oleic acid on alveolar and buccal epithelial cells in vitro have
also been studied; the in vitro and in vivo effects of oleic acid on rat
skin have been reported. Oleic acid is a moderate skin irritant; it
should not be used in eye preparations.
An acceptable daily intake for the calcium, sodium, and
potassium salts of oleic acid was not specified by the WHO since
the total daily intake of these materials in foods was such that they
did not pose a hazard to health.
LD
50 (mouse, IV): 0.23 g/kg
LD
50 (rat, IV): 2.4 mg/kg
LD
50 (rat, oral): 74 g/kg
Carcinogenicity
Some recent studies suggested that oleic acid may
decrease the incidence of mammary gland tumors of some
rodent species. In a reviewof several fatty acids, Ip concludes
that there is little evidence for the protective effect of oleic
acid on the development of cancer.
Lager
On exposure to air, oleic acid gradually absorbs oxygen, darkens in
color, and develops a more pronounced odor. At atmospheric
pressure, it decomposes when heated at 80–100°C.
Oleic acid should be stored in a well-filled, well-closed container,
protected from light, in a cool, dry place.
läuterung methode
Purify the acid by fractional crystallisation from its melt, followed by molecular distillation at 10 -3mm, or by conversion to its methyl ester, the free acid can be crystallised from acetone at -40o to -45o (12mL/g). For purification by the use of lead and lithium salts, see Keffler and McLean [J Soc Chem Ind (London) 54 176T 1935]. Purification based on direct crystallisation from acetone is described by Brown and Shinowara [J Am Chem Soc 59 6 1937, pK White J Am Chem Soc 72 1857 1950]. [Beilstein 2 H 463, 2 I 198, 2 II 429, 2 III 1387, 2 IV 1641.]
Inkompatibilitäten
Incompatible with aluminum, calcium, heavy metals, iodine
solutions, perchloric acid, and oxidizing agents. Oleic acid reacts
with alkalis to form soaps.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database
(inhalation and nasal aerosols, tablets, topical and transdermal
preparations). Included in nonparenteral medicines (metered dose
inhalers; oral capsules; oral prolonged release granules; topical
creams and gels) licensed in the UK. Included in the Canadian List of
Acceptable Non-medicinal Ingredients.
Oleic acid Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
