Oleic acid

Bezeichnung:Oleic acid

CAS-Nr112-80-1

Englisch Name:Oleic acid

CBNumberCB7228241

SummenformelC18H34O2

Molgewicht282.46

MOL-Datei112-80-1.mol

Synonyma

9-Octadecens?ure

9,10-Octadecens?ure

Oleins?ure

Oleic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	13-14 °C(lit.)
Siedepunkt	360 °C
Dichte	0.89 g/mL at 25 °C(lit.)
Dampfdichte	1.03 (vs air)
Dampfdruck	52 mm Hg ( 37 °C)
FEMA	2815 \| OLEIC ACID
Brechungsindex	n20/D 1.377
Flammpunkt	133 °F
storage temp.	-20°C
Löslichkeit	Miscible with ethanol, ether, acetone, chloroform, dimethyl formamide and dimethyl sulfoxide.
Aggregatzustand	Liquid
pka	pKa 5.35(H2O,t =25) (Uncertain)
Wichte	0.892 (20/4℃)
Farbe	Colorless to pale yellow
Geruch (Odor)	Peculiar Lard-Like
Geruchsart	fatty
Wasserlöslichkeit	negligible
Sensitive	Air Sensitive
Merck	14,6828
JECFA Number	333
BRN	1726542
hydrophiles-lipophiles Gleichgewicht (HLB)	1
Dielectric constant	2.5（20℃）
Stabilität	Stable. Combustible. Incompatible with strong oxidizing agents, aluminium.
InChIKey	ZQPPMHVWECSIRJ-KTKRTIGZSA-N
LogP	7.698 (est)
CAS Datenbank	112-80-1(CAS DataBase Reference)
NIST chemische Informationen	9-Octadecenoic acid (Z)-(112-80-1)
EPA chemische Informationen	Oleic acid (112-80-1)

Sicherheit

Kennzeichnung gefährlicher	T,Xi
R-Sätze:	23/24/25-34-40-43-36/37/38-38
S-Sätze:	36/37-37/39-26-36-36/37/39
RIDADR	UN 1198 3/PG 3
WGK Germany	2
RTECS-Nr.	LP8925000
F	10
Selbstentzündungstemperatur	363°C
TSCA	Yes
HS Code	29161500
Giftige Stoffe Daten	112-80-1(Hazardous Substances Data)
Toxizität	LD50 i.v. in mice: 230±18 mg/kg (Or, Wretlind)

Gefahreninformationscode (GHS)

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.
Beschreibung
Oleic acid is a monounsaturated fatty acid and a major component of membrane phospholipids that has been found in human plasma, cell membranes, and adipose tissue. It contributes approximately 17% of the total fatty acids esterified to phosphatidylcholine, the major phospholipid class in porcine platelets. Oleic acid inhibits collagen-stimulated platelet aggregation by approximately 90% when used at a concentration of 10 μg/ml. It also inhibits fMLF-induced neutrophil aggregation and degranulation by 55 and 68%, respectively, when used at a concentration of 5 μM, similar to arachidonic acid ( | 90010.1 | 10006607). Oleic acid (60 μM) induces release of intracellular calcium in human platelets. In vivo, oleic acid increases TNF-α, IL-8, IL-6, and IL-1β production, neutrophil accumulation, and apoptotic and necrotic cell death in mouse lung and has been used to induce lung injury in a mouse model of acute respiratory distress syndrome (ARDS).
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.
Verwenden
Oleic Acid is an unsaturated fatty acid that functions as a lubricant, binder, and defoamer.
Verwenden
oleic acid is also known as omega-9. oleic acid can improve the skinpenetration abilities of a preparation’s other components. An essential fatty acid, it is obtained from various animal and vegetable fats and oils, and may be mildly irritating to the skin.
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.
Reaktivität anzeigen
cis-9-Octadecenoic acid is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in cis-9-Octadecenoic acid to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.
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.
Biochem/physiol Actions
Oleic acid is a colourless, odourless fatty acid that blocks the glucose production and food intake when administered intracerebroventricularly.
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.
LD₅₀ (mouse, IV): 0.23 g/kg
LD₅₀ (rat, IV): 2.4 mg/kg
LD₅₀ (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

Oleic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

112-80-1, Oleic acid Verwandte Suche:

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