| Identification | More | [Name]
ETHYL OLEATE | [CAS]
111-62-6 | [Synonyms]
DELTA 9 CIS OCTADECENOIC ACID ETHYL ESTER
ETHYL OLEATE
ETHYL (Z)-9-OCTADECENOATE
FEMA 2450
OLEIC ACID ETHYL ESTER
(Z)-9-Octadecenoic acid ethyl ester
(Z)-9-Octadecenoicacidethylester
9-Octadecenoicacid(Z)-,ethylester
cis-octadec-9-enoicacidethylester
Ethyl (9Z)-9-octadecenoate
Ethyl cis-9-octadecenoate
Ethyl(Z)-9-octadeceneoate
ethylcis-9-octadecenoate
ethyloleate,mixtureofisomers
octadec-9-enoicacid,ethylester
oleic
ETHYL OLEATE, TECH., 70%
ETHYL OLEATE, BP
Ethyl oleate, mixture of homologeous fatty acid esters, 98%
Ethyl oleate, tech., mixture of isomers, 90% | [EINECS(EC#)]
203-889-5 | [Molecular Formula]
C20H38O2 | [MDL Number]
MFCD00009579 | [Molecular Weight]
310.51 | [MOL File]
111-62-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear pale yellow oily liquid | [Melting point ]
−32 °C(lit.)
| [Boiling point ]
216-218 °C15 mm Hg
| [density ]
0.87 g/mL at 25 °C(lit.)
| [FEMA ]
2450 | [refractive index ]
n20/D 1.451(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
−20°C
| [solubility ]
chloroform: soluble10% | [form ]
Oily Liquid | [color ]
Clear | [Odor]
at 100.00 %. fatty oily dairy milky waxy tallow | [Odor Type]
fatty | [Sensitive ]
Light Sensitive | [JECFA Number]
345 | [Merck ]
6828 | [BRN ]
1727318 | [Dielectric constant]
3.2（28℃） | [InChIKey]
LVGKNOAMLMIIKO-VAWYXSNFSA-N | [LogP]
8.69 | [CAS DataBase Reference]
111-62-6(CAS DataBase Reference) | [NIST Chemistry Reference]
9-Octadecenoic acid (Z)-, ethyl ester(111-62-6) | [EPA Substance Registry System]
111-62-6(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
2
| [RTECS ]
RG3715000
| [F ]
10-23 | [TSCA ]
Yes | [HS Code ]
29161900 | [Toxicity]
rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Chemical Toxicology. Vol. 20, Pg. 683, 1982. |
| Hazard Information | Back Directory | [Description]
Ethyl oleate(111-62-6) is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless to light yellow liquid. Ethyl oleate is produced by the body during ethanol intoxication. Ethyl oleate is used as a solvent for pharmaceutical drug preparations involving lipophilic substances such as steroids. It also finds use as a lubricant and a plasticizer. The Food and Drug Administration regulates its use as a food additive under "Food Additives Permitted for Direct Addition to Food for Human Consumption", 21CFR172.515. | [Chemical Properties]
Ethyl oleate is a pale yellow to almost colorless, mobile, oily liquid with a taste similar to olive oil and a slight odor that is not rancid. In the USP32-NF27, Ethyl oleate is described as consisting of esters of ethyl alcohol and high molecular weight fatty acids, principally oleic acid. It may contain a suitable antioxidant. | [Occurrence]
Reported found in cocoa, buckwheat, elderberry and babaco fruit (Carica pentagona Heilborn).
| [Uses]
Ethyl oleate is a flavoring and fragrance agent. Usually used to prepare the oily phase of self-microemulsifying drug delivery system (SMEDDS) for tacrolimus (Tac). It was obtained by the hydrolysis of various animal and vegetable fats and oils. | [Definition]
ChEBI: Ethyl oleate is a long-chain fatty acid ethyl ester resulting from the formal condensation of the carboxy group of oleic acid with the hydroxy group of ethanol. It has a role as a plant metabolite and an acaricide. It is functionally related to an oleic acid. | [Preparation]
Ethyl oleate is prepared by the reaction of ethanol with oleoyl chloride in the presence of a suitable hydrogen chloride acceptor. Or by direct esterification of oleic acid with ethyl alcohol in the presence of HCl at the boil; in the presence of Twitchell’s reagent or chlorosulfonic acid. | [Aroma threshold values]
Detection: 130 to 610 ppm | [General Description]
Ethyl oleate is a colourless to pale yellow oily liquid that has a faint, floral note. It is neutral and is a more lipid-soluble form of oleic acid. The compound contributed to approximately 17% of the total fatty acids esterified to phosphatidylcholine in porcine platelets. The compound is one of the fatty acid ethyl esters that is generated after the breakdown of ethanol in the body. Moreover, ethyl oleate usually acts as a toxic mediator of ethanol in the heart, liver, pancreas, and brain. | [Health effects]
Ethyl oleate is one of the fatty acid ethyl esters (FAEE) that is formed in the body after ingestion of ethanol. There is a growing body of research literature that implicates FAEEs such as ethyl oleate as the toxic mediators of ethanol in the body (pancreas, liver, heart, and brain). Among the speculations is that ethyl oleate may be the toxic mediator of alcohol in fetal alcohol syndrome. The oral ingestion of ethyl oleate has been carefully studied and due to rapid degradation in the digestive tract it appears safe for oral ingestion. Ethyl oleate is not currently approved by the U.S. Food and Drug Administration for any injectable use. However, it is used by compounding pharmacies as a vehicle for intramuscular drug delivery, in some cases to prepare the daily doses of progesterone in support of pregnancy. Studies which document the safe use of ethyl oleate in pregnancy for both the mother and the fetus have never been performed. | [Pharmaceutical Applications]
Ethyl oleate is primarily used as a vehicle in certain parenteral
preparations intended for intramuscular administration. It has also
been used as a solvent for drugs formulated as biodegradable
capsules for subdermal implantation) and in the preparation of
microemulsions containing cyclosporinand norcantharidin. | [Safety]
Ethyl oleate is generally considered to be of low toxicity but
ingestion should be avoided. Ethyl oleate has been found to cause
minimal tissue irritation. No reports of intramuscular irritation
during use have been recorded. | [Carcinogenicity]
Not listed by ACGIH, California
Proposition 65, IARC, NTP, or OSHA. | [storage]
Ethyl oleate should be stored in a cool, dry place in a small, wellfilled,
well-closed container, protected from light. When a partially
filled container is used, the air should be replaced by nitrogen or
another inert gas. Ethyl oleate oxidizes on exposure to air, resulting
in an increase in the peroxide value. It remains clear at 5°C, but
darkens in color on standing. Antioxidants are frequently used to
extend the shelf life of ethyl oleate. Protection from oxidation for
over 2 years has been achieved by storage in amber glass bottles
with the addition of combinations of propyl gallate, butylated
hydroxyanisole, butylated hydroxytoluene, and citric or ascorbic
acid. A concentration of 0.03% w/v of a mixture of propyl
gallate (37.5%), butylated hydroxytoluene (37.5%), and butylated
hydroxyanisole (25%) was found to be the best antioxidant for
ethyl oleate.
Ethyl oleate may be sterilized by heating at 150°C for 1 hour. | [Incompatibilities]
Ethyl oleate dissolves certain types of rubber and causes others to
swell. It may also react with oxidizing agents. | [Regulatory Status]
Included in the FDA Inactive Ingredients Database (transdermal
preparation). Included in parenteral (intramuscular injection) and
nonparenteral (transdermal patches) medicines licensed in the UK.
Included in the Canadian List of Acceptable Non-medicinal
Ingredients. |
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