ChemicalBook > Product Catalog > Chemical Reagents > Organic reagents > Esters > Other esters > TRIOCTANOIN
TRIOCTANOIN Chemical Properties
- Melting point:9-10 °C
- Boiling point:233 °C/1 mmHg (lit.)
- Density 0.956 g/mL at 20 °C (lit.)
- refractive index n
- Flash point:225 °C
- storage temp. -20°C
- solubility Miscible with most organic solvents including ethanol (95%). Captex 8000 is insoluble in water.
- form neat
- BRN 1717202
- CAS DataBase Reference538-23-8(CAS DataBase Reference)
- EPA Substance Registry SystemGlycerol trioctanoate (538-23-8)
TRIOCTANOIN Usage And Synthesis
- Description1,2,3-Trioctanoyl glycerol is a triacylglycerol that contains octanoic acid at the sn-1, sn-2, and sn-3 positions. Dietary administration of 1,2,3-trioctanoyl glycerol (260 g/kg diet) increases hepatic and adipose tissue glucose-6-phosphate dehydrogenase (G6PDH), citrate cleavage enzyme (CCE), and malic enzyme activities in rats.1 It induces nuclear edema and cytolysis in tumor cells, but not normal hepatic cells, in a murine hepatic carcinoma model.2
- Chemical PropertiesTricaprylin occurs as a clear, colorless to pale-yellow liquid. It forms crystals from acetone/ethanol (95%). Tricaprylin is odorless.
- Chemical Propertiesclear colorless to yellow viscous liquid
- Usesglyceryl trioctanoate is an emollient with skin-softening abilities.
- Usestricaprylin is a skin-conditioning agent.
- UsesGlytex(R) 273 is a low viscosity polyol ester suggested for use as a synthetic fiber lubricant. It offers a balance of moderate volatility and low varnishing behavior. For low to moderate denier polyester and nylon filament and staple yarn applications. Product Data Sheet
- DefinitionChEBI: A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.
- Production MethodsTricaprylin is a triglyceride manufactured by esterification of caprylic acid and glycerin.
- General DescriptionOdorless viscous clear colorless to amber-brown liquid.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileTRIOCTANOIN is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. TRIOCTANOIN is incompatible with strong oxidizers. .
- Fire HazardTRIOCTANOIN is combustible.
- Pharmaceutical ApplicationsTricaprylin is used in pharmaceutical preparations as a neutral
carrier, absorption promoter, and solubilizer for active drugs. It has
been used as an oily phase to prepare water-in-oil-in-water multiple
emulsions for incorporating water-soluble drugs such as cefadroxil, cephradine, 4-aminoantipyrine, and antipyrine, and also for
obtaining stable microcapsules.
Tricaprylin acts as a vehicle for topical creams and lotions, and cosmetic preparations. It is used as a penetration-enhancing lipid base with excellent emollient and skin-smoothing properties. Owing to its non-greasy components and low viscosity, it has very good spreadability. In spite of being skin-permeable, tricaprylin does not obstruct natural skin respiration, and hence it is used in baby oils, massage oils, and face masks. It is an excellent dispersant, and acts as a solubilizer, wetting agent and binder in color cosmetics. Being readily miscible with natural oils and surfactants, tricaprylin is used as the fat component in two-phase foam baths. It is used in sunscreen creams and oils because of its compatibility with organic and inorganic filter agents. It is also used as a fixative for perfumes/fragrances.
- Biochem/physiol ActionsGlyceryl trioctanoate might serve as a skin softening agent. It possesses caprylic acid as the aliphatic chain.
- Safety ProfilePoison by intraperitoneal route. Moderately toxic by intravenous route. Mildly toxic by ingestion. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
- SafetyTricaprylin is used in pharmaceutical and cosmetic formulations.
The Cosmetic Ingredient Review (CIR) Expert Panel found that
dermal application of tricaprylin has not been associated with
significant irritation in rabbit skin. However, as a penetration
enhancer, tricaprylin may allow other chemicals to penetrate deeper
into the skin, increasing their concentration so that they may reach
the bloodstream. Ocular exposures of tricaprylin were found to be
only mildly irritating to rabbit eyes. Little or no acute, subchronic,
or chronic oral toxicity was observed in animal studies unless levels
approached a significant percentage of caloric intake. Subcutaneous
injections of tricaprylin in rats over a period of 5 weeks
caused a granulomatous reaction.
Tricaprylin has not been found to be teratogenic in rats, mice, or hamsters, but some reproductive effects have been seen in rabbits. Dose-related central nervous system toxicity in dogs has also been observed.
LD50 (mouse, IP): >27.8 g/kg
LD50 (mouse, IV): 3.7 g/kg
LD50 (mouse, oral): 29.6 g/kg
LD50 (mouse, SC): >27.8 g/kg
LD50 (rat, IP): 0.05 g/kg
LD50 (rat, IV): 4 g/kg
LD50 (rat, oral): 33.3 g/kg
- CarcinogenicityIn F344 rats given 10 mL/kg of tricaprylin by gavage daily for 2 years, there is significant increase in the incidence of squamous cell papillomas of the forestomach, compared to controls .
- storageTricaprylin is classified as a stable compound. It has high stability
against oxidation and is not heat sensitive. Even in hot climates
cooling is not necessary. However, exposure to high temperatures
near the flash point (246℃) should be avoided. Owing to its very
low water content, it is not sensitive to hydrolytic and microbial
splitting. Although polymerization of tricaprylin will not occur, it is
reported to decompose into carbon monoxide and carbon dioxide.
Tricaprylin should be stored in well-closed containers, protected from light, in a dry place at ambient temperature. High-density polyethylene, polypropylene, metal (aluminum), and glass are suitable for packaging. Some plastics, especially those containing plasticizers, can become brittle or expand in the presence of tricaprylin. Polystyrene and polyvinyl chloride are not suitable for its storage. Tricaprylin has a high tendency to migrate, and therefore care should be taken when selecting seal-closure elastomer material.
- IncompatibilitiesTricaprylin is incompatible with strong oxidizing agents.
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (epidural injections).
Ethoxylated hydrogenated castor oil Dipotassium glycyrrhizinate MEDIUMCHAINTRIGLYCERIDES Citric acid Petrolatum Methylisothiazolinone Xanthan gum Triethanolamine 4'-Hydroxyacetophenone Glycerol 1,2,3-PROPANETRIOL TRIS(OCTANOATE-1-13C) Octanoic acid MONOCAPRYLIN Trioctanoin-d45 (tri-octyl-d45) Trioctanoin (Acid-1-13C) Trioctanoin(1,1,1-13C3,) (Glyceryl Trioctanoate) Tricaprylin?(Trioctanoin)?,trioctanoin,glyceryltri(2-ethylhexanoate
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