Triacetin

Chemical properties

Colorless, odorless oily liquid. It is miscible with ethanol, ether, benzene, chloroform and other organic solvents, soluble in acetone, insoluble in mineral oil. Slightly soluble in water. 25 ° C in water solubility of 5.9g / 100ml.

Uses

• As a plasticizer and fragrance fixative, ink solvent, also used in medicine and dye synthesis.
• As a chromatographic fixative, solvent, toughener and fragrance fixative.
• Humectants; carrier solvents; plasticizers; it can absorb carbon dioxide from the natural gas.
• In the production of cosmetics, pharmaceuticals and dyes, plasticizers for cigarette filter rods, and so on.
• Applied in cosmetics, casting, medicine, dyes and other industries. This product is non-toxic, non-irritating.
• As the substrate for the determination of lipase, perfume fixative, solvent, gas chromatographic fixative (maximum temperature of 85 ℃, solvent: methanol, chloroform), separation of gas and aldehyde analysis.

Production

It can be derived from the esterification of glycerol and acetic acid. After preheating glycerol to 50-60 ° C, add acetic acid, benzene and sulfuric acid. Heat and stir for refluxing dehydration, and recycle the benzene. Then add acetic anhydride for heating of 4h. After cooling, the mixture was neutralized with 5% sodium carbonate to pH 7, and the crude layer was dried and the crude oil was dried with calcium chloride. Distill under reduced pressure, collect the 128-131 ° C (0.93 kPa) fraction, namely glycerol triacetate.

Content analysis

Accurately weigh about 1g of the sample, put it into a suitable pressure bottle, add 25 mL of 1mol / L. potassium hydroxide solution and 15 mL of isopropyl alcohol, add stopper, wrap with cloth and put it in a canvas bag. Put it into the water bath of 98 ℃ ± 2 ℃ for 1h, and the water level in the water bath should be slightly higher than the bottle level. Take the bottle out from the bag, cool it to room temperature in the air, unfold the cloth and stopper to release the residual pressure in the bottle, and then remove the cloth. Add 6 to 8 drops of phenolphthalein test solution (TS-167), apply 0.5mol / L sulfuric acid for titration of excess alkali until the pink could just disappeared. At the same time, perform a blank test. Each mL of 0.5mol / L sulfuric acid is equivalent to 36.37 mg of glyceryl triacetate (C9H14O6).

Toxicity

ADI is not subject to special provisions (FAO / WHO, 2001).
GR.AS (FDA, § 182.1901, 2000).
LD50 3000mg / kg (rat, oral).

Description

§ 184.1901(a) Triacetin (C8H14O6), also known as 1,2,3-propanetriol triacetate or glyceryl triacetate, is the triester of glycerin and acetic acid. Triacetin can be prepared by heating glycerin with acetic anhydride alone or in the presence of finely divided potassium hydrogen sulfate. It can also be prepared by the reaction of oxygen with a liquid-phase mixture of allyl acetate and acetic acid using a bromide salt as a catalyst.

Chemical Properties

Colorless liquid; slight fatty odor; bitter taste. Slightly soluble in water; very soluble in alcohol, ether, and other organic solvents. Combustible.

Chemical Properties

Triacetin has a very faint, fruity odor. It has a mild, sweet taste that is bitter above 0.05%.

Chemical Properties

Triacetin is a colorless, viscous liquid with a slightly fatty odor.

Originator

Enzactin,Ayerst,US,1957

Occurrence

Reported found in papaya.

Uses

Triacetin is a colorless, oily liquid of slight fatty odor and bitter taste. It is soluble with water and is miscible with alcohol and ether. It functions in foods as a humectant and solvent.

Uses

As fixative in perfumery; solvent in manufacture of celluloid, photographic films. Technical triacetin (a mixture of mono-, di-, and small quantities of triacetin) as a solvent for basic dyes, particularly indulines, and tannin in dyeing.

Uses

Triacetin, a component of cigarette filters, induced a contact dermatitis in a worker at a cigarette manufacturers.

Definition

ChEBI: A triglyceride obtained by acetylation of the three hydroxy groups of glycerol. It has fungistatic properties (based on release of acetic acid) and has been used in the topical treatment of minor dermatophyte infections.

Preparation

By direct reaction of glycerol with acetic acid in the presence of Twitchell’s reagent, or in benzene solution of glycerol and boiling acetic acid in the presence of a cationic resin (Zeo-Karb H) pretreated with dilute H2SO4.

Production Methods

Triacetin is prepared by the esterification of glycerin with acetic anhydride.

Manufacturing Process

200 grams of allyl acetate, 450 grams of glacial acetic acid and 3.71 grams of cobaltous bromide were charged to the reactor and the mixture was heated to 100°C. Pure oxygen was then introduced into the reactor below the surface of the liquid reaction mixture at the rate of 0.5 standard cubic feet per hour. Initially, all of the oxygen was consumed, but after a period of time oxygen introduced into the mixture passed through unchanged. During the course of the reaction, a small quantity of gaseous hydrogen bromide (a total of 1.9 grams) was introduced into the reaction zone, along with the oxygen. The reaction was allowed to continue for 6 hours following which the reaction mixture was distilled. Essentially complete conversion of the allyl acetate took place. A yield of 116 grams of glycerol triacetate was obtained, this being accomplished by distilling the glycerol triacetate overhead from the reaction mixture, at an absolute pressure of approximately 13 mm of mercury.

Therapeutic Function

Topical antifungal

Taste threshold values

Sweet and creamy with an oily mouthfeel.

General Description

Triacetin is a triester of glycerin and acetic acid that occurs naturally in papaya. It is mainly used as a synthetic flavoring agent in ice-creams, nonalcoholic beverages and baked goods.

Pharmaceutical Applications

Triacetin is mainly used as a hydrophilic plasticizer in both aqueous and solvent-based polymeric coating of capsules, tablets, beads, and granules; typical concentrations used are 10–35% w/w.
Triacetin is used in cosmetics, perfumery, and foods as a solvent and as a fixative in the formulation of perfumes and flavors.

Contact allergens

Triacetin is a component of cigarette filters, which induced a contact dermatitis in a worker at a cigarette manufactory.

Clinical Use

Glyceryl triacetate (Enzactin, Fungacetin) is a colorless, oilyliquid with a slight odor and a bitter taste. The compound issoluble in water and miscible with alcohol and most organicsolvents.
The activity of triacetin is a result of the acetic acid releasedby hydrolysis of the compound by esterases presentin the skin. Acid release is a self-limiting process becausethe esterases are inhibited below pH 4.

Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal, subcutaneous, and intravenous routes. An eye irritant. Combustible when exposed to heat, flame, or powerful oxidizers. To fight fire, use alcohol foam, water, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

Triacetin is used in oral pharmaceutical formulations and is generally regarded as a relatively nontoxic and nonirritant material at the levels employed as an excipient.
LD50 (dog, IV): 1.5 g/kg
LD50 (mouse, IP): 1.4 g/kg
LD50 (mouse, IV): 1.6 g/kg
LD50 (mouse, oral): 1.1 g/kg
LD50 (mouse, SC): 2.3 g/kg
LD50 (rabbit, IV): 0.75 g/kg
LD50 (rat, IP): 2.1 g/kg
LD50 (rat, oral): 3 g/kg
LD50 (rat, SC): 2.8 g/kg

in vitro

Litton Bionetics, Inc. (1976) evaluated the mutagenic potential of Triacetin in a plate test using Salmonella typhimurium strains TA1535, TA1537, and TA1538 with and without metabolic activation. Test concentrations were 0.0013%, 0.00065%, and 0.000325% and the solvent was dimethyl sulfoxide (DMSO). A negative control (solvent) and appropriate positive controls were used and gave expected results. Triacetin was not mutagenic with or without metabolic activation.
Unichema Chemie B.V. (1994) reported that Triacetin was not mutagenic at 50 to 5000 μg/plate in an Ames test using S. typhimurium strains TA1535, TA1537, TA98, and TA100 with and without metabolic activation.

in vivo

The mutagenic potential of Triacetin was determined using adult Drosophila melanogaster (Efremova 1962). A dose of 0.2 to 0.3 mg Triacetin had a spontaneous mutation rate of approximately one mutation per 750 chromosomes.

storage

Triacetin is stable and should be stored in a well-closed, nonmetallic container, in a cool, dry place.

Incompatibilities

Triacetin is incompatible with metals and may react with oxidizing agents. Triacetin may destroy rayon fabric.

Regulatory Status

GRAS listed. Accepted in Europe as a food additive in certain applications. Included in the FDA Inactive Ingredients Database (oral capsules and tablets and gels). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.