Triacetin
Names | |
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Systematic IUPAC name
Propane-1,2,3-triyl triacetate | |
Other names
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.002.775 |
EC Number |
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E number | E1518 (additional chemicals) |
KEGG | |
PubChem CID
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RTECS number
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H14O6 | |
Molar mass | 218.205 g·mol−1 |
Appearance | Oily liquid |
Density | 1.155 g/cm3[3] |
Melting point | −78 °C (−108 °F; 195 K) at 760 mmHg[2] |
Boiling point | 259 °C (498 °F; 532 K) at 760 mmHg[2] |
6.1 g/100 mL[2] | |
Solubility | Miscible in EtOH Soluble in C6H6, (C2H5)2O, acetone[2] |
Vapor pressure | 0.051 Pa (11.09 °C) 0.267 Pa (25.12 °C) 2.08 Pa (45.05 °C)[4] ln(P/Pa)=22.819-4493/T(K)-807000/T(K)² |
Refractive index (nD)
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1.4301 (20 °C)[2] 1.4294 (24.5 °C)[4] |
Viscosity | 23 cP (20 °C)[3] |
Thermochemistry | |
Heat capacity (C)
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389 J/mol·K[5] |
Std molar
entropy (S⦵298) |
458.3 J/mol·K[5] |
Std enthalpy of (ΔfH⦵298)formation |
−1330.8 kJ/mol[5] |
Std enthalpy of (ΔcH⦵298)combustion |
4211.6 kJ/mol[5] |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 138 °C (280 °F; 411 K)[3] |
430 °C (806 °F; 703 K)[3] | |
Explosive limits
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7.73%[3] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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1100 mg/kg (mice, oral)[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triacetin is the organic compound with the formula C3H5(OCOCH3)3. It is classified as a triglyceride, i.e., the triester of glycerol with acetic acid.[6] It is a colorless, viscous, and odorless liquid with a high boiling point and a low melting point. It has a mild, sweet taste in concentrations lower than 500 ppm, but may appear bitter at higher concentrations.[7] It is one of the glycerine acetate compounds.
Uses
Triacetin is a common food additive, for instance as a solvent in flavorings, and for its humectant function, with E number E1518 and Australian approval code A1518. It is used as an excipient in pharmaceutical products, where it is used as a humectant, a plasticizer, and as a solvent.[8]
Potential uses
The plasticizing capabilities of triacetin have been utilized in the synthesis of a biodegradable phospholipid gel system for the dissemination of the cancer drug paclitaxel (PTX).[9] In the study, triacetin was combined with PTX, ethanol, a phospholipid and a medium chain triglyceride to form a gel-drug complex. This complex was then injected directly into the cancer cells of glioma-bearing mice. The gel slowly degraded and facilitated sustained release of PTX into the targeted glioma cells.
Triacetin can also be used as a
It has been considered as a possible source of
Synthesis
Triacetin was first prepared in 1854 by the French chemist Marcellin Berthelot.[12] Triacetin was prepared in the 19th century from glycerol and acetic acid.[13]
Its synthesis from acetic anhydride and glycerol is simple and inexpensive.
- 3 (CH3CO)2O + 1 C3H5(OH)3 → 1 C3H5(OCOCH3)3 + 3 CH3CO2H
This synthesis has been conducted with
Safety
The
Triacetin was not toxic to animals in studies of exposure through repeated inhalation over a relatively short period.[18]
References
- ^ Merck Index (11th ed.). p. 9405.
- ^ ISBN 978-1-4200-9084-0.
- ^ a b c d e f g "MSDS of Triacetin". fishersci.ca. Fisher Scientific. Retrieved 2014-06-20.
- ^ .
- ^ a b c d Triacetin in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
- S2CID 102384754.
- ISBN 978-0-931710-37-7.
- ^ "Triacetin". drugtopics.modernmedicine.com. Advanstar Communications, Inc. Archived from the original on 2012-02-19. Retrieved 2014-06-20.
- PMID 28596136.
- .
- PMID 12197534. Retrieved 2014-06-20.
- ^ Berthelot M (1854). "Sur les combinaisons de le glycérine avec les acides et sur la synthèse des principes immédiats des graisses des animaux" [On the compounds of glycerin with acids and on the synthesis of immediate principles of animal fats]. Annales de Chimie et de Physique. 3rd series (in French). 41: 216–319. ; see "Triacétine", pp. 282–283.
- .
- S2CID 96001761.
- .
- ^ "21 CFR § 184.1901 Listing of Specific Substances Affirmed as GRAS: Triacetin". eCFR.gov. FDA. 21 Feb 1989. Retrieved 25 Apr 2023.
- ^ "Glycerin and Glycerides". www.fda.gov. U.S. Food and Drug Administration. Archived from the original on 2017-10-31. Retrieved 2014-06-20.
Triacetin and two types of acetooleins have been found to be without toxic effects in long-term feeding tests in rats at levels that were several orders of magnitude greater than those to which consumers are exposed. Three types of acetostearins have been found to be without toxic effects in long-term feeding tests in rats at levels up to 5 g per kg per day. This contrasts with an estimated human consumption of a fraction of a milligram per kg per day. It is recognized that at an even higher feeding level (10 g per kg per day) male rats developed testicular atrophy and female rats, uterine discoloration. However, such a level which would amount to 50 g or more for an infant and 600 g for an adult per day, is vastly higher than would be possible in the consumption of foods to which acetostearins are added for functional purposes.
- PMID 14555416.