Triacetin

Triacetin

Names
IUPAC name 1,3-Diacetyloxypropan-2-yl acetate
Other names Glycerol triacetate
Identifiers
CAS Number	102-76-1 Y
ChEBI	CHEBI:9661 N
ChEMBL	ChEMBL1489254 N
ChemSpider	13835706 Y
Jmol 3D model	Interactive image
KEGG	D00384 Y
RTECS number	AK3675000
UNII	XHX3C3X673 Y
InChI InChI=1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3 Y Key: URAYPUMNDPQOKB-UHFFFAOYSA-N Y InChI=1/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3 Key: URAYPUMNDPQOKB-UHFFFAOYAH
SMILES CC(=O)OC(COC(=O)C)COC(C)=O
Properties
Chemical formula	C9H14O6
Molar mass	218.21 g·mol−1
Appearance	Oily liquid
Density	1.155 g/cm3
Melting point	−78 °C (−108 °F; 195 K) at 760 mmHg
Boiling point	259 °C (498 °F; 532 K) at 760 mmHg
Solubility in water	6.1 g/100 mL
Solubility	Miscible in EtOH Soluble in C6H6, (C2H5)2O, acetone
Vapor pressure	0.051 Pa (11.09 °C) 0.267 Pa (25.12 °C) 2.08 Pa (45.05 °C)
Refractive index (nD)	1.4301 (20 °C) 1.4294 (24.5 °C)
Viscosity	23 cP (20 °C)
Thermochemistry
Specific heat capacity (C)	389 J/mol·K
Std molar entropy (So298)	458.3 J/mol·K
Std enthalpy of formation (ΔfHo298)	−1330.8 kJ/mol
Std enthalpy of combustion (ΔcHo298)	4211.6 kJ/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

The triglyceride 1,2,3-triacetoxypropane is more generally known as triacetin and glycerin triacetate. It is the triester of glycerol and acetic acid.It is a colorless viscous liquid.

Uses

It is an artificial chemical compound, commonly used as a food additive, for instance as a solvent in flavourings, and for its humectant function, with E number E1518 and Australian approval code A1518. Triacetin is also a component of casting liquor with TG and as an excipient in pharmaceutical products, where it is used as a humectant, a plasticizer, and as a solvent.

Triacetin can also be used as a fuel additive as an antiknock agent which can reduce engine knocking in gasoline, and to improve cold and viscosity properties of biodiesel.

In a 1994 report released by five top cigarette companies, triacetin was listed as one of the 599 cigarette additives. The triacetin is applied to the filter as a plasticizer.

It has been considered as a possible source of food energy in artificial food regeneration systems on long space missions. It is believed to be safe to get over half of one's dietary energy from triacetin.

Safety

US Food and Drug Administration has approved it as Generally Regarded as Safe (GRAS) food additive and included it in the database according to the opinion from the Select Committee On GRAS Substances (SCOGS). "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." Triacetin is included in the SCOGS database since 1975.