Glycerols

Glycerol

Names
Preferred IUPAC name Propane-1,2,3-triol
Other names Glycerin Glycerine Propanetriol 1,2,3-Trihydroxypropane 1,2,3-Propanetriol
Identifiers
CAS Number	56-81-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17522 Y
ChEMBL	ChEMBL692 Y
ChemSpider	733 Y
DrugBank	DB04077 Y
ECHA InfoCard	100.000.263
E number	E422 (thickeners, ...)
IUPHAR/BPS	5195
KEGG	D00028 Y
PubChem	753
UNII	PDC6A3C0OX Y
InChI InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 Y Key: PEDCQBHIVMGVHV-UHFFFAOYSA-N Y InChI=1/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 Key: PEDCQBHIVMGVHV-UHFFFAOYAF
SMILES C(C(CO)O)O
Properties
Chemical formula	C3H8O3
Molar mass	92.09 g·mol−1
Appearance	colorless liquid hygroscopic
Odor	odorless
Density	1.261 g/cm3
Melting point	17.8 °C (64.0 °F; 290.9 K)
Boiling point	290 °C (554 °F; 563 K)
Solubility in water	miscible
Vapor pressure	0.003 mmHg (50°C)
Magnetic susceptibility (χ)	-57.06·10−6 cm3/mol
Refractive index (nD)	1.4746
Viscosity	1.412 Pa·s
Pharmacology
ATC code	A06AG04 (WHO) A06AX01 (WHO), QA16QA03 (WHO)
Hazards
Safety data sheet	See: data page JT Baker
NFPA 704	1 1 0
Flash point	160 °C (320 °F; 433 K) (closed cup) 176 °C (349 °F; 449 K) (open cup)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)
REL (Recommended)	None established
IDLH (Immediate danger)	N.D.
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Glycerol /ˈɡlɪsərɒl/ (also called glycerine or glycerin; see spelling differences) is a simple polyol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in all lipids known as triglycerides. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature.

Although achiral, glycerol is prochiral with respect to reactions of one of the two primary alcohols. Thus, in substituted derivatives, the stereospecific numbering labels each carbon as either sn-1, sn-2, or sn-3.

Glycerol is generally obtained from plant and animal sources where it occurs as triglycerides. Triglycerides are esters of glycerol with long-chain carboxylic acids. The hydrolysis, saponification, or transesterification of these triglycerides produces glycerol as well as the fatty acid derivative:

Triglycerides (1) are treated with an alcohol such as ethanol (2) with catalytic base to give ethyl esters of fatty acids (3) and glycerol (4):