FComEx: Glycerol (PC000506)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:59 UTC

Update date

2017-01-19 02:36:26 UTC

FoodComEx ID

PC000506

FoodDB Record

FDB000756

Chemical Information

Name

Glycerol

Description

Glycerol, also known as glycerin or glycyl alcohol, belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of sugars in which the carbonyl group (aldehyde or ketone of the reducing sugar) has been reduced to a primary or secondary hydroxyl group. Glycerol is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses, or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously.

CAS Number

56-81-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
1,2,3-Propanetriol	ChEBI
1,2,3-Propanetriol, 9CI	db_source
1,2,3-Trihydroxypropane	ChEBI
1,2,3-Trihydroxypropanol	biospider
Amylac	db_source
Babylax	db_source
Bulboid	db_source
Bulbold	HMDB
Cristal	db_source
e 422	HMDB
E422	db_source
Emery 916	HMDB
FEMA 2525	db_source
Glyceol opthalgan	HMDB
Glycerin	manual
Glycerine	ChEBI
Glyceritol	db_source
Glycerolum	ChEBI
Glycyl alcohol	manual
Glyrol	db_source
Glysanin	HMDB
Glyzerin	ChEBI
Gro	ChEBI
IFP	HMDB
Incorporation factor	HMDB
Luxoral	db_source
Mackstat H 66	HMDB
Meprolax	db_source
Oelsuess	ChEBI
Osmoglyn	db_source
Pricerine 9091	HMDB
Propane-1,2,3-triol	manual
Propanetriol	ChEBI
RG-S	HMDB
Trihydroxypropane	ChEBI
Tryhydroxypropane	HMDB

Chemical Formula

C3H8O3

IUPAC name

propane-1,2,3-triol

InChI Identifier

InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2

InChI Key

PEDCQBHIVMGVHV-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)CO

Average Molecular Weight

92.0938

Monoisotopic Molecular Weight

92.047344122

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

triol (CHEBI:17754 )
alditol (CHEBI:17754 )
Glycerols (C00116 )
a sugar alcohol (GLYCEROL )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	-1.76	HANSCH,C ET AL. (1995)
Experimental Water Solubility	1000 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	Mp 17.8°	DFC

Foods of Origin