Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2020-09-17 15:42:20 UTC
Primary IDFDB000756
Secondary Accession Numbers
  • FDB009508
Chemical Information
FooDB NameGlycerol
DescriptionGlycerol, 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 Number56-81-5
Structure
Thumb
Synonyms
SynonymSource
1,2,3-PropanetriolChEBI
1,2,3-TrihydroxypropaneChEBI
GlycerinChEBI
GlycerineChEBI
GlyceritolChEBI
GlycerolumChEBI
Glycyl alcoholChEBI
GlyzerinChEBI
GroChEBI
OelsuessChEBI
PropanetriolChEBI
TrihydroxypropaneChEBI
Concentrated glycerinKegg
Glycerin, concentratedKegg
BulboldHMDB
CristalHMDB
e 422HMDB
Emery 916HMDB
Glyceol opthalganHMDB
GlyrolHMDB
GlysaninHMDB
IFPHMDB
Incorporation factorHMDB
Mackstat H 66HMDB
OsmoglynHMDB
Pricerine 9091HMDB
RG-SHMDB
TryhydroxypropaneHMDB
2,5-Dihydroxyphenylacetic acidHMDB
2-(3,6-DIHYDROXYPHENYL)acetIC ACIDHMDB
2,5-DihydroxyphenylacetateHMDB
2-(3,6-DIHYDROXYPHENYL)acetateHMDB
HomogentisateHMDB
(2,5-Dihydroxyphenyl)-acetateHMDB
(2,5-Dihydroxyphenyl)-acetic acidHMDB
2,5-Dihydroxy-a-toluateHMDB
2,5-Dihydroxy-a-toluic acidHMDB
2,5-Dihydroxy-alpha-toluateHMDB
2,5-Dihydroxy-alpha-toluic acidHMDB
2,5-Dihydroxy-benzeneacetateHMDB
2,5-Dihydroxy-benzeneacetic acidHMDB
AlcaptonHMDB
Homogentisate acidHMDB
HomogentisinateHMDB
Homogentisinic acidHMDB
Melanic acidHMDB
Acid, homogentisicHMDB
GlcAaHMDB
GlcAalphaHMDB
D-GlucuronateHMDB
alpha-D-Glucopyranuronic acidHMDB
alpha-D-Glucuronic acidHMDB
alpha-delta-Glucopyranuronic acidHMDB
alpha-delta-Glucuronic acidHMDB
D-(+)-GlucuronateHMDB
D-(+)-Glucuronic acidHMDB
delta-(+)-GlucuronateHMDB
delta-(+)-Glucuronic acidHMDB
delta-GlucuronateHMDB
GCUHMDB
GlucosiduronateHMDB
Glucosiduronic acidHMDB
GlucuronateHMDB
Glucuronic acidHMDB
(2E)-2-Butenedioic acidHMDB
(e)-2-Butenedioic acidHMDB
e297HMDB
FumarsaeureHMDB
trans-1,2-Ethylenedicarboxylic acidHMDB
trans-But-2-enedioic acidHMDB
trans-Butenedioic acidHMDB
(2E)-2-ButenedioateHMDB
(e)-2-ButenedioateHMDB
trans-1,2-EthylenedicarboxylateHMDB
trans-But-2-enedioateHMDB
trans-ButenedioateHMDB
FumarateHMDB
(2E)-But-2-enedioateHMDB
(2E)-But-2-enedioic acidHMDB
2-(e)-ButenedioateHMDB
2-(e)-Butenedioic acidHMDB
AllomaleateHMDB
Allomaleic acidHMDB
BoletateHMDB
Boletic acidHMDB
FC 33HMDB
LichenateHMDB
Lichenic acidHMDB
Sodium fumarateHMDB
trans-2-ButenedioateHMDB
trans-2-Butenedioic acidHMDB
FuramagHMDB
Ammonium fumarateHMDB
Magnesium fumarateHMDB
MafusolHMDB
1,2,3-Propanetriol, 9CIdb_source
1,2,3-Trihydroxypropanolbiospider
Amylacdb_source
Babylaxdb_source
Bulboiddb_source
E422db_source
FEMA 2525db_source
Luxoraldb_source
Meprolaxdb_source
Propane-1,2,3-triolmanual
Predicted Properties
PropertyValueSource
Water Solubility1170 g/LALOGPS
logP-1.9ALOGPS
logP-1.8ChemAxon
logS1.1ALOGPS
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity20.52 m³·mol⁻¹ChemAxon
Polarizability8.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC3H8O3
IUPAC namepropane-1,2,3-triol
InChI IdentifierInChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2
InChI KeyPEDCQBHIVMGVHV-UHFFFAOYSA-N
Isomeric SMILESOCC(O)CO
Average Molecular Weight92.0938
Monoisotopic Molecular Weight92.047344122
Classification
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 39.13%; H 8.76%; O 52.12%DFC
Melting PointMp 17.8°DFC
Boiling PointBp20 182°DFC
Experimental Water Solubility1000 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.76HANSCH,C ET AL. (1995)
Experimental pKapKa1 14.4DFC
Isoelectric pointNot Available
Charge0
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd1515 1.27DFC
Refractive Indexn20D 1.4720DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3706109441e6d3017895Spectrum
GC-MSGlycerol, 3 TMS, GC-MS Spectrumsplash10-0fr2-0910000000-6497c0870b71585c6322Spectrum
GC-MSGlycerol, 3 TMS, GC-MS Spectrumsplash10-0ktb-0920000000-93408d69acffad6f48afSpectrum
GC-MSGlycerol, 3 TMS, GC-MS Spectrumsplash10-05mk-0940000000-778ba583836705f8fdf4Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-00kb-0920000000-2e4b358941c660851f0aSpectrum
GC-MSGlycerol, 3 TMS, GC-MS Spectrumsplash10-00dj-6920000000-6828d7b00cb31e84fac1Spectrum
GC-MSGlycerol, 3 TMS, GC-MS Spectrumsplash10-0le9-0940000000-e0b9bada9be26d720326Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-01ox-9000000000-3fe0c184a891364773a8Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-0fr2-0930000000-470b6694b25fde40d80fSpectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-0fr2-0910000000-6497c0870b71585c6322Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-0ktb-0920000000-93408d69acffad6f48afSpectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-05mk-0940000000-778ba583836705f8fdf4Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-00kb-0920000000-2e4b358941c660851f0aSpectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-00dj-6920000000-6828d7b00cb31e84fac1Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-0le9-0940000000-e0b9bada9be26d720326Spectrum
GC-MSGlycerol, non-derivatized, GC-MS Spectrumsplash10-00kb-0920000000-085a71f40d38f2729036Spectrum
Predicted GC-MSGlycerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01qc-9000000000-80cdb8c006ea00f55a64Spectrum
Predicted GC-MSGlycerol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0q4u-9280000000-1487e8921bcecbde6458Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-d7c139dc01453f61eb99Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-7d7844b4813b038012daSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9100000000-16029dbe79f139ab904aSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ox-9000000000-3fe0c184a891364773a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-a638e26fe3c3f48563c2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9000000000-d3fd9e9abd911eb0f88eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-ca218dca3a5d86196d81Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-b40367f5ca8d11288fbeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ba29a0647084e32d8704Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-4cd85379d414c16f95c0Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID733
ChEMBL IDCHEMBL692
KEGG Compound IDC00116
Pubchem Compound ID753
Pubchem Substance IDNot Available
ChEBI ID17754
Phenol-Explorer IDNot Available
DrugBank IDDB04077
HMDB IDHMDB00131
CRC / DFC (Dictionary of Food Compounds) IDBGV25-K:BGV25-K
EAFUS ID1512
Dr. Duke IDGLYCEROL|GLYCERIN
BIGG ID33915
KNApSAcK IDC00001163
HET IDGOL
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1008461
SuperScent IDNot Available
Wikipedia IDGlycerol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ear-wax52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti ketoticDUKE
anti Meniere's52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
arrhythmigenic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
emollientDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
hyperglycemic76916 A drug which increases the blood glucose level.DUKE
Enzymes
NameGene NameUniProt ID
Glutathione S-transferase PGSTP1P09211
Carnitine O-palmitoyltransferase 1, muscle isoformCPT1BQ92523
Carnitine O-palmitoyltransferase 1, liver isoformCPT1AP50416
Carnitine O-palmitoyltransferase 2, mitochondrialCPT2P23786
Alpha-galactosidase AGLAP06280
Lipoprotein lipaseLPLP06858
Monoglyceride lipaseMGLLQ99685
Alcohol dehydrogenase [NADP(+)]AKR1A1P14550
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1PAPSS1O43252
Lactase-phlorizin hydrolaseLCTP09848
Alpha-N-acetylgalactosaminidaseNAGAP17050
Glycerol kinase 2GK2Q14410
Glycerol kinaseGKP32189
Beta-galactosidaseGLB1P16278
Hematopoietic prostaglandin D synthaseHPGDSO60760
Glycophorin-BGYPBP06028
GlycodelinPAEPP09466
Putative glycerol kinase 3GK3PQ14409
Cardiolipin synthaseCRLS1Q9UJA2
Putative glycerol kinase 5GK5Q6ZS86
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6ENPP6Q6UWR7
Glycerophosphoinositol inositolphosphodiesterase GDPD2GDPD2Q9HCC8
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043 map00052
Glycerolipid MetabolismSMP00039 map00561
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.