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Showing Compound Glycerol (FDB000756)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3706109441e6d30178952014-09-20View Spectrum
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
Predicted GC-MSGlycerol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlycerol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-d7c139dc01453f61eb992012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-7d7844b4813b038012da2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9100000000-16029dbe79f139ab904a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ox-9000000000-3fe0c184a891364773a82012-08-31View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-a638e26fe3c3f48563c22015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9000000000-d3fd9e9abd911eb0f88e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-ca218dca3a5d86196d812015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-b40367f5ca8d11288fbe2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ba29a0647084e32d87042015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-4cd85379d414c16f95c02015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-1614392356273cb2b6a02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-9561fb02d4c00eb6eac12021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-7fe914cba67cae8073002021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-94d8bba653e2eee46dc32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-0c6df256e26adb060cbd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9000000000-edf49773503421d3897a2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.