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Record Information
Version1.0
Creation Date2016-09-30 22:19:58 UTC
Update Date2020-06-04 21:18:06 UTC
MCDB ID BMDB0000131
Secondary Accession Numbers
  • BMDB00131
Metabolite Identification
Common 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 carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Glycerol exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycerol exists in all living species, ranging from bacteria to humans. In cattle, glycerol is involved in the metabolic pathway called phospholipid biosynthesis pathway. Glycerol is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC3H8O3
Average Molecular Weight92.0938
Monoisotopic Molecular Weight92.047344122
IUPAC Namepropane-1,2,3-triol
Traditional Nameglycerol
CAS Registry Number56-81-5
SMILES
OCC(O)CO
InChI Identifier
InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2
InChI KeyPEDCQBHIVMGVHV-UHFFFAOYSA-N
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.
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point20 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-1.76HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0fr2-0910000000-6497c0870b71585c6322JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0ktb-0920000000-93408d69acffad6f48afJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-05mk-0940000000-778ba583836705f8fdf4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00kb-0920000000-2e4b358941c660851f0aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-6920000000-6828d7b00cb31e84fac1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0le9-0940000000-e0b9bada9be26d720326JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-9000000000-3fe0c184a891364773a8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0fr2-0930000000-470b6694b25fde40d80fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0910000000-6497c0870b71585c6322JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ktb-0920000000-93408d69acffad6f48afJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-05mk-0940000000-778ba583836705f8fdf4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0920000000-2e4b358941c660851f0aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-6920000000-6828d7b00cb31e84fac1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0le9-0940000000-e0b9bada9be26d720326JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00kb-0920000000-085a71f40d38f2729036JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01qc-9000000000-80cdb8c006ea00f55a64JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0q4u-9280000000-1487e8921bcecbde6458JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-9000000000-d7c139dc01453f61eb99JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9000000000-7d7844b4813b038012daJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9100000000-16029dbe79f139ab904aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-01ox-9000000000-3fe0c184a891364773a8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-a638e26fe3c3f48563c2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-9000000000-d3fd9e9abd911eb0f88eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-ca218dca3a5d86196d81JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-b40367f5ca8d11288fbeJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-ba29a0647084e32d8704JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9000000000-4cd85379d414c16f95c0JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-3706109441e6d3017895JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
HMDB IDHMDB0000131
DrugBank IDDB09462
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000756
KNApSAcK IDC00001163
Chemspider IDNot Available
KEGG Compound IDC00116
BioCyc IDGLYCEROL
BiGG IDNot Available
Wikipedia LinkGlycerol
METLIN IDNot Available
PubChem Compound753
PDB IDNot Available
ChEBI ID17754
References
Synthesis ReferenceYang, Yifang. Purification of glycerol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 3pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]
  3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.