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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:41:27 UTC
Update Date2022-03-07 02:52:51 UTC
HMDB IDHMDB0031175
Secondary Accession Numbers
  • HMDB31175
Metabolite Identification
Common NameTetrahydro-2-furanmethanol
DescriptionTetrahydro-2-furanmethanol, also known as tetrahydro-2-furfuryl alcohol or tetrahydrofuryl carbinol, belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Tetrahydro-2-furanmethanol is a faint, caramel, and cauliflower tasting compound. Based on a literature review very few articles have been published on Tetrahydro-2-furanmethanol.
Structure
Data?1563862091
Synonyms
ValueSource
2-(Hydroxymethyl)tetrahydrofuranChEBI
Tetrahydro-2-furancarbinolChEBI
Tetrahydro-2-furanylmethanolChEBI
Tetrahydro-2-furfuryl alcoholChEBI
Tetrahydrofuryl carbinolChEBI
THFAChEBI
2-Hydroxymethyl-tetrahydrofuranHMDB
2-HydroxymethyltetrahydrofuranHMDB
alpha-Tetrahydrofurfuryl alcoholHMDB
FEMA 3056HMDB
Oxolan-2-methanolHMDB
qo Tetrahydrofurfuryl alcoholHMDB
Tetrahydrofurfuryl alcohol, 8ciHMDB
TetrahydrofurylmethanolHMDB
Tetrahydrofurfuryl alcohol, (S)-isomerMeSH, HMDB
Tetrahydrofurfuryl alcohol, (R)-isomerMeSH, HMDB
Tetrahydro-2-furanmethanolChEBI
Chemical FormulaC5H10O2
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
IUPAC Nameoxolan-2-ylmethanol
Traditional Nametetrahydrofurfuryl alcohol
CAS Registry Number97-99-4
SMILES
OCC1CCCO1
InChI Identifier
InChI=1S/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2
InChI KeyBSYVTEYKTMYBMK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydrofurans
Sub ClassNot Available
Direct ParentTetrahydrofurans
Alternative Parents
Substituents
  • Tetrahydrofuran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -80 °CNot Available
Boiling Point178.00 to 179.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mL at 25 °CNot Available
LogP-0.367 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility279 g/LALOGPS
logP-0.28ALOGPS
logP-0.1ChemAxon
logS0.44ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.52 m³·mol⁻¹ChemAxon
Polarizability11.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+119.76731661259
DarkChem[M-H]-114.99431661259
DeepCCS[M+H]+128.40730932474
DeepCCS[M-H]-126.51230932474
DeepCCS[M-2H]-162.17930932474
DeepCCS[M+Na]+136.7230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Tetrahydro-2-furanmethanolOCC1CCCO11513.8Standard polar33892256
Tetrahydro-2-furanmethanolOCC1CCCO1903.8Standard non polar33892256
Tetrahydro-2-furanmethanolOCC1CCCO1894.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tetrahydro-2-furanmethanol,1TMS,isomer #1C[Si](C)(C)OCC1CCCO11039.5Semi standard non polar33892256
Tetrahydro-2-furanmethanol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1CCCO11262.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)splash10-006x-9000000000-9411d51655677813066a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)splash10-00dl-9000000000-c623d7fe47c3ac9514e42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)splash10-006x-9000000000-9411d51655677813066a2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)splash10-00dl-9000000000-c623d7fe47c3ac9514e42018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydro-2-furanmethanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9000000000-83aafc048b645c77b3952017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydro-2-furanmethanol GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9400000000-faa293567ff7736fa97e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tetrahydro-2-furanmethanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Positive-QTOFsplash10-0udi-2900000000-fbf530ec1063d3cf08182016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Positive-QTOFsplash10-0udr-9600000000-3f3da34e292d43f7510f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Positive-QTOFsplash10-0abl-9000000000-39da84f13eaffcb1b24f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Negative-QTOFsplash10-0udi-1900000000-923b4e8b9c6e9c821fdb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Negative-QTOFsplash10-0udi-9600000000-b90be65df448ce2c9d4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Negative-QTOFsplash10-002f-9000000000-0401e85759c5c9f4017a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Negative-QTOFsplash10-001i-9200000000-61868476761ad9b9dc432021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Negative-QTOFsplash10-0159-9100000000-0e6fd96aa4cd14b772962021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Negative-QTOFsplash10-014l-9000000000-e9580f612574a57033782021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Positive-QTOFsplash10-052o-9100000000-0a42aa2317d8ad004e282021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Positive-QTOFsplash10-052o-9000000000-909effcf903023813b612021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Positive-QTOFsplash10-00ko-9000000000-fac59974aa1e4ec376f92021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003193
KNApSAcK IDNot Available
Chemspider ID7082
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7360
PDB IDNot Available
ChEBI ID137944
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1034891
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Milosavljevic AR, Kocisek J, Papp P, Kubala D, Marinkovic BP, Mach P, Urban J, Matejcik S: Electron impact ionization of furanose alcohols. J Chem Phys. 2010 Mar 14;132(10):104308. doi: 10.1063/1.3352422. [PubMed:20232961 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Tetrahydro-2-furanmethanol → [(oxolan-2-yl)methoxy]sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Tetrahydro-2-furanmethanol → 3,4,5-trihydroxy-6-[(oxolan-2-yl)methoxy]oxane-2-carboxylic aciddetails