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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:27 UTC

Update Date

2023-02-21 17:19:57 UTC

HMDB ID

HMDB0031175

Secondary Accession Numbers

HMDB31175

Metabolite Identification

Common Name

Tetrahydro-2-furanmethanol

Description

Tetrahydro-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Hydroxymethyl)tetrahydrofuran	ChEBI
Tetrahydro-2-furancarbinol	ChEBI
Tetrahydro-2-furanylmethanol	ChEBI
Tetrahydro-2-furfuryl alcohol	ChEBI
Tetrahydrofuryl carbinol	ChEBI
THFA	ChEBI
2-Hydroxymethyl-tetrahydrofuran	HMDB
2-Hydroxymethyltetrahydrofuran	HMDB
alpha-Tetrahydrofurfuryl alcohol	HMDB
FEMA 3056	HMDB
Oxolan-2-methanol	HMDB
qo Tetrahydrofurfuryl alcohol	HMDB
Tetrahydrofurfuryl alcohol, 8ci	HMDB
Tetrahydrofurylmethanol	HMDB
Tetrahydrofurfuryl alcohol, (S)-isomer	MeSH, HMDB
Tetrahydrofurfuryl alcohol, (R)-isomer	MeSH, HMDB
Tetrahydro-2-furanmethanol	ChEBI

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

oxolan-2-ylmethanol

Traditional Name

tetrahydrofurfuryl alcohol

CAS Registry Number

97-99-4

SMILES

OCC1CCCO1

InChI Identifier

InChI=1S/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2

InChI Key

BSYVTEYKTMYBMK-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031175)
Cytoplasm (HMDB: HMDB0031175)

Source

Exogenous

Exogenous (HMDB: HMDB0031175)

Food

Food (HMDB: HMDB0031175)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0031175)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< -80 °C	Not Available
Boiling Point	178.00 to 179.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1000 mg/mL at 25 °C	Not Available
LogP	-0.367 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	279 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	-0.1	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	26.52 m³·mol⁻¹	ChemAxon
Polarizability	11.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	119.767	31661259
DarkChem	[M-H]-	114.994	31661259
DeepCCS	[M+H]+	128.407	30932474
DeepCCS	[M-H]-	126.512	30932474
DeepCCS	[M-2H]-	162.179	30932474
DeepCCS	[M+Na]+	136.72	30932474
AllCCS	[M+H]+	122.1	32859911
AllCCS	[M+H-H2O]+	117.1	32859911
AllCCS	[M+NH4]+	126.8	32859911
AllCCS	[M+Na]+	128.1	32859911
AllCCS	[M-H]-	121.4	32859911
AllCCS	[M+Na-2H]-	124.5	32859911
AllCCS	[M+HCOO]-	127.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.96 minutes	32390414
Predicted by Siyang on May 30, 2022	9.058 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.5 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	51.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1292.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	319.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	201.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	284.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	334.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	678.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	220.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	887.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	253.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	492.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	265.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	158.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydro-2-furanmethanol	OCC1CCCO1	1513.8	Standard polar	33892256
Tetrahydro-2-furanmethanol	OCC1CCCO1	903.8	Standard non polar	33892256
Tetrahydro-2-furanmethanol	OCC1CCCO1	894.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydro-2-furanmethanol,1TMS,isomer #1	C[Si](C)(C)OCC1CCCO1	1039.5	Semi standard non polar	33892256
Tetrahydro-2-furanmethanol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1CCCO1	1262.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)	splash10-006x-9000000000-9411d51655677813066a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)	splash10-00dl-9000000000-c623d7fe47c3ac9514e4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)	splash10-006x-9000000000-9411d51655677813066a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydro-2-furanmethanol EI-B (Non-derivatized)	splash10-00dl-9000000000-c623d7fe47c3ac9514e4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydro-2-furanmethanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9000000000-83aafc048b645c77b395	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydro-2-furanmethanol GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9400000000-faa293567ff7736fa97e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydro-2-furanmethanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Positive-QTOF	splash10-0udi-2900000000-fbf530ec1063d3cf0818	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Positive-QTOF	splash10-0udr-9600000000-3f3da34e292d43f7510f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Positive-QTOF	splash10-0abl-9000000000-39da84f13eaffcb1b24f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Negative-QTOF	splash10-0udi-1900000000-923b4e8b9c6e9c821fdb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Negative-QTOF	splash10-0udi-9600000000-b90be65df448ce2c9d4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Negative-QTOF	splash10-002f-9000000000-0401e85759c5c9f4017a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Negative-QTOF	splash10-001i-9200000000-61868476761ad9b9dc43	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Negative-QTOF	splash10-0159-9100000000-0e6fd96aa4cd14b77296	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Negative-QTOF	splash10-014l-9000000000-e9580f612574a5703378	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 10V, Positive-QTOF	splash10-052o-9100000000-0a42aa2317d8ad004e28	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 20V, Positive-QTOF	splash10-052o-9000000000-909effcf903023813b61	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydro-2-furanmethanol 40V, Positive-QTOF	splash10-00ko-9000000000-fac59974aa1e4ec376f9	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003193

KNApSAcK ID

Not Available

Chemspider ID

7082

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7360

PDB ID

Not Available

ChEBI ID

137944

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1034891

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

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 acid	details

Enzyme Details

2. UDP-glucuronosyltransferase 1-1

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 acid	details

Showing metabocard for Tetrahydro-2-furanmethanol (HMDB0031175)

MOL for HMDB0031175 (Tetrahydro-2-furanmethanol)

3D MOL for HMDB0031175 (Tetrahydro-2-furanmethanol)

3D SDF for HMDB0031175 (Tetrahydro-2-furanmethanol)

3D-SDF for HMDB0031175 (Tetrahydro-2-furanmethanol)

PDB for HMDB0031175 (Tetrahydro-2-furanmethanol)

3D PDB for HMDB0031175 (Tetrahydro-2-furanmethanol)

SMILES for HMDB0031175 (Tetrahydro-2-furanmethanol)

INCHI for HMDB0031175 (Tetrahydro-2-furanmethanol)

Structure for HMDB0031175 (Tetrahydro-2-furanmethanol)

3D Structure for HMDB0031175 (Tetrahydro-2-furanmethanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions