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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:28 UTC

Update Date

2023-02-21 17:19:58 UTC

HMDB ID

HMDB0031177

Secondary Accession Numbers

HMDB31177

Metabolite Identification

Common Name

Tetrahydrofurfuryl propionate

Description

Tetrahydrofurfuryl propionate 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. Tetrahydrofurfuryl propionate is a fruity, leaf, and oily tasting compound. Based on a literature review very few articles have been published on Tetrahydrofurfuryl propionate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Tetrahydrofurfuryl propionic acid	Generator
(+/-)-tetrahydrofurfuryl propionate	HMDB
2-Furanemethanol, tetrahydro-, propanoate	HMDB
2-Furanmethanol, tetrahydro-, 2-propanoate	HMDB
2-Furanmethanol, tetrahydro-, propanoate	HMDB
2-Tetrahydrofurylmethyl propionate	HMDB
DL-Tetrahydrofurfuryl propionate	HMDB
FEMA 3058	HMDB
Furfuryl alcohol, tetrahydro-, propionate	HMDB
N-Butyric acid tetrahydrofurfuryl ester	HMDB
N-Propionic acid tetrahydrofurfuryl ester	HMDB
Propionic acid, tetrahydrofurfuryl ester	HMDB
tetrahydro-2-Furanmethyl propanoate	HMDB
tetrahydro-2-Furanylmethyl propionate	HMDB
Tetrahydrofurfuryl alcohol propionate	HMDB
Tetrahydrofurfuryl propanoate	HMDB
(Oxolan-2-yl)methyl propanoic acid	Generator

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

oxolan-2-ylmethyl propanoate

Traditional Name

oxolan-2-ylmethyl propanoate

CAS Registry Number

637-65-0

SMILES

CCC(=O)OCC1CCCO1

InChI Identifier

InChI=1S/C8H14O3/c1-2-8(9)11-6-7-4-3-5-10-7/h7H,2-6H2,1H3

InChI Key

FMKCDSXOYLTWBR-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
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0031177)
Cytoplasm (HMDB: HMDB0031177)

Source

Endogenous

Endogenous (HMDB: HMDB0031177)

Exogenous

Food

Food (HMDB: HMDB0031177)

Exogenous (HMDB: HMDB0031177)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031177)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	205.00 to 207.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	0.858 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	16.9 g/L	ALOGPS
logP	1.03	ALOGPS
logP	1.04	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	40.29 m³·mol⁻¹	ChemAxon
Polarizability	17.38 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]+	136.252	31661259
DarkChem	[M-H]-	133.865	31661259
DeepCCS	[M+H]+	135.375	30932474
DeepCCS	[M-H]-	132.482	30932474
DeepCCS	[M-2H]-	169.079	30932474
DeepCCS	[M+Na]+	144.325	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	136.4	32859911
AllCCS	[M+Na-2H]-	138.0	32859911
AllCCS	[M+HCOO]-	139.7	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.	3.36 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0465 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.45 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1843.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	374.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	218.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	118.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	465.9 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	563.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	978.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.0 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	1182.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	418.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	388.2 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	80.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrofurfuryl propionate	CCC(=O)OCC1CCCO1	1683.1	Standard polar	33892256
Tetrahydrofurfuryl propionate	CCC(=O)OCC1CCCO1	1129.2	Standard non polar	33892256
Tetrahydrofurfuryl propionate	CCC(=O)OCC1CCCO1	1164.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofurfuryl propionate EI-B (Non-derivatized)	splash10-00di-9000000000-32e9a1d39997c3b8db61	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Tetrahydrofurfuryl propionate EI-B (Non-derivatized)	splash10-00di-9000000000-32e9a1d39997c3b8db61	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrofurfuryl propionate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05dl-9100000000-ce381fb893b89898caff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrofurfuryl propionate 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 - Tetrahydrofurfuryl propionate 10V, Positive-QTOF	splash10-0a4i-9700000000-616ceef04d29760de92a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 20V, Positive-QTOF	splash10-0a4r-9100000000-a5fecb7bf206082fd1ff	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 40V, Positive-QTOF	splash10-0a6r-9000000000-58b4d50ed2d2ee87ae29	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 10V, Negative-QTOF	splash10-0ab9-9500000000-0d10cd638472155f8dda	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 20V, Negative-QTOF	splash10-05fr-9100000000-1174e03c7a45cc12e365	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 40V, Negative-QTOF	splash10-0ab9-9000000000-ff27adfdcf01e94efd71	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 10V, Positive-QTOF	splash10-052r-9100000000-c046a2656b8120fc9d65	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 20V, Positive-QTOF	splash10-052u-9000000000-33e7309fb2af4386dc45	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 40V, Positive-QTOF	splash10-052o-9000000000-0350c2a2019f202e3168	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 10V, Negative-QTOF	splash10-00di-9200000000-d11f8dc9d33787ec6e7a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 20V, Negative-QTOF	splash10-00di-9000000000-b4f05a81ea82cae3d3f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrofurfuryl propionate 40V, Negative-QTOF	splash10-01bc-9000000000-95605294ee8cee0c8c82	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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+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

FDB003196

KNApSAcK ID

Not Available

Chemspider ID

55129

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61183

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1034911

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Tetrahydrofurfuryl propionate (HMDB0031177)

MOL for HMDB0031177 (Tetrahydrofurfuryl propionate)

3D MOL for HMDB0031177 (Tetrahydrofurfuryl propionate)

3D SDF for HMDB0031177 (Tetrahydrofurfuryl propionate)

3D-SDF for HMDB0031177 (Tetrahydrofurfuryl propionate)

PDB for HMDB0031177 (Tetrahydrofurfuryl propionate)

3D PDB for HMDB0031177 (Tetrahydrofurfuryl propionate)

SMILES for HMDB0031177 (Tetrahydrofurfuryl propionate)

INCHI for HMDB0031177 (Tetrahydrofurfuryl propionate)

Structure for HMDB0031177 (Tetrahydrofurfuryl propionate)

3D Structure for HMDB0031177 (Tetrahydrofurfuryl propionate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra