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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:02:57 UTC

Update Date

2023-02-21 17:24:06 UTC

HMDB ID

HMDB0034246

Secondary Accession Numbers

HMDB34246

Metabolite Identification

Common Name

Furfuryl acetate

Description

Furfuryl acetate belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Furfuryl acetate is a sweet, banana, and fruity tasting compound. Furfuryl acetate has been detected, but not quantified in, several different foods, such as welsh onions (Allium fistulosum), breakfast cereal, cocoa and cocoa products, cereals and cereal products, and robusta coffees (Coffea canephora). This could make furfuryl acetate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Furfuryl acetate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Furfuryl acetic acid	Generator
2-Acetoxymethylfuran	HMDB
2-Furanmethanol acetate	HMDB
2-Furanmethanol, 2-acetate	HMDB
2-Furanmethanol, acetate	HMDB
2-Furanmethyl acetate	HMDB
2-Furfuryl acetate	HMDB
2-Furfuryl-acetate	HMDB
2-Furylcarbinyl acetate	HMDB
2-Furylmethyl acetate	HMDB
Acetic acid furfuryl ester	HMDB
Acetic acid furfurylester	HMDB
FEMA 2490	HMDB
Furfuryl alcohol, acetate	HMDB
Furfuryl-ethanoate	HMDB
(Furan-2-yl)methyl acetic acid	Generator

Chemical Formula

C₇H₈O₃

Average Molecular Weight

140.1366

Monoisotopic Molecular Weight

140.047344122

IUPAC Name

furan-2-ylmethyl acetate

Traditional Name

2-furanmethanol, acetate

CAS Registry Number

623-17-6

SMILES

CC(=O)OCC1=CC=CO1

InChI Identifier

InChI=1S/C7H8O3/c1-6(8)10-5-7-3-2-4-9-7/h2-4H,5H2,1H3

InChI Key

CKOYRRWBOKMNRG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Heteroaromatic compound
Furan
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034246)
Cytoplasm (HMDB: HMDB0034246)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034246)

Source

Exogenous

Exogenous (HMDB: HMDB0034246)

Food

Food (HMDB: HMDB0034246)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Herb and spice

Herb

Welsh onion (FooDB: FOOD00241)

Vegetable

Onion-family vegetable

Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Cocoa and cocoa products (FooDB: FOOD00860)

Nut

Nuts (FooDB: FOOD00869)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Not Available

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0034246)

Biological role

Nutrient (HMDB: HMDB0034246)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	175.00 to 177.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	4825 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.102 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	14.7 g/L	ALOGPS
logP	1.33	ALOGPS
logP	0.71	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	34.42 m³·mol⁻¹	ChemAxon
Polarizability	13.79 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]+	129.979	31661259
DarkChem	[M-H]-	125.746	31661259
DeepCCS	[M+H]+	129.564	30932474
DeepCCS	[M-H]-	127.387	30932474
DeepCCS	[M-2H]-	163.065	30932474
DeepCCS	[M+Na]+	137.767	30932474
AllCCS	[M+H]+	128.6	32859911
AllCCS	[M+H-H2O]+	124.0	32859911
AllCCS	[M+NH4]+	132.9	32859911
AllCCS	[M+Na]+	134.1	32859911
AllCCS	[M-H]-	127.3	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	130.9	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.	3.44 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3042 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1044.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	429.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	273.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	364.9 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	533.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	240.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1006.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	350.7 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	1173.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	315.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	362.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	530.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	361.5 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	118.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Furfuryl acetate	CC(=O)OCC1=CC=CO1	1636.3	Standard polar	33892256
Furfuryl acetate	CC(=O)OCC1=CC=CO1	1014.1	Standard non polar	33892256
Furfuryl acetate	CC(=O)OCC1=CC=CO1	1032.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0f8d-9000000000-c56641f4bee3a25718dd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0f8c-9000000000-8acbf2c440658554923f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0ued-9000000000-5d41a76d32548e789aa7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0f8d-9100000000-92f20da69e1b9395abe5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0f8d-9000000000-c56641f4bee3a25718dd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0f8c-9000000000-8acbf2c440658554923f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0ued-9000000000-5d41a76d32548e789aa7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Furfuryl acetate EI-B (Non-derivatized)	splash10-0f8d-9100000000-92f20da69e1b9395abe5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furfuryl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-3f1f1ddbf47d4a264723	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Furfuryl acetate 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 - Furfuryl acetate 10V, Positive-QTOF	splash10-0006-1900000000-9fb23f18b69b9cc459b5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 20V, Positive-QTOF	splash10-0006-5900000000-25bb4617c60628b95d33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 40V, Positive-QTOF	splash10-0a4l-9100000000-097ccc8a5633fede4906	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 10V, Negative-QTOF	splash10-000i-4900000000-4a2e6a2685ad984246ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 20V, Negative-QTOF	splash10-000i-7900000000-ecfd7b6a3c67e88e919d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 40V, Negative-QTOF	splash10-0006-9000000000-fb83af71d86a1bd67833	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 10V, Negative-QTOF	splash10-00ks-9700000000-4164cb416eb2b4c5c3b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 20V, Negative-QTOF	splash10-014i-9000000000-891425c7cebab7746776	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 40V, Negative-QTOF	splash10-014i-9000000000-d8494f05a7fc29a7d7d8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 10V, Positive-QTOF	splash10-0006-9000000000-391728ea01afd37cd5b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 20V, Positive-QTOF	splash10-001i-9000000000-232f5b7b15de3f448d69	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Furfuryl acetate 40V, Positive-QTOF	splash10-0f76-9000000000-32b0b66faaf610537da4	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

FDB012559

KNApSAcK ID

C00053185

Chemspider ID

21105906

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12170

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1017931

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 Furfuryl acetate (HMDB0034246)

MOL for HMDB0034246 (Furfuryl acetate)

3D MOL for HMDB0034246 (Furfuryl acetate)

3D SDF for HMDB0034246 (Furfuryl acetate)

3D-SDF for HMDB0034246 (Furfuryl acetate)

PDB for HMDB0034246 (Furfuryl acetate)

3D PDB for HMDB0034246 (Furfuryl acetate)

SMILES for HMDB0034246 (Furfuryl acetate)

INCHI for HMDB0034246 (Furfuryl acetate)

Structure for HMDB0034246 (Furfuryl acetate)

3D Structure for HMDB0034246 (Furfuryl acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra