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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:53 UTC

Update Date

2023-02-21 17:23:06 UTC

HMDB ID

HMDB0033128

Secondary Accession Numbers

HMDB33128

Metabolite Identification

Common Name

4-(2-Furanyl)-3-buten-2-one

Description

4-(2-Furanyl)-3-buten-2-one 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. 4-(2-Furanyl)-3-buten-2-one is a sweet, balsam, and cinnamon tasting compound. 4-(2-Furanyl)-3-buten-2-one has been detected, but not quantified in, several different foods, such as alcoholic beverages, arabica coffees (Coffea arabica), coffee and coffee products, and robusta coffees (Coffea canephora). This could make 4-(2-furanyl)-3-buten-2-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-(2-Furanyl)-3-buten-2-one.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(3E)-4-(2-Furyl)-3-buten-2-one	HMDB
1-(2-Furyl)but-2-en-3-one	HMDB
2-(3-Oxobutenyl)furan	HMDB
2-Furalacetone	HMDB
2-Furfurylideneacetone	HMDB
2-Furfurylideneacetone polymer	HMDB
3-Buten-2-one, 4-(2-furanyl)-, homopolymer	HMDB
3-Buten-2-one, 4-(2-furanyl)-, polymers	HMDB
3-Buten-2-one, 4-(2-furyl)- (6ci,8ci)	HMDB
3-Buten-2-one, 4-(2-furyl)-, polymers	HMDB
3-Buten-2-one, 4-(2-furyl)-, polymers (8ci)	HMDB
4-(2-Furanyl)-3-butene-2-one	HMDB
4-(2-Furyl)-3-buten-2-one	HMDB
4-(2-Furyl)but-3-en-2-one	HMDB
beta -2-Furylideneacetone	HMDB
Fam (monomer)	HMDB
Fam polymer	HMDB
FEMA 2495	HMDB
Furfural acetone	HMDB
Furfuralacetone	HMDB
Furfuralacetone polymer	HMDB
Furfuryl acetone	HMDB
Furfurylidene acetone polymer	HMDB
Furfurylideneacetone	HMDB
Furfurylideneacetone resin	HMDB
Monofurfurylideneacetone	HMDB
Monomer fam	HMDB
Oramin R	HMDB
Oramin special GR	HMDB
Poly(monofurfurylideneacetone)	HMDB
Polyfurfurylidineacetone	HMDB
trans-Furfurylideneacetone	HMDB
Monofurfurylidene acetone	MeSH

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

IUPAC Name

(3Z)-4-(furan-2-yl)but-3-en-2-one

Traditional Name

(3Z)-4-(furan-2-yl)but-3-en-2-one

CAS Registry Number

623-15-4

SMILES

CC(=O)\C=C/C1=CC=CO1

InChI Identifier

InChI=1S/C8H8O2/c1-7(9)4-5-8-3-2-6-10-8/h2-6H,1H3/b5-4-

InChI Key

GBKGJMYPQZODMI-PLNGDYQASA-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
Alpha,beta-unsaturated ketone
Furan
Enone
Acryloyl-group
Ketone
Oxacycle
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: HMDB0033128)
Cytoplasm (HMDB: HMDB0033128)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033128)

Source

Exogenous

Exogenous (HMDB: HMDB0033128)

Food

Food (HMDB: HMDB0033128)

Coffee and coffee product

Coffee

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

Coffee and coffee products (FooDB: FOOD00861)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Coffea (HMDB: HMDB0033128)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033128)

Biological role

Nutrient (HMDB: HMDB0033128)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	39.5 °C	Not Available
Boiling Point	123.00 °C. @ 20.00 mm Hg	The Good Scents Company Information System
Water Solubility	6109 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.35	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.07 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.53	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	19.61	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	39 m³·mol⁻¹	ChemAxon
Polarizability	14.17 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
DeepCCS	[M+H]+	131.11	30932474
DeepCCS	[M-H]-	128.662	30932474
DeepCCS	[M-2H]-	164.464	30932474
DeepCCS	[M+Na]+	139.05	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	131.3	32859911
AllCCS	[M+Na]+	132.6	32859911
AllCCS	[M-H]-	126.2	32859911
AllCCS	[M+Na-2H]-	127.8	32859911
AllCCS	[M+HCOO]-	129.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(2-Furanyl)-3-buten-2-one	CC(=O)\C=C/C1=CC=CO1	1899.4	Standard polar	33892256
4-(2-Furanyl)-3-buten-2-one	CC(=O)\C=C/C1=CC=CO1	1126.7	Standard non polar	33892256
4-(2-Furanyl)-3-buten-2-one	CC(=O)\C=C/C1=CC=CO1	1157.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(2-Furanyl)-3-buten-2-one,1TMS,isomer #1	C=C(/C=C\C1=CC=CO1)O[Si](C)(C)C	1398.7	Semi standard non polar	33892256
4-(2-Furanyl)-3-buten-2-one,1TMS,isomer #1	C=C(/C=C\C1=CC=CO1)O[Si](C)(C)C	1362.8	Standard non polar	33892256
4-(2-Furanyl)-3-buten-2-one,1TBDMS,isomer #1	C=C(/C=C\C1=CC=CO1)O[Si](C)(C)C(C)(C)C	1634.5	Semi standard non polar	33892256
4-(2-Furanyl)-3-buten-2-one,1TBDMS,isomer #1	C=C(/C=C\C1=CC=CO1)O[Si](C)(C)C(C)(C)C	1587.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Furanyl)-3-buten-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-582fa970f302ae872c23	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 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 - 4-(2-Furanyl)-3-buten-2-one 10V, Positive-QTOF	splash10-00kr-1900000000-0b12cf860869ad68f576	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 20V, Positive-QTOF	splash10-014r-1900000000-c0377339c39debc4e28f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 40V, Positive-QTOF	splash10-0fr7-9000000000-ff851fe15df002beab1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 10V, Negative-QTOF	splash10-000i-0900000000-68bb0e7c93352b3d6402	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 20V, Negative-QTOF	splash10-000i-4900000000-2e7fef7a7bc6f2bd136f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 40V, Negative-QTOF	splash10-052u-9300000000-8d2aaf0806fb4c18f27e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 10V, Positive-QTOF	splash10-00kr-2900000000-561b01f8e1cd17fc3968	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 20V, Positive-QTOF	splash10-014i-9800000000-2871fa9e0b10cf79d47b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 40V, Positive-QTOF	splash10-0006-9000000000-98e31e2e1ae2159d6c46	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 10V, Negative-QTOF	splash10-000i-1900000000-4c9ff84c08bf3c3edb35	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 20V, Negative-QTOF	splash10-014i-9100000000-199bc116e7815041140b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(2-Furanyl)-3-buten-2-one 40V, Negative-QTOF	splash10-014m-9000000000-faae8a64dc5979b97dd6	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)	2021-09-25	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

FDB011129

KNApSAcK ID

Not Available

Chemspider ID

1266398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1549522

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1024531

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 4-(2-Furanyl)-3-buten-2-one (HMDB0033128)

MOL for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

3D MOL for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

3D SDF for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

3D-SDF for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

PDB for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

3D PDB for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

SMILES for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

INCHI for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

Structure for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

3D Structure for HMDB0033128 (4-(2-Furanyl)-3-buten-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra