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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:10 UTC

Update Date

2023-02-21 17:18:48 UTC

HMDB ID

HMDB0029563

Secondary Accession Numbers

HMDB29563

Metabolite Identification

Common Name

3-Acetyl-2,5-dimethylfuran

Description

3-Acetyl-2,5-dimethylfuran, also known as 2,5-dimethyl-3-acetylfuran or fema 3391, belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 3-Acetyl-2,5-dimethylfuran is a sweet, cocoa, and corn tasting compound. 3-Acetyl-2,5-dimethylfuran is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 3-Acetyl-2,5-dimethylfuran.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2,5-Dimethyl-3-furanyl)ethanone	ChEBI
1-(2,5-Dimethyl-3-furyl)ethan-1-one	ChEBI
1-(2,5-Dimethyl-3-furyl)ethanone	ChEBI
1-(2,5-Dimethylfuran-3-yl)ethan-1-one	ChEBI
2,5-Dimethyl-3-acetylfuran	ChEBI
2,5-Dimethyl-3-furyl methyl ketone	ChEBI
FEMA 3391	ChEBI
1-(2,5-Dimethyl-3-furanyl)-ethanone	HMDB
1-(2,5-Dimethyl-3-furanyl)ethanone, 9ci	HMDB
2,5-Dimethyl-3-furyl methyl ketone, 8ci	HMDB
3-Acetyl-2,5-dimethyl furan	HMDB
3-Acetyl-2-5-dimethylfuran	HMDB
Furan, 3-acetyl-2,5-dimethyl	HMDB
Ketone, 2,5-dimethyl-3-furyl methyl	HMDB

Chemical Formula

C₈H₁₀O₂

Average Molecular Weight

138.1638

Monoisotopic Molecular Weight

138.068079564

IUPAC Name

1-(2,5-dimethylfuran-3-yl)ethan-1-one

Traditional Name

1-(2,5-dimethylfuran-3-yl)ethanone

CAS Registry Number

10599-70-9

SMILES

CC(=O)C1=C(C)OC(C)=C1

InChI Identifier

InChI=1S/C8H10O2/c1-5-4-8(6(2)9)7(3)10-5/h4H,1-3H3

InChI Key

KBSVBCHYXYXDAG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl alkyl ketones

Alternative Parents

Substituents

Aryl alkyl ketone
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
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: HMDB0029563)
Cytoplasm (HMDB: HMDB0029563)

Source

Endogenous

Endogenous (HMDB: HMDB0029563)

Exogenous

Food

Food (HMDB: HMDB0029563)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029563)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	62.00 °C. @ 0.25 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	-0.294 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.41 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.07	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	15.43	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	1	ChemAxon
Refractivity	39.27 m³·mol⁻¹	ChemAxon
Polarizability	15.17 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
DarkChem	[M+H]+	130.941	31661259
DarkChem	[M-H]-	129.269	31661259
DeepCCS	[M+H]+	138.86	30932474
DeepCCS	[M-H]-	135.033	30932474
DeepCCS	[M-2H]-	172.582	30932474
DeepCCS	[M+Na]+	148.121	30932474
AllCCS	[M+H]+	127.4	32859911
AllCCS	[M+H-H2O]+	122.7	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	132.9	32859911
AllCCS	[M-H]-	127.2	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	130.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Acetyl-2,5-dimethylfuran	CC(=O)C1=C(C)OC(C)=C1	1187.1	Standard polar	33892256
3-Acetyl-2,5-dimethylfuran	CC(=O)C1=C(C)OC(C)=C1	1078.1	Standard non polar	33892256
3-Acetyl-2,5-dimethylfuran	CC(=O)C1=C(C)OC(C)=C1	1079.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetyl-2,5-dimethylfuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dv-9800000000-d79afaac0a8ab9c54798	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetyl-2,5-dimethylfuran 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 - 3-Acetyl-2,5-dimethylfuran 10V, Positive-QTOF	splash10-000i-0900000000-d8278b868ab5c8686690	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 20V, Positive-QTOF	splash10-01pa-7900000000-c5c186e43d210de6a3d6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 40V, Positive-QTOF	splash10-0umj-9200000000-e012f72c38f1b1de7efb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 10V, Negative-QTOF	splash10-000i-1900000000-e7d1d24f91b620e2895e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 20V, Negative-QTOF	splash10-000i-5900000000-29d0ef7acd53eba48278	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 40V, Negative-QTOF	splash10-014j-9100000000-7c54872df50ba6b44afb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 10V, Negative-QTOF	splash10-000i-2900000000-035d3c23946fd1c8b49b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 20V, Negative-QTOF	splash10-002n-9300000000-881c8af16ebb285146c4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 40V, Negative-QTOF	splash10-0006-9100000000-17ea9c5b6217cee1134d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 10V, Positive-QTOF	splash10-000i-3900000000-21587f9a2a941f2d4122	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 20V, Positive-QTOF	splash10-0007-9100000000-09cef65230a031e53aa1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,5-dimethylfuran 40V, Positive-QTOF	splash10-0006-9000000000-77dc60b69ff8b2cc69fa	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	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

FDB000718

KNApSAcK ID

Not Available

Chemspider ID

55447

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61527

PDB ID

Not Available

ChEBI ID

167367

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027711

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 3-Acetyl-2,5-dimethylfuran (HMDB0029563)

MOL for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

3D MOL for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

3D SDF for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

3D-SDF for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

PDB for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

3D PDB for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

SMILES for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

INCHI for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

Structure for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

3D Structure for HMDB0029563 (3-Acetyl-2,5-dimethylfuran)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra