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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 02:09:15 UTC

Update Date

2023-02-21 17:28:25 UTC

HMDB ID

HMDB0040594

Secondary Accession Numbers

HMDB40594

Metabolite Identification

Common Name

(±)-Furaneol

Description

(±)-Furaneol, also known as furaneol or HDMF, belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group (±)-Furaneol is a sweet, almond, and candy tasting compound (±)-Furaneol is found, on average, in the highest concentration within pineapples (Ananas comosus) (±)-Furaneol has also been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, fruits, nuts, and pulses. This could make (±)-furaneol a potential biomarker for the consumption of these foods (±)-Furaneol 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 (±)-Furaneol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,5-Dimethyl-3-hydroxy-4-oxo-4,5-dihydrofuran	ChEBI
2,5-Dimethyl-4-hydroxy-2,3-dihydrofuran-3-one	ChEBI
2,5-Dimethyl-4-hydroxy-3(2H)-furanone	ChEBI
4-Hydroxy-2,5-dimethyl-3(2H)-furanone	ChEBI
4-Hydroxy-2,5-dimethyl-furan-3(2H)-one	ChEBI
Dimethylhydroxy furanone	ChEBI
Furaneol	ChEBI
HDMF	ChEBI
Pineapple ketone	ChEBI
Furaneol, (R)-isomer	MeSH, HMDB
4-HDMF	MeSH, HMDB
Alletone	MeSH, HMDB
Furaneol, (S)-isomer	MeSH, HMDB

Chemical Formula

C₆H₈O₃

Average Molecular Weight

128.1259

Monoisotopic Molecular Weight

128.047344122

IUPAC Name

4-hydroxy-2,5-dimethyl-2,3-dihydrofuran-3-one

Traditional Name

furaneol

CAS Registry Number

Not Available

SMILES

CC1OC(C)=C(O)C1=O

InChI Identifier

InChI=1S/C6H8O3/c1-3-5(7)6(8)4(2)9-3/h3,8H,1-2H3

InChI Key

INAXVXBDKKUCGI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Furanones

Alternative Parents

Substituents

3-furanone
Vinylogous ester
Cyclic ketone
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

cyclic ketone (CHEBI:76247 )
furans (CHEBI:76247 )
enol (CHEBI:76247 )

Ontology

Not Available

Exogenous (HMDB: HMDB0040594)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	77 - 78 °C	Not Available
Boiling Point	215.53 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	18500 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.076 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	446 g/L	ALOGPS
logP	-0.33	ALOGPS
logP	0.21	ChemAxon
logS	0.54	ALOGPS
pKa (Strongest Acidic)	7.09	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.29 m³·mol⁻¹	ChemAxon
Polarizability	12.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	128.358	30932474
DeepCCS	[M-H]-	125.285	30932474
DeepCCS	[M-2H]-	162.137	30932474
DeepCCS	[M+Na]+	137.012	30932474
AllCCS	[M+H]+	127.3	32859911
AllCCS	[M+H-H2O]+	122.5	32859911
AllCCS	[M+NH4]+	131.7	32859911
AllCCS	[M+Na]+	133.0	32859911
AllCCS	[M-H]-	123.1	32859911
AllCCS	[M+Na-2H]-	125.2	32859911
AllCCS	[M+HCOO]-	127.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Furaneol	CC1OC(C)=C(O)C1=O	2023.5	Standard polar	33892256
(??)-Furaneol	CC1OC(C)=C(O)C1=O	976.0	Standard non polar	33892256
(??)-Furaneol	CC1OC(C)=C(O)C1=O	1021.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-Furaneol,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(=O)C(C)O1	1150.9	Semi standard non polar	33892256
(??)-Furaneol,1TMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C)=C(C)O1	1269.3	Semi standard non polar	33892256
(±)-Furaneol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)O1	1318.3	Semi standard non polar	33892256
(±)-Furaneol,2TMS,isomer #1	CC1=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C)O1	1383.6	Standard non polar	33892256
(??)-Furaneol,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(=O)C(C)O1	1410.3	Semi standard non polar	33892256
(??)-Furaneol,1TBDMS,isomer #2	CC1=C(O)C(O[Si](C)(C)C(C)(C)C)=C(C)O1	1540.6	Semi standard non polar	33892256
(±)-Furaneol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C)O1	1791.2	Semi standard non polar	33892256
(±)-Furaneol,2TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C)O1	1808.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Furaneol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9100000000-8c4cb8aa573b16fcfb70	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Furaneol GC-MS (1 TMS) - 70eV, Positive	splash10-0adu-9600000000-2c6fe7e0e944a33c5cc9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Furaneol 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 - (±)-Furaneol 10V, Positive-QTOF	splash10-004i-1900000000-2a171214e5cd4706888f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Positive-QTOF	splash10-004i-3900000000-31e666e61cc7b8411876	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Positive-QTOF	splash10-054p-9000000000-af02647aeeb779640073	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Negative-QTOF	splash10-004i-0900000000-357e93488390a2976c9d	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Negative-QTOF	splash10-004i-1900000000-602820cb95c6f5aecaae	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Negative-QTOF	splash10-0a4i-9100000000-4e8ccb8034b60b5362d0	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Negative-QTOF	splash10-004i-2900000000-f04fe270624eef9c155b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Negative-QTOF	splash10-006x-9000000000-996faea12712159d1b18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Negative-QTOF	splash10-0a4l-9000000000-0c6cf150442af99bad61	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 10V, Positive-QTOF	splash10-004i-7900000000-afb6007af0c955aff56b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 20V, Positive-QTOF	splash10-0avl-9000000000-61679df963f1143460b0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Furaneol 40V, Positive-QTOF	splash10-05mp-9000000000-67eb08c0013c727e892e	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)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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+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

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

FDB020380

KNApSAcK ID

C00052712

Chemspider ID

18218

KEGG Compound ID

Not Available

BioCyc ID

CPD-10198

BiGG ID

Not Available

Wikipedia Link

Furaneol

METLIN ID

Not Available

PubChem Compound

19309

PDB ID

Not Available

ChEBI ID

76247

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1000931

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 (±)-Furaneol (HMDB0040594)

MOL for HMDB0040594 ((±)-Furaneol)

3D MOL for HMDB0040594 ((±)-Furaneol)

3D SDF for HMDB0040594 ((±)-Furaneol)

3D-SDF for HMDB0040594 ((±)-Furaneol)

PDB for HMDB0040594 ((±)-Furaneol)

3D PDB for HMDB0040594 ((±)-Furaneol)

SMILES for HMDB0040594 ((±)-Furaneol)

INCHI for HMDB0040594 ((±)-Furaneol)

Structure for HMDB0040594 ((±)-Furaneol)

3D Structure for HMDB0040594 ((±)-Furaneol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra