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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:47:45 UTC

Update Date

2023-02-21 17:28:04 UTC

HMDB ID

HMDB0040260

Secondary Accession Numbers

HMDB40260

Metabolite Identification

Common Name

5,5-Dimethyl-2(5H)-furanone

Description

5,5-Dimethyl-2(5H)-furanone belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 5,5-Dimethyl-2(5H)-furanone has been detected, but not quantified in, fishes and herbs and spices. This could make 5,5-dimethyl-2(5H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,5-Dimethyl-2(5H)-furanone.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,4-Dimethyl-2-buten-4-olide	HMDB
4,4-Dimethyl-2-butenolide	HMDB
4,4-Dimethylbut-2-enolide	HMDB
5,5-Dimethyl-2-furanone	HMDB
5,5-Dimethylbut-3-enolide	HMDB
5,5-Dimethylfuran-2(5H)-one	HMDB

Chemical Formula

C₆H₈O₂

Average Molecular Weight

112.1265

Monoisotopic Molecular Weight

112.0524295

IUPAC Name

5,5-dimethyl-2,5-dihydrofuran-2-one

Traditional Name

5,5-dimethylfuran-2-one

CAS Registry Number

20019-64-1

SMILES

CC1(C)OC(=O)C=C1

InChI Identifier

InChI=1S/C6H8O2/c1-6(2)4-3-5(7)8-6/h3-4H,1-2H3

InChI Key

YNKQMZRTPPVLLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dihydrofurans

Sub Class

Furanones

Direct Parent

Butenolides

Alternative Parents

Substituents

2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040260)
Cytoplasm (HMDB: HMDB0040260)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040260)

Source

Exogenous

Exogenous (HMDB: HMDB0040260)

Food

Food (HMDB: HMDB0040260)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Aquatic origin

Fish

Fishes (FooDB: FOOD00865)

Endogenous

Plant

Plant (HMDB: HMDB0040260)

Animal

Animal (HMDB: HMDB0040260)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040260)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	202.00 to 203.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	53750 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.247 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	26.4 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.23	ChemAxon
logS	-0.63	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.3 m³·mol⁻¹	ChemAxon
Polarizability	11.32 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]+	122.633	31661259
DarkChem	[M-H]-	118.895	31661259
DeepCCS	[M+H]+	125.426	30932474
DeepCCS	[M-H]-	121.72	30932474
DeepCCS	[M-2H]-	159.202	30932474
DeepCCS	[M+Na]+	134.372	30932474
AllCCS	[M+H]+	120.7	32859911
AllCCS	[M+H-H2O]+	115.8	32859911
AllCCS	[M+NH4]+	125.3	32859911
AllCCS	[M+Na]+	126.6	32859911
AllCCS	[M-H]-	121.2	32859911
AllCCS	[M+Na-2H]-	123.8	32859911
AllCCS	[M+HCOO]-	126.7	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.	3.53 minutes	32390414
Predicted by Siyang on May 30, 2022	11.3982 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.64 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1486.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	391.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	123.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	252.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	59.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	365.9 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	484.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	823.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	200.7 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	1039.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	271.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	579.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	340.6 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	81.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,5-Dimethyl-2(5H)-furanone	CC1(C)OC(=O)C=C1	1669.9	Standard polar	33892256
5,5-Dimethyl-2(5H)-furanone	CC1(C)OC(=O)C=C1	893.2	Standard non polar	33892256
5,5-Dimethyl-2(5H)-furanone	CC1(C)OC(=O)C=C1	962.1	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 - 5,5-Dimethyl-2(5H)-furanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fb9-9100000000-a8387a61eb346d029179	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 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 - 5,5-Dimethyl-2(5H)-furanone 10V, Positive-QTOF	splash10-03di-1900000000-5b7f8f61b822f7d0646d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 20V, Positive-QTOF	splash10-03di-4900000000-9aa5950cc436a76f746f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 40V, Positive-QTOF	splash10-0gb9-9000000000-835b34a04e1481c16b45	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 10V, Negative-QTOF	splash10-03di-2900000000-ff5907c92f17b672e30d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 20V, Negative-QTOF	splash10-03xr-8900000000-30370745bd4e4e775950	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 40V, Negative-QTOF	splash10-014i-9000000000-3331adc7961da35ca92a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 10V, Negative-QTOF	splash10-02t9-9800000000-429482f1d61d1e9b3531	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 20V, Negative-QTOF	splash10-014i-9200000000-b8ec20373473d490c5dd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 40V, Negative-QTOF	splash10-0ldi-9000000000-bc8fd3c37c15eb860e6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 10V, Positive-QTOF	splash10-03xr-9600000000-499dd7c41327b7e23bf8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 20V, Positive-QTOF	splash10-014l-9000000000-c1dad4ba3f6a01b611fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,5-Dimethyl-2(5H)-furanone 40V, Positive-QTOF	splash10-0uxu-9000000000-ecd1c88f0b04c84ede06	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)	2021-09-24	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+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

FDB019977

KNApSAcK ID

Not Available

Chemspider ID

27792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

29909

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1428431

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 5,5-Dimethyl-2(5H)-furanone (HMDB0040260)

MOL for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

3D MOL for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

3D SDF for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

3D-SDF for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

PDB for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

3D PDB for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

SMILES for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

INCHI for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

Structure for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

3D Structure for HMDB0040260 (5,5-Dimethyl-2(5H)-furanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra