Showing Compound 5-Methyl-2(3H)-furanone (FDB000776)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:42 UTC

Update date

2019-11-26 02:55:23 UTC

Primary ID

FDB000776

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

5-Methyl-2(3H)-furanone

Description

5-Methyl-2(3H)-furanone, also known as beta-angelicalacton or 2-penten-4-olide, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 5-Methyl-2(3H)-furanone is a sweet, coumarin, and nutty tasting compound. 5-Methyl-2(3H)-furanone has been detected, but not quantified in, blackberries (Rubus) and evergreen blackberries (Rubus laciniatus). This could make 5-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5-Methyl-2(3H)-furanone.

CAS Number

591-12-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
2(3H)-Furanone, 5-methyl-	biospider
2,3-dihydro-5-Methyl-2-furanone	HMDB
2,3-Dihydro-5-methyl-2-furanone	biospider
2-Penten-4-olide	ChEBI
3-Pentenoic acid, 4-hydroxy-, gamma-lactone	HMDB
3-Pentenoic acid, 4-hydroxy-, laquo gammaraquo -lactone	HMDB
3-Pentenoic acid, 4-hydroxy-, «gamma»-lactone	biospider
3-PENTENOIC ACID,4-hydroxy,lactone alpha-angelica-lactone	HMDB
3-PENTENOIC ACID,4-HYDROXY,LACTONE ALPHA-ANGELICA-LACTONE	biospider
4-Hydroxy-2-pentenoate g-lactone	Generator

Showing 1 to 10 of 83 entries

Predicted Properties

Property	Value	Source
Water Solubility	100 g/L	ALOGPS
logP	0.53	ALOGPS
logP	0.95	ChemAxon
logS	0.01	ALOGPS
pKa (Strongest Acidic)	7.6	ChemAxon
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	25.67 m³·mol⁻¹	ChemAxon
Polarizability	9.44 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

Chemical Formula

C5H6O2

IUPAC name

5-methyl-2,5-dihydrofuran-2-one

InChI Identifier

InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3

InChI Key

BGLUXFNVVSVEET-UHFFFAOYSA-N

Isomeric SMILES

CC1OC(=O)C=C1

Average Molecular Weight

98.0999

Monoisotopic Molecular Weight

98.036779436

Classification

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

butenolide (CHEBI:36436 )
angelica lactone (CHEBI:36436 )

Ontology

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp12 53°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	50 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 61.22%; H 6.16%; O 32.62%	DFC
Melting Point	Mp 18°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	5-Methyl-2(3H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udi-9000000000-d924660fd05b0a4f24ee	Spectrum
Predicted GC-MS	5-Methyl-2(3H)-furanone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-8664120e7c9085a6c96e	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-455a07b16bc61387238b	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-9000000000-51dfe2fb573308864135	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-7bfecdf1510b67f2f505	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-9000000000-7dbf786cff83ed69720c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9000000000-a2e2372374e257c02f4c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-9ab2cbf1d22ebb0d9233	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w39-9000000000-ec0a82f3905d92f31ae2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-546d854a71bcb0920317	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-81f2c4b9955bbe4aea22	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9000000000-d866a621060ee919d07f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-9000000000-4cce45b0c86e4783eecc	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

11070

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

11558

Pubchem Substance ID

Not Available

ChEBI ID

36433

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29609

CRC / DFC (Dictionary of Food Compounds) ID

BHB48-E:BHB48-E

EAFUS ID

1776

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1029001

SuperScent ID

11559

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Blackberry	Expected but not quantified	Not Available	Dimitris N. Georgilopoulos and Annie N. Gallois. Volatile flavour compounds in heated blackberry juices. Z LebensmUnters Forsch (1987) 185:299-306

Showing 1 to 1 of 1 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
coumarin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
nutty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
solvent	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tobacco	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.