Showing Compound gamma-Butyrolactone (FDB003392)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:47 UTC

Update date

2019-11-26 02:59:09 UTC

Primary ID

FDB003392

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

gamma-Butyrolactone

Description

gamma-Butyrolactone, also known as 1,4-butanolide or 4-hydroxy-butanoate, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, gamma-butyrolactone is considered to be a fatty ester lipid molecule. gamma-Butyrolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. gamma-Butyrolactone exists in all living species, ranging from bacteria to humans. gamma-Butyrolactone is a sweet, caramel, and creamy tasting compound. gamma-Butyrolactone has been detected, but not quantified in, several different foods, such as tortilla chips, red bell peppers, tea, green bell peppers, and evergreen blackberries. This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. gamma-Butyrolactone is a potentially toxic compound.

CAS Number

96-48-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Butanolide	ChEBI
1,4-Butanolide	ChEBI
1,4-Lactone	ChEBI
4-Butyrolactone	ChEBI
4-Deoxytetronic acid	ChEBI
4-Hydroxybutyric acid lactone	ChEBI
Butyrolactone	ChEBI
Dihydro-2(3H)-furanone	ChEBI
gamma-Butanolactone	ChEBI
gamma-Hydroxybutyric acid lactone	ChEBI
gamma-Hydroxybutyrolactone	ChEBI
Tetrahydrofuran-2-one	ChEBI
4-Deoxytetronate	Generator
4-Hydroxybutyrate lactone	Generator
g-Butanolactone	Generator
Γ-butanolactone	Generator
g-Hydroxybutyrate lactone	Generator
g-Hydroxybutyric acid lactone	Generator
gamma-Hydroxybutyrate lactone	Generator
Γ-hydroxybutyrate lactone	Generator
Γ-hydroxybutyric acid lactone	Generator
g-Hydroxybutyrolactone	Generator
Γ-hydroxybutyrolactone	Generator
g-Butyrolactone	Generator
Γ-butyrolactone	Generator
1-Oxacyclopentan-2-one	HMDB
2,3,4,5-Tetrahydro-2-furanone	HMDB
2-Oxolanone	HMDB
2-Oxotetrahydrofuran	HMDB
4,5-Dihydro-2(3H)-furanone	HMDB
4-Butanolide	HMDB
4-Hydroxy-butanoate	HMDB
4-Hydroxy-butanoic acid	HMDB
4-Hydroxy-butanoic acid g-lactone	HMDB
4-Hydroxybutanoate	HMDB
4-Hydroxybutanoic acid	HMDB
4-Hydroxybutanoic acid lactone	HMDB
Butyric acid lactone	HMDB
g-Butalactone	HMDB
g-Butyryllactone	HMDB
gamma-Butalactone	HMDB
gamma-Butyryllactone	HMDB
GBL	HMDB
Paint clean g	HMDB
Tetrahydro-2-furanone	HMDB
4 Butyrolactone	HMDB
gamma Butyrolactone	HMDB
Furanone, tetrahydro 2	HMDB
1,4 Butanolide	HMDB
4 Hydroxybutyric acid lactone	HMDB
Lactone, 4-hydroxybutyric acid	HMDB
gamma-Butyrolactone	MeSH
1-Oxacyclopentane-2-one	biospider
1,4-Butyrolactone	biospider
2-Dihydrofuranone	biospider
2(3H)-dihydrofuranone	biospider
3-Hydroxybutyric acid lactone	biospider
4-Hydroxy-Butanoic acid g-lactone	biospider
4-Hydroxybutanoic acid, «gamma»-lactone	biospider
4-Hydroxybutyric acid, «gamma»-lactone	biospider
Butyryl lactone	biospider
Butyrylactone	biospider
Dihydro-2-furanone	biospider
Dihydrofuran-2(3H)-one	biospider
Dihyro-2-furanone	biospider
FEMA 3291	db_source
gamma-Hydroxybutyric acid cyclic ester	biospider
gamma-Lactone 4-hydroxy-butanoic acid	biospider
gamma-Lactone 4-hydroxy-butyric acid	biospider
gamma-Lactone 4-hydroxybutanoic acid	biospider
gamma-Lactone 4-hydroxybutyric acid	biospider
Hydroxybutanoic acid lactone	biospider
γ-butanolactone	Generator
γ-butyrolactone	Generator
γ-hydroxybutyrate lactone	Generator
γ-hydroxybutyric acid lactone	Generator
γ-hydroxybutyrolactone	Generator

Predicted Properties

Property	Value	Source
Water Solubility	238 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	0.15	ChemAxon
logS	0.44	ALOGPS
pKa (Strongest Basic)	-7	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	20.31 m³·mol⁻¹	ChemAxon
Polarizability	8.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C4H6O2

IUPAC name

oxolan-2-one

InChI Identifier

InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2

InChI Key

YEJRWHAVMIAJKC-UHFFFAOYSA-N

Isomeric SMILES

O=C1CCCO1

Average Molecular Weight

86.0892

Monoisotopic Molecular Weight

86.036779436

Classification

Description

belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Tetrahydrofuran
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

butan-4-olide (CHEBI:42639 )
Lactones (LMFA07040004 )

Ontology

Physiological effect

Health effect:

Health condition:

General disorders and administration site conditions:

Hypothermia

Respiratory, thoracic and mediastinal disorders:

Apnea

Renal and urinary disorders:

Urinary incontinence

Vascular disorders:

Nervous system disorders:

Headache

Psychiatric disorders:

Metabolism and nutrition disorders:

Acidosis

Ingestion

Source:

Biological:

Plant:

Fabaceae

Biological location:

Tissue and substructures:

Adipose tissue

Cell and elements:

Cell:

Nerve cell

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Indirect biological role:

Neurotoxin

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 55.81%; H 7.02%; O 37.17%	DFC
Melting Point	-45
Boiling Point	Bp12 89°	DFC
Experimental Water Solubility	1000 mg/mL	WEAST,RC (1972)
Experimental logP	-0.64	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d0 1.44	DFC
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9000000000-500445dc73cb69119e6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-9000000000-d3df175d3315ed446e14	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9000000000-500445dc73cb69119e6b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-9000000000-d3df175d3315ed446e14	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-bd4b413f20907d13a107	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-4a6de93563809aa51a33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-4a6de93563809aa51a33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-b5163f6eb1e8004e61a9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-004l-9000000000-1066d349a6023c66dd64	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0006-9000000000-c2f6d51e7b2f9ce1e9f1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-002f-9000000000-d3df175d3315ed446e14	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-507998514018a44c4cf0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-9000000000-d4ec4947321dfb11fab4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b2a1436205f5365513b0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-fb7c9ada825a0c62979f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-9000000000-95fda8a898d02f7e71ff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9000000000-c8282365f175b61ca8c0	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-004l-9000000000-2fc3f4165b5808b41e93	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

42639

Phenol-Explorer ID

Not Available

DrugBank ID

DB04699

HMDB ID

HMDB00549

CRC / DFC (Dictionary of Food Compounds) ID

CXH55-B:CXH55-B

EAFUS ID

1728

Dr. Duke ID

GAMMA-BUTYROLACTONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

GBL

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

96-48-0

GoodScent ID

rw1028441

SuperScent ID

Not Available

Wikipedia ID

4-Hydroxybutyric acid lactone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
neurotoxic	50910	A poison that interferes with the functions of the nervous system.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
caramel	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
creamy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oily	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound gamma-Butyrolactone (FDB003392)

Structure for FDB003392 (gamma-Butyrolactone)