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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:24:04 UTC

Update Date

2023-02-21 17:24:48 UTC

HMDB ID

HMDB0035422

Secondary Accession Numbers

HMDB35422

Metabolite Identification

Common Name

4-Butyl-gamma-butyrolactone

Description

4-Butyl-gamma-butyrolactone, also known as 4-octanolide or 5-butyldihydro-2(3H)-furanone, 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, 4-butyl-gamma-butyrolactone is considered to be a fatty ester. 4-Butyl-gamma-butyrolactone is a sweet, coconut, and creamy tasting compound. 4-Butyl-gamma-butyrolactone is found, on average, in the highest concentration within pineapples (Ananas comosus) and bilberries (Vaccinium myrtillus). 4-Butyl-gamma-butyrolactone has also been detected, but not quantified in, several different foods, such as asparagus (Asparagus officinalis), tortilla chip, peaches (Prunus persica), blackberries (Rubus), and papayas (Carica papaya). This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods. 4-Butyl-gamma-butyrolactone 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 4-Butyl-gamma-butyrolactone.

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-Octanolide	ChEBI
5-Butyldihydro-2(3H)-furanone	ChEBI
5-Butyloxolan-2-one	ChEBI
8-oxo-5-Octanolide	ChEBI
Dihydro-5-butyl-2(3H)-furanone	ChEBI
gamma-Butyl-gamma-butyrolactone	ChEBI
gamma-Butylbutyrolactone	ChEBI
gamma-N-Butyl-gamma-butyrolactone	ChEBI
gamma-Octanoic lactone	ChEBI
Octan-4-olide	ChEBI
Octano-1,4-lactone	ChEBI
g-Butyl-g-butyrolactone	Generator
Γ-butyl-γ-butyrolactone	Generator
g-Butylbutyrolactone	Generator
Γ-butylbutyrolactone	Generator
g-N-Butyl-g-butyrolactone	Generator
Γ-N-butyl-γ-butyrolactone	Generator
g-Octanoic lactone	Generator
Γ-octanoic lactone	Generator
4-Butyl-g-butyrolactone	Generator
4-Butyl-γ-butyrolactone	Generator
4-Butyl-4-hydroxybutyric acid lactone	HMDB
4-Hydroxyoctanoic acid lactone	HMDB
5-Butyl-tetrahydro-furan-2-one	HMDB
5-Butyldihydrofuran-2(3H)-one	HMDB
5-butylhydro-2(3H)-Furanone	HMDB
5-butyltetrahydro-2-Furanone	HMDB
FEMA 2796	HMDB
gamma-Octalactone	HMDB
gamma-Octanolactone	HMDB
Octanoic acid, gamma lactone	HMDB
Octanolide-1,4	HMDB
g-Octanolide	Generator
Γ-octanolide	Generator
(R)-4-Octanolide	MeSH

Chemical Formula

C₈H₁₄O₂

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

IUPAC Name

5-butyloxolan-2-one

Traditional Name

5-butyloxolan-2-one

CAS Registry Number

104-50-7

SMILES

CCCCC1CCC(=O)O1

InChI Identifier

InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3

InChI Key

IPBFYZQJXZJBFQ-UHFFFAOYSA-N

Chemical Taxonomy

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

Lactones (LMFA07040016 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0035422)
Cytoplasm (HMDB: HMDB0035422)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035422)

Source

Exogenous

Food

Food (HMDB: HMDB0035422)

Vegetable

Shoot vegetable

Asparagus (FooDB: FOOD00021)

Fruit

Berry

Tropical fruit

Papaya (FooDB: FOOD00041)
Pineapple (FooDB: FOOD00012)

Drupe

Peach (FooDB: FOOD00149)

Fruits (FooDB: FOOD00871)

Snack

Tortilla chip (FooDB: FOOD00721)

Endogenous

Plant

Plant (HMDB: HMDB0035422)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035422)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035422)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	234.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	1.432 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.96 g/L	ALOGPS
logP	1.94	ALOGPS
logP	1.98	ChemAxon
logS	-1.9	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	3	ChemAxon
Refractivity	38.45 m³·mol⁻¹	ChemAxon
Polarizability	16.25 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]+	131.552	31661259
DarkChem	[M-H]-	128.286	31661259
DeepCCS	[M+H]+	137.316	30932474
DeepCCS	[M-H]-	134.553	30932474
DeepCCS	[M-2H]-	171.495	30932474
DeepCCS	[M+Na]+	146.287	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.0	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	138.0	32859911
AllCCS	[M-H]-	134.5	32859911
AllCCS	[M+Na-2H]-	136.3	32859911
AllCCS	[M+HCOO]-	138.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Butyl-gamma-butyrolactone	CCCCC1CCC(=O)O1	1926.3	Standard polar	33892256
4-Butyl-gamma-butyrolactone	CCCCC1CCC(=O)O1	1191.6	Standard non polar	33892256
4-Butyl-gamma-butyrolactone	CCCCC1CCC(=O)O1	1274.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Butyl-gamma-butyrolactone EI-B (Non-derivatized)	splash10-000i-9000000000-b38e079f829f45a525dd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Butyl-gamma-butyrolactone EI-B (Non-derivatized)	splash10-000i-9000000000-b38e079f829f45a525dd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Butyl-gamma-butyrolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9100000000-1ba786a1eb6b754fd600	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Butyl-gamma-butyrolactone 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 - 4-Butyl-gamma-butyrolactone 10V, Positive-QTOF	splash10-0006-4900000000-8714044bd4ab585a2f69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Positive-QTOF	splash10-000x-9200000000-1001b4cf846542fcb2e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Positive-QTOF	splash10-0006-9000000000-a476386c50ad13ec24a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 10V, Negative-QTOF	splash10-0006-3900000000-d0af9ad440391bb2c058	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Negative-QTOF	splash10-0007-9700000000-5dbe2305cdbd99c63dbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Negative-QTOF	splash10-0007-9000000000-247831545f03580fc9cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 10V, Negative-QTOF	splash10-0006-0900000000-5720fb1a64f78a262794	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Negative-QTOF	splash10-0006-2900000000-65c7450bb61b4b3696f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Negative-QTOF	splash10-0006-9100000000-24ceeecd97274ff6ec49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 10V, Positive-QTOF	splash10-0a4l-9300000000-6bd6c22f833b03943fd0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 20V, Positive-QTOF	splash10-05po-9000000000-d22b0d5f17d4f20fe77b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Butyl-gamma-butyrolactone 40V, Positive-QTOF	splash10-052f-9000000000-ee08758371db084712ce	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)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB014100

KNApSAcK ID

Not Available

Chemspider ID

7418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7704

PDB ID

Not Available

ChEBI ID

145738

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1006542

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 4-Butyl-gamma-butyrolactone (HMDB0035422)

MOL for HMDB0035422 (4-Butyl-gamma-butyrolactone)

3D MOL for HMDB0035422 (4-Butyl-gamma-butyrolactone)

3D SDF for HMDB0035422 (4-Butyl-gamma-butyrolactone)

3D-SDF for HMDB0035422 (4-Butyl-gamma-butyrolactone)

PDB for HMDB0035422 (4-Butyl-gamma-butyrolactone)

3D PDB for HMDB0035422 (4-Butyl-gamma-butyrolactone)

SMILES for HMDB0035422 (4-Butyl-gamma-butyrolactone)

INCHI for HMDB0035422 (4-Butyl-gamma-butyrolactone)

Structure for HMDB0035422 (4-Butyl-gamma-butyrolactone)

3D Structure for HMDB0035422 (4-Butyl-gamma-butyrolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra