Showing Compound 4-Butyl-gamma-butyrolactone (FDB014100)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:05 UTC

Update date

2019-11-26 03:09:31 UTC

Primary ID

FDB014100

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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 blackberries (Rubus), evergreen blackberries (Rubus laciniatus), asparagus (Asparagus officinalis), papayas (Carica papaya), and fruits. This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Butyl-gamma-butyrolactone.

CAS Number

104-50-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(R)-4-Octanolide	MeSH
4-Butyl-4-hydroxybutyric acid lactone	HMDB
4-Butyl-g-butyrolactone	Generator
4-Butyl-gamma-butyrolactone	biospider
4-Butyl-γ-butyrolactone	Generator
4-Hydroxyoctanoic acid lactone	HMDB
4-Octanolide	ChEBI
5-Butyl-tetrahydro-furan-2-one	HMDB
5-Butyldihydro-2(3H)-furanone	ChEBI
5-Butyldihydrofuran-2(3H)-one	HMDB

Showing 1 to 10 of 39 entries

Predicted 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

Chemical Formula

C8H14O2

IUPAC name

5-butyloxolan-2-one

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

Isomeric SMILES

CCCCC1CCC(=O)O1

Average Molecular Weight

142.1956

Monoisotopic Molecular Weight

142.099379692

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

Lactones (LMFA07040016 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp5.5 102-105°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 67.57%; H 9.92%; O 22.50%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	4-Butyl-gamma-butyrolactone, non-derivatized, GC-MS Spectrum	splash10-000i-9000000000-b38e079f829f45a525dd	Spectrum
GC-MS	4-Butyl-gamma-butyrolactone, non-derivatized, GC-MS Spectrum	splash10-000i-9000000000-b38e079f829f45a525dd	Spectrum
Predicted GC-MS	4-Butyl-gamma-butyrolactone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-052f-9100000000-1ba786a1eb6b754fd600	Spectrum
Predicted GC-MS	4-Butyl-gamma-butyrolactone, 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	splash10-0006-4900000000-8714044bd4ab585a2f69	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-9200000000-1001b4cf846542fcb2e1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a476386c50ad13ec24a2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-3900000000-d0af9ad440391bb2c058	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9700000000-5dbe2305cdbd99c63dbf	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9000000000-247831545f03580fc9cc	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-5720fb1a64f78a262794	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-2900000000-65c7450bb61b4b3696f2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-24ceeecd97274ff6ec49	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-9300000000-6bd6c22f833b03943fd0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05po-9000000000-d22b0d5f17d4f20fe77b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-ee08758371db084712ce	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

7418

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

7704

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35422

CRC / DFC (Dictionary of Food Compounds) ID

JJR08-S:JNW32-W

EAFUS ID

2746

Dr. Duke ID

GAMMA-OCTALACTONE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

104-50-7

GoodScent ID

rw1006541

SuperScent ID

Not Available

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

Processing...

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
coconut	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.
creamy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dairy	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.
sweet	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.
waxy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.