gamma-Decalactone (YMDB01697)

Identification

YMDB ID

YMDB01697

Name

gamma-Decalactone

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

xi-5-Hexyldihydro-2(3H)-furanone, also known as gamma-hexyl-gamma-butyrolactone or 4-hydroxydecanoic acid g-lactone, 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. Based on a literature review a significant number of articles have been published on xi-5-Hexyldihydro-2(3H)-furanone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-Decalactone
2(3H)-Furanone, 5-hexyldihydro-
4-Decalactone
4-Decanolide
4-Hexyl-«
4-Hexyl-4-butanolide
4-Hydroxydecanoic acid lactone
4-Hydroxydecanoic acid, «
5-Hexyldihydro-2(3H)-furanone
5-Hexyltetrahydro-2-furanone
Decan-4-olide
Decanoic acid, 4-hydroxy-, «
Decanolactone
Decanolide-1,4
Hydroxydecanoic acid «
4-Hexyl-gamma-butyrolactone
4-Hydroxydecanoic acid gamma-lactone
5-Hexyloxolan-2-one
gamma-Decanolactone
gamma-Hexyl-gamma-butyrolactone
gamma-N-Decalactone
gamma-N-Hexyl-gamma-butyrolactone
4-Hexyl-g-butyrolactone
4-Hexyl-γ-butyrolactone
4-Hydroxydecanoate g-lactone
4-Hydroxydecanoate gamma-lactone
4-Hydroxydecanoate γ-lactone
4-Hydroxydecanoic acid g-lactone
4-Hydroxydecanoic acid γ-lactone
g-Decanolactone
Γ-decanolactone
g-Hexyl-g-butyrolactone
Γ-hexyl-γ-butyrolactone
g-N-Decalactone
Γ-N-decalactone
g-N-Hexyl-g-butyrolactone
Γ-N-hexyl-γ-butyrolactone
gamma-Lactone decanoic acid
gamma-Decalactone

CAS number

706-14-9

Weight

Average: 170.2487
Monoisotopic: 170.13067982

InChI Key

IFYYFLINQYPWGJ-UHFFFAOYSA-N

InChI

InChI=1S/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3

IUPAC Name

5-hexyloxolan-2-one

Traditional IUPAC Name

gamma-decalactone

Chemical Formula

C₁₀H₁₈O₂

SMILES

CCCCCCC1CCC(=O)O1

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

Not Available

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	2.72 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	3.52	ALOGPS
logP	2.87	ChemAxon
logS	-3.1	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	5	ChemAxon
Refractivity	47.65 m³·mol⁻¹	ChemAxon
Polarizability	20.38 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

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Buttery	FDB016224
Coconut	FDB016224
Fat	FDB016224
Fresh	FDB016224
Oily	FDB016224
Peach	FDB016224
Sweet	FDB016224
Waxy	FDB016224

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9000000000-4b166790a11e7c302d92	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9000000000-4b166790a11e7c302d92	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ap3-9100000000-b00c7215590a3d9b2e9d	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udr-0900000000-d70fbbe72766763b45e2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-052s-4900000000-0e9fb29ea39a5db8b46d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052s-4900000000-ca7c24e9577963b4e53e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0900000000-d70fbbe72766763b45e2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-052s-4900000000-0e9fb29ea39a5db8b46d	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-290b1fa859383e242f93	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-9800000000-93589434f6ecccc40d35	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d48426fb0e1a4c1a49a7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-63a514b1d1c53dbcbd66	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016r-2900000000-d4ee5269c414e9f521f4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-9b6a92e807e7ae4e5fd5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-efbd93a1a83feefc94df	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1900000000-175297cb580811c14bb1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-9db65c438d4cb8beba4f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fu-9500000000-c1c23158375af766301b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9100000000-032097fa4e962fbd8056	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-15c616405145e21bbc24	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9100000000-5c41e313dc97eb12ddd5	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	145740
HMDB ID	HMDB0037217
Pubchem Compound ID	7710
Kegg ID	Not Available
ChemSpider ID	12285
FOODB ID	FDB016224
Wikipedia ID	Gamma-Decalactone
BioCyc ID	Not Available

Structure for #<Compound:0xa9305094>