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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:46 UTC

Update Date

2023-02-21 17:20:43 UTC

HMDB ID

HMDB0031514

Secondary Accession Numbers

HMDB31514

Metabolite Identification

Common Name

6-Butyltetrahydro-2H-pyran-2-one

Description

6-Butyltetrahydro-2H-pyran-2-one belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. 6-Butyltetrahydro-2H-pyran-2-one is a sweet, coconut, and coumarin tasting compound. Based on a literature review very few articles have been published on 6-Butyltetrahydro-2H-pyran-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0031514
HETATM    1  C1  UNL     1       3.672  -0.974   0.021  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.871   0.192  -0.572  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.407  -0.053  -0.185  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.604   1.075  -0.754  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.861   0.978  -0.458  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.415  -0.292  -1.032  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.875  -0.372  -0.606  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.851  -0.620   0.903  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.309   0.632   1.500  1.00  0.00           C  
HETATM   10  O1  UNL     1      -2.873   1.126   2.485  1.00  0.00           O  
HETATM   11  O2  UNL     1      -1.178   1.164   0.884  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.743  -1.811  -0.726  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.706  -0.596   0.169  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.205  -1.347   0.935  1.00  0.00           H  
HETATM   15  H4  UNL     1       3.009   0.178  -1.664  1.00  0.00           H  
HETATM   16  H5  UNL     1       3.230   1.141  -0.135  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.381  -0.032   0.913  1.00  0.00           H  
HETATM   18  H7  UNL     1       1.096  -1.052  -0.517  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.056   2.021  -0.382  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.765   1.078  -1.852  1.00  0.00           H  
HETATM   21  H10 UNL     1      -1.354   1.820  -1.027  1.00  0.00           H  
HETATM   22  H11 UNL     1      -1.392  -0.255  -2.137  1.00  0.00           H  
HETATM   23  H12 UNL     1      -0.933  -1.203  -0.633  1.00  0.00           H  
HETATM   24  H13 UNL     1      -3.309   0.627  -0.749  1.00  0.00           H  
HETATM   25  H14 UNL     1      -3.423  -1.160  -1.146  1.00  0.00           H  
HETATM   26  H15 UNL     1      -2.106  -1.409   1.107  1.00  0.00           H  
HETATM   27  H16 UNL     1      -3.867  -0.855   1.259  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3   15   16
CONECT    3    4   17   18
CONECT    4    5   19   20
CONECT    5    6   11   21
CONECT    6    7   22   23
CONECT    7    8   24   25
CONECT    8    9   26   27
CONECT    9   10   10   11
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2H-Pyran-2-one, tetrahydro-6-butyl	HMDB
5-Butyl-5-hydroxypentanoic acid lactone	HMDB
5-Butyl-delta-valerolactone	HMDB
5-Hydroxynonanoic acid delta-lactone	HMDB
5-Hydroxynonanoic acid, lactone	HMDB
5-Nonalactone	HMDB
5-Nonanolide	HMDB
6-butyltetrahydro-2H-Pyran-2-one, 9ci	HMDB
beta -Nonalactone	HMDB
delta-Butyl-delta-valerolactone	HMDB
delta-Hydroxypelargonic acid lactone	HMDB
delta-Nonalactone	HMDB
FEMA 3356	HMDB
Hydroxynonanoic acid delta-lactone	HMDB
laquo deltaraquo -Nonanolide	HMDB
Nonanoic acid, 5-hydroxy-, delta-lactone	HMDB
5-Butyl-δ-valerolactone	Generator

Chemical Formula

C₉H₁₆O₂

Average Molecular Weight

156.2221

Monoisotopic Molecular Weight

156.115029756

IUPAC Name

6-butyloxan-2-one

Traditional Name

6-butyloxan-2-one

CAS Registry Number

3301-94-8

SMILES

CCCCC1CCCC(=O)O1

InChI Identifier

InChI=1S/C9H16O2/c1-2-3-5-8-6-4-7-9(10)11-8/h8H,2-7H2,1H3

InChI Key

PXRBWNLUQYZAAX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta_valerolactone
Delta valerolactone
Oxane
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

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031514)
Cytoplasm (HMDB: HMDB0031514)

Source

Endogenous

Endogenous (HMDB: HMDB0031514)

Exogenous

Food

Food (HMDB: HMDB0031514)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031514)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	253.33 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1201 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.959 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.73 g/L	ALOGPS
logP	2.47	ALOGPS
logP	2.42	ChemAxon
logS	-2.3	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	43.05 m³·mol⁻¹	ChemAxon
Polarizability	18.26 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]+	135.935	31661259
DarkChem	[M-H]-	132.247	31661259
DeepCCS	[M+H]+	140.173	30932474
DeepCCS	[M-H]-	137.193	30932474
DeepCCS	[M-2H]-	174.356	30932474
DeepCCS	[M+Na]+	149.348	30932474
AllCCS	[M+H]+	136.1	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.5	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	140.2	32859911
AllCCS	[M+HCOO]-	141.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6-Butyltetrahydro-2H-pyran-2-one	CCCCC1CCCC(=O)O1	2072.1	Standard polar	33892256
6-Butyltetrahydro-2H-pyran-2-one	CCCCC1CCCC(=O)O1	1322.2	Standard non polar	33892256
6-Butyltetrahydro-2H-pyran-2-one	CCCCC1CCCC(=O)O1	1406.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one EI-B (Non-derivatized)	splash10-006y-9000000000-726e12b176464d011270	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one EI-B (Non-derivatized)	splash10-006y-9000000000-726e12b176464d011270	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9200000000-1617f26d15ffb7699bfc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 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 - 6-Butyltetrahydro-2H-pyran-2-one 10V, Positive-QTOF	splash10-0a4i-2900000000-d6b1cac193cdbe928a5d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 20V, Positive-QTOF	splash10-014i-9200000000-b9996ddabbd417ebc1cf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 40V, Positive-QTOF	splash10-0006-9000000000-45a0c7db4fd983f7a939	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 10V, Negative-QTOF	splash10-0bt9-0900000000-5cbee3403780bf081940	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 20V, Negative-QTOF	splash10-0bt9-4900000000-f24d8812566998420494	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 40V, Negative-QTOF	splash10-0006-9100000000-4f81d90a891348c946d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 10V, Negative-QTOF	splash10-0a4i-1900000000-f83fe54ea78d76444f90	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 20V, Negative-QTOF	splash10-0a4i-2900000000-bf4aba677a660f68b349	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 40V, Negative-QTOF	splash10-0a6u-9500000000-05449238c6af6bd591a1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 10V, Positive-QTOF	splash10-0a4i-8900000000-487d7cee920414eb0c9c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 20V, Positive-QTOF	splash10-07bp-9500000000-4cbe556fd76350976785	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6-Butyltetrahydro-2H-pyran-2-one 40V, Positive-QTOF	splash10-0006-9000000000-c295f9c62891f1ff82e4	2021-09-24	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

FDB008107

KNApSAcK ID

Not Available

Chemspider ID

17658

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18698

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1554781

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 6-Butyltetrahydro-2H-pyran-2-one (HMDB0031514)

MOL for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

3D MOL for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

3D SDF for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

3D-SDF for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

PDB for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

3D PDB for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

SMILES for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

INCHI for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

Structure for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

3D Structure for HMDB0031514 (6-Butyltetrahydro-2H-pyran-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra