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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:42:33 UTC

Update Date

2023-02-21 17:27:48 UTC

HMDB ID

HMDB0040165

Secondary Accession Numbers

HMDB40165

Metabolite Identification

Common Name

Butyl levulinate

Description

Butyl levulinate belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. Butyl levulinate is a bitter, caramel, and fruity tasting compound. Based on a literature review a significant number of articles have been published on Butyl levulinate.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.977   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.026   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.644   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.358   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.025   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.976   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.692   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.691   2.104   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.692  -0.206   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.691   3.644   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.357   1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    8                                                            
CONECT    3    1    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    8                                                       
CONECT    6    5    9                                                       
CONECT    7    4   12                                                       
CONECT    8    2    5   10                                                  
CONECT    9    6   11   12                                                  
CONECT   10    8                                                            
CONECT   11    9                                                            
CONECT   12    7    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

COMPND    HMDB0040165
HETATM    1  C1  UNL     1       4.079  -0.624   0.940  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.114   0.705   0.218  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.712   1.273   0.184  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.768   0.335  -0.540  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.457   0.856  -0.578  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.543   0.156  -1.186  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.316  -0.947  -1.714  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.912   0.701  -1.224  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.691   0.030  -0.121  1.00  0.00           C  
HETATM   10  C8  UNL     1      -4.087   0.473  -0.029  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.954  -0.118   1.018  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.501   1.308  -0.804  1.00  0.00           O  
HETATM   13  H1  UNL     1       3.372  -0.532   1.796  1.00  0.00           H  
HETATM   14  H2  UNL     1       5.059  -0.897   1.376  1.00  0.00           H  
HETATM   15  H3  UNL     1       3.703  -1.382   0.226  1.00  0.00           H  
HETATM   16  H4  UNL     1       4.466   0.604  -0.818  1.00  0.00           H  
HETATM   17  H5  UNL     1       4.802   1.379   0.755  1.00  0.00           H  
HETATM   18  H6  UNL     1       2.399   1.388   1.264  1.00  0.00           H  
HETATM   19  H7  UNL     1       2.705   2.296  -0.234  1.00  0.00           H  
HETATM   20  H8  UNL     1       1.780  -0.625   0.041  1.00  0.00           H  
HETATM   21  H9  UNL     1       2.176   0.162  -1.538  1.00  0.00           H  
HETATM   22  H10 UNL     1      -2.398   0.419  -2.204  1.00  0.00           H  
HETATM   23  H11 UNL     1      -1.926   1.805  -1.141  1.00  0.00           H  
HETATM   24  H12 UNL     1      -2.138   0.140   0.833  1.00  0.00           H  
HETATM   25  H13 UNL     1      -2.712  -1.070  -0.357  1.00  0.00           H  
HETATM   26  H14 UNL     1      -5.316  -1.108   0.637  1.00  0.00           H  
HETATM   27  H15 UNL     1      -4.330  -0.331   1.927  1.00  0.00           H  
HETATM   28  H16 UNL     1      -5.767   0.564   1.271  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   12   12
CONECT   11   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Butyl levulinic acid	Generator
4-Ketopentanoic acid butyl ester	HMDB
Butyl 4-ketovalerate	HMDB
Butyl 4-oxopentanoate	HMDB
Butyl acetylpropionate	HMDB
Butyl laevulinate	HMDB
FEMA 2207	HMDB
Levulinic acid N-butyl ester	HMDB
Levulinic acid, butyl ester	HMDB
N-Butyl 4-oxopentanoate	HMDB
N-Butyl laevulinate	HMDB
N-Butyl levulinate	HMDB
Pentanoic acid, 4-oxo-, butyl ester	HMDB
Butyl 4-oxopentanoic acid	Generator

Chemical Formula

C₉H₁₆O₃

Average Molecular Weight

172.2215

Monoisotopic Molecular Weight

172.109944378

IUPAC Name

butyl 4-oxopentanoate

Traditional Name

butyl 4-oxopentanoate

CAS Registry Number

2052-15-5

SMILES

CCCCOC(=O)CCC(C)=O

InChI Identifier

InChI=1S/C9H16O3/c1-3-4-7-12-9(11)6-5-8(2)10/h3-7H2,1-2H3

InChI Key

ISBWNEKJSSLXOD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Fatty acid ester
Fatty acyl
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040165)
Cytoplasm (HMDB: HMDB0040165)

Source

Exogenous

Food

Food (HMDB: HMDB0040165)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040165)

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040165)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	106.00 to 108.00 °C. @ 5.50 mm Hg	The Good Scents Company Information System
Water Solubility	4940 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.457 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.91 g/L	ALOGPS
logP	1.36	ALOGPS
logP	1.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	17.54	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.73 m³·mol⁻¹	ChemAxon
Polarizability	19.55 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.097	31661259
DarkChem	[M-H]-	137.415	31661259
DeepCCS	[M+H]+	144.07	30932474
DeepCCS	[M-H]-	140.771	30932474
DeepCCS	[M-2H]-	178.224	30932474
DeepCCS	[M+Na]+	153.387	30932474
AllCCS	[M+H]+	142.1	32859911
AllCCS	[M+H-H2O]+	138.4	32859911
AllCCS	[M+NH4]+	145.6	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	142.1	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	145.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butyl levulinate	CCCCOC(=O)CCC(C)=O	1961.9	Standard polar	33892256
Butyl levulinate	CCCCOC(=O)CCC(C)=O	1169.2	Standard non polar	33892256
Butyl levulinate	CCCCOC(=O)CCC(C)=O	1276.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butyl levulinate,1TMS,isomer #1	CCCCOC(=O)CC=C(C)O[Si](C)(C)C	1459.0	Semi standard non polar	33892256
Butyl levulinate,1TMS,isomer #1	CCCCOC(=O)CC=C(C)O[Si](C)(C)C	1402.8	Standard non polar	33892256
Butyl levulinate,1TMS,isomer #2	C=C(CCC(=O)OCCCC)O[Si](C)(C)C	1418.1	Semi standard non polar	33892256
Butyl levulinate,1TMS,isomer #2	C=C(CCC(=O)OCCCC)O[Si](C)(C)C	1405.0	Standard non polar	33892256
Butyl levulinate,1TBDMS,isomer #1	CCCCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1668.1	Semi standard non polar	33892256
Butyl levulinate,1TBDMS,isomer #1	CCCCOC(=O)CC=C(C)O[Si](C)(C)C(C)(C)C	1614.8	Standard non polar	33892256
Butyl levulinate,1TBDMS,isomer #2	C=C(CCC(=O)OCCCC)O[Si](C)(C)C(C)(C)C	1617.9	Semi standard non polar	33892256
Butyl levulinate,1TBDMS,isomer #2	C=C(CCC(=O)OCCCC)O[Si](C)(C)C(C)(C)C	1594.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butyl levulinate EI-B (Non-derivatized)	splash10-0007-9000000000-dd754b510d9a5b964618	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butyl levulinate EI-B (Non-derivatized)	splash10-0007-9000000000-dd754b510d9a5b964618	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl levulinate GC-MS (Non-derivatized) - 70eV, Positive	splash10-052g-9000000000-2aa9aa6898ccc66696af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl levulinate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butyl levulinate 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 - Butyl levulinate 10V, Positive-QTOF	splash10-0ab9-4900000000-3b30aa503d4b32ce4e18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 20V, Positive-QTOF	splash10-0a4i-9200000000-c275c9ef2dd4689bbe7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 40V, Positive-QTOF	splash10-0a4l-9000000000-5fb37db543ff458e2c03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 10V, Negative-QTOF	splash10-00dj-7900000000-eb3fb3bd06b7a50ba5b9	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 20V, Negative-QTOF	splash10-00r2-9600000000-cae40c7bc236f0fa944f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 40V, Negative-QTOF	splash10-0002-9000000000-ae41ac4c19ae4a4bf2b3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 10V, Positive-QTOF	splash10-0aba-9200000000-b1bce0e3a06994d6dc4d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 20V, Positive-QTOF	splash10-0ac3-9000000000-4f2ab0be26cee0b64cb3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 40V, Positive-QTOF	splash10-0a4l-9000000000-34ab516a8864b5b5fb15	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 10V, Negative-QTOF	splash10-00dj-9000000000-f301c1f868e7fb9a2c55	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 20V, Negative-QTOF	splash10-052e-9200000000-e74fbd3beb52ecbd8ea5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butyl levulinate 40V, Negative-QTOF	splash10-0a4l-9000000000-741689e5fae24b15ecc9	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

FDB019874

KNApSAcK ID

Not Available

Chemspider ID

15496

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16331

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1013561

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 Butyl levulinate (HMDB0040165)

MOL for HMDB0040165 (Butyl levulinate)

3D MOL for HMDB0040165 (Butyl levulinate)

3D SDF for HMDB0040165 (Butyl levulinate)

3D-SDF for HMDB0040165 (Butyl levulinate)

PDB for HMDB0040165 (Butyl levulinate)

3D PDB for HMDB0040165 (Butyl levulinate)

SMILES for HMDB0040165 (Butyl levulinate)

INCHI for HMDB0040165 (Butyl levulinate)

Structure for HMDB0040165 (Butyl levulinate)

3D Structure for HMDB0040165 (Butyl levulinate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra