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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:05:33 UTC

Update Date

2023-02-21 17:23:16 UTC

HMDB ID

HMDB0033376

Secondary Accession Numbers

HMDB33376

Metabolite Identification

Common Name

Phenylmethyl butanoate

Description

Phenylmethyl butanoate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Phenylmethyl butanoate is an apricot, berry, and butter tasting compound. Phenylmethyl butanoate has been detected, but not quantified in, several different foods, such as black tea, herbal tea, teas (Camellia sinensis), red tea, and green tea. This could make phenylmethyl butanoate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phenylmethyl butanoate.

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       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    6                                                       
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    2   11                                                       
CONECT    7    4   10                                                       
CONECT    8    5   10                                                       
CONECT    9   10   13                                                       
CONECT   10    7    8    9                                                  
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0033376
HETATM    1  C1  UNL     1       3.081   1.103   0.470  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.491  -0.337   0.264  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.516  -1.084  -0.604  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.148  -1.107  -0.015  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.955  -0.533   1.088  1.00  0.00           O  
HETATM    6  O2  UNL     1       0.085  -1.719  -0.606  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.225  -1.798  -0.144  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.917  -0.529   0.057  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.977   0.032   1.309  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.640   1.250   1.498  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.228   1.884   0.441  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.178   1.341  -0.806  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.514   0.121  -0.994  1.00  0.00           C  
HETATM   14  H1  UNL     1       3.789   1.788  -0.006  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.110   1.316   1.565  1.00  0.00           H  
HETATM   16  H3  UNL     1       2.049   1.261   0.064  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.674  -0.840   1.235  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.465  -0.335  -0.266  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.919  -2.104  -0.772  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.516  -0.575  -1.598  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.777  -2.467  -0.867  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.190  -2.425   0.798  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.543  -0.397   2.202  1.00  0.00           H  
HETATM   24  H11 UNL     1      -2.701   1.709   2.462  1.00  0.00           H  
HETATM   25  H12 UNL     1      -3.741   2.830   0.594  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.651   1.862  -1.623  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.517  -0.246  -2.011  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   21   22
CONECT    8    9    9   13
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Phenylmethyl butanoic acid	Generator
Benzyl butanoate	HMDB
Benzyl butyrate	HMDB
Benzyl N-butanoate	HMDB
Benzyl N-butyrate	HMDB
Benzyl-N-butyrate	HMDB
Benzylester kyseliny maselne	HMDB
Benzylsuccinate	HMDB
Butanoic acid, benzyl ester	HMDB
Butanoic acid, phenylmethyl ester	HMDB
Butyric acid, benzyl ester	HMDB
FEMA 2140	HMDB
N-Butyric acid benzyl ester	HMDB
Phenylmethyl butyrate	HMDB
Benzyl butanoic acid	Generator

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

benzyl butanoate

Traditional Name

benzyl butanoate

CAS Registry Number

103-37-7

SMILES

CCCC(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H14O2/c1-2-6-11(12)13-9-10-7-4-3-5-8-10/h3-5,7-8H,2,6,9H2,1H3

InChI Key

VONGZNXBKCOUHB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0033376)
Cell membrane (HMDB: HMDB0033376)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033376)

Source

Exogenous

Exogenous (HMDB: HMDB0033376)

Food

Food (HMDB: HMDB0033376)

Tea

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0033376)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033376)
Flavor (HMDB: HMDB0033376)

Biological role

Nutrient (HMDB: HMDB0033376)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	21.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	238.00 to 240.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	136 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.017 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.79	ChemAxon
logS	-3.2	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	51.25 m³·mol⁻¹	ChemAxon
Polarizability	20.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	140.648	31661259
DarkChem	[M-H]-	137.768	31661259
DeepCCS	[M+H]+	138.286	30932474
DeepCCS	[M-H]-	134.458	30932474
DeepCCS	[M-2H]-	171.913	30932474
DeepCCS	[M+Na]+	147.452	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.8	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	142.9	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	145.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylmethyl butanoate	CCCC(=O)OCC1=CC=CC=C1	1888.4	Standard polar	33892256
Phenylmethyl butanoate	CCCC(=O)OCC1=CC=CC=C1	1344.7	Standard non polar	33892256
Phenylmethyl butanoate	CCCC(=O)OCC1=CC=CC=C1	1375.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl butanoate EI-B (Non-derivatized)	splash10-052f-9400000000-4eefa0ad170d4001c1c0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl butanoate EI-B (Non-derivatized)	splash10-0a4l-8900000000-0f526f57eacec955c243	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl butanoate EI-B (Non-derivatized)	splash10-0006-9300000000-360016726e255d4d2859	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl butanoate EI-B (Non-derivatized)	splash10-052f-9400000000-4eefa0ad170d4001c1c0	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl butanoate EI-B (Non-derivatized)	splash10-0a4l-8900000000-0f526f57eacec955c243	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl butanoate EI-B (Non-derivatized)	splash10-0006-9300000000-360016726e255d4d2859	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethyl butanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-80b2eac4bd47057d362b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethyl butanoate 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 - Phenylmethyl butanoate 10V, Positive-QTOF	splash10-004l-9800000000-49aa581b1925d3bbe209	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 20V, Positive-QTOF	splash10-0006-9100000000-4a4cde916787e572d1b7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 40V, Positive-QTOF	splash10-0006-9000000000-386e89b556479b98563d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 10V, Negative-QTOF	splash10-00or-6900000000-03d864153d2fb0e01ac9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 20V, Negative-QTOF	splash10-0170-9300000000-e08a845e9a1bbdb9b195	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 40V, Negative-QTOF	splash10-004l-9000000000-5e371f0c8d799c268fa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 10V, Positive-QTOF	splash10-0006-9000000000-32906eeab0d9d2f55c5d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 20V, Positive-QTOF	splash10-0006-9000000000-5dba089e656e19d35bcc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 40V, Positive-QTOF	splash10-0006-9000000000-94b88ae45ba520852cb7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 10V, Negative-QTOF	splash10-056r-2900000000-deeadee3f3f8988cd58c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 20V, Negative-QTOF	splash10-0a4r-9100000000-cc517953fc5c93f03b2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl butanoate 40V, Negative-QTOF	splash10-054o-9000000000-675df8981c82a0125615	2021-09-22	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

Membrane

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

FDB011406

KNApSAcK ID

Not Available

Chemspider ID

7367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7650

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1022171

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 Phenylmethyl butanoate (HMDB0033376)

MOL for HMDB0033376 (Phenylmethyl butanoate)

3D MOL for HMDB0033376 (Phenylmethyl butanoate)

3D SDF for HMDB0033376 (Phenylmethyl butanoate)

3D-SDF for HMDB0033376 (Phenylmethyl butanoate)

PDB for HMDB0033376 (Phenylmethyl butanoate)

3D PDB for HMDB0033376 (Phenylmethyl butanoate)

SMILES for HMDB0033376 (Phenylmethyl butanoate)

INCHI for HMDB0033376 (Phenylmethyl butanoate)

Structure for HMDB0033376 (Phenylmethyl butanoate)

3D Structure for HMDB0033376 (Phenylmethyl butanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra