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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:53 UTC

Update Date

2023-02-21 17:20:12 UTC

HMDB ID

HMDB0031250

Secondary Accession Numbers

HMDB31250

Metabolite Identification

Common Name

Phenylmethyl 2-methylpropanoate

Description

Phenylmethyl 2-methylpropanoate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Phenylmethyl 2-methylpropanoate is a sweet, fruity, and jasmine tasting compound. Phenylmethyl 2-methylpropanoate has been detected, but not quantified in, a few different foods, such as alcoholic beverages, fruits, and spearmints (Mentha spicata). This could make phenylmethyl 2-methylpropanoate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Phenylmethyl 2-methylpropanoate.

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       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8   10   13                                                       
CONECT    9    1    2   11                                                  
CONECT   10    6    7    8                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0031250
HETATM    1  C1  UNL     1      -2.584  -1.092  -1.000  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.554  -0.496   0.394  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.696   0.495   0.473  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.259   0.103   0.727  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.596  -0.325   1.710  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.688   1.153   0.007  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.554   1.732   0.318  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.668   0.751   0.251  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.916   1.048   0.759  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.967   0.170   0.711  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.808  -1.074   0.138  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.570  -1.392  -0.375  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.516  -0.495  -0.320  1.00  0.00           C  
HETATM   14  H1  UNL     1      -1.994  -2.027  -1.034  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.637  -1.373  -1.198  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.302  -0.361  -1.777  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.779  -1.309   1.107  1.00  0.00           H  
HETATM   18  H5  UNL     1      -3.499   1.337  -0.252  1.00  0.00           H  
HETATM   19  H6  UNL     1      -4.633  -0.005   0.228  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.752   0.977   1.473  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.580   2.175   1.332  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.752   2.507  -0.448  1.00  0.00           H  
HETATM   23  H10 UNL     1       3.080   2.010   1.214  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.952   0.392   1.106  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.648  -1.778   0.099  1.00  0.00           H  
HETATM   26  H13 UNL     1       2.429  -2.353  -0.823  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.534  -0.770  -0.740  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   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 2-methylpropanoic acid	Generator
Benzyl 2-methyl propionate	HMDB
Benzyl 2-methylpropanoate	HMDB
Benzyl 2-methylpropionate	HMDB
Benzyl isobutanoate	HMDB
Benzyl isobutyrate	HMDB
Benzylester kyseliny isomaselne	HMDB
FEMA 2141	HMDB
Isobutyric acid, benzyl ester	HMDB
Propanoic acid, 2-methyl-, phenylmethyl ester	HMDB
Benzyl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

benzyl 2-methylpropanoate

Traditional Name

benzyl 2-methylpropanoate

CAS Registry Number

103-28-6

SMILES

CC(C)C(=O)OCC1=CC=CC=C1

InChI Identifier

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

InChI Key

UIKJRDSCEYGECG-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
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

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031250)
Cell membrane (HMDB: HMDB0031250)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031250)

Source

Endogenous

Endogenous (HMDB: HMDB0031250)

Plant

Plant (HMDB: HMDB0031250)

Exogenous

Food

Food (HMDB: HMDB0031250)

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0031250)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031250)
Flavor (HMDB: HMDB0031250)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	229.00 to 230.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	157.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.861 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.17 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.89	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-7.1	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	4	ChemAxon
Refractivity	51.23 m³·mol⁻¹	ChemAxon
Polarizability	20.08 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]+	140.961	31661259
DarkChem	[M-H]-	136.692	31661259
DeepCCS	[M+H]+	139.52	30932474
DeepCCS	[M-H]-	136.159	30932474
DeepCCS	[M-2H]-	173.17	30932474
DeepCCS	[M+Na]+	148.709	30932474
AllCCS	[M+H]+	138.1	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.0	32859911
AllCCS	[M+Na]+	143.2	32859911
AllCCS	[M-H]-	141.3	32859911
AllCCS	[M+Na-2H]-	142.3	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylmethyl 2-methylpropanoate	CC(C)C(=O)OCC1=CC=CC=C1	1865.0	Standard polar	33892256
Phenylmethyl 2-methylpropanoate	CC(C)C(=O)OCC1=CC=CC=C1	1306.5	Standard non polar	33892256
Phenylmethyl 2-methylpropanoate	CC(C)C(=O)OCC1=CC=CC=C1	1318.8	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 2-methylpropanoate EI-B (Non-derivatized)	splash10-0006-9100000000-b537162bf87c98d73dae	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylmethyl 2-methylpropanoate EI-B (Non-derivatized)	splash10-0006-9100000000-b537162bf87c98d73dae	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethyl 2-methylpropanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-2fc6424c43c2d85ad461	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethyl 2-methylpropanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylmethyl 2-methylpropanoate 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 2-methylpropanoate 10V, Positive-QTOF	splash10-004l-9700000000-4ddc5666375257bf84a0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 20V, Positive-QTOF	splash10-0006-9100000000-201cb6d83c9b0aa5d1c6	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 40V, Positive-QTOF	splash10-0006-9000000000-8f08ea032e32c88b6d20	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 10V, Negative-QTOF	splash10-004i-2900000000-6e1dfe9c0e45a411a52a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 20V, Negative-QTOF	splash10-002r-9300000000-76cfc694f2af373dae2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 40V, Negative-QTOF	splash10-00p0-9000000000-cfa7c8a546b05cb3698e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 10V, Negative-QTOF	splash10-056r-2900000000-a86ed40d809a153ad4f6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 20V, Negative-QTOF	splash10-0a6u-9400000000-9eb8c6935d855bc75ca3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 40V, Negative-QTOF	splash10-002f-9000000000-dcd74fcd6df94f1473b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 10V, Positive-QTOF	splash10-0006-9000000000-47d2029de8830d06652e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 20V, Positive-QTOF	splash10-0006-9000000000-65895cd21982c35821ec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylmethyl 2-methylpropanoate 40V, Positive-QTOF	splash10-0006-9000000000-1e2f35db79e468f0bc15	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	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

FDB003280

KNApSAcK ID

Not Available

Chemspider ID

7363

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7646

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1001711

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 2-methylpropanoate (HMDB0031250)

MOL for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

3D MOL for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

3D SDF for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

3D-SDF for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

PDB for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

3D PDB for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

SMILES for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

INCHI for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

Structure for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

3D Structure for HMDB0031250 (Phenylmethyl 2-methylpropanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra