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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:58:02 UTC

Update Date

2023-02-21 17:25:58 UTC

HMDB ID

HMDB0037708

Secondary Accession Numbers

HMDB37708

Metabolite Identification

Common Name

p-Tolyl isobutyrate

Description

p-Tolyl isobutyrate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. p-Tolyl isobutyrate is an animal, floral, and fruity tasting compound. Based on a literature review very few articles have been published on p-Tolyl isobutyrate.

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      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    6    9                                                       
CONECT    5    7    9                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    4    5                                                  
CONECT   10    6    7   13                                                  
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0037708
HETATM    1  C1  UNL     1       4.715  -0.821   0.601  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.320  -0.384   0.302  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.802   0.792   0.805  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.517   1.196   0.531  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.735   0.396  -0.269  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.570   0.746  -0.584  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.668   0.372   0.176  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.443  -0.317   1.199  1.00  0.00           O  
HETATM    9  C7  UNL     1      -3.066   0.736  -0.145  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.989   0.163   0.893  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.367   0.108  -1.512  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.259  -0.777  -0.768  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.547  -1.191  -0.498  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.075  -1.498  -0.183  1.00  0.00           H  
HETATM   15  H2  UNL     1       5.333   0.114   0.581  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.725  -1.309   1.590  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.419   1.435   1.443  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.074   2.108   0.903  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.182   1.835  -0.262  1.00  0.00           H  
HETATM   20  H7  UNL     1      -3.477   0.032   1.889  1.00  0.00           H  
HETATM   21  H8  UNL     1      -4.309  -0.874   0.600  1.00  0.00           H  
HETATM   22  H9  UNL     1      -4.907   0.753   0.984  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.626   0.582  -2.209  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.091  -0.966  -1.452  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.401   0.282  -1.820  1.00  0.00           H  
HETATM   26  H13 UNL     1       0.633  -1.395  -1.394  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.946  -2.120  -0.899  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   13
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   12
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   11   19
CONECT   10   20   21   22
CONECT   11   23   24   25
CONECT   12   13   13   26
CONECT   13   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
p-Tolyl isobutyric acid	Generator
4-Methylphenyl 2-methylpropanoate	HMDB
FEMA 3075	HMDB
Isobutyric acid, P-tolyl ester	HMDB
P-Cresyl isobutyrate	HMDB
P-Methylphenyl 2-methylpropanoate	HMDB
P-Methylphenyl isobutyrate	HMDB
P-Tolyl 2-methylpropanoate	HMDB
Para-tolyl isobutyrate	HMDB
Paracresyl isobutyrate	HMDB
Proapnoic acid, 2-methyl-, 4-methylphenyl ester	HMDB
Propanoic acid, 2-methyl-, 4-methylphenyl ester	HMDB
4-Methylphenyl 2-methylpropanoic acid	Generator

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

4-methylphenyl 2-methylpropanoate

Traditional Name

p-tolyl isobutyrate

CAS Registry Number

103-93-5

SMILES

CC(C)C(=O)OC1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C11H14O2/c1-8(2)11(12)13-10-6-4-9(3)5-7-10/h4-8H,1-3H3

InChI Key

UPPSFGGDKACIKP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Toluene
Monocyclic benzene moiety
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: HMDB0037708)
Cell membrane (HMDB: HMDB0037708)

Source

Exogenous

Exogenous (HMDB: HMDB0037708)

Food

Food (HMDB: HMDB0037708)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037708)

Biological role

Nutrient (HMDB: HMDB0037708)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.34	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	-7.2	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	51.43 m³·mol⁻¹	ChemAxon
Polarizability	20.12 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]+	142.699	31661259
DarkChem	[M-H]-	138.745	31661259
DeepCCS	[M+H]+	142.957	30932474
DeepCCS	[M-H]-	140.178	30932474
DeepCCS	[M-2H]-	176.116	30932474
DeepCCS	[M+Na]+	151.654	30932474
AllCCS	[M+H]+	137.6	32859911
AllCCS	[M+H-H2O]+	133.4	32859911
AllCCS	[M+NH4]+	141.6	32859911
AllCCS	[M+Na]+	142.7	32859911
AllCCS	[M-H]-	140.8	32859911
AllCCS	[M+Na-2H]-	141.7	32859911
AllCCS	[M+HCOO]-	142.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.99 minutes	32390414
Predicted by Siyang on May 30, 2022	16.567 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	28.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2184.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	588.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	352.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	266.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	694.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	724.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	137.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1348.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	544.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1490.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	433.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	459.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Tolyl isobutyrate	CC(C)C(=O)OC1=CC=C(C)C=C1	1799.7	Standard polar	33892256
p-Tolyl isobutyrate	CC(C)C(=O)OC1=CC=C(C)C=C1	1289.5	Standard non polar	33892256
p-Tolyl isobutyrate	CC(C)C(=O)OC1=CC=C(C)C=C1	1324.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - p-Tolyl isobutyrate EI-B (Non-derivatized)	splash10-0a4l-9700000000-7f3009ff6f506c7ee841	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - p-Tolyl isobutyrate EI-B (Non-derivatized)	splash10-0a4l-9700000000-7f3009ff6f506c7ee841	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Tolyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9600000000-8c1a5cb3db7263b6169f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Tolyl isobutyrate 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 - p-Tolyl isobutyrate 10V, Positive-QTOF	splash10-004i-3900000000-7a9ad8306d2aedd6038d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 20V, Positive-QTOF	splash10-00fu-9300000000-1f3c1833b43ba805ab0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 40V, Positive-QTOF	splash10-05fu-9000000000-2ffcc75dbc17c85974de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 10V, Negative-QTOF	splash10-004i-0900000000-6e7b0a2ac81982ca91d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 20V, Negative-QTOF	splash10-004i-1900000000-3ae02da818ce6df2050a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 40V, Negative-QTOF	splash10-0a4i-9600000000-95ac89d8b92f48c62e75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 10V, Negative-QTOF	splash10-004i-0900000000-583273c8100f9e55b4bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 20V, Negative-QTOF	splash10-056r-1900000000-63572ccb77119862bc0f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 40V, Negative-QTOF	splash10-0a4i-8900000000-f2d1fbc52a04d6b031f5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 10V, Positive-QTOF	splash10-004l-8900000000-60793204412dcffc53c7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 20V, Positive-QTOF	splash10-0006-9100000000-f5c106141721fbeea84e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Tolyl isobutyrate 40V, Positive-QTOF	splash10-0006-9000000000-45ccceef90b7efa3c139	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

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

FDB016836

KNApSAcK ID

Not Available

Chemspider ID

7401

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7685

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 p-Tolyl isobutyrate (HMDB0037708)

MOL for HMDB0037708 (p-Tolyl isobutyrate)

3D MOL for HMDB0037708 (p-Tolyl isobutyrate)

3D SDF for HMDB0037708 (p-Tolyl isobutyrate)

3D-SDF for HMDB0037708 (p-Tolyl isobutyrate)

PDB for HMDB0037708 (p-Tolyl isobutyrate)

3D PDB for HMDB0037708 (p-Tolyl isobutyrate)

SMILES for HMDB0037708 (p-Tolyl isobutyrate)

INCHI for HMDB0037708 (p-Tolyl isobutyrate)

Structure for HMDB0037708 (p-Tolyl isobutyrate)

3D Structure for HMDB0037708 (p-Tolyl isobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra