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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:58:09 UTC

Update Date

2023-02-21 17:28:14 UTC

HMDB ID

HMDB0040426

Secondary Accession Numbers

HMDB40426

Metabolite Identification

Common Name

Isopropyl phenylacetate

Description

Isopropyl phenylacetate belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Isopropyl phenylacetate is a sweet, honeysuckle, and powdery tasting compound. Based on a literature review very few articles have been published on Isopropyl phenylacetate.

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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       5.335   3.080   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   11                                                       
CONECT    9    1    2   13                                                  
CONECT   10    6    7    8                                                  
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0040426
HETATM    1  C1  UNL     1       3.955   0.165   0.699  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.759  -0.094  -0.167  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.808   0.692  -1.462  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.540   0.121   0.518  1.00  0.00           O  
HETATM    5  C4  UNL     1       0.559  -0.825   0.694  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.734  -1.973   0.208  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.654  -0.439   1.445  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.830  -0.221   0.614  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.519  -1.238   0.018  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.647  -1.001  -0.772  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.075   0.311  -0.950  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.382   1.341  -0.347  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.274   1.077   0.425  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.742  -0.627   0.598  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.429   1.164   0.481  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.639   0.164   1.776  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.774  -1.161  -0.474  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.630   1.774  -1.288  1.00  0.00           H  
HETATM   19  H6  UNL     1       3.823   0.538  -1.895  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.004   0.283  -2.109  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.807  -1.272   2.198  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.396   0.468   2.052  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.214  -2.266   0.140  1.00  0.00           H  
HETATM   24  H11 UNL     1      -4.192  -1.798  -1.248  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.960   0.528  -1.565  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.718   2.378  -0.489  1.00  0.00           H  
HETATM   27  H14 UNL     1      -1.727   1.911   0.903  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19   20
CONECT    4    5
CONECT    5    6    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
Isopropyl phenylacetic acid	Generator
1-Methylethyl benzeneacetate	HMDB
Acetic acid, phenyl-, isopropyl ester	HMDB
Benzeneacetic acid 1-methylethyl ester	HMDB
Benzeneacetic acid, 1-methylethyl ester	HMDB
FEMA 2956	HMDB
Isopropyl alpha-toluate	HMDB
Phenylacetic acid, isopropyl ester	HMDB
Propan-2-yl 2-phenylacetic acid	Generator

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

propan-2-yl 2-phenylacetate

Traditional Name

isopropyl 2-phenylacetate

CAS Registry Number

4861-85-2

SMILES

CC(C)OC(=O)CC1=CC=CC=C1

InChI Identifier

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

InChI Key

SSMBXPJYHMZLOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040426)
Cell membrane (HMDB: HMDB0040426)

Source

Exogenous

Food

Food (HMDB: HMDB0040426)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0040426)

Biological role

Nutrient (HMDB: HMDB0040426)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	157.00 to 165.00 °C. @ 12.00 mm Hg	The Good Scents Company Information System
Water Solubility	157.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.774 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.97	ALOGPS
logP	2.53	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	51.3 m³·mol⁻¹	ChemAxon
Polarizability	19.84 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]+	142.018	31661259
DarkChem	[M-H]-	137.762	31661259
DeepCCS	[M+H]+	141.912	30932474
DeepCCS	[M-H]-	138.127	30932474
DeepCCS	[M-2H]-	175.597	30932474
DeepCCS	[M+Na]+	151.136	30932474
AllCCS	[M+H]+	139.9	32859911
AllCCS	[M+H-H2O]+	135.7	32859911
AllCCS	[M+NH4]+	143.8	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	142.1	32859911
AllCCS	[M+Na-2H]-	143.0	32859911
AllCCS	[M+HCOO]-	144.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopropyl phenylacetate	CC(C)OC(=O)CC1=CC=CC=C1	1768.2	Standard polar	33892256
Isopropyl phenylacetate	CC(C)OC(=O)CC1=CC=CC=C1	1247.9	Standard non polar	33892256
Isopropyl phenylacetate	CC(C)OC(=O)CC1=CC=CC=C1	1291.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isopropyl phenylacetate EI-B (Non-derivatized)	splash10-0006-9000000000-1f974656022600dc0f4a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isopropyl phenylacetate EI-B (Non-derivatized)	splash10-0006-9000000000-1f974656022600dc0f4a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropyl phenylacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-3b0ff306a147483c092b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopropyl phenylacetate 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 - Isopropyl phenylacetate 10V, Positive-QTOF	splash10-00or-2900000000-2e107d4096d05d9a9605	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 20V, Positive-QTOF	splash10-02tc-8900000000-68a489ae25edc6434cfe	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 40V, Positive-QTOF	splash10-0006-9200000000-c2211006818b0a972d46	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 10V, Negative-QTOF	splash10-004i-4900000000-937cf2697d7b5147a4f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 20V, Negative-QTOF	splash10-0a4i-9400000000-6cbaac8985c46d3e50b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 40V, Negative-QTOF	splash10-0a4i-9200000000-79117c5d21904c17df0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 10V, Positive-QTOF	splash10-00mx-3900000000-23523e766f2bcdd8e850	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 20V, Positive-QTOF	splash10-0006-9200000000-6019b3ec76aef868d414	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 40V, Positive-QTOF	splash10-0006-9100000000-204632f111a8da98bcb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 10V, Negative-QTOF	splash10-0a4i-9000000000-c9b5b1f1bc0a663bcdb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 20V, Negative-QTOF	splash10-0a4l-9100000000-b81681a3b20d6bc10c4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopropyl phenylacetate 40V, Negative-QTOF	splash10-0006-9000000000-102e8a0747098ababc08	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

FDB020159

KNApSAcK ID

Not Available

Chemspider ID

56320

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62553

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1004471

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 Isopropyl phenylacetate (HMDB0040426)

MOL for HMDB0040426 (Isopropyl phenylacetate)

3D MOL for HMDB0040426 (Isopropyl phenylacetate)

3D SDF for HMDB0040426 (Isopropyl phenylacetate)

3D-SDF for HMDB0040426 (Isopropyl phenylacetate)

PDB for HMDB0040426 (Isopropyl phenylacetate)

3D PDB for HMDB0040426 (Isopropyl phenylacetate)

SMILES for HMDB0040426 (Isopropyl phenylacetate)

INCHI for HMDB0040426 (Isopropyl phenylacetate)

Structure for HMDB0040426 (Isopropyl phenylacetate)

3D Structure for HMDB0040426 (Isopropyl phenylacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra