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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:57:12 UTC

Update Date

2023-02-21 17:24:33 UTC

HMDB ID

HMDB0035013

Secondary Accession Numbers

HMDB35013

Metabolite Identification

Common Name

2-Phenylethyl propanoate

Description

2-Phenylethyl propanoate 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. 2-Phenylethyl propanoate is a balsam, floral, and fruity tasting compound. 2-Phenylethyl propanoate has been detected, but not quantified in, several different foods, such as alcoholic beverages, ceylon cinnamons (Cinnamomum verum), fruits, milk and milk products, and nuts. This could make 2-phenylethyl propanoate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Phenylethyl propanoate.

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

COMPND    HMDB0035013
HETATM    1  C1  UNL     1       4.844  -0.189   0.400  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.922  -0.513  -0.773  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.497  -0.578  -0.306  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.939  -1.690  -0.111  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.759   0.560  -0.076  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.423   0.622   0.361  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.491  -0.061  -0.621  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.899  -0.007  -0.271  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.554  -0.942   0.461  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.904  -0.770   0.736  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.598   0.325   0.284  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.944   1.290  -0.466  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.613   1.111  -0.731  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.029  -1.055   1.024  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.277   0.580   1.004  1.00  0.00           H  
HETATM   16  H3  UNL     1       5.754   0.303  -0.018  1.00  0.00           H  
HETATM   17  H4  UNL     1       4.271  -1.459  -1.188  1.00  0.00           H  
HETATM   18  H5  UNL     1       4.055   0.313  -1.501  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.164   1.647   0.583  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.350  -0.005   1.297  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.193  -1.123  -0.784  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.346   0.416  -1.618  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.018  -1.802   0.818  1.00  0.00           H  
HETATM   24  H11 UNL     1      -4.459  -1.507   1.322  1.00  0.00           H  
HETATM   25  H12 UNL     1      -5.653   0.491   0.478  1.00  0.00           H  
HETATM   26  H13 UNL     1      -4.491   2.165  -0.835  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.118   1.878  -1.317  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   19   20
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
2-Phenylethyl propanoic acid	Generator
2-Phenethyl propionate	HMDB
2-Phenethylpropionate	HMDB
2-Phenyl ethyl propanoate	HMDB
2-Phenylethanol, propanoate	HMDB
2-Phenylethyl propionate	HMDB
Benzylcarbinyl propionate	HMDB
beta -Phenylethyl propionate	HMDB
beta-Phenylethyl propionate	HMDB
ecopco Acu	HMDB
FEMA 2867	HMDB
Japanese beetle bait	HMDB
Phenethyl alcohol, propionate	HMDB
Phenethyl popanoate	HMDB
Phenethyl propanoate	HMDB
Phenethyl propionate	HMDB
Phenylethanol propanoate	HMDB
Phenylethyl N-propionate	HMDB
Phenylethyl propanoate	HMDB
Phenylethyl propionate	HMDB
Propanoic acid, 2-phenylethyl ester	HMDB
PROPANOIC ACID,3-(ethyl,2-phenyl) ester MFC11 H14 O2	HMDB
Propionic acid, 2-phenylethyl ester	HMDB
Propionic acid, phenethyl ester	HMDB

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

2-phenylethyl propanoate

Traditional Name

2-phenylethyl propionate

CAS Registry Number

122-70-3

SMILES

CCC(=O)OCCC1=CC=CC=C1

InChI Identifier

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

InChI Key

HVGZQCSMLUDISR-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

Cellular substructure

Membrane (HMDB: HMDB0035013)
Cell membrane (HMDB: HMDB0035013)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035013)

Source

Exogenous

Exogenous (HMDB: HMDB0035013)

Food

Food (HMDB: HMDB0035013)

Herb and spice

Spice

Ceylon cinnamon (FooDB: FOOD00051)

Nut

Nuts (FooDB: FOOD00869)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Milk and milk product

Milk and milk products (FooDB: FOOD00863)

Endogenous

Plant

Plant (HMDB: HMDB0035013)

Animal

Animal (HMDB: HMDB0035013)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035013)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	244.00 to 245.00 °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	2.808 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.64	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	51.41 m³·mol⁻¹	ChemAxon
Polarizability	20.18 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]+	141.157	31661259
DarkChem	[M-H]-	137.616	31661259
DeepCCS	[M+H]+	137.798	30932474
DeepCCS	[M-H]-	134.148	30932474
DeepCCS	[M-2H]-	171.491	30932474
DeepCCS	[M+Na]+	147.029	30932474
AllCCS	[M+H]+	139.4	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.3	32859911
AllCCS	[M+Na]+	144.4	32859911
AllCCS	[M-H]-	142.6	32859911
AllCCS	[M+Na-2H]-	143.5	32859911
AllCCS	[M+HCOO]-	144.6	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.	7.24 minutes	32390414
Predicted by Siyang on May 30, 2022	15.2643 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.54 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2135.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	512.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	311.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	629.2 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	685.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1335.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	513.8 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	1402.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	456.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	434.9 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	26.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Phenylethyl propanoate	CCC(=O)OCCC1=CC=CC=C1	1964.9	Standard polar	33892256
2-Phenylethyl propanoate	CCC(=O)OCCC1=CC=CC=C1	1311.0	Standard non polar	33892256
2-Phenylethyl propanoate	CCC(=O)OCCC1=CC=CC=C1	1388.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Phenylethyl propanoate EI-B (Non-derivatized)	splash10-0zfr-9800000000-234d53df7898caf22a51	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Phenylethyl propanoate EI-B (Non-derivatized)	splash10-0zfr-9800000000-234d53df7898caf22a51	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Phenylethyl propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-054o-9200000000-ee8c4a5397d243c35040	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Phenylethyl propanoate 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 - 2-Phenylethyl propanoate 10V, Positive-QTOF	splash10-056r-3900000000-5bc88c7a39ef259c07ad	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 20V, Positive-QTOF	splash10-0a4i-6900000000-e5f084861f9942ced6fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 40V, Positive-QTOF	splash10-0a6r-9300000000-9ef3b5833a6f505b51f6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 10V, Negative-QTOF	splash10-056r-7900000000-f5ce0fd30ad0a24326bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 20V, Negative-QTOF	splash10-05fr-9200000000-6ecc75f6312c3747ddbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 40V, Negative-QTOF	splash10-0a4i-9000000000-e3e68fb2729c5b9aebb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 10V, Negative-QTOF	splash10-00di-9000000000-a18665b48b96b6efae4c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 20V, Negative-QTOF	splash10-00di-9000000000-9c5cbfe3ebac90be0161	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 40V, Negative-QTOF	splash10-00di-9000000000-e577c6aa8ecccc953bfb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 10V, Positive-QTOF	splash10-0a4i-1900000000-29d7f396fe2571e76b81	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 20V, Positive-QTOF	splash10-052f-9500000000-64371c6dd4cc2eb7d719	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Phenylethyl propanoate 40V, Positive-QTOF	splash10-0a6u-9700000000-07011da2843a2936fa67	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

FDB013618

KNApSAcK ID

C00056663

Chemspider ID

28965

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31225

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1012692

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 2-Phenylethyl propanoate (HMDB0035013)

MOL for HMDB0035013 (2-Phenylethyl propanoate)

3D MOL for HMDB0035013 (2-Phenylethyl propanoate)

3D SDF for HMDB0035013 (2-Phenylethyl propanoate)

3D-SDF for HMDB0035013 (2-Phenylethyl propanoate)

PDB for HMDB0035013 (2-Phenylethyl propanoate)

3D PDB for HMDB0035013 (2-Phenylethyl propanoate)

SMILES for HMDB0035013 (2-Phenylethyl propanoate)

INCHI for HMDB0035013 (2-Phenylethyl propanoate)

Structure for HMDB0035013 (2-Phenylethyl propanoate)

3D Structure for HMDB0035013 (2-Phenylethyl propanoate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra