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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:05:19 UTC

Update Date

2023-02-21 17:25:30 UTC

HMDB ID

HMDB0036905

Secondary Accession Numbers

HMDB36905

Metabolite Identification

Common Name

2-Propenyl phenylacetate

Description

2-Propenyl 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. 2-Propenyl phenylacetate is a sweet, fruity, and honey tasting compound. Based on a literature review very few articles have been published on 2-Propenyl 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       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       8.002   6.160   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      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      10.669   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    8                                                       
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    2   13                                                       
CONECT    9   10   11                                                       
CONECT   10    6    7    9                                                  
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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Propenyl phenylacetic acid	Generator
2-Propenyl benzeneacetate	HMDB
Acetic acid, phenyl-, allyl ester	HMDB
Allyl alpha-toluate	HMDB
Allyl phenylacetate	HMDB
Benzeneacetic acid, 2-propen-1-yl ester	HMDB
Benzeneacetic acid, 2-propenyl ester	HMDB
Phenylacetic acid allyl ester	HMDB
Prop-2-en-1-yl 2-phenylacetic acid	Generator

Chemical Formula

C₁₁H₁₂O₂

Average Molecular Weight

176.2118

Monoisotopic Molecular Weight

176.083729628

IUPAC Name

prop-2-en-1-yl 2-phenylacetate

Traditional Name

prop-2-en-1-yl 2-phenylacetate

CAS Registry Number

1797-74-6

SMILES

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

InChI Identifier

InChI=1S/C11H12O2/c1-2-8-13-11(12)9-10-6-4-3-5-7-10/h2-7H,1,8-9H2

InChI Key

ZCDYAMJXVAUTIM-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

Sweet

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0036905)
Cell membrane (HMDB: HMDB0036905)

Source

Exogenous

Exogenous (HMDB: HMDB0036905)

Food

Food (HMDB: HMDB0036905)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036905)

Biological role

Nutrient (HMDB: HMDB0036905)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	239.00 to 240.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	181.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.661 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.49	ChemAxon
logS	-2.9	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	5	ChemAxon
Refractivity	51.3 m³·mol⁻¹	ChemAxon
Polarizability	19.12 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]+	140.377	31661259
DarkChem	[M-H]-	136.656	31661259
DeepCCS	[M+H]+	136.485	30932474
DeepCCS	[M-H]-	133.352	30932474
DeepCCS	[M-2H]-	170.34	30932474
DeepCCS	[M+Na]+	145.879	30932474
AllCCS	[M+H]+	137.9	32859911
AllCCS	[M+H-H2O]+	133.7	32859911
AllCCS	[M+NH4]+	141.9	32859911
AllCCS	[M+Na]+	143.0	32859911
AllCCS	[M-H]-	139.8	32859911
AllCCS	[M+Na-2H]-	140.6	32859911
AllCCS	[M+HCOO]-	141.5	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.	7.14 minutes	32390414
Predicted by Siyang on May 30, 2022	15.1311 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2208.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	516.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	328.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	279.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	615.2 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	706.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1336.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	495.3 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	1374.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	388.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	433.8 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	22.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Propenyl phenylacetate	C=CCOC(=O)CC1=CC=CC=C1	1899.6	Standard polar	33892256
2-Propenyl phenylacetate	C=CCOC(=O)CC1=CC=CC=C1	1259.9	Standard non polar	33892256
2-Propenyl phenylacetate	C=CCOC(=O)CC1=CC=CC=C1	1358.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl phenylacetate CI-B (Non-derivatized)	splash10-004i-0900000000-933cb8074ca2bf3472b3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl phenylacetate EI-B (Non-derivatized)	splash10-0006-9100000000-646b8c316cbe73398d54	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl phenylacetate EI-B (Non-derivatized)	splash10-0006-9000000000-10bb6fc9d1f1d1892d00	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl phenylacetate CI-B (Non-derivatized)	splash10-004i-0900000000-933cb8074ca2bf3472b3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl phenylacetate EI-B (Non-derivatized)	splash10-0006-9100000000-646b8c316cbe73398d54	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Propenyl phenylacetate EI-B (Non-derivatized)	splash10-0006-9000000000-10bb6fc9d1f1d1892d00	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl phenylacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-b27e2880b03a2949ee4f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Propenyl 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 - 2-Propenyl phenylacetate 10V, Positive-QTOF	splash10-004l-4900000000-44c838cb757b40ba5490	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 20V, Positive-QTOF	splash10-0006-9300000000-98fd1b7afc7fc03a69a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 40V, Positive-QTOF	splash10-0006-9100000000-b63dcbd7858dbff5b5bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 10V, Negative-QTOF	splash10-00p0-2900000000-c69ee1934aed4bf9af90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 20V, Negative-QTOF	splash10-00kr-4900000000-7795c98f020a4817243c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 40V, Negative-QTOF	splash10-014u-9600000000-caea430688f30c35a4e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 10V, Positive-QTOF	splash10-002f-8900000000-dfcb685bce16b56425b7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 20V, Positive-QTOF	splash10-0006-9200000000-df673db1f07d0ea10d62	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 40V, Positive-QTOF	splash10-0006-9000000000-72aa8c10d030b3fd5557	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 10V, Negative-QTOF	splash10-0a4i-9000000000-f6e7e9ce8de840809c83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 20V, Negative-QTOF	splash10-0006-9000000000-5ad167046c2b923d6ace	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Propenyl phenylacetate 40V, Negative-QTOF	splash10-0006-9000000000-345556e6708cf63e28a3	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

FDB015868

KNApSAcK ID

Not Available

Chemspider ID

14946

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15717

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1002911

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-Propenyl phenylacetate (HMDB0036905)

MOL for HMDB0036905 (2-Propenyl phenylacetate)

3D MOL for HMDB0036905 (2-Propenyl phenylacetate)

3D SDF for HMDB0036905 (2-Propenyl phenylacetate)

3D-SDF for HMDB0036905 (2-Propenyl phenylacetate)

PDB for HMDB0036905 (2-Propenyl phenylacetate)

3D PDB for HMDB0036905 (2-Propenyl phenylacetate)

SMILES for HMDB0036905 (2-Propenyl phenylacetate)

INCHI for HMDB0036905 (2-Propenyl phenylacetate)

Structure for HMDB0036905 (2-Propenyl phenylacetate)

3D Structure for HMDB0036905 (2-Propenyl phenylacetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra