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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:06:08 UTC

Update Date

2023-02-21 17:23:18 UTC

HMDB ID

HMDB0033386

Secondary Accession Numbers

HMDB33386

Metabolite Identification

Common Name

3-Phenylpropyl acetate

Description

3-Phenylpropyl acetate, also known as hydrocinnamyl acetate, 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. 3-Phenylpropyl acetate is a sweet, balsam, and bitter tasting compound. 3-Phenylpropyl acetate is found, on average, in the highest concentration within ceylon cinnamons (Cinnamomum verum). 3-Phenylpropyl acetate has also been detected, but not quantified in, several different foods, such as alcoholic beverages, chinese cinnamons (Cinnamomum aromaticum), fruits, and muskmelons (Cucumis melo). This could make 3-phenylpropyl acetate a potential biomarker for the consumption of these foods. 3-Phenylpropyl acetate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 3-Phenylpropyl acetate.

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      10.669   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002   3.080   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    8    9                                                       
CONECT    6    3   11                                                       
CONECT    7    4   11                                                       
CONECT    8    5   11                                                       
CONECT    9    5   13                                                       
CONECT   10    1   12   13                                                  
CONECT   11    6    7    8                                                  
CONECT   12   10                                                            
CONECT   13    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0033386
HETATM    1  C1  UNL     1       4.749  -0.439   0.645  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.431  -0.267  -0.070  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.514   0.305  -1.180  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.252  -0.702   0.456  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.044  -0.525  -0.234  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.698   0.905  -0.481  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.608   1.072  -1.221  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.717   0.473  -0.434  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.443   1.191   0.492  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.476   0.585   1.207  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.781  -0.744   0.991  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.072  -1.477   0.075  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.057  -0.862  -0.620  1.00  0.00           C  
HETATM   14  H1  UNL     1       5.367  -1.191   0.118  1.00  0.00           H  
HETATM   15  H2  UNL     1       5.252   0.554   0.580  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.545  -0.697   1.702  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.243  -0.938   0.448  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.985  -1.157  -1.139  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.607   1.487   0.453  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.494   1.391  -1.075  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.799   2.161  -1.296  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.606   0.579  -2.209  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.187   2.223   0.642  1.00  0.00           H  
HETATM   24  H11 UNL     1      -4.010   1.187   1.916  1.00  0.00           H  
HETATM   25  H12 UNL     1      -4.578  -1.177   1.555  1.00  0.00           H  
HETATM   26  H13 UNL     1      -3.348  -2.518  -0.060  1.00  0.00           H  
HETATM   27  H14 UNL     1      -1.495  -1.418  -1.337  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   17   18
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
Hydrocinnamyl acetate	Kegg
Hydrocinnamyl acetic acid	Generator
3-Phenylpropyl acetic acid	Generator
(3-Acetoxypropyl)benzene	HMDB
1-Acetoxy-3-phenylpropane	HMDB
1-Propanol, 3-phenyl-, acetate	HMDB
3-Acetoxy-1-phenylpropane	HMDB
3-Phenyl-1-propanol, acetate	HMDB
3-Phenyl-1-propyl acetate	HMDB
Benzenepropanol, 1-acetate	HMDB
Benzenepropanol, acetate	HMDB
Benzenepropyl acetate	HMDB
FEMA 2890	HMDB
laquo gammaraquo -Phenylpropyl acetate	HMDB
Phenylpropyl acetate	HMDB

Chemical Formula

C₁₁H₁₄O₂

Average Molecular Weight

178.2277

Monoisotopic Molecular Weight

178.099379692

IUPAC Name

3-phenylpropyl acetate

Traditional Name

benzenepropanol, acetate

CAS Registry Number

122-72-5

SMILES

CC(=O)OCCCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H14O2/c1-10(12)13-9-5-8-11-6-3-2-4-7-11/h2-4,6-7H,5,8-9H2,1H3

InChI Key

JRJGKUTZNBZHNK-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

benzenes (CHEBI:81257 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0033386)
Cell membrane (HMDB: HMDB0033386)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033386)

Source

Exogenous

Exogenous (HMDB: HMDB0033386)

Food

Food (HMDB: HMDB0033386)

Gourd

Muskmelon (FooDB: FOOD00064)

Herb and spice

Spice

Chinese cinnamon (FooDB: FOOD00050)
Ceylon cinnamon (FooDB: FOOD00051)

Fruit

Fruits (FooDB: FOOD00871)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Endogenous

Plant

Plant (HMDB: HMDB0033386)
Cucurbitaceae (HMDB: HMDB0033386)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033386)
Flavor (HMDB: HMDB0033386)

Fragrance (HMDB: HMDB0033386)

Biological role

Nutrient (HMDB: HMDB0033386)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	2.847 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.045 g/L	ALOGPS
logP	2.88	ALOGPS
logP	2.38	ChemAxon
logS	-3.6	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	51.38 m³·mol⁻¹	ChemAxon
Polarizability	20.3 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]+	141.139	31661259
DarkChem	[M-H]-	136.402	31661259
DeepCCS	[M+H]+	137.77	30932474
DeepCCS	[M-H]-	134.55	30932474
DeepCCS	[M-2H]-	171.592	30932474
DeepCCS	[M+Na]+	147.13	30932474
AllCCS	[M+H]+	139.0	32859911
AllCCS	[M+H-H2O]+	134.8	32859911
AllCCS	[M+NH4]+	142.9	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	143.0	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	145.0	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.	7.35 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6739 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.46 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2130.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	477.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	289.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	612.9 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	671.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	103.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1336.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	495.5 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	1427.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	421.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	337.2 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	27.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Phenylpropyl acetate	CC(=O)OCCCC1=CC=CC=C1	1997.5	Standard polar	33892256
3-Phenylpropyl acetate	CC(=O)OCCCC1=CC=CC=C1	1323.1	Standard non polar	33892256
3-Phenylpropyl acetate	CC(=O)OCCCC1=CC=CC=C1	1400.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Phenylpropyl acetate EI-B (Non-derivatized)	splash10-014i-4900000000-c81ecf44d44f2a4f762f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Phenylpropyl acetate EI-B (Non-derivatized)	splash10-014l-4900000000-88035a3fdb2f5791bea9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Phenylpropyl acetate EI-B (Non-derivatized)	splash10-014l-6900000000-37831f4980d74f7589d5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Phenylpropyl acetate EI-B (Non-derivatized)	splash10-014i-4900000000-c81ecf44d44f2a4f762f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Phenylpropyl acetate EI-B (Non-derivatized)	splash10-014l-4900000000-88035a3fdb2f5791bea9	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Phenylpropyl acetate EI-B (Non-derivatized)	splash10-014l-6900000000-37831f4980d74f7589d5	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Phenylpropyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-ab6da2f371bcb3642272	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Phenylpropyl acetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Phenylpropyl acetate 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 - 3-Phenylpropyl acetate 10V, Positive-QTOF	splash10-004i-1900000000-c82eb511ff256437184e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 20V, Positive-QTOF	splash10-014i-2900000000-147583abcd97452349d6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 40V, Positive-QTOF	splash10-0006-9400000000-f654e098d65302179401	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 10V, Negative-QTOF	splash10-004i-3900000000-b6598a77646f0ed4eb77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 20V, Negative-QTOF	splash10-0a4i-9400000000-897b15af3830f0ac70cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 40V, Negative-QTOF	splash10-0a4l-9100000000-eda29dbd870d3599cdcc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 10V, Negative-QTOF	splash10-0a4i-9200000000-150ed1ad00d4968c8659	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 20V, Negative-QTOF	splash10-0a4i-9200000000-4d22694ec7b837caa51f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 40V, Negative-QTOF	splash10-052f-9000000000-addddde8b8293250d3bc	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 10V, Positive-QTOF	splash10-05mo-4900000000-110dceac8e3dd5b6b00d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 20V, Positive-QTOF	splash10-00kf-9500000000-8b6aff48b6de2a29cd1c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Phenylpropyl acetate 40V, Positive-QTOF	splash10-0006-9000000000-63327ba5e0b484ea4e8b	2021-09-25	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

31226

PDB ID

Not Available

ChEBI ID

81257

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1015191

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 3-Phenylpropyl acetate (HMDB0033386)

MOL for HMDB0033386 (3-Phenylpropyl acetate)

3D MOL for HMDB0033386 (3-Phenylpropyl acetate)

3D SDF for HMDB0033386 (3-Phenylpropyl acetate)

3D-SDF for HMDB0033386 (3-Phenylpropyl acetate)

PDB for HMDB0033386 (3-Phenylpropyl acetate)

3D PDB for HMDB0033386 (3-Phenylpropyl acetate)

SMILES for HMDB0033386 (3-Phenylpropyl acetate)

INCHI for HMDB0033386 (3-Phenylpropyl acetate)

Structure for HMDB0033386 (3-Phenylpropyl acetate)

3D Structure for HMDB0033386 (3-Phenylpropyl acetate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra