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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:59:03 UTC

Update Date

2023-02-21 17:28:38 UTC

HMDB ID

HMDB0041315

Secondary Accession Numbers

HMDB41315

Metabolite Identification

Common Name

Cinnamyl propionate

Description

Cinnamyl propionate belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety. Cinnamyl propionate is a sweet, balsam, and fruity tasting compound. Based on a literature review a small amount of articles have been published on Cinnamyl propionate.

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       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   3.080   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       5.335   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1   12                                                       
CONECT    3    4    5                                                       
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10                                                       
CONECT    7    4   11                                                       
CONECT    8    5   11                                                       
CONECT    9    6   11                                                       
CONECT   10    6   14                                                       
CONECT   11    7    8    9                                                  
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0041315
HETATM    1  C1  UNL     1       5.172   0.332  -0.037  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.900   0.305   0.793  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.803  -0.389   0.039  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.991  -0.852  -1.107  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.592  -0.500   0.642  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.437  -1.156   0.001  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.101  -0.414  -1.209  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.030   0.139  -1.455  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.199   0.147  -0.643  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.065   1.246  -0.835  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.266   1.347  -0.199  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.711   0.387   0.667  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.900  -0.701   0.881  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.674  -0.790   0.223  1.00  0.00           C  
HETATM   15  H1  UNL     1       5.660  -0.663  -0.075  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.878   1.008   0.483  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.995   0.760  -1.043  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.613   1.368   0.951  1.00  0.00           H  
HETATM   19  H5  UNL     1       4.124  -0.175   1.748  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.705  -2.181  -0.239  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.333  -1.044   0.794  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.931  -0.356  -1.952  1.00  0.00           H  
HETATM   23  H9  UNL     1      -1.060   0.670  -2.458  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.755   2.031  -1.511  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.882   2.199  -0.379  1.00  0.00           H  
HETATM   26  H12 UNL     1      -5.660   0.468   1.170  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.224  -1.473   1.559  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.141  -1.713   0.399  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   20   21
CONECT    7    8    8   22
CONECT    8    9   23
CONECT    9   10   10   14
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cinnamyl propionic acid	Generator
(2E)-3-Phenyl-2-propenyl propionate	HMDB
2-Propen-1-ol, 3-phenyl-, 1-propanoate	HMDB
2-Propen-1-ol, 3-phenyl-, propanoate	HMDB
3-Phenyl-2-propen-1-ol propanoate	HMDB
3-Phenyl-2-propen-1-yl propionate	HMDB
3-Phenyl-2-propenyl propanoate	HMDB
3-Phenyl-2-propenyl propionate	HMDB
3-Phenylallyl propionate	HMDB
Cinnamyl alcohol, propionate	HMDB
Cinnamyl N-propionate	HMDB
FEMA 2301	HMDB
gamma-Phenylallyl propionate	HMDB
Propionic acid, cinnamyl ester	HMDB
trans-Cinnamyl propionate	HMDB
(2Z)-3-Phenylprop-2-en-1-yl propanoic acid	Generator

Chemical Formula

C₁₂H₁₄O₂

Average Molecular Weight

190.2384

Monoisotopic Molecular Weight

190.099379692

IUPAC Name

(2Z)-3-phenylprop-2-en-1-yl propanoate

Traditional Name

(2Z)-3-phenylprop-2-en-1-yl propanoate

CAS Registry Number

103-56-0

SMILES

CCC(=O)OC\C=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C12H14O2/c1-2-12(13)14-10-6-9-11-7-4-3-5-8-11/h3-9H,2,10H2,1H3/b9-6-

InChI Key

KGDJMNKPBUNHGY-TWGQIWQCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as styrenes. These are organic compounds containing an ethenylbenzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Styrenes

Direct Parent

Styrenes

Alternative Parents

Substituents

Styrene
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: HMDB0041315)
Cell membrane (HMDB: HMDB0041315)

Source

Exogenous

Exogenous (HMDB: HMDB0041315)

Food

Food (HMDB: HMDB0041315)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041315)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	288.00 to 289.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	68.97 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.150 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	3.36	ALOGPS
logP	2.96	ChemAxon
logS	-3.4	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	56.97 m³·mol⁻¹	ChemAxon
Polarizability	21.61 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]+	146.945	31661259
DarkChem	[M-H]-	143.49	31661259
DeepCCS	[M+H]+	139.172	30932474
DeepCCS	[M-H]-	136.673	30932474
DeepCCS	[M-2H]-	172.042	30932474
DeepCCS	[M+Na]+	147.305	30932474
AllCCS	[M+H]+	142.2	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.0	32859911
AllCCS	[M+Na]+	147.1	32859911
AllCCS	[M-H]-	145.9	32859911
AllCCS	[M+Na-2H]-	146.6	32859911
AllCCS	[M+HCOO]-	147.4	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.	8.43 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1924 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.6 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2550.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	539.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	340.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	334.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	692.8 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	755.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1458.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	546.8 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	1416.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	445.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	485.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	452.9 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	17.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cinnamyl propionate	CCC(=O)OC\C=C/C1=CC=CC=C1	2240.8	Standard polar	33892256
Cinnamyl propionate	CCC(=O)OC\C=C/C1=CC=CC=C1	1485.4	Standard non polar	33892256
Cinnamyl propionate	CCC(=O)OC\C=C/C1=CC=CC=C1	1582.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl propionate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0690-9700000000-0d124e6af5d896121916	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cinnamyl propionate 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 - Cinnamyl propionate 10V, Positive-QTOF	splash10-00kf-3900000000-3f355a1660e018826a80	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 20V, Positive-QTOF	splash10-014i-4900000000-5ee29569df7524dd8d05	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 40V, Positive-QTOF	splash10-0pvu-9300000000-c9eac3478fdb92cd72fa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 10V, Negative-QTOF	splash10-052r-6900000000-34db6b3e07f4dfc619d3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 20V, Negative-QTOF	splash10-05fr-9300000000-784f3c72c00a1b2ea4d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 40V, Negative-QTOF	splash10-0a4i-9300000000-f4bc926420b98cac8673	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 10V, Negative-QTOF	splash10-00xr-8900000000-a8e323cd69df11ce43b9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 20V, Negative-QTOF	splash10-0gi0-7900000000-af8dd47d99174b202c77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 40V, Negative-QTOF	splash10-0ab9-9000000000-e5bfe909dfc5d1ed5d48	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 10V, Positive-QTOF	splash10-014i-1900000000-fb7193a1ab5bdeada791	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 20V, Positive-QTOF	splash10-014l-2900000000-b9651719d5d604122718	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cinnamyl propionate 40V, Positive-QTOF	splash10-014l-9700000000-3c6bcc63de597786d982	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

FDB021234

KNApSAcK ID

Not Available

Chemspider ID

30777555

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57500615

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1024271

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 Cinnamyl propionate (HMDB0041315)

MOL for HMDB0041315 (Cinnamyl propionate)

3D MOL for HMDB0041315 (Cinnamyl propionate)

3D SDF for HMDB0041315 (Cinnamyl propionate)

3D-SDF for HMDB0041315 (Cinnamyl propionate)

PDB for HMDB0041315 (Cinnamyl propionate)

3D PDB for HMDB0041315 (Cinnamyl propionate)

SMILES for HMDB0041315 (Cinnamyl propionate)

INCHI for HMDB0041315 (Cinnamyl propionate)

Structure for HMDB0041315 (Cinnamyl propionate)

3D Structure for HMDB0041315 (Cinnamyl propionate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra