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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:43 UTC

Update Date

2023-02-21 17:18:55 UTC

HMDB ID

HMDB0029640

Secondary Accession Numbers

HMDB29640

Metabolite Identification

Common Name

3-(4-Methylphenyl)-2-propenal

Description

3-(4-Methylphenyl)-2-propenal belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal. 3-(4-Methylphenyl)-2-propenal is a cinnamon and spicy tasting compound. Based on a literature review very few articles have been published on 3-(4-Methylphenyl)-2-propenal.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-3-(4-Methylphenyl)-2-propenal	HMDB
3-(P-Methylphenyl)propenal	HMDB
3-P-Tolylacrolein	HMDB
3-P-Tolylacrylaldehyde	HMDB
3-P-Tolylprop-2-enal	HMDB
3-P-Tolylpropenal	HMDB
4-Methylcinnamaldehyde	HMDB
FEMA 3640	HMDB
P-Methyl-cinnamaldehyde	HMDB
P-Methylcinnamaldehyde	HMDB
P-Methylcinnamaldehyde, 8ci	HMDB

Chemical Formula

C₁₀H₁₀O

Average Molecular Weight

146.1858

Monoisotopic Molecular Weight

146.073164942

IUPAC Name

(2E)-3-(4-methylphenyl)prop-2-enal

Traditional Name

(2E)-3-(4-methylphenyl)prop-2-enal

CAS Registry Number

1504-75-2

SMILES

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

InChI Identifier

InChI=1S/C10H10O/c1-9-4-6-10(7-5-9)3-2-8-11/h2-8H,1H3/b3-2+

InChI Key

DKOUYOVAEBQFHU-NSCUHMNNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamaldehydes. These are organic aromatic compounds containing a cinnamlaldehyde moiety, consisting of a benzene and an aldehyde group to form 3-phenylprop-2-enal.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamaldehydes

Sub Class

Not Available

Direct Parent

Cinnamaldehydes

Alternative Parents

Substituents

Cinnamaldehyde
Styrene
Toluene
Benzenoid
Monocyclic benzene moiety
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0029640)
Cytoplasm (HMDB: HMDB0029640)

Source

Endogenous

Endogenous (HMDB: HMDB0029640)

Exogenous

Food

Food (HMDB: HMDB0029640)

Exogenous (HMDB: HMDB0029640)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0029640)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	41.5 °C	Not Available
Boiling Point	154.00 °C. @ 25.00 mm Hg	The Good Scents Company Information System
Water Solubility	752.8 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.583 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.49	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.18 m³·mol⁻¹	ChemAxon
Polarizability	16.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	136.414	31661259
DarkChem	[M-H]-	132.986	31661259
DeepCCS	[M+H]+	132.885	30932474
DeepCCS	[M-H]-	129.746	30932474
DeepCCS	[M-2H]-	166.823	30932474
DeepCCS	[M+Na]+	142.34	30932474
AllCCS	[M+H]+	129.0	32859911
AllCCS	[M+H-H2O]+	124.4	32859911
AllCCS	[M+NH4]+	133.4	32859911
AllCCS	[M+Na]+	134.7	32859911
AllCCS	[M-H]-	130.5	32859911
AllCCS	[M+Na-2H]-	131.7	32859911
AllCCS	[M+HCOO]-	133.1	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.	6.55 minutes	32390414
Predicted by Siyang on May 30, 2022	14.383 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.83 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2181.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	505.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	205.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	341.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	625.6 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	657.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	243.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1359.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	532.1 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	1329.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	403.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	383.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	530.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	422.7 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	41.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Methylphenyl)-2-propenal	CC1=CC=C(\C=C\C=O)C=C1	2031.0	Standard polar	33892256
3-(4-Methylphenyl)-2-propenal	CC1=CC=C(\C=C\C=O)C=C1	1288.3	Standard non polar	33892256
3-(4-Methylphenyl)-2-propenal	CC1=CC=C(\C=C\C=O)C=C1	1378.6	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 - 3-(4-Methylphenyl)-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kb-1900000000-95203e9b3d8d9b2c1a88	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methylphenyl)-2-propenal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methylphenyl)-2-propenal 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-(4-Methylphenyl)-2-propenal 10V, Positive-QTOF	splash10-0002-0900000000-e177f14a0bed69afa254	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 20V, Positive-QTOF	splash10-002b-1900000000-a5b23f58a50f41900c2d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 40V, Positive-QTOF	splash10-0ar0-9800000000-ab421492b93814c7d2d1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 10V, Negative-QTOF	splash10-0002-0900000000-df53ea1d98a797d323e1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 20V, Negative-QTOF	splash10-0002-0900000000-5c11869d6648f7ddfaaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 40V, Negative-QTOF	splash10-002f-6900000000-fd8579805633950a42e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 10V, Positive-QTOF	splash10-0002-0900000000-e0368a38b17bf4fe1fb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 20V, Positive-QTOF	splash10-00or-5900000000-e3ff46938c73e02ec762	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 40V, Positive-QTOF	splash10-004i-9500000000-8410270b776cce957f63	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 10V, Negative-QTOF	splash10-014i-0900000000-6f02d30135a562271682	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 20V, Negative-QTOF	splash10-014i-2900000000-deaf05383a2c333e5c03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)-2-propenal 40V, Negative-QTOF	splash10-014i-3900000000-fa7191dd62aaedc309a1	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]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB000810

KNApSAcK ID

Not Available

Chemspider ID

4522224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5371802

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1032331

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-(4-Methylphenyl)-2-propenal (HMDB0029640)

MOL for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

3D MOL for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

3D SDF for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

3D-SDF for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

PDB for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

3D PDB for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

SMILES for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

INCHI for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

Structure for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

3D Structure for HMDB0029640 (3-(4-Methylphenyl)-2-propenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra