Cinnamaldehyde (YMDB01654)

Identification

YMDB ID

YMDB01654

Name

Cinnamaldehyde

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Cinnamaldehyde, also known as 3-fenylpropenal or 3-phenylacrolein, 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. Based on a literature review a significant number of articles have been published on Cinnamaldehyde.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2E)-3-Phenyl-2-propenal
(2E)-3-Phenylacrylaldehyde
(e)-3-Phenyl-2-propenal
(e)-3-Phenyl-propenal
(e)-3-Phenylpropenal
(e)-Cinnamaldehyde
(e)-Cinnamic aldehyde
(e)-Phenylvinyl aldehyde
3-Fenylpropenal
3-Phenyl-2-propen-1-al
3-Phenyl-2-propenaldehyde
3-Phenylacrolein
3-Phenylacrylaldehyde
3-Phenylprop-2-enal
3-Phenylprop-2-enaldehyde
3-Phenylpropenal
Benzylideneacetaldehyde
beta-Phenylacrolein
beta-Phenylcrolein
Cinnamal
Cinnamic aldehyde
Cinnamic aldehyde, (e)-isomer
Cinnamyl aldehyde
Cinnamylaldehyde
Cinnemaldehyde
Supercinnamaldehyde
trans-3-Phenyl-2-propenal
trans-3-Phenylprop-2-enaldehyde
trans-Cinnamaldehyde
trans-Cinnamic aldehyde
trans-Cinnamylaldehyde
2E)-3-Phenyl-2-propenal
(E)-3-Phenylacrolein
(E)-3-Phenylprop-2-en-1-al
(E)-3-Phenylprop-2-enal
(E)-3-Phenylprop-2-enone
E-Cinnamyl aldehyde
trans-3-Phenylpropenal
trans-Benzenepropenal
3-Phenyl-2-propenal
3-Phenyl-2-propene-1-al

CAS number

104-55-2

Weight

Average: 132.1592
Monoisotopic: 132.057514878

InChI Key

KJPRLNWUNMBNBZ-QPJJXVBHSA-N

InChI

InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+

IUPAC Name

(2E)-3-phenylprop-2-enal

Traditional IUPAC Name

cinnamal

Chemical Formula

C₉H₈O

SMILES

O=C\C=C\C1=CC=CC=C1

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
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

cinnamaldehydes (CHEBI:16731 )
Monolignols (C00903 )

Physical Properties

State

Liquid

Charge

Melting point

-7.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1.42 mg/mL at 25 oC [VALVANI,SC et al. (1981)]	PhysProp
LogP	1.90 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	2	ALOGPS
logP	1.98	ChemAxon
logS	-2.5	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	42.13 m³·mol⁻¹	ChemAxon
Polarizability	14.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Cinnamon	FDB030727
Clove	FDB030727
Red hots	FDB030727
Spice	FDB030727
Sweet	FDB030727
Warm	FDB030727

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0059-3900000000-52db83b595237437ab08	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f89-5900000000-540c43f6893b35e8a105	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f89-5900000000-482f8b5c30c53689d8eb	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-3900000000-9d274f5e3981ab662650	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0900000000-4f0ad7748ac21b7320c9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f89-6900000000-ecaba4b9d657020c3f4c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-001i-0900000000-c02b7869dea8f1113cb4	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-2900000000-d89aa99ef7a6ae16b942	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ugi-8900000000-14f14e29c81360ebdd4b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0059-3900000000-52db83b595237437ab08	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-4900000000-e9eb0053986096f21c83	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a59-5900000000-a125425df0f09bb01129	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-056r-9300000000-043ea317ed08a1cbacfb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9000000000-39ab07ef5d737e851671	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0f89-5900000000-f27dd11a8900d729bd19	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0f89-5900000000-4e11cf955911f9ca7da2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive	splash10-001i-3900000000-9d274f5e3981ab662650	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (SHIMADZU QP-1000) , Positive	splash10-001i-0900000000-4f0ad7748ac21b7320c9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0f89-6900000000-e363e674a4ec6e092f26	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - CI-B (HITACHI M-80) , Positive	splash10-001i-0900000000-c02b7869dea8f1113cb4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-001i-2900000000-7339e3ff66ab63ba3409	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0ugi-8900000000-1b72d0d216af15365444	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-067i-2900000000-76d2db81f3822a698f0a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-067i-2900000000-76d2db81f3822a698f0a	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1900000000-4b1b083c8fdb2a27206b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-2900000000-eee6045375789bd7b511	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9400000000-ffef407879854d06bd7e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-074611feed644fd89c07	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-cbf5bec188b738c514af	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p6-9600000000-5eb930cf87b199a5f449	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-827b27666b5028c8cf77	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-138b8c24fd394024a31a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-93f143b30bbb2b4ff778	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lu-2900000000-eda42d3592c23cd1e4bd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-5900000000-5757a78bf103c73ab434	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-9300000000-8784eab3c86fc7a1a721	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16731
HMDB ID	HMDB03441
Pubchem Compound ID	637511
Kegg ID	C00903
ChemSpider ID	553117
FOODB ID	FDB030727
Wikipedia ID	Cinnamaldehyde
BioCyc ID	Not Available

Structure for #<Compound:0xae563b74>