Human Metabolome Database: Showing metabocard for Cinnamaldehyde (HMDB0003441)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Detected but not Quantified

Creation Date

2006-08-12 20:46:08 UTC

Update Date

2020-04-22 23:33:26 UTC

HMDB ID

HMDB0003441

Secondary Accession Numbers

HMDB03441

Metabolite Identification

Common Name

Cinnamaldehyde

Description

Cinnamaldehyde is the aldehyde that gives cinnamon its flavor and odor. Cinnamaldehyde occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum like camphor and cassia. These trees are the natural source of cinnamon, and the essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde is also used as a fungicide. Proven effective on over 40 different crops, cinnamaldehyde is typically applied to the root systems of plants. Its low toxicity and well-known properties make it ideal for agriculture. To a lesser extent, cinnamaldehyde is an effective insecticide, and its scent is also known to repel animals like cats and dogs. Cinnamaldehyde is also known as a corrosion inhibitor for steel and other ferrous alloys in corrosive fluids. It can be used in combination with additional components such as dispersing agents, solvents and other surfactants. Concentrated cinnamaldehyde is a skin irritant, and the chemical is toxic in large doses, but no agencies suspect the compound is a carcinogen or poses a long-term health hazard. Most cinnamaldehyde is excreted in urine as cinnamic acid, an oxidized form of cinnamaldehyde.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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

Chemical Formula

C₉H₈O

Average Molecular Weight

132.1592

Monoisotopic Molecular Weight

132.057514878

IUPAC Name

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

Traditional Name

cinnamal

CAS Registry Number

104-55-2

SMILES

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

InChI Identifier

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

InChI Key

KJPRLNWUNMBNBZ-QPJJXVBHSA-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
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 )

Ontology

Physiological effect

Health effect:

Health condition:

Eczema

Immune system disorders:

Allergy

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Organ and components:

Skin

Cell and elements:

Cell:

Nerve cell

Subcellular:

Biofluid and excreta:

Feces

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Asthma

Role

Industrial application:

Food and nutrition

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-7.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.42 mg/mL at 25 °C	Not Available
LogP	1.90	HANSCH,C ET AL. (1995)

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

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

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Feces

Tissue Locations

Epidermis
Neuron

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19167006	details

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

Cinnamaldehyde

METLIN ID

6931

PubChem Compound

637511

PDB ID

Not Available

ChEBI ID

16731

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

References

Synthesis Reference

Liu, Xue-mei. Synthesis of cinnamaldehyde. Qufu Shifan Daxue Xuebao, Ziran Kexueban (2005), 31(2), 96-98.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Muller G, Biering A, Graubaum K, Jeschkeit H, Neubert K, Kleine R, Klapperstuck M: [The PABA test]. Dtsch Z Verdau Stoffwechselkr. 1984;44(5):219-31. [PubMed:6334604 ]
Smith CK, Moore CA, Elahi EN, Smart AT, Hotchkiss SA: Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Toxicol Appl Pharmacol. 2000 Nov 1;168(3):189-99. [PubMed:11042091 ]
Bandell M, Story GM, Hwang SW, Viswanath V, Eid SR, Petrus MJ, Earley TJ, Patapoutian A: Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin. Neuron. 2004 Mar 25;41(6):849-57. [PubMed:15046718 ]
Smith CK, Cheung C, Elahi EN, Hotchkiss SA: High-performance liquid chromatography method for the quantification of non-radiolabelled cinnamic compounds in analytes derived from human skin absorption and metabolism experiments. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):249-64. [PubMed:11486835 ]
Bruze M, Johansen JD, Andersen KE, Frosch P, Lepoittevin JP, Rastogi S, Wakelin S, White I, Menne T: Deodorants: an experimental provocation study with cinnamic aldehyde. J Am Acad Dermatol. 2003 Feb;48(2):194-200. [PubMed:12582388 ]

Showing metabocard for Cinnamaldehyde (HMDB0003441)

Structure for HMDB0003441 (Cinnamaldehyde)