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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:35:02 UTC

Update Date

2023-02-21 17:23:38 UTC

HMDB ID

HMDB0033813

Secondary Accession Numbers

HMDB33813

Metabolite Identification

Common Name

3-(3,4-Methylenedioxyphenyl)propenal

Description

3-(3,4-Methylenedioxyphenyl)propenal belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. 3-(3,4-Methylenedioxyphenyl)propenal has been detected, but not quantified in, several different foods, such as black tea, teas (Camellia sinensis), red tea, herbs and spices, and herbal tea. This could make 3-(3,4-methylenedioxyphenyl)propenal a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(3,4-Methylenedioxyphenyl)propenal.

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      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.788   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    8                                                       
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    1   11                                                       
CONECT    6    8   10                                                       
CONECT    7   12   13                                                       
CONECT    8    2    3    6                                                  
CONECT    9    4   10   12                                                  
CONECT   10    6    9   13                                                  
CONECT   11    5                                                            
CONECT   12    7    9                                                       
CONECT   13    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Methylenedioxycinnamaldehyde	HMDB
3,4-Methylenedioxycinnamaldehyde, 8ci	HMDB
3-(1,3-Benzodioxol-5-yl)-2-propenal, 9ci	HMDB
3-(1,3-Benzodioxol-5-yl)acrylaldehyde	HMDB
3-(3,4-Methylenedioxyphenyl)acrolein	HMDB
Piperonylacrolein	HMDB
Piperonylideneacetaldehyde	HMDB

Chemical Formula

C₁₀H₈O₃

Average Molecular Weight

176.1687

Monoisotopic Molecular Weight

176.047344122

IUPAC Name

(2Z)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enal

Traditional Name

(2Z)-3-(2H-1,3-benzodioxol-5-yl)prop-2-enal

CAS Registry Number

14756-00-4

SMILES

O=C\C=C/C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C10H8O3/c11-5-1-2-8-3-4-9-10(6-8)13-7-12-9/h1-6H,7H2/b2-1-

InChI Key

HZUFMSJUNLSDSZ-UPHRSURJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Styrene
Benzenoid
Enal
Alpha,beta-unsaturated aldehyde
Oxacycle
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033813)
Cytoplasm (HMDB: HMDB0033813)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033813)

Source

Exogenous

Exogenous (HMDB: HMDB0033813)

Food

Food (HMDB: HMDB0033813)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0033813)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033813)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	84 - 85 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1425 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.48 g/L	ALOGPS
logP	1.79	ALOGPS
logP	1.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.9 m³·mol⁻¹	ChemAxon
Polarizability	17.66 Å³	ChemAxon
Number of Rings	2	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]+	142.497	31661259
DarkChem	[M-H]-	137.782	31661259
DeepCCS	[M+H]+	137.659	30932474
DeepCCS	[M-H]-	135.263	30932474
DeepCCS	[M-2H]-	170.657	30932474
DeepCCS	[M+Na]+	145.116	30932474
AllCCS	[M+H]+	137.0	32859911
AllCCS	[M+H-H2O]+	132.5	32859911
AllCCS	[M+NH4]+	141.1	32859911
AllCCS	[M+Na]+	142.3	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	138.0	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.	5.45 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5943 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1867.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	416.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	261.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	507.3 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	569.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	189.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1166.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	391.1 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	1274.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	353.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	517.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	443.2 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	56.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(3,4-Methylenedioxyphenyl)propenal	O=C\C=C/C1=CC2=C(OCO2)C=C1	2578.7	Standard polar	33892256
3-(3,4-Methylenedioxyphenyl)propenal	O=C\C=C/C1=CC2=C(OCO2)C=C1	1483.5	Standard non polar	33892256
3-(3,4-Methylenedioxyphenyl)propenal	O=C\C=C/C1=CC2=C(OCO2)C=C1	1610.9	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-(3,4-Methylenedioxyphenyl)propenal GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1900000000-66f2647243c75d4dde1b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3,4-Methylenedioxyphenyl)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-(3,4-Methylenedioxyphenyl)propenal 10V, Positive-QTOF	splash10-004i-0900000000-9b66b1c2ef5b09ef6f87	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Positive-QTOF	splash10-004i-1900000000-75427a933490a5c63826	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Positive-QTOF	splash10-0pba-7900000000-24513de0b932e7ee1c44	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 10V, Negative-QTOF	splash10-004i-0900000000-ce45ddf94696c7737e49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Negative-QTOF	splash10-004i-0900000000-52f8e4472ba209a44059	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Negative-QTOF	splash10-004j-2900000000-77fbed4965ba80679c47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 10V, Positive-QTOF	splash10-004i-0900000000-d0bb884df17a68411daa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Positive-QTOF	splash10-004i-0900000000-2b0cfa5a186f594dc39b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Positive-QTOF	splash10-004i-5900000000-68ff198bbdba3c500093	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 10V, Negative-QTOF	splash10-004i-0900000000-4a803894b4fd0ab0e5a4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 20V, Negative-QTOF	splash10-0002-0900000000-eafab4756929a1d839fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3,4-Methylenedioxyphenyl)propenal 40V, Negative-QTOF	splash10-014j-3900000000-a5027aca8830808e8b6d	2021-09-23	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

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

FDB011976

KNApSAcK ID

C00034385

Chemspider ID

4511077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5355018

PDB ID

Not Available

ChEBI ID

173812

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1390361

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-(3,4-Methylenedioxyphenyl)propenal (HMDB0033813)

MOL for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

3D MOL for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

3D SDF for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

3D-SDF for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

PDB for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

3D PDB for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

SMILES for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

INCHI for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

Structure for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

3D Structure for HMDB0033813 (3-(3,4-Methylenedioxyphenyl)propenal)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra