Piperonal (YMDB01776)

Identification

YMDB ID

YMDB01776

Name

Piperonal

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

3,4-Methylenedioxybenzaldehyde, also known as heliotropin or piperonyl aldehyde, 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. Based on a literature review a significant number of articles have been published on 3,4-Methylenedioxybenzaldehyde.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1,3-Benzodioxole-5-carbaldehyde
1,3-Benzodioxole-5-carboxaldehyde
3, 4-(Methylenedioxy)benzaldehyde
3, 4-Bis(methylenedioxy)benzaldehyde
3,4-(Methylenedioxy)benzaldehyde
3,4-Bis(methylenedioxy)benzaldehyde
3,4-Dihydroxybenzaldehyde methylene ketal
3,4-Methylene-dihydroxybenzaldehyde
3,4-methylenedioxybenzaldehyde
5-Formyl-1,3-benzodioxole
Benzaldehyde, 3,4-(methylenedioxy)-
Blue P
Dioxymethylene-protocatechuic aldehyde
Geliotropin
Heliotropin
Heliotropine
Heliotropine (Piperonal)
Piperanal
Piperonal
Piperonaldehyde
piperonyl aldehyde
Piperonylaldehyde
Protocatechuic aldehyde methylene ether
1,3-Benzodioxole-5-carboxaldehyde, 9ci
3,4-(Methylenedioxy)-benzaldehyde
3,4-Dimethylenedioxybenzaldehyde
3,4-METHYLEN-dioxy-benzaldehyde
Dioxymethylene protocatechuic aldehyde
FEMA 2911
Piperonal, 8ci
Heliotrin

CAS number

120-57-0

Weight

Average: 150.1314
Monoisotopic: 150.031694058

InChI Key

SATCULPHIDQDRE-UHFFFAOYSA-N

InChI

InChI=1S/C8H6O3/c9-4-6-1-2-7-8(3-6)11-5-10-7/h1-4H,5H2

IUPAC Name

2H-1,3-benzodioxole-5-carbaldehyde

Traditional IUPAC Name

piperonal

Chemical Formula

C₈H₆O₃

SMILES

O=CC1=CC2=C(OCO2)C=C1

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
Aryl-aldehyde
Benzenoid
Oxacycle
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:8240 )
arenecarbaldehyde (CHEBI:8240 )

Physical Properties

State

Solid

Charge

Melting point

37 °C

Experimental Properties

Property	Value	Reference
Water Solubility	3.5 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	1.05 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	8.28 g/L	ALOGPS
logP	0.79	ALOGPS
logP	1.31	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-4.7	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	1	ChemAxon
Refractivity	38.41 m³·mol⁻¹	ChemAxon
Polarizability	14.25 Å³	ChemAxon
Number of Rings	2	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
Bitter	FDB010553
Coconut	FDB010553
Flower	FDB010553
Heliotrope	FDB010553
Powdery	FDB010553
Sweet	FDB010553
Vanilla	FDB010553
Violet	FDB010553

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 - EI-B (Non-derivatized)	splash10-0f6t-5900000000-deaf6988b3684d4c20e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udj-0900000000-b5bce0817d3b7da073b5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udj-2900000000-dd3223a5400ccb92654c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6t-5900000000-f62030c087954cb17793	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gvk-5900000000-8a0279ec82445d96e75a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6t-5900000000-deaf6988b3684d4c20e3	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-0udj-0900000000-b5bce0817d3b7da073b5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udj-2900000000-dd3223a5400ccb92654c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f6t-5900000000-f62030c087954cb17793	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gvk-5900000000-8a0279ec82445d96e75a	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-5900000000-18459b3a00c1178d35a1	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0udi-0900000000-b5b6834400d9d6682544	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0udi-0900000000-84dd85011e2ee53f2419	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-1900000000-62ac1d8f95baaaa86cdc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0udi-2900000000-845d915e801880fe515e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0ukc-4900000000-a2da771088f9bd903b28	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0fdo-7900000000-6d6138acd0b07ffaf80f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0006-9600000000-50b7e072efe444eab046	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-0006-9400000000-a00479fe5850665b281a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00kf-9100000000-d767f739422c110699e1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-014i-9000000000-2c58ea01cf6deb1fd0cb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-014i-9000000000-e1b8a3928f36d4c767f0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-014i-9000000000-9a1a6e1587039d548c14	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014i-9000000000-8cba8d9c4f8d5695ce7f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-00di-1900000000-54afeb3dfd71c9fcd607	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-014i-9000000000-02653bad35d931248654	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004i-9000000000-791c4364189bf936d4c3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0006-9000000000-e67da0571423f0e6b4b8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-1900000000-94cc28f3d5f593c40e43	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-00di-1900000000-64a29a0890bb37965f42	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-e5e34bc7a3df137e69de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-7dea1b5613bf810c5aa5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0l90-7900000000-0505f5c9e1fbdc94057b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-b0c81ffa7cb223383909	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-7ff4ed41bbe2ad283eda	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-9700000000-abb6ae8bee74f8c6ae31	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

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	8240
HMDB ID	HMDB0032612
Pubchem Compound ID	8438
Kegg ID	C10812
ChemSpider ID	13859497
FOODB ID	FDB010553
Wikipedia ID	Piperonal
BioCyc ID	Not Available

Structure for #<Compound:0xa90e9274>