Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:47 UTC

Update Date

2023-02-21 17:22:29 UTC

HMDB ID

HMDB0032614

Secondary Accession Numbers

HMDB32614

Metabolite Identification

Common Name

Piperonyl acetate

Description

Piperonyl acetate 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. Piperonyl acetate is a sweet, bitter, and floral tasting compound. Piperonyl acetate has been detected, but not quantified in, green vegetables. This could make piperonyl acetate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Piperonyl acetate.

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      12.789   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.455  -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      11.455  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.122   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    8   10                                                       
CONECT    5    8   12                                                       
CONECT    6   13   14                                                       
CONECT    7    1   11   12                                                  
CONECT    8    2    4    5                                                  
CONECT    9    3   10   13                                                  
CONECT   10    4    9   14                                                  
CONECT   11    7                                                            
CONECT   12    5    7                                                       
CONECT   13    6    9                                                       
CONECT   14    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Piperonyl acetic acid	Generator
(3,4-Methylenedioxy)benzyl acetate	HMDB
1,3-Benzodioxol, 5-(acetoxymethyl)	HMDB
1,3-Benzodioxol-5-ylmethyl acetate	HMDB
1,3-Benzodioxole-5-methanol, 5-acetate	HMDB
1,3-Benzodioxole-5-methanol, acetate	HMDB
3,4-Methylenedioxybenzyl acetate	HMDB
Acetic acid, (3, 4-methylenedioxy)benzyl ester	HMDB
Acetic acid, (3,4-methylenedioxy)benzyl ester	HMDB
FEMA 2912	HMDB
Heliotropin acetate	HMDB
Heliotropyl acetate	HMDB
Methyl 1,3-benzodioxol-5-ylacetate	HMDB
Piperonal acetate	HMDB
Piperonyl alcohol, acetate	HMDB
Piperonyl alcohol, acetate (6ci,7ci,8ci)	HMDB
Piperonylacetate	HMDB
(2H-1,3-Benzodioxol-5-yl)methyl acetic acid	Generator
1,3-Benzodioxole-5-methanol acetate	MeSH
Piperonyl acetate	MeSH

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

IUPAC Name

2H-1,3-benzodioxol-5-ylmethyl acetate

Traditional Name

piperonyl acetate

CAS Registry Number

326-61-4

SMILES

CC(=O)OCC1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C10H10O4/c1-7(11)12-5-8-2-3-9-10(4-8)14-6-13-9/h2-4H,5-6H2,1H3

InChI Key

PFWYHTORQZAGCA-UHFFFAOYSA-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
Benzenoid
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032614)
Cytoplasm (HMDB: HMDB0032614)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032614)

Source

Endogenous

Endogenous (HMDB: HMDB0032614)

Plant

Plant (HMDB: HMDB0032614)

Exogenous

Food

Food (HMDB: HMDB0032614)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Industrial application

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0032614)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	51 °C	Not Available
Boiling Point	150.00 to 151.00 °C. @ 10.00 mm Hg	The Good Scents Company Information System
Water Solubility	0 slightly	The Good Scents Company Information System
LogP	1.938 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.17 g/L	ALOGPS
logP	1.4	ALOGPS
logP	1.27	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.79 m³·mol⁻¹	ChemAxon
Polarizability	19.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.407	31661259
DarkChem	[M-H]-	140.872	31661259
DeepCCS	[M+H]+	136.669	30932474
DeepCCS	[M-H]-	134.273	30932474
DeepCCS	[M-2H]-	169.574	30932474
DeepCCS	[M+Na]+	144.033	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.6	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.9	32859911
AllCCS	[M-H]-	142.8	32859911
AllCCS	[M+Na-2H]-	143.1	32859911
AllCCS	[M+HCOO]-	143.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piperonyl acetate	CC(=O)OCC1=CC2=C(OCO2)C=C1	2446.9	Standard polar	33892256
Piperonyl acetate	CC(=O)OCC1=CC2=C(OCO2)C=C1	1513.7	Standard non polar	33892256
Piperonyl acetate	CC(=O)OCC1=CC2=C(OCO2)C=C1	1586.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Piperonyl acetate EI-B (Non-derivatized)	splash10-0f76-4900000000-92da8e820031602709c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Piperonyl acetate EI-B (Non-derivatized)	splash10-0f76-4900000000-92da8e820031602709c7	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperonyl acetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-4900000000-e40b664e869f3f27ae75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piperonyl acetate 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 - Piperonyl acetate 10V, Positive-QTOF	splash10-0002-0900000000-fae17415db827f864dab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 20V, Positive-QTOF	splash10-0002-0900000000-466494e8eb86c24650dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 40V, Positive-QTOF	splash10-0006-9800000000-ba12bb6a6e41a820a746	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 10V, Negative-QTOF	splash10-0006-2900000000-4620fb177da88172db65	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 20V, Negative-QTOF	splash10-0006-2900000000-540e08888772c4194626	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 40V, Negative-QTOF	splash10-0006-9500000000-0280106f7a7edf9f86d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 10V, Positive-QTOF	splash10-000i-0900000000-4aa46a9717b95d9ed721	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 20V, Positive-QTOF	splash10-000i-0900000000-44a492319107ab04e6ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 40V, Positive-QTOF	splash10-0006-9600000000-694e5b64c4e6746504ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 10V, Negative-QTOF	splash10-0udi-0900000000-1750905022a298264c01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 20V, Negative-QTOF	splash10-0fk9-0900000000-f2187ed17caab45933a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piperonyl acetate 40V, Negative-QTOF	splash10-00di-5900000000-af92226ec7c8bc1af18d	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

FDB010555

KNApSAcK ID

C00057346

Chemspider ID

9101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9473

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020671

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 Piperonyl acetate (HMDB0032614)

MOL for HMDB0032614 (Piperonyl acetate)

3D MOL for HMDB0032614 (Piperonyl acetate)

3D SDF for HMDB0032614 (Piperonyl acetate)

3D-SDF for HMDB0032614 (Piperonyl acetate)

PDB for HMDB0032614 (Piperonyl acetate)

3D PDB for HMDB0032614 (Piperonyl acetate)

SMILES for HMDB0032614 (Piperonyl acetate)

INCHI for HMDB0032614 (Piperonyl acetate)

Structure for HMDB0032614 (Piperonyl acetate)

3D Structure for HMDB0032614 (Piperonyl acetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra