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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:10:18 UTC

Update Date

2023-02-21 17:28:44 UTC

HMDB ID

HMDB0041481

Secondary Accession Numbers

HMDB41481

Metabolite Identification

Common Name

4-(3,4-Methylenedioxyphenyl)-2-butanone

Description

4-(3,4-Methylenedioxyphenyl)-2-butanone 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. 4-(3,4-Methylenedioxyphenyl)-2-butanone is a sweet, candy, and cotton tasting compound. Based on a literature review very few articles have been published on 4-(3,4-Methylenedioxyphenyl)-2-butanone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061312422D          

 14 15  0  0  0  0            999 V2000
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11 10  2  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041481

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCC1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O3/c1-8(12)2-3-9-4-5-10-11(6-9)14-7-13-10/h4-6H,2-3,7H2,1H3

> <INCHI_KEY>
TZJLGGWGVLADDN-UHFFFAOYSA-N

> <FORMULA>
C11H12O3

> <MOLECULAR_WEIGHT>
192.2112

> <EXACT_MASS>
192.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.38030252431934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2H-1,3-benzodioxol-5-yl)butan-2-one

> <ALOGPS_LOGP>
1.59

> <JCHEM_LOGP>
2.0084217606666668

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.591524746909016

> <JCHEM_PKA_STRONGEST_BASIC>
-4.740143072065347

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
51.28460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piperonyl acetone

> <JCHEM_VEBER_RULE>
1

$$$$

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      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.121   2.310   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      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.455  -2.310   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    8                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    5    9                                                       
CONECT    5    4   10                                                       
CONECT    6    9   11                                                       
CONECT    7   13   14                                                       
CONECT    8    1    2   12                                                  
CONECT    9    3    4    6                                                  
CONECT   10    5   11   13                                                  
CONECT   11    6   10   14                                                  
CONECT   12    8                                                            
CONECT   13    7   10                                                       
CONECT   14    7   11                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0041481
HETATM    1  C1  UNL     1      -4.162   0.797  -0.094  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.463  -0.018   0.934  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.108  -0.476   1.862  1.00  0.00           O  
HETATM    4  C3  UNL     1      -2.014  -0.318   0.906  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.320   0.296  -0.283  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.119  -0.059  -0.221  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.560  -1.214  -0.832  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.890  -1.544  -0.776  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.824  -0.759  -0.123  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.392   0.401   0.492  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.051   0.722   0.428  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.527   0.971   1.053  1.00  0.00           O  
HETATM   13  C11 UNL     1       4.693   0.391   0.512  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.194  -0.876   0.069  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.336   1.848   0.280  1.00  0.00           H  
HETATM   16  H2  UNL     1      -5.134   0.337  -0.373  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.497   0.932  -0.989  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.579   0.127   1.825  1.00  0.00           H  
HETATM   19  H5  UNL     1      -1.798  -1.405   0.891  1.00  0.00           H  
HETATM   20  H6  UNL     1      -1.425   1.403  -0.297  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.718  -0.080  -1.247  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.138  -1.876  -1.364  1.00  0.00           H  
HETATM   23  H9  UNL     1       2.215  -2.470  -1.271  1.00  0.00           H  
HETATM   24  H10 UNL     1       0.733   1.621   0.908  1.00  0.00           H  
HETATM   25  H11 UNL     1       5.495   0.259   1.238  1.00  0.00           H  
HETATM   26  H12 UNL     1       5.000   0.990  -0.381  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5   18   19
CONECT    5    6   20   21
CONECT    6    7    7   11
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   14
CONECT   10   11   11   12
CONECT   11   24
CONECT   12   13
CONECT   13   14   25   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-METHYLENEDIOXYBENZYL acetone	HMDB
3,4-Methylenedioxybenzylacetone	HMDB
3,4-METHYLENEDIOXYBENZYLIDENE acetone	HMDB
4-(1,3-Benzodioxol-5-yl)-2-butanone	HMDB
4-(1,3-Benzodioxol-5-yl)butan-2-one	HMDB
4-(3,4-Methylenedioxyphenyl)-2-butanone, 9ci	HMDB
FEMA 2701	HMDB
Heliotropylacetone	HMDB
Piperonyl acetone	HMDB
Piperonylacetone	HMDB
Piperonylidene acetone	HMDB

Chemical Formula

C₁₁H₁₂O₃

Average Molecular Weight

192.2112

Monoisotopic Molecular Weight

192.07864425

IUPAC Name

4-(2H-1,3-benzodioxol-5-yl)butan-2-one

Traditional Name

piperonyl acetone

CAS Registry Number

55418-52-5

SMILES

CC(=O)CCC1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C11H12O3/c1-8(12)2-3-9-4-5-10-11(6-9)14-7-13-10/h4-6H,2-3,7H2,1H3

InChI Key

TZJLGGWGVLADDN-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
Ketone
Oxacycle
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

Physiological effect

Organoleptic effect

Taste

Sweet

Odor

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041481)
Cytoplasm (HMDB: HMDB0041481)

Source

Exogenous

Food

Food (HMDB: HMDB0041481)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041481)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	55 °C	Not Available
Boiling Point	176.00 °C. @ 17.00 mm Hg	The Good Scents Company Information System
Water Solubility	892.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.148	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.53 g/L	ALOGPS
logP	1.59	ALOGPS
logP	2.01	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
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	3	ChemAxon
Refractivity	51.28 m³·mol⁻¹	ChemAxon
Polarizability	20.38 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]+	145.355	31661259
DarkChem	[M-H]-	141.527	31661259
DeepCCS	[M+H]+	138.489	30932474
DeepCCS	[M-H]-	136.093	30932474
DeepCCS	[M-2H]-	171.418	30932474
DeepCCS	[M+Na]+	145.907	30932474
AllCCS	[M+H]+	141.4	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	145.4	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	144.7	32859911
AllCCS	[M+Na-2H]-	145.0	32859911
AllCCS	[M+HCOO]-	145.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(3,4-Methylenedioxyphenyl)-2-butanone	CC(=O)CCC1=CC2=C(OCO2)C=C1	2513.9	Standard polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone	CC(=O)CCC1=CC2=C(OCO2)C=C1	1554.3	Standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone	CC(=O)CCC1=CC2=C(OCO2)C=C1	1597.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #1	CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C	1780.1	Semi standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #1	CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C	1657.9	Standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #2	C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C	1723.2	Semi standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TMS,isomer #2	C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C	1672.8	Standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #1	CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C	2040.1	Semi standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #1	CC(=CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C	1891.8	Standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C	1972.8	Semi standard non polar	33892256
4-(3,4-Methylenedioxyphenyl)-2-butanone,1TBDMS,isomer #2	C=C(CCC1=CC=C2OCOC2=C1)O[Si](C)(C)C(C)(C)C	1886.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-4900000000-ac9b2fea1878e5144c7b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 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 - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Positive-QTOF	splash10-002f-0900000000-3525e495d33bc9c77b76	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Positive-QTOF	splash10-004l-1900000000-02446f80e5cc5ec58745	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Positive-QTOF	splash10-0ufr-6900000000-28a8fba4a202c974ba17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-40956cbf99ffbda4c174	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Negative-QTOF	splash10-0006-0900000000-60cdb8101c4256073c4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Negative-QTOF	splash10-00bc-2900000000-b7f00bb66442755efbe9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Negative-QTOF	splash10-0006-0900000000-3b8fc77e2c5dffca7765	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Negative-QTOF	splash10-0006-0900000000-2a48ae6e31f71b3aae8d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Negative-QTOF	splash10-00ng-5900000000-0167e286bc12b3d6421a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 10V, Positive-QTOF	splash10-002o-0900000000-2ea49a60ba6fb44bd91f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 20V, Positive-QTOF	splash10-002r-0900000000-1eb2b873735859ee5412	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-(3,4-Methylenedioxyphenyl)-2-butanone 40V, Positive-QTOF	splash10-004l-8900000000-00d9f819c51027719d2f	2021-09-24	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

FDB021444

KNApSAcK ID

Not Available

Chemspider ID

55934

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

62098

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1012851

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 4-(3,4-Methylenedioxyphenyl)-2-butanone (HMDB0041481)

MOL for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

3D MOL for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

3D SDF for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

3D-SDF for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

PDB for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

3D PDB for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

SMILES for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

INCHI for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

Structure for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

3D Structure for HMDB0041481 (4-(3,4-Methylenedioxyphenyl)-2-butanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra