ContaminantDB: Piperonyl butoxide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (19)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:44 UTC

Update Date

2016-11-09 01:09:09 UTC

Accession Number

CHEM003484

Identification

Common Name

Piperonyl butoxide

Class

Small Molecule

Description

Piperonyl butoxide (PBO) is an organic compound used as a component of pesticide formulations. It is a waxy white solid. It is a synergist. That is, despite having no pesticidal activity of its own, it enhances the potency of certain pesticides such as especially for carbamates, pyrethrins, pyrethroids, and rotenone. It is a semisynthetic derivative of safrole.

Contaminant Sources

Clean Air Act Chemicals
EPA Endocrine Screening
HPV EPA Chemicals
IARC Carcinogens Group 3
My Exposome Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ether
Household Toxin
Organic Compound
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3,4-Methylenedioxy-6-propylbenzyl) (butyl) diethylene glycol ether	ChEBI
(Butylcarbityl)(6-propylpiperonyl)ether	ChEBI
2-(2-Butoxyethoxy)ethyl 6-propylpiperonyl ether	ChEBI
5-Propyl-4-(2,5,8-trioxa-dodecyl)-1,3-benzodioxole	ChEBI
6-Propylpiperonyl butyl diethylene glycol ether	ChEBI
alpha-(2-(2-N-Butoxyethoxy)-ethoxy)-4,5-methylenedioxy-2-propyltoluene	ChEBI
alpha-[2-(2-Butoxyethoxy)ethoxy]-4,5-(methylenedioxy)-2-propyltoluene	ChEBI
Butyl carbitol 6-propylpiperonyl ether	ChEBI
Para pio	Kegg
Rid mousse	Kegg
a-(2-(2-N-Butoxyethoxy)-ethoxy)-4,5-methylenedioxy-2-propyltoluene	Generator
Α-(2-(2-N-butoxyethoxy)-ethoxy)-4,5-methylenedioxy-2-propyltoluene	Generator
a-[2-(2-Butoxyethoxy)ethoxy]-4,5-(methylenedioxy)-2-propyltoluene	Generator
Α-[2-(2-butoxyethoxy)ethoxy]-4,5-(methylenedioxy)-2-propyltoluene	Generator
Butoxide, piperonyl	MeSH

Chemical Formula

C₁₉H₃₀O₅

Average Molecular Mass

338.439 g/mol

Monoisotopic Mass

338.209 g/mol

CAS Registry Number

51-03-6

IUPAC Name

5-{[2-(2-butoxyethoxy)ethoxy]methyl}-6-propyl-2H-1,3-benzodioxole

Traditional Name

piperonyl butoxide

SMILES

CCCCOCCOCCOCC1=CC2=C(OCO2)C=C1CCC

InChI Identifier

InChI=1S/C19H30O5/c1-3-5-7-20-8-9-21-10-11-22-14-17-13-19-18(23-15-24-19)12-16(17)6-4-2/h12-13H,3-11,14-15H2,1-2H3

InChI Key

FIPWRIJSWJWJAI-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
Oxacycle
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:32687 )
Synergist (C18880 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cell surface
Cytosol
Endoplasmic reticulum
Extracellular
Membrane
Microsome
Microtubule
Mitochondrial Membrane
Mitochondrion
Plasma Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Cell cycle	Not Available	map04110
Anticonvulsants	Not Available	Not Available
Apoptosis	Not Available	map04210
Metabolic Pathways	Not Available	Not Available

Applications

pesticide synergist

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	180°C (0.13 kPa)
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0061 g/L	ALOGPS
logP	3.07	ALOGPS
logP	4.1	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	46.15 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	93.6 m³·mol⁻¹	ChemAxon
Polarizability	40.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-004i-0900000000-83a568261ed03ec9a2ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-004i-0090000000-7f8c0c60f00b77cf3fb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 28V, positive	splash10-004i-0090000000-a6b6459c8dfb544e77ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-03di-0900000000-ef2b2f7b7a6f98cb2e33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative	splash10-03e9-0900000000-e11e12fcf6e8688cb65f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-001i-0900000000-fd66d18958b4e959166a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 26V, negative	splash10-0bt9-9400000000-d77c812ecba12a04a592	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-03e9-0900000000-e11e12fcf6e8688cb65f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-ef2b2f7b7a6f98cb2e33	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0090000000-7f8c0c60f00b77cf3fb7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-83a568261ed03ec9a2ee	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-000i-0009000000-a8b8ed9c0d32ae5fc67d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0900000000-fd66d18958b4e959166a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-0109000000-1a8b29cb1a5b44dc668d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00n0-0902000000-9eb3ea566e2af2d8f02e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-00bl-1900000000-c75b103603964ff92d16	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-004u-1900000000-8ddf1c337724ccbd2e8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-004i-1900000000-21a606b5cf7421bf55b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-2619000000-000e675745b2a31606dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9722000000-2cb812d5895c28068389	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9710000000-313b68d43467f69fe0f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-2339000000-9f3d34c953c6df5d8e4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-8797000000-527927977cf352299b16	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06xx-7920000000-a2edfe60bbf2682d413f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-edf43c4a8ef3e628b1f3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09350

HMDB ID

HMDB0256579

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00056079

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Piperonyl_Butoxide

Chemspider ID

5590

ChEBI ID

32687

PubChem Compound ID

Not Available

Kegg Compound ID

C18880

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Piperonyl butoxide (CHEM003484)

Structure for CHEM003484: Piperonyl butoxide