T3DB: Monoisobutyl phthalic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (4)XML

Targets (4)

Record Information

Version

2.0

Creation Date

2014-08-29 04:47:20 UTC

Update Date

2014-12-24 20:26:35 UTC

Accession Number

T3D3960

Identification

Common Name

Monoisobutyl phthalic acid

Class

Small Molecule

Description

Monoisobutyl phthalic acid is a phthalate metabolite that has been found in human meconium and in semen , saliva , and urine Phthalate esters are a family of multifunctional compounds widely used as plasticizers, solvents, or additives in many diverse products such as poly(vinyl chloride) (PVC) materials, pharmaceuticals and medical devices, pesticides, lubricants, and personal care products. Humans have been exposed to phthalates through the manufacture, ubiquitous use, and disposal of PVC materials and other phthalate-containing products. (1, 2, 3, 1).

Compound Type

Animal Toxin
Ester
Ether
Food Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Pesticide
Plasticizer
Solvent

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym
Isobutyl hydrogen phthalate
MIBP
Mono-iso-butyl phthalate
Monoisobutyl phthalate

Chemical Formula

C₁₂H₁₄O₄

Average Molecular Mass

222.237 g/mol

Monoisotopic Mass

222.089 g/mol

CAS Registry Number

30833-53-5

IUPAC Name

2-[(2-methylpropoxy)carbonyl]benzoic acid

Traditional Name

MIBP

SMILES

CC(C)COC(=O)C1=CC=CC=C1C(O)=O

InChI Identifier

InChI=1S/C12H14O4/c1-8(2)7-16-12(15)10-6-4-3-5-9(10)11(13)14/h3-6,8H,7H2,1-2H3,(H,13,14)

InChI Key

InChIKey=RZJSUWQGFCHNFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoic acid
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

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	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.88	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.08 m³·mol⁻¹	ChemAxon
Polarizability	22.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4910000000-ac2484b74eb5cfd5b690	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-6390000000-4ca9de5bf766a991b3dc	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0089-0930000000-d249a5cd21193a8a3cd2	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-13d64e3eb0a1e3e235be	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0089-0930000000-3a306e5ce6ca6a0e9127	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-0900000000-b4a2e5d94dccaced84c1	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-6690000000-8f32418bd6ccde0549c0	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9720000000-286cdd7561a043eef3d0	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9500000000-6c3aca6817c2db6bb804	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1790000000-2d20ca2ec96d84986321	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0100-2910000000-46c6c191f37b2782021a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-6900000000-0d9a0ca1ebdbc964dac0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4j-0940000000-827565da796a34bbd6b1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-1900000000-bfe543859b406a2dae92	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-8cb1cf43ad6057fc27c8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0930000000-2a9d225bebcec6f94629	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-6910000000-2ae4c65b2cf89d2dde5a	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-c321d909ae49bc32f15a	2021-09-25	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Phthalates are synthetic industrial compounds capable of disrupting the endocrine system. The phthalates have been the most common chemical compounds with the ability to disrupt the endocrine system. Phthalates, when acting in a critical period of the development of genital tract, lead to disturbances in the androgen-signaling pathway. Fetal testicular dysgenesis syndrome, otherwise known as the ”phthalate syndrome” in rodents, is a consequence of reduced level of fetal testosterone, insulin-like growth factor-3 (IGF-3) and follicule stimulating hormone (FSH). A negative correlation between levels in breast milk and free testosterone of babies was observed, while there was a positive correlation between mono-ethyl phthalate (MEP) and mono-butyl (MBP) with sex hormone bingind globuline (SHBG) and mono-metyl phthalate (MMP) and MEP and MBP with the ratio of lutenzing hormone (LH) and free testosterone. Exposure to phthalates is significantly associated with the duration of pregnancy. According to some studies, the chemical structure of some phthalates and prostaglandin/thromboxane, interleukin-1 connects the phthalates with induction of intrauterine inflammatory processes as well as shortening of pregnancy. (4)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is a natural compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB02056

PubChem Compound ID

92272

ChEMBL ID

Not Available

ChemSpider ID

83306

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Ke, Changying. Esterification synthesis of diisobutyl phthalate. Huaxue Shijie (1986), 27(10), 440-2.

MSDS

Not Available

General References

Kato K, Silva MJ, Needham LL, Calafat AM: Quantifying phthalate metabolites in human meconium and semen using automated off-line solid-phase extraction coupled with on-line SPE and isotope-dilution high-performance liquid chromatography--tandem mass spectrometry. Anal Chem. 2006 Sep 15;78(18):6651-5. [16970347 ]
Silva MJ, Reidy JA, Samandar E, Herbert AR, Needham LL, Calafat AM: Detection of phthalate metabolites in human saliva. Arch Toxicol. 2005 Nov;79(11):647-52. Epub 2005 Jul 2. [15995852 ]
Silva MJ, Slakman AR, Reidy JA, Preau JL Jr, Herbert AR, Samandar E, Needham LL, Calafat AM: Analysis of human urine for fifteen phthalate metabolites using automated solid-phase extraction. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Jun 5;805(1):161-7. [15113553 ]
Bajkin I, Bjelica A, Icin T, Dobric V, Zavisic BK, Stojanoska MM: Effects of phthalic acid esters on fetal health. Med Pregl. 2014 May-Jun;67(5-6):172-5. [25033577 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Androgen receptor

General Function:: Zinc ion binding
Specific Function:: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:: AR
Uniprot ID:: P10275
Molecular Weight:: 98987.9 Da

Target Details

2. Insulin-like growth factor-binding protein 3

General Function:: Protein tyrosine phosphatase activator activity
Specific Function:: IGF-binding proteins prolong the half-life of the IGFs and have been shown to either inhibit or stimulate the growth promoting effects of the IGFs on cell culture. They alter the interaction of IGFs with their cell surface receptors. Also exhibits IGF-independent antiproliferative and apoptotic effects mediated by its receptor TMEM219/IGFBP-3R.
Gene Name:: IGFBP3
Uniprot ID:: P17936
Molecular Weight:: 31673.87 Da

Target Details

3. Interleukin-1 alpha

General Function:: Cytokine activity
Specific Function:: Produced by activated macrophages, IL-1 stimulates thymocyte proliferation by inducing IL-2 release, B-cell maturation and proliferation, and fibroblast growth factor activity. IL-1 proteins are involved in the inflammatory response, being identified as endogenous pyrogens, and are reported to stimulate the release of prostaglandin and collagenase from synovial cells.
Gene Name:: IL1A
Uniprot ID:: P01583
Molecular Weight:: 30606.29 Da

Target Details

4. Interleukin-1 beta

General Function:: Protein domain specific binding
Specific Function:: Potent proinflammatory cytokine. Initially discovered as the major endogenous pyrogen, induces prostaglandin synthesis, neutrophil influx and activation, T-cell activation and cytokine production, B-cell activation and antibody production, and fibroblast proliferation and collagen production. Promotes Th17 differentiation of T-cells.
Gene Name:: IL1B
Uniprot ID:: P01584
Molecular Weight:: 30747.7 Da

Monoisobutyl phthalic acid (T3D3960)

Structure for T3D3960: Monoisobutyl phthalic acid

Targets