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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2009-11-30 15:51:40 UTC
Update Date2019-01-11 19:32:16 UTC
HMDB IDHMDB0013248
Secondary Accession Numbers
  • HMDB13248
Metabolite Identification
Common NameMonoethylhexyl phthalic acid
DescriptionMonoethylhexyl phthalic acid (MEHP) is an active metabolite of Bis(2-ethylhexyl)phthalate (DEHP). DEHP measured from the blood of pregnant women have been significantly associated with the decreased penis width, shorter anogenital distance, and the incomplete descent of testes of their newborn sons, replicating effects identified in animals(Wikipedia). DEHP hydrolyzes to MEHP via the enzyme Bis(2-ethylhexyl)phthalate acylhydrolase(3.1.1.60)and subsequently to phthalate salts. The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid.
Structure
Data?1547235136
Synonyms
ValueSource
(2-Ethylhexyl) hydrogen phthalateChEBI
1,2-Benzenedicarboxylic acid, mono(2-ethylhexyl) esterChEBI
2-([(2-Ethylhexyl)oxy]carbonyl)benzoic acidChEBI
2-Ethylhexyl hydrogen phthalateChEBI
2-Ethylhexyl phthalateChEBI
MEHPChEBI
mono(2-Ethylhexyl)phthalateChEBI
mono-(2-Ethylhexyl)phthalateChEBI
mono-2-Ethylhexyl phthalateChEBI
Monoethylhexyl phthalateChEBI
Phthalic acid, 2-ethylhexyl esterChEBI
(2-Ethylhexyl) hydrogen phthalic acidGenerator
1,2-Benzenedicarboxylate, mono(2-ethylhexyl) esterGenerator
2-([(2-Ethylhexyl)oxy]carbonyl)benzoateGenerator
2-Ethylhexyl hydrogen phthalic acidGenerator
2-Ethylhexyl phthalic acidGenerator
mono(2-Ethylhexyl)phthalic acidGenerator
mono-(2-Ethylhexyl)phthalic acidGenerator
mono-2-Ethylhexyl phthalic acidGenerator
Phthalate, 2-ethylhexyl esterGenerator
1,2-Benzenedicarboxylicacid,mono(2-ethylhexyl)esterHMDB
mono-EthylhexylHMDB
mono-EthylhexylphthalateHMDB
Monoethylhexyl phthalate (mehp)HMDB
MonoethylhexylphthalateHMDB
MONOOCTYL phthalATEHMDB
Phthalic acid 1-hydrogen 2-(2-ethylhexyl) esterHMDB
Phthalic acid hydrogen 1-(2-ethylhexyl) esterHMDB
PHTHALIC ACID mono-2-ethylhexyl esterHMDB
PHTHALIC ACID monooctyl esterHMDB
Phthalicacid,2-ethylhexylesterHMDB
phthalicacidmono-2-ETHYLEXYLESTERHMDB
PHTHALICACIDMONOETHYLHEXYLHMDB
PhthalicacidmonoethylhexylesterHMDB
mono-(2-Ethylhexyl)phthalate, sodium saltMeSH
Chemical FormulaC16H22O4
Average Molecular Weight278.3435
Monoisotopic Molecular Weight278.151809192
IUPAC Name2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid
Traditional Namebar 1
CAS Registry Number4376-20-9
SMILES
CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C16H22O4/c1-3-5-8-12(4-2)11-20-16(19)14-10-7-6-9-13(14)15(17)18/h6-7,9-10,12H,3-5,8,11H2,1-2H3,(H,17,18)
InChI KeyDJDSLBVSSOQSLW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP4.36ALOGPS
logP4.66ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity77.49 m³·mol⁻¹ChemAxon
Polarizability30.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-2970000000-346112e2dd7eb2ef672fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00dj-2970000000-346112e2dd7eb2ef672fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-5920000000-6756fbba86aadca647ceJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7392000000-fd40ccd8c52320562e5cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fr-0790000000-972234c38f1e6baf9909JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4930000000-1ab987bce4973d4f07f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9500000000-53028683cce560c7a65bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0490000000-44a004dad8099c4e00deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00w9-1940000000-8169435369a241584a63JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-6900000000-56a7cc157be52d6494f3JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0002-4900000000-af0f2c76a7c01b845a00JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.00109 (0.000971-0.00123) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
details
UrineDetected and Quantified0.000865 (0.000772-0.000975) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF details
Associated Disorders and Diseases
Disease References
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029358
KNApSAcK IDNot Available
Chemspider ID19208
KEGG Compound IDC03343
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20393
PDB IDNot Available
ChEBI ID17243
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hasmall S, Orphanides G, James N, Pennie W, Hedley K, Soames A, Kimber I, Roberts R: Downregulation of lactoferrin by PPARalpha ligands: role in perturbation of hepatocyte proliferation and apoptosis. Toxicol Sci. 2002 Aug;68(2):304-13. [PubMed:12151626 ]
  2. Hasmall SC, James NH, Macdonald N, West D, Chevalier S, Cosulich SC, Roberts RA: Suppression of apoptosis and induction of DNA synthesis in vitro by the phthalate plasticizers monoethylhexylphthalate (MEHP) and diisononylphthalate (DINP): a comparison of rat and human hepatocytes in vitro. Arch Toxicol. 1999 Nov;73(8-9):451-6. [PubMed:10650916 ]
  3. Anderson WA, Barnes KA, Castle L, Damant AP, Scotter MJ: Determination of isotopically labelled monoesterphthalates in urine by high performance liquid chromatography-mass spectrometry. Analyst. 2002 Sep;127(9):1193-7. [PubMed:12375842 ]
  4. Marttinen SK, Kettunen RH, Sormunen KM, Rintala JA: Removal of bis(2-ethylhexyl) phthalate at a sewage treatment plant. Water Res. 2003 Mar;37(6):1385-93. [PubMed:12598201 ]
  5. Quintana JB, Rodil R, Reemtsma T: Determination of phosphoric acid mono- and diesters in municipal wastewater by solid-phase extraction and ion-pair liquid chromatography-tandem mass spectrometry. Anal Chem. 2006 Mar 1;78(5):1644-50. [PubMed:16503618 ]
  6. Luisi S, Latini G, de Felice C, Sanseverino F, di Pasquale D, Mazzeo P, Petraglia F: Low serum concentrations of di-(2-ethylhexyl)phthalate in women with uterine fibromatosis. Gynecol Endocrinol. 2006 Feb;22(2):92-5. [PubMed:16603434 ]
  7. Howdeshell KL, Furr J, Lambright CR, Rider CV, Wilson VS, Gray LE Jr: Cumulative effects of dibutyl phthalate and diethylhexyl phthalate on male rat reproductive tract development: altered fetal steroid hormones and genes. Toxicol Sci. 2007 Sep;99(1):190-202. Epub 2007 Mar 30. [PubMed:17400582 ]
  8. Lovekamp-Swan T, Davis BJ: Mechanisms of phthalate ester toxicity in the female reproductive system. Environ Health Perspect. 2003 Feb;111(2):139-45. [PubMed:12573895 ]
  9. Kambia K, Dine T, Gressier B, Dupin-Spriet T, Luyckx M, Brunet C: Evaluation of the direct toxicity of trioctyltrimellitate (TOTM), di(2-ethylhexyl) phthalate (DEHP) and their hydrolysis products on isolated rat hepatocytes. Int J Artif Organs. 2004 Nov;27(11):971-8. [PubMed:15636055 ]
  10. Rosado-Berrios CA, Velez C, Zayas B: Mitochondrial permeability and toxicity of diethylhexyl and monoethylhexyl phthalates on TK6 human lymphoblasts cells. Toxicol In Vitro. 2011 Dec;25(8):2010-6. doi: 10.1016/j.tiv.2011.08.001. Epub 2011 Aug 16. [PubMed:21864672 ]
  11. Rokos CL, Ledwith BJ: Peroxisome proliferators activate extracellular signal-regulated kinases in immortalized mouse liver cells. J Biol Chem. 1997 May 16;272(20):13452-7. [PubMed:9148971 ]
  12. Forgacs AL, Ding Q, Jaremba RG, Huhtaniemi IT, Rahman NA, Zacharewski TR: BLTK1 murine Leydig cells: a novel steroidogenic model for evaluating the effects of reproductive and developmental toxicants. Toxicol Sci. 2012 Jun;127(2):391-402. doi: 10.1093/toxsci/kfs121. Epub 2012 Mar 29. [PubMed:22461451 ]
  13. Janer G, Verhoef A, Gilsing HD, Piersma AH: Use of the rat postimplantation embryo culture to assess the embryotoxic potency within a chemical category and to identify toxic metabolites. Toxicol In Vitro. 2008 Oct;22(7):1797-805. doi: 10.1016/j.tiv.2008.07.007. Epub 2008 Jul 15. [PubMed:18675337 ]
  14. Theunissen PT, Robinson JF, Pennings JL, van Herwijnen MH, Kleinjans JC, Piersma AH: Compound-specific effects of diverse neurodevelopmental toxicants on global gene expression in the neural embryonic stem cell test (ESTn). Toxicol Appl Pharmacol. 2012 Aug 1;262(3):330-40. doi: 10.1016/j.taap.2012.05.011. Epub 2012 May 23. [PubMed:22634333 ]
  15. Hoppin JA, Brock JW, Davis BJ, Baird DD: Reproducibility of urinary phthalate metabolites in first morning urine samples. Environ Health Perspect. 2002 May;110(5):515-8. [PubMed:12003755 ]
  16. Kato K, Shoda S, Takahashi M, Doi N, Yoshimura Y, Nakazawa H: Determination of three phthalate metabolites in human urine using on-line solid-phase extraction-liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 May 25;788(2):407-11. [PubMed:12705982 ]
  17. Koo HJ, Lee BM: Human monitoring of phthalates and risk assessment. J Toxicol Environ Health A. 2005 Aug 27;68(16):1379-92. [PubMed:16009652 ]
  18. Kim SH, Chun S, Jang JY, Chae HD, Kim CH, Kang BM: Increased plasma levels of phthalate esters in women with advanced-stage endometriosis: a prospective case-control study. Fertil Steril. 2011 Jan;95(1):357-9. doi: 10.1016/j.fertnstert.2010.07.1059. Epub 2010 Aug 25. [PubMed:20797718 ]
  19. Ge RS, Chen GR, Dong Q, Akingbemi B, Sottas CM, Santos M, Sealfon SC, Bernard DJ, Hardy MP: Biphasic effects of postnatal exposure to diethylhexylphthalate on the timing of puberty in male rats. J Androl. 2007 Jul-Aug;28(4):513-20. Epub 2007 Feb 7. [PubMed:17287459 ]
  20. Hoppin JA, Ulmer R, London SJ: Phthalate exposure and pulmonary function. Environ Health Perspect. 2004 Apr;112(5):571-4. [PubMed:15064163 ]
  21. Barron MG, Schultz IR, Hayton WL: Presystemic branchial metabolism limits di-2-ethylhexyl phthalate accumulation in fish. Toxicol Appl Pharmacol. 1989 Mar 15;98(1):49-57. [PubMed:2929021 ]
  22. Holm A, Solbu K, Molander P, Lundanes E, Greibrokk T: Sensitive biomonitoring of phthalate metabolites in human urine using packed capillary column switching liquid chromatography coupled to electrospray ionization ion-trap mass spectrometry. Anal Bioanal Chem. 2004 Apr;378(7):1762-8. Epub 2004 Jan 31. [PubMed:14758462 ]
  23. Christen V, Crettaz P, Oberli-Schrammli A, Fent K: Some flame retardants and the antimicrobials triclosan and triclocarban enhance the androgenic activity in vitro. Chemosphere. 2010 Nov;81(10):1245-52. doi: 10.1016/j.chemosphere.2010.09.031. Epub 2010 Oct 12. [PubMed:20943248 ]
  24. Ellero-Simatos S, Claus SP, Benelli C, Forest C, Letourneur F, Cagnard N, Beaune PH, de Waziers I: Combined transcriptomic-(1)H NMR metabonomic study reveals that monoethylhexyl phthalate stimulates adipogenesis and glyceroneogenesis in human adipocytes. J Proteome Res. 2011 Dec 2;10(12):5493-502. doi: 10.1021/pr200765v. Epub 2011 Nov 9. [PubMed:22017230 ]
  25. Rose ML, Rivera CA, Bradford BU, Graves LM, Cattley RC, Schoonhoven R, Swenberg JA, Thurman RG: Kupffer cell oxidant production is central to the mechanism of peroxisome proliferators. Carcinogenesis. 1999 Jan;20(1):27-33. [PubMed:9934846 ]