mono-2-(ethylhexyl)phthalate

Synonyms: "mono(2-ethylhexyl)phthalate", "monoethylhexyl phthalate", "2-ethylhexyl hydrogen phthalate", "(2-Ethylhexyl) hydrogen phthalate", "phthalic acid mono-2-ethylhexyl ester", "MEHP"

Source: mono-2-(ethylhexyl)phthalate is a metabolite of di-(2-ethylhexyl) phthalate (DEHP).

Identifiers:

IUPAC Name: 2-(2-ethylhexoxycarbonyl)benzoic acid
CAS Number: 4376-20-9
PubChem ID: 20393
InChiKey: DJDSLBVSSOQSLW-UHFFFAOYSA-N
Canonical SMILES: CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)O

Structural Properties:

Molecular Formula: C₁₆H₂₂O₄
Molecular Weight: 278.344

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 3
Number of atoms different from hydrogen: 20

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3D structure (.sdf)
3D structure (.mol2)
3D structure (.pdb)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Hurst CH, Waxman DJ. 2003. Activation of PPARalpha and PPARgamma by environmental phthalate monoesters. Toxicol Sci 74(2):297-308.

Lampen A, Zimnik S, Nau H. 2003. Teratogenic phthalate esters and metabolites activate the nuclear receptors PPARs and induce differentiation of F9 cells. Toxicol Appl Pharmacol 188(1):14-23, DOI: 10.1016/S0041-008X(03)00014-0.

Lloyd SC, Foster PMD. 1988. Effect of mono-(2-ethylhexyl)phthalate on follicle-stimulating hormone responsiveness of cultured rat Sertoli cells. Toxicol Appl Pharmacol 95(3):484-489.

Thysen B, Morris PL, Gatz M, Bloch E. 1990. The effect of mono(2-ethylhexyl) phthalate on Sertoli cell transferrin secretion in vitro. Toxicol Appl Pharmacol 106(1):154-157.Treinen KA, Dodson WC, Heindel JJ. 1990. Inhibition of FSH-stimulated cAMP accumulation and progesterone production by mono(2-ethylhexyl) phthalate in rat granulosa cell cultures. Toxicol Appl Pharmacol 106(2):334-340.