MONO(ETHYLHEXYL) PHTHALATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H22O4
Molecular Weight	278.3435
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DJDSLBVSSOQSLW-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C16H22O4
Molecular Weight	278.3435
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7038132 | https://www.ncbi.nlm.nih.gov/pubmed/26529 | https://www.ncbi.nlm.nih.gov/pubmed/18077825

Mono(ethylhexyl) phthalate (MEHP) is an active metabolite of Bis(2-ethylhexyl)phthalate (DEHP). DEHP is a widely used plasticizer. MEHP has been shown to be moderately toxic. Studies involving orally administered MEHP revealed the mild hepatic changes occurred but there was no bioaccumulation of the monoester. Studies of the rat and rabbit indicated that MEHP has no teratogenic effects. This compound was readily absorbed from the gastrointestinal tract. Radioactivity following intravenous administration of 14C-MEHP was rapidly distributed in tissues, with the highest levels occurring in the liver, kidney, and urinary bladder. Mono(ethylhexyl) phthalate is a member of a class of chemical compounds with known adverse effects on the male reproductive system.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 17A1 8 Target ID: CHEMBL4430 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22087261	Inhibitor 8504
LDL-associated phospholipase A2 2 Target ID: CHEMBL3514 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3203637	Inhibitor 8504		37.0 mM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Kinetics of the phthalate metabolites mono-2-ethylhexyl phthalate (MEHP) and mono-n-butyl phthalate (MnBP) in male subjects after a single oral dose.	2016-06-11	27091076
Mono-(2-ethylhexyl) phthalate directly alters the expression of Leydig cell genes and CYP17 lyase activity in cultured rat fetal testis.	2011	22087261
Plasticizers and inhibition of leukocyte function in vitro.	1999-02-05	9932661
Effects of hepatic peroxisome proliferators and 12-O-tetradecanoyl phorbol-13-acetate on catalase and other enzyme activities of embryonic cells in vitro.	1990-02-01	2306265
Morphological transformation and catalase activity of Syrian hamster embryo cells treated with hepatic peroxisome proliferators, TPA and nickel sulphate.	1990-01	2334865
Various short-term assays and two long-term studies with the plasticizer di(2-ethylhexyl)phthalate in the Syrian golden hamster.	1988-01	3335045
Effect of peroxisome proliferator carcinogens on unscheduled DNA synthesis in rat hepatocytes determined by autoradiography.	1986-12	3802057

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The direct mechanisms of action of mono(ethylhexyl) phthalate (MEHP) on the rat fetal testis, focusing on Leydig cell steroidogenesis in particular was investigated. the production of 5 alpha-dihydrotestosterone (5α-DHT) (-68%) and androstenedione (-54%) was also inhibited by 10 µM MEHP, whereas 17 alpha-hydroxyprogesterone (17α-OHP) production was found to increase (+41%).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:54:24 GMT 2025` Edited by `admin` on `Mon Mar 31 20:54:24 GMT 2025`
Record UNII	FU2EWB60RT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MONO(ETHYLHEXYL) PHTHALATE

Systematic Name

English

MEHP

Preferred Name

English

1,2-BENZENEDICARBOXYLIC ACID, 1-(2-ETHYLHEXYL) ESTER

Systematic Name

English

2-((2-(ETHYL)HEXYLOXY)CARBONYL)BENZOIC ACID

Systematic Name

English

PHTHALIC ACID, MONO(2-ETHYLHEXYL) ESTER

Systematic Name

English

1,2-BENZENEDICARBOXYLIC ACID, MONO(2-ETHYLHEXYL) ESTER

Systematic Name

English

2-ETHYLHEXYL HYDROGEN PHTHALATE

Systematic Name

English

PHTHALIC ACID, 2-ETHYLHEXYL ESTER

Systematic Name

English

MONO(2-ETHYLHEXYL) PHTHALATE

Systematic Name

English

Code System Code Type Description

CHEBI

17243