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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 of MONO(ETHYLHEXYL) PHTHALATE

SMILES

CCCCC(CC)COC(=O)C1=CC=CC=C1C(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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
37.0 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Plasticizers and inhibition of leukocyte function in vitro.
1998 Nov-Dec
Mono-(2-ethylhexyl) phthalate directly alters the expression of Leydig cell genes and CYP17 lyase activity in cultured rat fetal testis.
2011
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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%).
Name Type Language
MONO(ETHYLHEXYL) PHTHALATE
Systematic 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
MEHP
Common 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
Created by admin on Thu Jul 06 07:52:38 UTC 2023 , Edited by admin on Thu Jul 06 07:52:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
224-477-1
Created by admin on Thu Jul 06 07:52:38 UTC 2023 , Edited by admin on Thu Jul 06 07:52:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID2025680
Created by admin on Thu Jul 06 07:52:38 UTC 2023 , Edited by admin on Thu Jul 06 07:52:38 UTC 2023
PRIMARY
CAS
4376-20-9
Created by admin on Thu Jul 06 07:52:38 UTC 2023 , Edited by admin on Thu Jul 06 07:52:38 UTC 2023
PRIMARY
FDA UNII
FU2EWB60RT
Created by admin on Thu Jul 06 07:52:38 UTC 2023 , Edited by admin on Thu Jul 06 07:52:38 UTC 2023
PRIMARY
PUBCHEM
20393
Created by admin on Thu Jul 06 07:52:38 UTC 2023 , Edited by admin on Thu Jul 06 07:52:38 UTC 2023
PRIMARY