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
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)
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of peroxisome proliferator carcinogens on unscheduled DNA synthesis in rat hepatocytes determined by autoradiography. | 1986 Dec |
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| Various short-term assays and two long-term studies with the plasticizer di(2-ethylhexyl)phthalate in the Syrian golden hamster. | 1988 Jan |
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| Effects of hepatic peroxisome proliferators and 12-O-tetradecanoyl phorbol-13-acetate on catalase and other enzyme activities of embryonic cells in vitro. | 1990 Feb 1 |
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| Morphological transformation and catalase activity of Syrian hamster embryo cells treated with hepatic peroxisome proliferators, TPA and nickel sulphate. | 1990 Jan |
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| Plasticizers and inhibition of leukocyte function in vitro. | 1998 Nov-Dec |
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| Mono-(2-ethylhexyl) phthalate directly alters the expression of Leydig cell genes and CYP17 lyase activity in cultured rat fetal testis. | 2011 |
|
| 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 Jun 11 |
Sample Use Guides
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%).
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17243
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224-477-1
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DTXSID2025680
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4376-20-9
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FU2EWB60RT
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20393
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SUBSTANCE RECORD
