Monobenzyl phthalate does not have a specific pharmacological target as it is a metabolite and biomarker rather than a therapeutic drug. It is used as a urinary biomarker for phthalate exposure. Its "target" in research is as an indicator of environmental exposure to phthalates, which are known endocrine disruptors. The compound is associated with reproductive health effects, including preterm deliveries.

In vitro activity of Monobenzyl phthalate is not evaluated as a bioactive compound with pharmacological effects. Its utility lies in its role as a biomarker and analytical reference standard. It may be used in in vitro assays to study phthalate metabolism or to validate analytical methods for detecting phthalate exposure. Its "activity" is reflected in its presence in biological samples.

In vivo, Monobenzyl phthalate is a urinary metabolite that reflects exposure to butyl benzyl phthalate and other phthalates. It serves as a biomarker for phthalate exposure in human and animal studies. Levels of MBzP in urine are measured to assess the extent of phthalate exposure and to study the association between phthalate exposure and health outcomes, including reproductive effects.

In vitro enzyme assays with Monobenzyl phthalate typically involve studying esterases that hydrolyze phthalate esters to their monoester metabolites. The compound can be used as a substrate or product in assays to characterize the activity of these enzymes. Standard assays involve incubating the compound with enzyme preparations and analyzing the products by HPLC or LC-MS.

Monobenzyl phthalate is not typically used in cell culture experiments as a bioactive compound. However, it may be employed in studies investigating the effects of phthalate metabolites on cellular function, particularly in endocrine or reproductive cells. Cells could be treated with the compound to assess its potential endocrine-disrupting effects. Its primary use is as an analytical standard for biomarker measurement.

In vivo animal experiments with Monobenzyl phthalate typically involve administering phthalate esters (e.g., BBP) to animals and measuring MBzP levels in urine as a biomarker of exposure. Alternatively, the compound itself could be administered to study its pharmacokinetics and metabolism. These studies are used to understand the metabolic fate of phthalates and their potential toxicological effects.

The pharmacokinetic (PK) properties of Monobenzyl phthalate reflect its role as a metabolite. Following exposure to BBP or other phthalates, MBzP is formed through hydrolysis by esterases. It is rapidly excreted in urine, making it a useful biomarker for recent phthalate exposure. Its half-life in the body is relatively short, consistent with its role as a metabolite of a rapidly cleared parent compound.

Monobenzyl phthalate is classified as an irritant (Xi) with risk of eye irritation. Safety precautions should be taken when handling. It has a melting point of 106°C and is a white to off-white solid. As a phthalate metabolite, it is used as a biomarker for phthalate exposure. Comprehensive toxicology data are available from phthalate toxicity studies.

[1]. Positive Association of Low-Level Environmental Phthalate Exposure With Sperm Motility Was Mediated by DNA Methylation: A Pilot Study. Chemosphere. 2019 Apr;220:459-467.

Monobenzyl phthalate is a phthalic acid monoester formed by the condensation of a carboxyl group of phthalic acid with the hydroxyl group of benzyl alcohol. It is the main metabolite of the plasticizer butyl benzyl phthalate (BBP). It has the effects of isoestrogens and xenobiotic metabolites, and its function is related to that of benzyl alcohol. Monobenzyl phthalate has been reported to be detected in tobacco (Nicotiana tabacum), and relevant data are available. Monobenzyl phthalate is a phthalate ester metabolite that can be found in human biological fluids. Phthalate esters are industrial chemicals added to plastics to impart flexibility and elasticity, and are commonly referred to as plasticizers. Phthalate esters can also be used as solubilizers or stabilizers in other applications. Phthalates may be present in many products, such as adhesives, automotive plastics, detergents, lubricants, certain medical devices and pharmaceuticals; plastic raincoats; solvents; vinyl tiles and flooring; and personal care products such as soaps, shampoos, deodorants, lotions, perfumes, hairsprays, and nail polish. Phthalates are commonly used in polyvinyl chloride (PVC) plastics, such as plastic packaging films and sheets, garden hoses, inflatable recreational toys, blood product storage bags, intravenous infusion catheters, and toys. Because phthalates are not chemically bonded to the added plastics, they are released into the environment during the use or disposal of products. People are exposed to phthalates through ingestion, inhalation, and (less commonly) skin contact with products containing phthalates. Phthalates have low acute animal toxicity. In animal studies, phthalates exert anti-androgenic effects by reducing testosterone production and, at high concentrations, also reduce estrogen production; these effects may be achieved by inhibiting testicular and ovarian steroid production.

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Monobenzyl phthalate (MBzP) is a hydroxylated phthalate metabolite and a major metabolite of the plasticizer butyl benzyl phthalate (BBP). It is used as an analytical reference standard for the quantification of phthalate metabolites in biological samples. The compound is not a drug and has no therapeutic indications. It is available for laboratory research use only as a biomarker for environmental exposure assessment.

C15H12O4

256.25

256.073

2528-16-7

Monobenzyl phthalate-d4;478954-83-5

31736

White to off-white solid powder

1.3±0.1 g/cm3

441.1±28.0 °C at 760 mmHg

106 °C

167.8±17.5 °C

0.0±1.1 mmHg at 25°C

1.609

2.9

1

4

5

19

320

0

C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2C(=O)O

XIKIUQUXDNHBFR-UHFFFAOYSA-N

InChI=1S/C15H12O4/c16-14(17)12-8-4-5-9-13(12)15(18)19-10-11-6-2-1-3-7-11/h1-9H,10H2,(H,16,17)

2-phenylmethoxycarbonylbenzoic acid

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO: 100 mg/mL (390.24 mM)
H2O: < 0.1 mg/mL

Solubility in Formulation 1: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

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Solubility in Formulation 2: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (9.76 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

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 (Please use freshly prepared in vivo formulations for optimal results.)