Monobenzyl phthalate (2-((Benzyloxy)carbonyl)benzoic acid) is a urinary metabolite after exposure to phthalates (eg, diethylhexyl phthalate).

Physicochemical Properties

Molecular Formula	C15H12O4
Molecular Weight	256.25
Exact Mass	256.073
CAS #	2528-16-7
Related CAS #	Monobenzyl phthalate-d4;478954-83-5
PubChem CID	31736
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	441.1±28.0 °C at 760 mmHg
Melting Point	106 °C
Flash Point	167.8±17.5 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.609
LogP	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Heavy Atom Count	19
Complexity	320
Defined Atom Stereocenter Count	0
InChi Key	XIKIUQUXDNHBFR-UHFFFAOYSA-N
InChi Code	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)
Chemical Name	2-phenylmethoxycarbonylbenzoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[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.

Additional Infomation

Monobenzyl phthalate is a phthalic acid monoester resulting from the formal condensation of one of the carboxy groups of phthalic acid with the hydroxy group of benzyl alcohol. It is a major metabolite of the plasticiser butyl benzyl phthalate (BBP). It has a role as a xenoestrogen and a xenobiotic metabolite. It is functionally related to a benzyl alcohol. Monobenzyl phthalate has been reported in Nicotiana tabacum with data available. Mono-benzyl phthalate is a phthalate metabolite that can be found in human biofluids. Phthalates are industrial chemicals that are added to plastics to impart flexibility and resilience and are often referred to as plasticizers. Phthalates also are used as solubilizing or stabilizing agents in other applications. There are numerous products that may contain phthalates: adhesives; automotive plastics; detergents; lubricating oils; some medical devices and pharmaceuticals; plastic raincoats; solvents; vinyl tiles and flooring; and personal-care products, such as soap, shampoo, deodorants, lotions, fragrances, hair spray, and nail polish. Phthalates are often used in polyvinyl chloride type plastics, such as plastic packaging film and sheet, garden hoses, inflatable recreational toys, blood product storage bags, intravenous medical tubing, and toys. Because they are not chemically bound to the plastics to which they are added, phthalates can be released into the environment during use or disposal of the product. People are exposed to phthalates through ingestion, inhalation, and, to a lesser extent, dermal contact with products that contain phthalates. Phthalates have low acute animal toxicity. In animals, phthalates produced anti-androgenic effects by reducing testosterone production and, at very high levels, reducing estrogen production, effects that may be mediated by inhibiting testicular and ovarian steroidogenesis.

Solubility Data

Solubility (In Vitro)

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

Solubility (In Vivo)

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

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.9024 mL	19.5122 mL	39.0244 mL
	5 mM	0.7805 mL	3.9024 mL	7.8049 mL
	10 mM	0.3902 mL	1.9512 mL	3.9024 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.