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| Targets |
Monobutyl phthalate does not have a therapeutic target but instead acts as an endocrine-disrupting chemical. It is a potent antagonist of the androgen receptor (AR), with an IC50 of 1.22 × 10^-7 M, making it 8.6-fold more potent as an AR antagonist than its parent compound DBP. It is also 4.7-fold more potent as a thyroid hormone receptor (TR) antagonist. By blocking AR and TR signaling, monobutyl phthalate disrupts normal endocrine function, leading to a range of adverse effects, particularly on male reproductive development. The compound's anti-androgenic effects are well-established in both in vitro and in vivo models, and it is considered a critical biomarker for assessing human exposure to phthalates.
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| ln Vitro |
In vitro studies have demonstrated that monobutyl phthalate is a potent anti-androgenic compound. Reporter gene assays in cells expressing the androgen receptor have shown that monobutyl phthalate inhibits AR-mediated transcriptional activity with an IC50 of 1.22 × 10^-7 M. This activity is significantly more potent than that of its parent compound DBP. In addition to AR antagonism, monobutyl phthalate has been shown to antagonize the thyroid hormone receptor. These in vitro findings are consistent with the compound's role as an endocrine disruptor and its association with reproductive and developmental toxicity. The compound has a molecular weight of 222.24 g/mol and a molecular formula of C12H14O4. It is a colorless, oily liquid at room temperature and is soluble in organic solvents.
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| ln Vivo |
In vivo, monobutyl phthalate is the biologically active metabolite responsible for the toxicity associated with DBP exposure. Animal studies have shown that exposure to DBP or its metabolite monobutyl phthalate during critical windows of development leads to male reproductive tract malformations, including hypospadias, cryptorchidism, and reduced anogenital distance. These effects are mediated through the compound's anti-androgenic activity, which disrupts normal testosterone signaling during fetal development. Monobutyl phthalate is also an embryotoxicant, causing adverse effects on embryonic development. The compound's in vivo effects have been extensively studied in rodent models, and these studies have provided the basis for human risk assessments and regulatory limits on phthalate exposure.
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| Enzyme Assay |
The in vitro enzyme/receptor binding assays for monobutyl phthalate focus on its antagonism of the androgen receptor. In these assays, cells expressing the human androgen receptor are transfected with a reporter gene construct containing an androgen-responsive element. The cells are treated with a potent androgen agonist (e.g., dihydrotestosterone) in the presence of varying concentrations of monobutyl phthalate, and the inhibition of reporter gene activity is measured. The IC50 for AR antagonism is determined from dose-response curves. Similar assays are used to assess antagonism of the thyroid hormone receptor. These receptor-binding assays are critical for understanding the molecular basis of monobutyl phthalate's endocrine-disrupting effects.
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| Cell Assay |
Cellular assays for monobutyl phthalate involve treating cells with the compound and measuring its effects on hormone-sensitive endpoints. For androgen receptor antagonism, cells expressing AR are treated with monobutyl phthalate, and the inhibition of androgen-induced gene expression is measured by qRT-PCR or reporter gene assays. The compound's effects on cell proliferation, differentiation, and apoptosis can also be assessed in relevant cell lines. These cellular assays provide functional confirmation of the receptor-binding data and help elucidate the mechanisms underlying phthalate toxicity.
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| Animal Protocol |
In vivo animal experiments for monobutyl phthalate are conducted to evaluate its reproductive and developmental toxicity. Pregnant rodents are exposed to monobutyl phthalate or its parent compound DBP during gestation, and the offspring are examined for reproductive tract malformations. Parameters such as anogenital distance, testicular descent, and the structure of the reproductive organs are assessed. The compound's effects on fertility and embryonic development are also studied in these models. These animal studies have been critical for establishing the link between phthalate exposure and adverse reproductive outcomes and for informing regulatory decisions on phthalate use.
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| ADME/Pharmacokinetics |
Monobutyl phthalate is not a therapeutic agent and does not have pharmacokinetic properties relevant to drug development. However, as a metabolite of DBP, its formation and elimination in the body have been studied in the context of human exposure assessment. Monobutyl phthalate is detected in urine as a biomarker of DBP exposure, with a median concentration of 60.7 μg/L in the general population. The compound has a molecular weight of 222.24 g/mol and a molecular formula of C12H14O4. Its chemical structure consists of a phthalate moiety with a butyl ester and a free carboxylic acid group, which is characteristic of monoester metabolites of phthalates.
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| Toxicity/Toxicokinetics |
Monobutyl phthalate is a toxicologically significant compound rather than a therapeutic agent. It is classified as an endocrine disruptor with well-documented anti-androgenic and embryotoxic effects. The compound is the primary active metabolite of dibutyl phthalate, a widely used plasticizer. Its mechanism of action involves antagonism of the androgen receptor and thyroid hormone receptor, leading to disruption of normal endocrine function. Monobutyl phthalate is routinely used as an analytical reference standard for biomonitoring studies and as a tool in mechanistic toxicology research. Its established role in male reproductive toxicity makes it an essential compound for studies focused on low-molecular-weight phthalate toxicity.
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| References |
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| Additional Infomation |
Monobutyl phthalate (MBP) is a phthalate monoester that functions similarly to n-butanol. It has been reported to be found in Oecophylla smaragdina and Glycyrrhiza glabra, with relevant data available. MBP is the active metabolite of dibutyl phthalate (DBP). DBP is a commonly used plasticizer and can also be used as an additive in adhesives or printing inks. It is soluble in many organic solvents, such as alcohols, ethers, and benzene. DBP is also used as an ectoparasite killer. In November 2006, DBP was added to California Proposition 65 (1986) as a suspected teratogen. It is a suspected endocrine disruptor and was previously used in some nail polishes. In the fall of 2006, all major manufacturers began banning this chemical from their nail polishes. Dibutyl phthalate (DBP) has been permanently banned for use in children's toys. Dibutyl phthalate inhibits steroid production by downregulating the expression of acute regulatory proteins involved in steroid production.
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| Molecular Formula |
C12H14O4
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| Molecular Weight |
222.24
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| Exact Mass |
222.089
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| CAS # |
131-70-4
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| Related CAS # |
Monobutyl phthalate-d4;478954-81-3
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| PubChem CID |
8575
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| Appearance |
White to off-white solid powder
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| Density |
1.173g/cm3
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| Boiling Point |
363.5ºC at 760mmHg
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| Melting Point |
73 °C
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| Flash Point |
138.2ºC
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| LogP |
2.341
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
16
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| Complexity |
249
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
YZBOVSFWWNVKRJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H14O4/c1-2-3-8-16-12(15)10-7-5-4-6-9(10)11(13)14/h4-7H,2-3,8H2,1H3,(H,13,14)
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| Chemical Name |
2-butoxycarbonylbenzoic acid
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| Synonyms |
NSC-8479; NSC 8479; Monobutyl phthalate
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~449.96 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.25 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 (11.25 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.25 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4996 mL | 22.4982 mL | 44.9964 mL | |
| 5 mM | 0.8999 mL | 4.4996 mL | 8.9993 mL | |
| 10 mM | 0.4500 mL | 2.2498 mL | 4.4996 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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