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| Targets |
Benzophenone is a known metabolite of cinnarizine in humans. It has been shown to have anti-inflammatory effects. It is a photosensitizer that absorbs UV light, transfers its energy to DNA, and triggers DNA damage. It also exhibits estrogenic activity.
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| ln Vitro |
In vitro, benzophenone has been shown to have anti-inflammatory effects. It absorbs UV light and acts as a photosensitizer, transferring energy to DNA and causing DNA damage. It exhibits estrogenic activity in cell-based assays.
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| ln Vivo |
In vivo, benzophenone (0-160 mg/kg, oral administration for 105 weeks) exhibits potential carcinogenic risks in rat and mouse models under long-term exposure, especially in the kidney and liver. It also increases uterine weight, endometrial height and stromal cells, and keratinizes vaginal epithelial cells in animal studies.
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| Enzyme Assay |
Cell-free assays for benzophenone involve studying its photoinitiating properties and its ability to absorb UV light. The compound's photochemical properties are characterized using UV-Vis spectroscopy and measurements of its ability to generate free radicals upon UV irradiation.
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| Cell Assay |
In vitro cellular assays evaluate the estrogenic activity of benzophenone using estrogen-responsive cell lines (e.g., MCF-7). Cells are treated with benzophenone, and cell proliferation or reporter gene activity (e.g., luciferase under an estrogen-responsive promoter) is measured to assess its estrogenic potential.
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| Animal Protocol |
In vivo toxicity studies have been conducted in rats and mice, with benzophenone administered orally at doses of 0-160 mg/kg for up to 105 weeks. Organ weights, histopathology (especially of kidney and liver), and tumor incidence are evaluated to assess its carcinogenic potential.
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Benzophenone is a known metabolite of cinnarizine in humans. Paraoxygenase (PON1) is a key enzyme in organophosphate metabolism. PON1 can inactivate certain organophosphates through hydrolysis. PON1 hydrolyzes active metabolites in various organophosphate pesticides and nerve agents (such as soman, sarin, and VX). The existence of PON1 polymorphism leads to differences in the enzyme activity level and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effects of organophosphate exposure. Benzophenone (C13H10O) has a molecular weight of 182.22 g/mol. It is a pale yellow solid that is soluble in organic solvents but insoluble in water. It is used as a photosensitizer, that absorbs UV light and transfers its energy to DNA. |
| Toxicity/Toxicokinetics |
Toxicity Summary
Benzophenone is a cholinesterase, or acetylcholinesterase (AChE) inhibitor. Cholinesterase inhibitors (or "anticholinesterases") inhibit the activity of acetylcholinesterase. Because acetylcholinesterase plays a vital physiological role, chemicals that interfere with its activity are potent neurotoxins; even low doses can cause excessive salivation and lacrimation, followed by muscle spasms and ultimately death. Substances used in nerve gases and many pesticides have been shown to exert their effects by binding to serine residues at the active site of acetylcholinesterase, thus completely inhibiting the enzyme's activity. Acetylcholinesterase breaks down the neurotransmitter acetylcholine, which is released at the neuromuscular junction, causing muscle or organ relaxation. The mechanism of action of acetylcholinesterase inhibitors is to allow acetylcholine to accumulate and exert its sustained effect, ensuring the continuous transmission of nerve impulses and preventing muscle contraction from ceasing. The most common acetylcholinesterase inhibitors are phosphorus-containing compounds designed to bind to the enzyme's active site. Its structural requirements include a phosphorus atom with two lipophilic groups, a leaving group (such as a halogen or thiocyanate group), and a terminal oxygen atom. The toxicity of benzophenone includes potential carcinogenic risks in rat and mouse models under long-term exposure, especially in the kidney and liver. It is a skin, eye, and respiratory tract irritant. Liver changes similar to chronic hepatitis have been noted in high-dose animal studies. |
| Additional Infomation |
Benzophenone may be carcinogenic under California labor law. Benzophenone is the simplest member of the benzophenone family; it is a formaldehyde molecule in which two hydrogen atoms are replaced by phenyl groups. It is a photosensitizer and a plant metabolite. Benzophenone is an organic compound. Substituted benzophenones, such as oxybenzone and dioxybenzone, are used in sunscreens. Benzophenone has been reported to be found in soybeans, Streptomyces, and other organisms with relevant data. Benzophenone is found in fruits, such as grapes. Benzophenone is a flavoring agent. Benzophenone is a common photosensitizer in photochemistry. It transitions from the Sn1 state to the triplet state in almost 100% yield. The resulting diradical abstracts a hydrogen atom from a suitable hydrogen donor, forming a keto radical. Benzophenone is an organic compound with the molecular formula (C6H5)2CO, often abbreviated as Ph2CO. Benzophenone is a widely used structural unit in organic chemistry, its parent compound being a diaryl ketone. Benzophenone has been shown to have anti-inflammatory effects. Benzophenone belongs to the benzophenone class of compounds. These organic compounds consist of one ketone group linked to two phenyl groups (A3203). Benzophenone is a metabolite found or produced in Saccharomyces cerevisiae. See also: ADP-D-glycerol-β-D-mannohepose (note moved to...).
Benzophenone is a component of many consumer products. It is primarily used as a photoinitiator and as a fragrance enhancer. It is also used as an ultraviolet curing agent, flavor ingredient, as a polymerization inhibitor, and in the manufacture of insecticides, agricultural chemicals, hypnotics, and other pharmaceuticals. It is a known metabolite of cinnarizine in humans. |
| Exact Mass |
182.073
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| CAS # |
119-61-9
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| Related CAS # |
Benzophenone-d10;22583-75-1;Benzophenone-d5;2694-78-2;Benzophenone-13C;32488-48-5
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| PubChem CID |
3102
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
305.4±0.0 °C at 760 mmHg
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| Melting Point |
47-51 °C(lit.)
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| Flash Point |
123.7±13.7 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.584
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| LogP |
3.18
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
165
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C1C([H])=C([H])C([H])=C([H])C=1[H])C1C([H])=C([H])C([H])=C([H])C=1[H]
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| InChi Key |
RWCCWEUUXYIKHB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
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| Chemical Name |
diphenylmethanone
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| Synonyms |
Benzophenone Diphenylketone Diphenyl ketone
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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 (~548.79 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.72 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 (13.72 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 (13.72 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
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.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT00530387 | COMPLETED | Drug: 19 organic sunscreen filters and 5 topical NSAIDs | Dermatitis, Photocontact | NHS Tayside | 2008-07 | Not Applicable |
| NCT01695356 | COMPLETED | Drug: 290-400 nm sunscreen Drug: 290-800 nm sunscreen |
Melasma | Universidad Autonoma de San Luis Potosí | 2012-09 | Phase 4 |
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