| Record Information |
|---|
| Version | 2.0 |
|---|
| Creation Date | 2014-08-29 04:48:25 UTC |
|---|
| Update Date | 2014-12-24 20:26:35 UTC |
|---|
| Accession Number | T3D3976 |
|---|
| Identification |
|---|
| Common Name | Benzophenone |
|---|
| Class | Small Molecule |
|---|
| Description | Benzophenone is found in fruits. Benzophenone is present in grapes. Benzophenone is a flavouring agent Benzophenone is a common photosensitizer in photochemistry. It crosses from the S1 state into the triplet state with nearly 100% yield. The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical. Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.
Benzophenone has been shown to exhibit anti-inflammatory function
Benzophenone belongs to the family of Benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. (1). |
|---|
| Compound Type | - Ester
- Flavouring Agent
- Food Toxin
- Household Toxin
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Photosensitizing Agent
- Plant Toxin
|
|---|
| Chemical Structure | |
|---|
| Synonyms | | Synonym | | 1dzp | | A-Oxodiphenylmethane | | A-Oxoditane | | Adjutan 6016 | | ADK STAB 1413 | | alpha -oxodiphenylmethane | | alpha -oxoditane | | alpha-Oxodiphenylmethane | | alpha-Oxoditane | | Benzopheneone | | BENZOPHENONE (8CI) | | Benzophenone (diphenyl-ketone) | | Benzoyl-Benzene | | Benzoylbenzene | | BZQ | | Di(phenyl)methanone | | Diphenyl ketone | | Diphenyl-methanon | | Diphenyl-Methanone | | Diphenylketone | | Diphenylmethanone | | Diphenylmethanone, 9CI | | FEMA 2134 | | Kayacure BP | | Ketone, diphenyl | | METHANONE, DIPHENYL- (9CI) | | Phenyl ketone |
|
|---|
| Chemical Formula | C13H10O |
|---|
| Average Molecular Mass | 182.218 g/mol |
|---|
| Monoisotopic Mass | 182.073 g/mol |
|---|
| CAS Registry Number | 119-61-9 |
|---|
| IUPAC Name | diphenylmethanone |
|---|
| Traditional Name | benzophenone |
|---|
| SMILES | O=C(C1=CC=CC=C1)C1=CC=CC=C1 |
|---|
| InChI Identifier | InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H |
|---|
| InChI Key | InChIKey=RWCCWEUUXYIKHB-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Benzenoids |
|---|
| Class | Benzene and substituted derivatives |
|---|
| Sub Class | Benzophenones |
|---|
| Direct Parent | Benzophenones |
|---|
| Alternative Parents | |
|---|
| Substituents | - Benzophenone
- Aryl-phenylketone
- Diphenylmethane
- Aryl ketone
- Benzoyl
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
|
|---|
| Molecular Framework | Aromatic homomonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Biological Properties |
|---|
| Status | Detected and Not Quantified |
|---|
| Origin | Exogenous |
|---|
| Cellular Locations | |
|---|
| Biofluid Locations | Not Available |
|---|
| Tissue Locations | Not Available |
|---|
| Pathways | Not Available |
|---|
| Applications | |
|---|
| Biological Roles | |
|---|
| Chemical Roles | Not Available |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Appearance | White powder. |
|---|
| Experimental Properties | | Property | Value |
|---|
| Melting Point | 26°C | | Boiling Point | 305.4°C (581.7°F) | | Solubility | 0.137 mg/mL at 25°C | | LogP | 3.18 |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
|---|
| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-b948527870febd59c85e | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-4900000000-93e6c7526327719d728d | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-3900000000-23d78741cacbe9443a57 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-eb0842414a2a12ff24b3 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20 | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-7c028c0aa3b44d2ee6be | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-b948527870febd59c85e | 2018-05-18 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-4900000000-93e6c7526327719d728d | 2018-05-18 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a4i-3900000000-23d78741cacbe9443a57 | 2018-05-18 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-eb0842414a2a12ff24b3 | 2018-05-18 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20 | 2018-05-18 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0a6r-6900000000-7c028c0aa3b44d2ee6be | 2018-05-18 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a59-3900000000-94e3675023c8e5cf8b46 | 2016-09-22 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - ESI-ITFT , positive | splash10-0a4i-0900000000-1f9db6636ef926e9a822 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - APCI-ITFT , positive | splash10-0a4i-0900000000-c08dc4bd854f23a10ab6 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0a4i-0900000000-1f9db6636ef926e9a822 | 2021-09-20 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-f048592c39e6448959f3 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053r-0900000000-35d1d32df051465b3618 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-3900000000-4e792aa67452f41d4fd0 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-2ea2893ee5ce1f203589 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900000000-fb40d9e5c26915affa0d | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-7900000000-d9d95ec382ac97a7af66 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-052cd8aa2cc34939880f | 2021-09-22 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053r-0900000000-f0b9223dd578ae5d011f | 2021-09-22 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fb9-9200000000-4239c3243d5a26b7658f | 2021-09-22 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-2aea314e447f6c21a0a5 | 2021-09-22 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900000000-81ba80bd5ec599f30980 | 2021-09-22 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0059-2900000000-2142e08d17da4d6f92a3 | 2021-09-22 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0a6r-6900000000-e66f1faddf56bc55ae47 | 2014-09-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
|
|---|
| Toxicity Profile |
|---|
| Route of Exposure | Not Available |
|---|
| Mechanism of Toxicity | Benzophenone is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
|---|
| Metabolism | Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure. |
|---|
| Toxicity Values | Not Available |
|---|
| Lethal Dose | Not Available |
|---|
| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. (3) |
|---|
| Uses/Sources | Benzophenone is found in fruits. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone. |
|---|
| Minimum Risk Level | Not Available |
|---|
| Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
|---|
| Symptoms | Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result. |
|---|
| Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
|---|
| Normal Concentrations |
|---|
| Not Available |
|---|
| Abnormal Concentrations |
|---|
| Not Available |
|---|
| External Links |
|---|
| DrugBank ID | DB01878 |
|---|
| HMDB ID | HMDB32049 |
|---|
| PubChem Compound ID | 3102 |
|---|
| ChEMBL ID | CHEMBL90039 |
|---|
| ChemSpider ID | 2991 |
|---|
| KEGG ID | C06354 |
|---|
| UniProt ID | Not Available |
|---|
| OMIM ID | |
|---|
| ChEBI ID | 3034 |
|---|
| BioCyc ID | Not Available |
|---|
| CTD ID | Not Available |
|---|
| Stitch ID | Not Available |
|---|
| PDB ID | BZQ |
|---|
| ACToR ID | Not Available |
|---|
| Wikipedia Link | Benzophenone |
|---|
| References |
|---|
| Synthesis Reference | Mitsuru Kondo, Hiroshi Iwasaki, Kiyoshi Yasui, Makoto Miyake, “Process for preparing benzophenone derivatives.” U.S. Patent US4323700, issued September, 1963. |
|---|
| MSDS | Link |
|---|
| General References | - Vigorita MG, Previtera T, Trovato A, Monforte MT, Barbera R, Bisignano G: N-trifluoroacetyl derivatives as pharmacological agents. IV--Antiinflammatory and related properties; antimicrobial activity of some polyaromatic trifluoroacetamides. Farmaco. 1989 Feb;44(2):173-84. [2775414 ]
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
|
|---|
| Gene Regulation |
|---|
| Up-Regulated Genes | Not Available |
|---|
| Down-Regulated Genes | Not Available |
|---|
