Tmic
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Record Information
Version2.0
Creation Date2014-08-29 04:48:25 UTC
Update Date2014-12-24 20:26:35 UTC
Accession NumberT3D3976
Identification
Common NameBenzophenone
ClassSmall Molecule
DescriptionBenzophenone 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
Thumb
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 FormulaC13H10O
Average Molecular Mass182.218 g/mol
Monoisotopic Mass182.073 g/mol
CAS Registry Number119-61-9
IUPAC Namediphenylmethanone
Traditional Namebenzophenone
SMILESO=C(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
InChI KeyInChIKey=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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Aryl-phenylketone
  • Diphenylmethane
  • Aryl ketone
  • Benzoyl
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point26°C
Boiling Point305.4°C (581.7°F)
Solubility0.137 mg/mL at 25°C
LogP3.18
Predicted Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP3.03ALOGPS
logP3.43ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-7.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity56.63 m³·mol⁻¹ChemAxon
Polarizability20.19 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-b948527870febd59c85eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-4900000000-93e6c7526327719d728dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3900000000-23d78741cacbe9443a57View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-eb0842414a2a12ff24b3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-7c028c0aa3b44d2ee6beView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-b948527870febd59c85eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-4900000000-93e6c7526327719d728dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3900000000-23d78741cacbe9443a57View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-eb0842414a2a12ff24b3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-7c028c0aa3b44d2ee6beView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-3900000000-94e3675023c8e5cf8b46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-1f9db6636ef926e9a822View in MoNA
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0a4i-0900000000-c08dc4bd854f23a10ab6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-f048592c39e6448959f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0900000000-35d1d32df051465b3618View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-4e792aa67452f41d4fd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-2ea2893ee5ce1f203589View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-fb40d9e5c26915affa0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7900000000-d9d95ec382ac97a7af66View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a6r-6900000000-e66f1faddf56bc55ae47View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityBenzophenone 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.
MetabolismParaoxonase (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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/SourcesBenzophenone is found in fruits. Benzophenone is a widely used building block in organic chemistry, being the parent diarylketone.
Minimum Risk LevelNot Available
Health EffectsAcute 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.
SymptomsSymptoms 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.
TreatmentIf 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
DrugBank IDDB01878
HMDB IDHMDB32049
PubChem Compound ID3102
ChEMBL IDCHEMBL90039
ChemSpider ID2991
KEGG IDC06354
UniProt IDNot Available
OMIM ID
ChEBI ID3034
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDBZQ
ACToR IDNot Available
Wikipedia LinkBenzophenone
References
Synthesis Reference

Mitsuru Kondo, Hiroshi Iwasaki, Kiyoshi Yasui, Makoto Miyake, “Process for preparing benzophenone derivatives.” U.S. Patent US4323700, issued September, 1963.

MSDSLink
General References
  1. 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 ]
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Serine hydrolase activity
Specific Function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular Weight:
67795.525 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory>100 uMNot AvailableBindingDB 22726
References
  1. Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
General Function:
Proteoglycan binding
Specific Function:
Thiol protease which is believed to participate in intracellular degradation and turnover of proteins. Has also been implicated in tumor invasion and metastasis.
Gene Name:
CTSB
Uniprot ID:
P07858
Molecular Weight:
37821.35 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
IC50288.8 uMNot AvailableBindingDB 22726
References
  1. Martins FT, Assis DM, Dos Santos MH, Camps I, Veloso MP, Juliano MA, Alves LC, Doriguetto AC: Natural polyprenylated benzophenones inhibiting cysteine and serine proteases. Eur J Med Chem. 2009 Mar;44(3):1230-9. doi: 10.1016/j.ejmech.2008.09.018. Epub 2008 Sep 24. [18995931 ]
General Function:
Methylumbelliferyl-acetate deacetylase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular Weight:
61806.41 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory>100 uMNot AvailableBindingDB 22726
References
  1. Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [16079615 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Matsumoto H, Adachi S, Suzuki Y: [Estrogenic activity of ultraviolet absorbers and the related compounds]. Yakugaku Zasshi. 2005 Aug;125(8):643-52. [16079615 ]
General Function:
Triglyceride lipase activity
Specific Function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular Weight:
62520.62 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory>100 uMNot AvailableBindingDB 22726
References
  1. Wadkins RM, Hyatt JL, Wei X, Yoon KJ, Wierdl M, Edwards CC, Morton CL, Obenauer JC, Damodaran K, Beroza P, Danks MK, Potter PM: Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15. [15828829 ]
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
TP53
Uniprot ID:
P04637
Molecular Weight:
43652.79 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.01 uMAPR_p53Act_72h_dnApredica
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]