Benzophenone (CHEM002936)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2014-08-29 04:48:25 UTC
Update Date2026-05-14 17:19:25 UTC
Accession NumberCHEM002936
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).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • Suspected Compounds – Schymanski Project
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Flavouring Agent
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • PMT
  • Photosensitizing Agent
  • Plant Toxin
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
alpha-OxodiphenylmethaneChEBI
alpha-OxoditaneChEBI
BenzoylbenzeneChEBI
Diphenyl ketoneChEBI
DIPHENYLMETHANONEChEBI
PH2COChEBI
a-OxodiphenylmethaneGenerator
Α-oxodiphenylmethaneGenerator
a-OxoditaneGenerator
Α-oxoditaneGenerator
1DZPHMDB
Adjutan 6016HMDB
ADK stab 1413HMDB
alpha -OxodiphenylmethaneHMDB
alpha -OxoditaneHMDB
BenzopheneoneHMDB
BENZOPHENONE (8ci)HMDB
Benzophenone (diphenyl-ketone)HMDB
Benzoyl-benzeneHMDB
BZQHMDB
Di(phenyl)methanoneHMDB
Diphenyl-methanonHMDB
Diphenyl-methanoneHMDB
DiphenylketoneHMDB
Diphenylmethanone, 9ciHMDB
FEMA 2134HMDB
Kayacure BPHMDB
Ketone, diphenylHMDB
METHANONE, diphenyl- (9ci)HMDB
Phenyl ketoneHMDB
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 KeyRWCCWEUUXYIKHB-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
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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-b948527870febd59c85eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-4900000000-93e6c7526327719d728dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3900000000-23d78741cacbe9443a57Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-eb0842414a2a12ff24b3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-7c028c0aa3b44d2ee6beSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-b948527870febd59c85eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-4900000000-93e6c7526327719d728dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-3900000000-23d78741cacbe9443a57Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-eb0842414a2a12ff24b3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-7900000000-95f4bdf3395ce8c0bc20Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-6900000000-7c028c0aa3b44d2ee6beSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-3900000000-94e3675023c8e5cf8b46Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-0a4i-0900000000-1f9db6636ef926e9a822Spectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-0a4i-0900000000-c08dc4bd854f23a10ab6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-0900000000-1f9db6636ef926e9a822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-f048592c39e6448959f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0900000000-35d1d32df051465b3618Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-4e792aa67452f41d4fd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-2ea2893ee5ce1f203589Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-fb40d9e5c26915affa0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-7900000000-d9d95ec382ac97a7af66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-052cd8aa2cc34939880fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0900000000-f0b9223dd578ae5d011fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9200000000-4239c3243d5a26b7658fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-2aea314e447f6c21a0a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-81ba80bd5ec599f30980Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-2900000000-2142e08d17da4d6f92a3Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-6900000000-e66f1faddf56bc55ae47Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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. (2)
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.
Concentrations
StatusValueUnitSample LocationReference
DrugBank IDDB01878
HMDB IDHMDB0032049
FooDB IDFDB008753
Phenol Explorer IDNot Available
KNApSAcK IDC00055728
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDBZQ
Wikipedia LinkBenzophenone
Chemspider ID2991
ChEBI ID41308
PubChem Compound ID3102
Kegg Compound IDC06354
YMDB IDYMDB02308
ECMDB IDNot Available
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. https://www.ncbi.nlm.nih.gov/pubmed/?term=10728861
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10864504
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10877357
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14673848
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15373829
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15672204
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16212356
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16820853
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16853025
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16999485
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=17955805
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19388040
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=19655709
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=19939518
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=20534002
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21238557
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=21277784
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=21919502
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23963450
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24226914
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=25788150
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=26254646
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=26282042
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=30720459
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=32736220
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=33682414
28. 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.
29. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.