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    Also known as: 119-61-9, Diphenylmethanone, Diphenyl ketone, Benzoylbenzene, Methanone, diphenyl-, Phenyl ketone
    Molecular Formula
    C13H10O
    Molecular Weight
    182.22  g/mol
    InChI Key
    RWCCWEUUXYIKHB-UHFFFAOYSA-N
    FDA UNII
    701M4TTV9O
    Benzophenone
    Diphenylketone is a metabolite found in or produced by Saccharomyces cerevisiae.
    1 2D Structure

    Benzophenone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    diphenylmethanone
    2.1.2 InChI
    InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
    2.1.3 InChI Key
    RWCCWEUUXYIKHB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C(C=C1)C(=O)C2=CC=CC=C2
    2.2 Other Identifiers
    2.2.1 UNII
    701M4TTV9O
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 119-61-9

    2. Diphenylmethanone

    3. Diphenyl Ketone

    4. Benzoylbenzene

    5. Methanone, Diphenyl-

    6. Phenyl Ketone

    7. Ketone, Diphenyl

    8. Alpha-oxoditane

    9. Benzene, Benzoyl-

    10. Alpha-oxodiphenylmethane

    11. Diphenylketone

    12. Diphenyl-methanone

    13. Kayacure Bp

    14. .alpha.-oxoditane

    15. Adjutan 6016

    16. Fema No. 2134

    17. .alpha.-oxodiphenylmethane

    18. Diphenyl-methanon

    19. 1dzp

    20. Nsc 8077

    21. Mfcd00003076

    22. Chembl90039

    23. 701m4ttv9o

    24. Dtxsid0021961

    25. Chebi:41308

    26. Nsc-8077

    27. Ncgc00090787-05

    28. Dsstox_cid_1961

    29. Dsstox_rid_76429

    30. Dsstox_gsid_21961

    31. Diphenylmethanone (benzophenone)

    32. Caswell No. 081g

    33. Cas-119-61-9

    34. Ccris 629

    35. Hsdb 6809

    36. Wln: Rvr

    37. Einecs 204-337-6

    38. Epa Pesticide Chemical Code 000315

    39. Benzophenone (8ci)

    40. Phenylketone

    41. Unii-701m4ttv9o

    42. Benzopheneone

    43. Benzophenon

    44. Benzophenone-

    45. Benzoyl-benzene

    46. A-oxoditane

    47. Ai3-00754

    48. Meta-benzophenone

    49. Alpha -oxoditane

    50. Fema 2134

    51. Benzophenone Flakes

    52. Di(phenyl)methanone

    53. A-oxodiphenylmethane

    54. Methanone, Diphenyl- (9ci)

    55. Ph2co

    56. Speedcure Bp

    57. Darocur Bp

    58. Diphenylmethanone, 9ci

    59. Alpha -oxodiphenylmethane

    60. Dimenhydrinate Impurity J

    61. Benzophenone [mi]

    62. Benzophenone [fcc]

    63. Upcmld-dp071

    64. Benzophenone [fhfi]

    65. Benzophenone [hsdb]

    66. Benzophenone [iarc]

    67. Benzophenone [inci]

    68. Ec 204-337-6

    69. Bidd:pxr0008

    70. Schembl17745

    71. Mls001055400

    72. Adk Stab 1413

    73. Benzophenone [usp-rs]

    74. Benzophenone [who-dd]

    75. Bidd:er0022

    76. Benzophenone (diphenyl-ketone)

    77. Benzophenone (diphenylmethanone)

    78. Upcmld-dp071:001

    79. Bdbm22726

    80. Benzophenone, Analytical Standard

    81. Diphenhydramine Impurity E

    82. Amy7704

    83. Nsc8077

    84. Hms2268a24

    85. Zinc968233

    86. Benzophenone [usp Impurity]

    87. Benzophenone, >=99%, Fcc, Fg

    88. Hy-y0546

    89. Tox21_113465

    90. Tox21_202425

    91. Tox21_300058

    92. Benzophenone, Reagentplus(r), 99%

    93. S4438

    94. Stl363250

    95. Benzophenone, For Synthesis, 98.0%

    96. Akos000119029

    97. Tox21_113465_1

    98. Benzophenone (diphenyl-ketone)

    99. Db01878

    100. Benzophenone 100 Microg/ml In Methanol

    101. Benzophenone, Purum, >=99.0% (gc)

    102. Benzophenone, Reagentplus(r), >=99%

    103. Ncgc00090787-01

    104. Ncgc00090787-03

    105. Ncgc00090787-04

    106. Ncgc00090787-06

    107. Ncgc00090787-07

    108. Ncgc00090787-08

    109. Ncgc00254183-01

    110. Ncgc00259974-01

    111. Bp-21212

    112. Smr000112143

    113. Phenytoin Impurity A [ep Impurity]

    114. Benzophenone, Saj First Grade, >=99.0%

    115. Db-061602

    116. B0083

    117. Cs-0015323

    118. Ft-0622720

    119. Ft-0693251

    120. Benzophenone, Purified By Sublimation, >=99%

    121. Benzophenone, Vetec(tm) Reagent Grade, 98%

    122. C06354

    123. D72506

    124. Dimenhydrinate Impurity J [ep Impurity]

    125. Phenytoin Sodium Impurity A [ep Impurity]

    126. Q409482

    127. Melting Point Standard 47-49c, Analytical Standard

    128. Q-200691

    129. Phenytoin Impurity Benzophenone [usp Impurity]

    130. F0001-0309

    131. Z1245792986

    132. Benzophenone, European Pharmacopoeia (ep) Reference Standard

    133. Diphenhydramine Hydrochloride Impurity E [ep Impurity]

    134. Mettler-toledo Calibration Substance Me 18870, Benzophenone

    135. Phenytoin Sodium Impurity Benzophenone [usp Impurity]

    136. Benzophenone, United States Pharmacopeia (usp) Reference Standard

    137. Hydrocodone Hydrogen Tartrate 2.5-hydrate Impurity H [ep Impurity]

    138. Benzophenone, Pharmaceutical Secondary Standard; Certified Reference Material

    139. Mettler-toledo Calibration Substance Me 18870, Benzophenone, For The Calibration Of The Thermosystem 900, Traceable To Primary Standards (lgc)

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 182.22 g/mol
    Molecular Formula C13H10O
    XLogP33.4
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count2
    Exact Mass182.073164938 g/mol
    Monoisotopic Mass182.073164938 g/mol
    Topological Polar Surface Area17.1 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity165
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Photosensitizing Agents

    Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

    4.2 Absorption, Distribution and Excretion

    The percutaneous absorption of benzophenone was determined in vivo in monkeys. Absorption through occluded skin was approximately 70% of the applied dose in 24 hr. Under unoccluded conditions skin penetration was reduced to 44%, presumably because of evaporation from the site of application.

    European Commission/European Chemical Substances Information System; IUCLID Dataset, Benzophenone (CAS No. 119-61-9) (2000). Available from, as of March 18, 2015: https://esis.jrc.ec.europa.eu/

    /The authors/ gave /benzophenone/ orally ... (100 or 400 mg/kg) ... once per day for 3 days, to ovariectomized Sprague-Dawley (SD) rats, and all rats were killed 24 h after being given the last dose. ... At 24 hr after the last dose, the mean serum concentrations of benzophenone, benzhydrol and p-hydroxybenzophenone in the high-dosed rats were 10.4+/-1.0, 1.5+/-0.3, and 0.7+/-0.2 (mean +/- SE) umol/L, respectively, whereas in the serum of low-dosed rats these compounds were not detected. When a single oral administration of benzophenone (100 or 400 mg/kg) was given to intact female rats, serum concentrations of benzophenone, benzhydrol and p-hydroxybenzophenone increased in a dose-dependent manner 6 hr later. ...

    PMID:1245144 Nakagawa Y, Tayama K; Arch Toxicol 76 (12): 727-31 (2002)

    ... The percutaneous absorption of the fragrances benzyl acetate and five other benzyl derivatives (benzyl alcohol, benzyl benzoate, benzamide, benzoin and benzophenone) was determined in vivo in monkeys. Absorption through occluded skin was high for all cmpd (approx 70% of the applied dose in 24 hr) and no significant differences between the values for the different cmpd were observed. No correlations were seen between skin penetration of these cmpd and their octanol-water partition coefficients. Under unoccluded conditions skin penetration of the fragrances was reduced and there was great variability between cmpd, presumably because of variations in the rates of evaporation from the site of application.

    PMID:2379896 Bronaugh RL et al; Food Chem Toxicol 28 (5): 369-73 (1990)

    4.3 Metabolism/Metabolites

    In male Sprague-Dawley rats that received benzophenone by gavage, 1% of the administered dose was detected as p-hydroxybenzophenone in enzymetreated urine samples, but not in unhydrolyzed urine (Stocklinski et al., 1979). No p-hydroxybenzophenone was detected in the feces.

    DHHS/NTP; Toxicology and Carcinogenesis Studies of Benzophenone (CAS No. 119-61-9) Toxicity Report Series No. 61 NIH Pub No. 00-3943. Available from, as of March 18, 2015: https://ntp-server.niehs.nih.gov

    The results from recent studies show that some benzophenones (BPs) and their hydroxylated metabolites can function as weak estrogens (E2) in the environment. However, little is known about the structure-activity relationship of these molecules. We have examined the effects of exposure to ten different BPs on the proliferation of estrogen receptor (ER)-positive breast cancer cells and on the transcriptional activity of E2-target genes. We analyzed two genes that are tightly linked with estrogen-mediated proliferation, the CXCL12 and amphiregulin genes and two classical estrogen-responsive genes, the pS2 and progesterone receptor. Significant differences in the BPs efficiency to induce cell proliferation and endogenous E2-target gene expressions were observed. Using ERE-, Sp1-, AP1- and C3-reporter genes that contain different ER-binding sites in their promoter, we also showed significant differences in the BPs efficiency in activation of the ER transactivation. Together, our analyzes showed that the most active molecule is 4-hydroxy-BP. Docking analysis of the interaction of BPs in the ligand-binding pocket of ERa suggests that the minimum structural requirement for the estrogenic activity of BPs is a hydroxyl (OH) group in the phenyl A-ring that allows interaction with Glu-353, Arg-394 or Phe-404, which enhances the stability between BPs and ERa. Our modeling also indicates a loss of interaction between the OH groups of the phenyl B-ring and His-524. In addition, the presence of some OH groups in the phenyl B-ring can create repulsion forces, which may constrain helix 12 in an unfavorable position, explaining the differential estrogenic effects of BPs. These results, together with our analysis of BPs for their potency in activation of cell proliferation and ER-mediated transcription, report an improved understanding of the mechanism and structure-activity relationship of BPs. /benzophenones/

    Kerdivel G et al; PLoS One. 8(4):e60567 (2013)

    Benzophenone's main metabolic pathway in the rabbit is by reduction to benzhydrol, which is excreted in urine conjugated with glucoronic acid. Small amount (1%) is converted to p-hydroxybenzophenone following oral administration to rats. No p-hydroxybenzohydrol was detected in urine or feces.

    European Commission/European Chemical Substances Information System; IUCLID Dataset, Benzophenone (CAS No. 119-61-9) (2000). Available from, as of March 18, 2015: https://esis.jrc.ec.europa.eu/

    Benzophenone is a known human metabolite of cinnarizine.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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BHARUCH. 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    02-Jan-2021
    30-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (USD/KGS)    		 Number of Transactions

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