BENZOPHENONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10O
Molecular Weight	182.2179
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=RWCCWEUUXYIKHB-UHFFFAOYSA-N

InChI=1S/C13H10O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

HIDE SMILES / InChI

Description
Sources: http://www.drugbank.ca/drugs/DB01878
Curator's Comment: Description was created using several sources including: http://apps.who.int/iris/bitstream/10665/42578/1/WHO_TRS_909.pdf; http://www.fda.gov/food/ingredientspackaginglabeling/foodadditivesingredients/ucm091048.htm; http://www.fda.gov/downloads/drugs/developmentapprovalprocess/developmentresources/over-the-counterotcdrugs/statusofotcrulemakings/ucm090435.pdf; https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5a68508b-f1fa-4f03-b28a-554e24cf58d6; https://clinicaltrials.gov/ct2/show/NCT01695356?term=BENZOPHENONE&rank=1; https://clinicaltrials.gov/ct2/show/NCT01695356?term=BENZOPHENONE&rank=1; https://www.ncbi.nlm.nih.gov/pubmed/26753716

Benzophenone is the organic compound. It is a flavouring agent evaluated as safe at current levels of intake by joint FAO/WHO Expert Committee on Food Additives (JECFA) and approved by FDA as a food additive and as UV protector. Substituted benzophenones such as oxybenzone (benzophenone-3) and dioxybenzone are used in sunscreens in cosmetics and as a sunscreen ingredients in some topical drugs in combination with skin lighteners for gradual fading of dark (brownish) areas in the skin such as freckles, age and liver spots or treatment of melanosis. Benzophenone derivatives can be used as a photo initiators. Benzophenone used in practical synthesis of some drugs.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Skin pigmentation 4 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=dcf6ec95-78bc-42cc-8f0c-60b6d2d1fb08	Primary		Approved 8429	METASOL Approved Use For the gradual fading of dark (brownish) areas in the skin such as freckles, age and liver spots

PubMed

Title	Date	PubMed
Hydrogen abstraction from ionic liquids by benzophenone triplet excited states.	2001 Nov 21	12240077
Photoimmobilization of biomolecules within a 3-dimensional hydrogel matrix.	2002	12182548
Structure based design of benzophenone-based non-thiol farnesyltransferase inhibitors.	2002	12171543
The use of a photoactivatable kaempferol analogue to probe the role of flavonol 3-O-galactosyltransferase in pollen germination.	2002	12083465
Evaluating the potential for recycling all PET bottles into new food packaging.	2002	11962702
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.	2002 Apr	12147041
Complete LC/MS analysis of a Tinnevelli senna pod extract and subsequent isolation and identification of two new benzophenone glucosides.	2002 Apr	11988861
Quinoxaline 1,4-dioxides: hypoxia-selective therapeutic agents.	2002 Apr	11933073
Oxygen transfer from sulfoxides: oxidation of alkylarenes catalyzed by a polyoxomolybdate, [PMo12O40]3-.	2002 Apr 24	11960434
[Determination of alkylphenols, bisphenol A, benzophenone and phthalates in containers of baby food, and migration into food simulants].	2002 Aug	12436722
New photoactivators for multiphoton excited three-dimensional submicron cross-linking of proteins: bovine serum albumin and type 1 collagen.	2002 Aug	12194208
4,4'-Benzophenone-O,O'-disulfamate: a potent inhibitor of steroid sulfatase.	2002 Aug 19	12127511
The development of an improved carrier system for sunscreen formulations based on crystalline lipid nanoparticles.	2002 Aug 21	12176282
Triplet energy distribution in photoinitiators containing two dissociable groups.	2002 Aug 23	12182651
Genotoxic activation of benzophenone and its two metabolites by human cytochrome P450s in SOS/umu assay.	2002 Aug 26	12160905
Oligonucleotides containing 7-vinyl-7-deazaguanine as a facile strategy for expanding the functional diversity of DNA.	2002 Aug 5	12113802
Migration of surrogate contaminants in paper and paperboard into water through polyethylene coating layer.	2002 Dec	12623681
Benzophenone-induced estrogenic potency in ovariectomized rats.	2002 Dec	12451449
Structure-reactivity relationships in the photoreduction of n,pi*-excited ketones and azoalkanes: the effect of reaction thermodynamics, excited-state electrophilicity, and antibonding character in the transition state.	2002 Feb	12659131
Stereoselective intramolecular hydrogen abstraction by a chiral benzophenone derivative.	2002 Feb 7	12120404
Methionine proximity assay, a novel method for exploring peptide ligand-receptor interaction.	2002 Feb-Nov	12503623
[Results of a French nationwide survey of cutaneous side effects of ketoprofen gel reported between September 1996 and August 2000].	2002 Jan-Feb	12090148
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002 Jul	12224631
New cytotoxic coumarins and prenylated benzophenone derivatives from the bark of Ochrocarpos punctatus from the Madagascar rainforest.	2002 Jul	12141854
Identification of the principal binding site for RGD-containing ligands in the alpha(V)beta(3) integrin: a photoaffinity cross-linking study.	2002 Jul 2	12081480
Hydrogenation without a transition-metal catalyst: on the mechanism of the base-catalyzed hydrogenation of ketones.	2002 Jul 24	12121113
Identification of two tamoxifen target proteins by photolabeling with 4-(2-morpholinoethoxy)benzophenone.	2002 Jul-Aug	12121132
Stability indicating methods for the determination of loratadine in the presence of its degradation product.	2002 Jun 15	12049969
Synthesis and protein kinase inhibitory activity of balanol analogues with modified benzophenone subunits.	2002 Jun 6	12036372
Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum.	2002 Mar	11882941
Photochemistry of benzophenone immobilized in a major groove of DNA: formation of thermally reversible interstrand cross-link.	2002 Mar 13	11878957
Oxidation of sulfides and disulfides under electron transfer or singlet oxygen photosensitization using soluble or grafted sensitizers.	2002 May	12653474
[Cross-reaction potentials of ketoprofen].	2002 May 12	12063858
Molecular structure of the solvated proton in isolated salts. Short, strong, low barrier (SSLB) H-bonds.	2002 Nov 20	12431118
p-Nitrobenzenesulfenate esters as precursors for laser flash photolysis studies of alkyl radicals.	2002 Nov 29	12444656
Photoinduced electron transfer cleavage of oxetane adducts of uracil and cytosine.	2002 Sep	12665298
Biotransformation of cyclizine in greyhounds. 2: N(1)-dealkylation and identification of some neutral and phenolic metabolites in canine urine by gas chromatography-mass spectrometry.	2002 Sep	12396277
Modulation of GABA(A) receptor-mediated currents by benzophenone derivatives in isolated rat Purkinje neurones.	2002 Sep	12367621
Identification of the extracellular loop 2 as the point of interaction between the N terminus of the chemokine MIP-1alpha and its CCR1 receptor.	2002 Sep	12181451
Catalytic asymmetric Mannich reactions of glycine derivatives with imines. A new approach to optically active alpha,beta-diamino acid derivatives.	2003 Apr 4	12662026
Biochemical and structural studies with prenyl diphosphate analogues provide insights into isoprenoid recognition by protein farnesyl transferase.	2003 Apr 8	12667062
Structure-activity relationships of novel anti-malarial agents: part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides.	2003 Feb 10	12565929
Determination of benzophenones in a cosmetic matrix by supercritical fluid extraction and capillary electrophoresis.	2003 Feb 14	12613821
Cryptophycin affinity labels: synthesis and biological activity of a benzophenone analogue of cryptophycin-24.	2003 Feb 24	12639575
Three-fold interpenetrating three-dimensional networks based on C-methylcalix[4]resorcinarene incorporating benzophenone guest molecules.	2003 Feb 7	12613638
New series of N-substituted phenyl ketone oxime ethers: synthesis and bovine beta3-adrenergic agonistic activities.	2003 Jan	12622245
Tuning copper-dioxygen reactivity and exogenous substrate oxidations via alterations in ligand electronics.	2003 Jan 22	12526654
Unexpected differences in the alpha-halogenation and related reactivity of sulfones with perhaloalkanes in KOH-t-BuOH.	2003 Jan 24	12530877
High-intensity ultrasound-promoted reformatsky reactions.	2003 Jan 24	12530861
Diazotrifluoropropionamido-containing prenylcysteines: syntheses and applications for studying isoprenoid-protein interactions.	2003 Mar 6	12605471

Patents

Sample Use Guides

In Vivo Use Guide

Apply a small amount of gel as a thin layer on the affected area twice daily, or use as directed by a doctor (50 g of gel contains 1 g of hydroquinone and 0.05 g benzophenone)

Route of Administration: Topical

In Vitro Use Guide

The patterned co-culture of different types of living cells in a microfluidic device is crucial for the analysis of cellular interactions and cell-cell communication. Cell patterning was achieved by photocrosslinking 0.2 M benzophenone-4-isocyocyanate in a microfluidic channel. Patterning and co-culture of non-adherent K562 cells and adherent RF-6A cells was achieved by successive rounds of patterning. The present approach is expected to be useful for the development of in vitro methods for studying cell signaling.

Name

Type

Language

BENZOPHENONE

Official Name

English

Benzophenone [WHO-DD]

Common Name

English

BENZOPHENONE [HSDB]

Common Name

English

DIPHENYLMETHANONE

Systematic Name

English

PHENYTOIN SODIUM IMPURITY A [EP IMPURITY]

Common Name

English

PHENYTOIN IMPURITY BENZOPHENONE [USP IMPURITY]

Common Name

English

HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY H [EP IMPURITY]

Common Name

English

BENZOPHENONE [USP IMPURITY]

Common Name

English

KAYACURE BP

Common Name

English

DIMENHYDRINATE IMPURITY J [EP IMPURITY]

Common Name

English

FEMA NO. 2134

Code

English

BENZOPHENONE [FHFI]

Common Name

English

DIMENHYDRINATE IMPURITY J

Common Name

English

BENZOYLBENZENE

Systematic Name

English

ADJUTAN 6016

Common Name

English

PHENYL KETONE

Systematic Name

English

PHENYTOIN SODIUM IMPURITY BENZOPHENONE [USP IMPURITY]

Common Name

English

DIPHENHYDRAMINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Common Name

English

DIPHENYL KETONE

Systematic Name

English

NSC-8077

Code

English

.ALPHA.-OXODIPHENYLMETHANE

Common Name

English

BENZOPHENONE [INCI]

Common Name

English

BENZOPHENONE [FCC]

Common Name

English

DAROCUR BP

Common Name

English

DIPHENHYDRAMINE IMPURITY E

Common Name

English

.ALPHA.-OXODITANE

Common Name

English

BENZOPHENONE [MI]

Common Name

English

BENZOPHENONE [IARC]

Common Name

English

SPEEDCURE BP

Common Name

English

BENZOPHENONE [USP-RS]

Common Name

English

PHENYTOIN IMPURITY A [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

BENZOPHENONE