U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of BENZOPHENONE

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

Molecular Formula C13H10O
Molecular Weight 182.2179
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment: C. S. Marvel and W. M. Sperry described the synthesis of benzothenone in 1928

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
METASOL

Approved Use

For the gradual fading of dark (brownish) areas in the skin such as freckles, age and liver spots
PubMed

PubMed

TitleDatePubMed
Time-resolved spectroscopy of sulfur- and carboxy-substituted N-alkylphthalimides.
2001 Apr 1
Synthesis, molecular modeling, and structure-activity relationship of benzophenone-based CAAX-peptidomimetic farnesyltransferase inhibitors.
2001 Aug 30
Benzophenone derivatives and related compounds as potent histamine H3-receptor antagonists and potential PET/SPECT ligands.
2001 Feb
Three xanthones and a benzophenone from Garcinia mangostana.
2001 Jul
Synthesis and biological evaluation of didemnin photoaffinity analogues.
2001 Jul 23
Structure-activity relationships of novel anti-malarial agents: 1. arylacyl and cyclohexylacyl derivatives of 5-amino-2-tolylacetylaminobenzophenone.
2001 Jun
An iridoid gentiobioside, a benzophenone glucoside and acylated flavone C-glycosides from Tripterospermum japonicum (Sieb. et Zucc.) Maxim.
2001 Jun
Unusual temperature-dependent diastereoselectivity in the [2 + 2] photocycloaddition (Paternò-Büchi reaction) of benzophenone to cis- and trans-cyclooctene through conformational control.
2001 Mar 14
Reactions of PhSCH(2)Li and NCCH(2)Li with benzaldehyde and benzophenone: when does the mechanism change from ET to polar?
2001 Mar 23
[Allergies to ketoprofen gels].
2001 Mar 31
Report of 19 cases of photoallergic contact dermatitis to sunscreens seen at the Skin and Cancer Foundation.
2001 Nov
Pestalone, a new antibiotic produced by a marine fungus in response to bacterial challenge.
2001 Nov
Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems.
2001 Nov 16
Synthesis, structure, and reactions of (acylimino)triaryl-lambda(5)-bismuthanes: first comparative study of the (acylimino)pnictorane series.
2001 Nov 7
The [2+2]-photocycloaddition of aromatic aldehydes and ketones to 3,4-dihydro-2-pyridones: regioselectivity, diastereoselectivity, and reductive ring opening of the product oxetanes.
2001 Oct 15
Solid-phase microextraction and gas chromatography-mass spectrometry analysis of p,p' -DDE in biological samples.
2001 Sep 15
The use of a photoactivatable kaempferol analogue to probe the role of flavonol 3-O-galactosyltransferase in pollen germination.
2002
Experimental study on phototoxicity and the photosensitization potential of ketoprofen, suprofen, tiaprofenic acid and benzophenone and the photocross-reactivity in guinea pigs.
2002 Apr
Two benzophenone O-arabinosides and a chromone from Hypericum annulatum.
2002 Apr
Quinoxaline 1,4-dioxides: hypoxia-selective therapeutic agents.
2002 Apr
A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from alpha-oxy-substituted derivatives through Norrish-type I cleavage.
2002 Apr 17
New photoactivators for multiphoton excited three-dimensional submicron cross-linking of proteins: bovine serum albumin and type 1 collagen.
2002 Aug
4,4'-Benzophenone-O,O'-disulfamate: a potent inhibitor of steroid sulfatase.
2002 Aug 19
Benzophenone-induced estrogenic potency in ovariectomized rats.
2002 Dec
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
Structure-based design of cyclooxygenase-2 selectivity into ketoprofen.
2002 Feb 25
Stereoselective intramolecular hydrogen abstraction by a chiral benzophenone derivative.
2002 Feb 7
Methionine proximity assay, a novel method for exploring peptide ligand-receptor interaction.
2002 Feb-Nov
The polymer-supported phospholipid bilayer: tethering as a new approach to substrate-membrane stabilization.
2002 Jan-Feb
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
New cytotoxic coumarins and prenylated benzophenone derivatives from the bark of Ochrocarpos punctatus from the Madagascar rainforest.
2002 Jul
Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum.
2002 Mar
Photochemistry of benzophenone immobilized in a major groove of DNA: formation of thermally reversible interstrand cross-link.
2002 Mar 13
Photoinduced electron transfer cleavage of oxetane adducts of uracil and cytosine.
2002 Sep
Biochemical and structural studies with prenyl diphosphate analogues provide insights into isoprenoid recognition by protein farnesyl transferase.
2003 Apr 8
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
Determination of benzophenones in a cosmetic matrix by supercritical fluid extraction and capillary electrophoresis.
2003 Feb 14
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 16 15:46:17 UTC 2022
Edited
by admin
on Fri Dec 16 15:46:17 UTC 2022
Record UNII
701M4TTV9O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZOPHENONE
FCC   FHFI   HSDB   INCI   MI   USP-RS   WHO-DD  
INCI  
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
EP  
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
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
CFR 21 CFR 172.515
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
EPA PESTICIDE CODE 315
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
Code System Code Type Description
EPA CompTox
DTXSID0021961
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
HSDB
6809
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
RS_ITEM_NUM
1056130
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
CAS
119-61-9
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
EVMPD
SUB13019MIG
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
WIKIPEDIA
BENZOPHENONE
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
NSC
8077
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
PUBCHEM
3102
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
MERCK INDEX
M2370
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY Merck Index
CHEBI
41308
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
FDA UNII
701M4TTV9O
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
ECHA (EC/EINECS)
204-337-6
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
DRUG BANK
DB01878
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
RXCUI
18997
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY RxNorm
MESH
C047723
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
DAILYMED
701M4TTV9O
Created by admin on Fri Dec 16 15:46:17 UTC 2022 , Edited by admin on Fri Dec 16 15:46:17 UTC 2022
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY