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
O-Methylephedrine: a versatile and highly efficient ortho-directing group. Synthesis of enantiopure 1,2-disubstituted ferrocene derivatives.
2001 Dec 28
Strategy for on-line preconcentration in chromatographic separations.
2001 Nov 15
Hydrogen abstraction from ionic liquids by benzophenone triplet excited states.
2001 Nov 21
Polymer-supported lipid bilayers on benzophenone-modified substrates.
2001 Spring
Photoimmobilization of biomolecules within a 3-dimensional hydrogel matrix.
2002
The use of a photoactivatable kaempferol analogue to probe the role of flavonol 3-O-galactosyltransferase in pollen germination.
2002
Evaluating the potential for recycling all PET bottles into new food packaging.
2002
Complete LC/MS analysis of a Tinnevelli senna pod extract and subsequent isolation and identification of two new benzophenone glucosides.
2002 Apr
Two benzophenone O-arabinosides and a chromone from Hypericum annulatum.
2002 Apr
Unusual temperature dependence in the cis/trans-oxetane formation discloses competitive syn versus anti attack for the Paternò-Büchi reaction of triplet-excited ketones with cis- and trans-cylooctenes. Conformational control of diastereoselectivity in the cyclization and cleavage of preoxetane diradicals.
2002 Apr 10
Oxygen transfer from sulfoxides: oxidation of alkylarenes catalyzed by a polyoxomolybdate, [PMo12O40]3-.
2002 Apr 24
[Determination of alkylphenols, bisphenol A, benzophenone and phthalates in containers of baby food, and migration into food simulants].
2002 Aug
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
The development of an improved carrier system for sunscreen formulations based on crystalline lipid nanoparticles.
2002 Aug 21
Triplet energy distribution in photoinitiators containing two dissociable groups.
2002 Aug 23
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
4-[18F]fluoroarylalkylethers via an improved synthesis of n.c.a. 4-[18F]fluorophenol.
2002 Feb
Non-thiol farnesyltransferase inhibitors: N-(4-Acylamino-3-benzoylphenyl)-4-nitrocinnamic acid amides.
2002 Feb
Mechanistic studies on the B(C(6)F(5))(3) catalyzed allylstannation of aromatic aldehydes with ortho donor substituents.
2002 Feb 20
Structure-based design of cyclooxygenase-2 selectivity into ketoprofen.
2002 Feb 25
Highly chemoselective hydrogenolysis of iodoarenes.
2002 Feb 8
Methionine proximity assay, a novel method for exploring peptide ligand-receptor interaction.
2002 Feb-Nov
Comparison of reporter gene assay and immature rat uterotrophic assay of twenty-three chemicals.
2002 Jan 15
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
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
Hydrogenation without a transition-metal catalyst: on the mechanism of the base-catalyzed hydrogenation of ketones.
2002 Jul 24
Synthesis and protein kinase inhibitory activity of balanol analogues with modified benzophenone subunits.
2002 Jun 6
Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum.
2002 Mar
Non-thiol farnesyltransferase inhibitors: structure-activity relationships of benzophenone-based bisubstrate analogue farnesyltransferase inhibitors.
2002 Mar
Photochemistry of benzophenone immobilized in a major groove of DNA: formation of thermally reversible interstrand cross-link.
2002 Mar 13
Oxidation of sulfides and disulfides under electron transfer or singlet oxygen photosensitization using soluble or grafted sensitizers.
2002 May
[Cross-reaction potentials of ketoprofen].
2002 May 12
Molecular structure of the solvated proton in isolated salts. Short, strong, low barrier (SSLB) H-bonds.
2002 Nov 20
p-Nitrobenzenesulfenate esters as precursors for laser flash photolysis studies of alkyl radicals.
2002 Nov 29
Photoinduced electron transfer cleavage of oxetane adducts of uracil and cytosine.
2002 Sep
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
Modulation of GABA(A) receptor-mediated currents by benzophenone derivatives in isolated rat Purkinje neurones.
2002 Sep
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
Catalytic asymmetric Mannich reactions of glycine derivatives with imines. A new approach to optically active alpha,beta-diamino acid derivatives.
2003 Apr 4
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
Cryptophycin affinity labels: synthesis and biological activity of a benzophenone analogue of cryptophycin-24.
2003 Feb 24
New series of N-substituted phenyl ketone oxime ethers: synthesis and bovine beta3-adrenergic agonistic activities.
2003 Jan
Tuning copper-dioxygen reactivity and exogenous substrate oxidations via alterations in ligand electronics.
2003 Jan 22
High-intensity ultrasound-promoted reformatsky reactions.
2003 Jan 24
Diazotrifluoropropionamido-containing prenylcysteines: syntheses and applications for studying isoprenoid-protein interactions.
2003 Mar 6
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 15 14:57:47 GMT 2023
Edited
by admin
on Fri Dec 15 14:57:47 GMT 2023
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 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
EPA PESTICIDE CODE 315
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID0021961
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
HSDB
6809
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
RS_ITEM_NUM
1056130
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
CAS
119-61-9
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
EVMPD
SUB13019MIG
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
WIKIPEDIA
BENZOPHENONE
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
NSC
8077
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
PUBCHEM
3102
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
MERCK INDEX
m2370
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY Merck Index
SMS_ID
100000077159
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
CHEBI
41308
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
FDA UNII
701M4TTV9O
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-337-6
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
DRUG BANK
DB01878
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
RXCUI
18997
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY RxNorm
MESH
C047723
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
DAILYMED
701M4TTV9O
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
JECFA MONOGRAPH
745
Created by admin on Fri Dec 15 14:57:47 GMT 2023 , Edited by admin on Fri Dec 15 14:57:47 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY