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benzophenone

Chemical Structure

General Material Information

Preferred name benzophenone
Trivial Name Benzophenone
Short Description diphenylketone
Formula C13 H10 O
CAS Number 119-61-9
Deleted CAS Number 852361-03-6
FEMA Number 2134
FDA UNII 701M4TTV9O
Nikkaji Number J2.481C
Beilstein Number 1238185
MDL MFCD00003076
COE Number 166
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 831 benzophenone
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 119-61-9 ; BENZOPHENONE
Synonyms
  • adjutan 6016
  • benzene, benzoyl-
  • benzophenone cryst.
  • benzophenone crystals
  • benzophenone extra pure
  • benzophenone FCC
  • benzophenone flake
  • benzophenone flakes
  • benzoyl benzene
  • benzoylbenzene
  • diphenyl ketone
  • alpha-oxo diphenyl methane
  • diphenyl methanone
  • diphenyl-methanone
  • diphenylketone
  • a-oxo diphenylmethane
  • diphenylmethanone
  • kayacure BP
  • ketone, diphenyl
  • methanone, diphenyl-
  • a- oxoditane
  • alpha- oxoditane
  • phenyl ketone
  • speedcure BP
  • α-Oxodiphenylmethane
  • α-Oxoditane
  • Darocur BP
  • Lowlite 24
  • NSC 8077
  • Kayacure BP 100
  • BLS 531
  • Runtecure 1020
  • BP
  • Irgacure BP
  • Winure BP
  • JRCure 1020
  • Daracure 1137
  • Gencure BP
  • PI BP
  • Photoinitiator BP
  • Hycure Benzophenone
  • B 0083
  • Omnirad BP
  • SB-PI 710
  • Chemcure BP

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

diphenylmethanone
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:119-61-9
Pubchem (cid):3102
Pubchem (sid):134974554
Pherobase:View
Publications by PubMed
The FEMA GRAS assessment of aromatic substituted secondary alcohols, ketones, and related esters used as flavor ingredients.
Toxicology and carcinogenesis studies of benzophenone (CAS No. 119-61-9) in F344/N rats and B6C3F1 mice (feed studies).
NTP technical report on the toxicity studies of benzophenone (CAS No. 119-61-9). Administered in feed to F344/N rats and B6C3F mice.
Safety evaluation of benzophenone.
Comparison between solid phase microextraction (SPME) and hollow fiber liquid phase microextraction (HFLPME) for determination of extractables from post-consumer recycled PET into food simulants.
Post-harvest UV-B irradiation induces changes of phenol contents and corresponding biosynthetic gene expression in peaches and nectarines.
Migration study of optical brighteners from polymer packing materials to jam squeeze and fruit drink by spectrofluorimetry and RP-HPLC methods.
Molecular evolution and sequence divergence of plant chalcone synthase and chalcone synthase-Like genes.
Model studies of migration from paper and board into fruit and vegetables and into Tenax™ as a food simulant.
Printing ink compounds in foods: UK survey results.
Measurement of urinary biomarkers of parabens, benzophenone-3, and phthalates in a Belgian population.
Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives.
Iriflophenone-3-C-glucoside from Cyclopia genistoides: isolation and quantitative comparison of antioxidant capacity with mangiferin and isomangiferin using on-line HPLC antioxidant assays.
Induction of p21(Waf1/Cip1) by garcinol via downregulation of p38-MAPK signaling in p53-independent H1299 lung cancer.
Urinary concentrations of environmental phenols in pregnant women in a pilot study of the National Children's Study.
Optimization of matrix solid-phase dispersion for the rapid determination of salicylate and benzophenone-type UV absorbing substances in marketed fish.
Evaluation of the migration of 15 photo-initiators from cardboard packaging into Tenax(®) using ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS).
Optimisation of an analytical method and results from the inter-laboratory comparison of the migration of regulated substances from food packaging into the new mandatory European Union simulant for dry foodstuffs.
Bio-based coatings as potential barriers to chemical contaminants from recycled paper and board for food packaging.
Childhood exposure to DEHP, DBP and BBP under existing chemical management systems: a comparative study of sources of childhood exposure in Korea and in Denmark.
Widespread occurrence of bisphenol A diglycidyl ethers, p-hydroxybenzoic acid esters (parabens), benzophenone type-UV filters, triclosan, and triclocarban in human urine from Athens, Greece.
Solvent-assisted dispersive solid phase extraction.
Survey on the occurrence of photo-initiators and amine synergists in cartonboard packaging on the German market and their migration into the packaged foodstuffs.
Rapid screening method to study the reactivity of UV filter substances towards skin proteins by high-performance thin-layer chromatography.
Regulation of lipid and glucose homeostasis by mango tree leaf extract is mediated by AMPK and PI3K/AKT signaling pathways.
Molecular design, synthesis and biological evaluation of BP-O-DAPY and O-DAPY derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors.
[Determination of the migration of seven photoinitiators in food packaging materials into aqueous solvent].
Synthesis and characterization of polymerizable one-component photoinitiator based on sesamol.
Targeted multidimensional gas chromatography using a heart-cutting device and cryogenic focusing for the determination of benzophenone derivatives in foodstuffs.
Isolation, structural elucidation, MS profiling, and evaluation of triglyceride accumulation inhibitory effects of benzophenone C-glucosides from leaves of Mangifera indica L.
Food ingredient extracts of Cyclopia subternata (Honeybush): variation in phenolic composition and antioxidant capacity.
Effect of relative humidity on the migration of benzophenone from paperboard into the food simulant Tenax® and modelling hereof.
An amperometric sensor for the determination of benzophenone in food packaging materials based on the electropolymerized molecularly imprinted poly-o-phenylenediamine film.
Potential role of garcinol as an anticancer agent.
Urinary levels of triclosan and parabens are associated with aeroallergen and food sensitization.
Simultaneous analysis and monitoring of 16 UV filters in cosmetics by high-performance liquid chromatography.
The power of hyphenated chromatography/time-of-flight mass spectrometry in public health laboratories.
Identification and quantification of the migration of chemicals from plastic baby bottles used as substitutes for polycarbonate.
7-epiclusianone, the natural prenylated benzophenone, inhibits superoxide anions in the neutrophil respiratory burst.
Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain).
Preventing false negatives with high-resolution mass spectrometry: the benzophenone case.
Identification of benzophenone C-glucosides from mango tree leaves and their inhibitory effect on triglyceride accumulation in 3T3-L1 adipocytes.
[Determination of photoinitiators in printing inks used in food contact materials].
[Safety verification for reuse of PET and glass bottles].
Garcinol inhibits cell proliferation and promotes apoptosis in pancreatic adenocarcinoma cells.
Metabolism of a new herbicide, [(14)c]pyribenzoxim, in rice.
4-Methylbenzophenone and benzophenone are inactive in the micronucleus assay.
Garcinol promotes neurogenesis in rat cortical progenitor cells through the duration of extracellular signal-regulated kinase signaling.
Effect of 2,4-dihydroxybenzophenone (BP1) on early life-stage development of the marine copepod Acartia tonsa at different temperatures and salinities.
A new method for the determination of carbonyl compounds in wines by headspace solid-phase microextraction coupled to gas chromatography-ion trap mass spectrometry.
Photoinduced reduction of divalent mercury in ice by organic matter.
A rapid High Performance Liquid Chromatographic (HPLC) method for the simultaneous determination of seven UV filters found in sunscreen and cosmetics.
Rapid multi-analyte quantification of benzophenone, 4-methylbenzophenone and related derivatives from paperboard food packaging.
Analysis of benzophenone and 4-methylbenzophenone in breakfast cereals using ultrasonic extraction in combination with gas chromatography-tandem mass spectrometry (GC-MS(n)).
Evaluation of sub-critical water as an extraction fluid for model contaminants from recycled PET for reuse as food packaging material.
[Hazards for health related to migration of substances from packaging into food].
Widespread occurrence of estrogenic UV-filters in aquatic ecosystems in Switzerland.
Importance of prey and predator feeding behaviors for trophic transfer and secondary poisoning.
Migration of photoinitiators by gas phase into dry foods.
Study of the migration of photoinitiators used in printed food-packaging materials into food simulants.
Determination of low-level ink photoinitiator residues in packaged milk by solid-phase extraction and LC-ESI/MS/MS using triple-quadrupole mass analyzer.
Photostability and phytotoxicity of selected sunscreen agents and their degradation mixtures in water.
Identification and determination butylmethoxydibenzoylmethane in the presence benzophenone-3 and ethylhexylmethoxycinnamate in suncare preparation.
Synthesis and antifungal activity of 2-azetidinonyl-5-(2-benzoylphenoxy)methyl-1,3,4-oxadiazoles against seed-borne pathogens of Eleusine coracana (L.) Gaertn.
Bioassay and ultraperformance liquid chromatography/mass spectrometry guided isolation of apoptosis-inducing benzophenones and xanthone from the pericarp of Garcinia yunnanensis Hu.
Migration measurement and modelling from poly(ethylene terephthalate) (PET) into soft drinks and fruit juices in comparison with food simulants.
Polyisoprenylated benzophenones and an unusual polyisoprenylated tetracyclic xanthone from the fruits of Garcinia cambogia.
Determination of ink photoinitiators in packaged beverages by gas chromatography-mass spectrometry and liquid chromatography-mass spectrometry.
SiOx layer as functional barrier in polyethylene terephthalate (PET) bottles against potential contaminants from post-consumer recycled PET.
Development of a method to study the migration of six photoinitiators into powdered milk.
Development of a multimethod for the determination of photoinitiators in beverage packaging.
Development of an analytical method for the determination of photoinitiators used for food packaging materials with potential to migrate into milk.
In utero exposure to benzophenone-2 causes hypospadias through an estrogen receptor dependent mechanism.
Migration of organic compounds from a multilayer plastic-paper material intended for food packaging.
1,3-diene probes for detection of triplet carbonyls in biological systems.
Soil metabolism of a new herbicide, [14C]Pyribenzoxim, under flooded conditions.
Carcinogenesis studies of benzophenone in rats and mice.
The FEMA GRAS assessment of aromatic substituted secondary alcohols, ketones, and related esters used as flavor ingredients.
[Migration of bisphenol A and benzophenones from paper and paperboard products used in contact with food].
A two-generation reproductive toxicity study of benzophenone in rats.
Application of Finite Element Analysis (FEA) for the simulation of release of additives from multilayer polymeric packaging structures.
Migration of contaminants by gas phase transfer from carton board and corrugated board box secondary packaging into foods.
Identification of rat urinary and fecal metabolites of a new herbicide, pyribenzoxim.
[Estrogenic activity of ultraviolet absorbers and the related compounds].
Estrogenic and antiandrogenic activities of 17 benzophenone derivatives used as UV stabilizers and sunscreens.
Determination of sixteen UV filters in suncare formulations by high-performance liquid chromatography.
Characterization of gallotannins and benzophenone derivatives from mango (Mangifera indica L. cv. 'Tommy Atkins') peels, pulp and kernels by high-performance liquid chromatography/electrospray ionization mass spectrometry.
Chemical analysis and genotoxicological safety assessment of paper and paperboard used for food packaging.
Effectiveness of polypropylene film as a barrier to migration from recycled paperboard packaging to fatty and high-moisture food.
Contaminants and levels of occurrence in washed and shredded poly(ethylene terephthalate) from curbside collection. Part 1: Extraction conditions.
Benzophenone in cartonboard packaging materials and the factors that influence its migration into food.
Migration of surrogate contaminants in paper and paperboard into water through polyethylene coating layer.
[Determination of alkylphenols, bisphenol A, benzophenone and phthalates in containers of baby food, and migration into food simulants].
Evaluating the potential for recycling all PET bottles into new food packaging.
Induction of apoptosis by garcinol and curcumin through cytochrome c release and activation of caspases in human leukemia HL-60 cells.
Analytical procedure for quantifying five compounds suspected as possible contaminants in recycled paper/paperboard for food packaging.
Free radical scavenging activity and antiulcer activity of garcinol from Garcinia indica fruit rind.
Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind.
A polyisoprenylated benzophenone from Cuban propolis.
Migration studies from paper and board food packaging materials. Part 2. Survey for residues of dialkylamino benzophenone UV-cure ink photoinitiators.
Migration studies from paper and board food packaging materials. 1. Compositional analysis.
Safety evaluation of benzophenone-3 after dermal administration in rats.
Current research on food contact materials undertaken by the UK Ministry of Agriculture, Fisheries and Food.
Safety evaluation of benzophenone.
Cysteine-374 of actin resides at the gelsolin contact site in the EGTA-resistant actin-gelsolin complex.
In vivo percutaneous absorption of fragrance ingredients in rhesus monkeys and humans.
Effect of food on absorption of 450191-S, a 1H-1,2,4-triazolyl benzophenone derivative from rat small intestine.
[Pharmacological studies on drug dependence. (III): Intravenous self-administration of some CNS-affecting drugs and a new sleep-inducer, 1H-1, 2, 4-triazolyl benzophenone derivative (450191-S), in rats].
U.v. absorbers in sun cosmetics 1978.
[Migration of UV stabilizers, derivatives of benzophenone].

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C06354
HMDB (The Human Metabolome Database):HMDB32049
FooDB:FDB008753
YMDB (Yeast Metabolome Database):YMDB02308
Export Tariff Code:2914.39.9000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
free from chlorine; also food chemicals codex

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 182.22189331055
Melting Point 47 to 51°C @ 760 mm Hg
Boiling Point 305 to 307°C @ 760 mm Hg
Boiling Point 170 to 171°C @ 15 mm Hg
Vapor Pressure 0.001 mmHg @ 25 °C
Vapor Density 6.3
Flash Point TCC Value 100 °C TCC
logP (o/w) 3.18
Shelf life 36 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
fixed oils Yes
paraffin oil Yes
water, 137 mg/L @ 25 °C (exp) Yes
glycerin No
Stability
bath foam Unspecified
non-discoloring in most media Unspecified
powder Unspecified
shampoo Unspecified

Organoleptic Properties

Odor Type: Balsamic
balsamic, rose, metallic, powdery, geranium, herbal
Odor strength medium , recommend smelling in a 10.00 % solution or less
Substantivity 394 hour(s) at 100.00 %
Luebke, William tgsc, (1981) At 10.00 % in dipropylene glycol. balsam rose metallic powdery geranium
Flavor Type: Geranium
plastic, geranium, herbal, metallic, rose, phenolic
Luebke, William tgsc, (1997) Plastic geranium herbal metallic rose phenolic
Useful in: sweet others. Slightly citrus, somewhat fruity
General comment Citric, slightly fruity

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi N - Irritant, Dangerous for the environment.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
R 51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
S 02 - Keep out of the reach of children.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Carcinogenicity (Category 2), H351
Acute aquatic toxicity (Category 1), H400
Chronic aquatic toxicity (Category 1), H410
GHS Label elements, including precautionary statements
Pictogramhealth-hazard.jpgenvironment.jpg
Signal word Warning
Hazard statement(s)
H351 - Suspected of causing cancer
H400 - Very toxic to aquatic life
H410 - Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
P201 - Obtain special instructions before use.
P202 - Do not handle until all safety precautions have been read and understood.
P273 - Avoid release to the environment.
P281 - Use personal protective equipment as required.
P308 + P313 - IF exposed or concerned: Get medical advice/attention.
P391 - Collect spillage. Hazardous to the aquatic environment
P405 - Store locked up.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Human Experience:
6 % solution: non-sensitising.
Oral/Parenteral Toxicity:
oral-rat LD50 > 10000 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 873, 1973.

oral-mouse LD50 2895 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
European Journal of Toxicology and Environmental Hygiene. Vol. 9, Pg. 99, 1976.

intraperitoneal-mouse LD50 727 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: TREMOR BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
European Journal of Toxicology and Environmental Hygiene. Vol. 9, Pg. 99, 1976.

Dermal Toxicity:
skin-rabbit LD50 3535 mg/kg
Food and Cosmetics Toxicology. Vol. 11, Pg. 873, 1973.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for benzophenone usage levels up to:
6.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 23.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 11.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 3.7 (μg/person/day)
Threshold of Concern:90 (μg/person/day)
Structure Class: III
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -2.40000
beverages(nonalcoholic): -0.50000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.61000
fruit ices: -0.61000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -1.70000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 69, (FGE.69)[1] - Consideration of aromatic substituted secondary alcohols, ketones and related esters evaluated by JECFA (57th meeting) structurally related to aromatic ketones from chemical group 21 evaluated by EFSA in FGE.16 (2006) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Toxicological evaluation of benzophenone
View page or View pdf

Report of ESCO WG on non-plastic Food Contact Materials
View page or View pdf

Safety of benzophenone to be used as flavouring
View page or View pdf

Safety and efficacy of 4-phenylbut-3-en-2-one and benzophenone belonging to chemical group 21 when used as flavouring compounds for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 69, Revision 1 (FGE.69Rev1): consideration of aromatic substituted secondary alcohols, ketones and related esters evaluated by JECFA (57th meeting), structurally related to aromatic ketones from chemical group 21 evaluated by EFSA in FGE.16Rev2
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
NIOSH International Chemical Safety Cards:search
Chemical Carcinogenesis Research Information System:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):119-61-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3102
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 3077
WGK Germany:2
diphenylmethanone
Chemidplus:0000119619
EPA/NOAA CAMEO:hazardous materials
RTECS:119-61-9