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Basic Information
CAS No.: 131-57-7
Name: Oxybenzone
Molecular Structure:
Molecular Structure of 131-57-7 (Oxybenzone)
Formula: C14H12O3
Molecular Weight: 228.247
Synonyms: Ultraviolet absorbent UV-9;2-Hydroxy-4-methoxy benzophenone(UV9);Uvinul 9;Sunscreen UV-15;UV 9;2-Hydroxy-4-methoxybenzophenone;Usaf cy-9;Aduvex 24;MOB;UF 3;ASL 24;Oxybenzon;Methanone,(2-hydroxy-4-methoxyphenyl)- phenyl-;Benzophenone, 2-hydroxy-4-methoxy-;Ongrostab HMB;Chimassorb 90;4-Methoxy-2-hydroxybenzophenone;Advastab 45;Sumisorb 110;Seesorb 101;Oxybenzone,131-57-7;UV-9 / BP-3;Methanone, (2-hydroxy-4-methoxyphenyl)phenyl-;2-hydroxyl-4-methylbenzophenone;
EINECS: 205-031-5
Density: 1.201 g/cm3
Melting Point: 62-64 °C(lit.)
Boiling Point: 370.3 °C at 760 mmHg
Flash Point: 140.5 °C
Solubility: water: <0.1 g/100 mL at 20 °C
Appearance: white to light yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 46.53000
LogP: 2.63180
Synthetic route
926236-29-5

2-hydroxy-4-methoxybenzhydrol

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen In acetonitrile at 60℃; for 0.5h;97%
With triethylamine; pyridinium chlorochromate In dichloromethane at 20℃;
131-56-6

2,4-dihydroxybenzophenone

616-38-6

carbonic acid dimethyl ester

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With sodium carbonate at 160 - 170℃; for 10h;94%
With tetrabutylammomium bromide; sodium carbonate In methanol at 170 - 175℃; under 22502.3 - 30003 Torr; Temperature; Reagent/catalyst; Pressure; Large scale;86.1%
131-56-6

2,4-dihydroxybenzophenone

74-87-3

methylene chloride

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride; sodium carbonate In tert-butyl methyl ether; water; chlorobenzene at 100℃; under 2250.23 Torr; for 2h; Temperature; Solvent; Reagent/catalyst; Pressure; Autoclave;91%
3555-84-8

2,4-dimethoxybenzophenone

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With beryllium(II) chloride In toluene for 3h; Heating;90%
With boron trichloride In dichloromethane at 0℃; Inert atmosphere;
With aluminum (III) chloride In dichloromethane at 20℃;
98-88-4

benzoyl chloride

151-10-0

1,3-Dimethoxybenzene

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane 1) 0-5 deg C -> r.t., 2 h 2) reflux, 1h;85%
With aluminium trichloride; zinc(II) chloride
150-19-6

O-methylresorcine

98-88-4

benzoyl chloride

131-57-7

Benzophenone-3

Conditions
ConditionsYield
boron trichloride In benzene for 10h; Heating;85%

C14H12O6S

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; triphenylphosphine In tetrahydrofuran at 25℃; for 8h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;85%

N-(3-methoxyphenoxy)acetamide

611-73-4

Benzoylformic acid

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With dipotassium peroxodisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate; silver carbonate In N,N-dimethyl-formamide at 120℃; for 24h; Sealed tube;82%
123-73-9

trans-Crotonaldehyde

42059-56-3

7-methoxy-3-formylchromone

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With piperidine In ethanol at 80℃; Green chemistry;82%
131-56-6

2,4-dihydroxybenzophenone

74-88-4

methyl iodide

131-57-7

Benzophenone-3

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 0 - 20℃; for 17h;81%
With caesium carbonate In acetonitrile at 0 - 20℃;
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Standards and Recommendations

ASSAY: 98.0%
MELTING POINT: 60 oC min
COLOR: 5 max (10% sol.)

Specification

1.Introduction of Oxybenzone

Oxybenzone, with its CAS NO 131-57-7, is a kind of white or light yellow crystalline powder. It has synonyms of Ultraviolet absorbent UV-9;2-Hydroxy-4-methoxy benzophenone(UV9);Uvinul 9;Sunscreen UV-15;UV 9;2-Hydroxy-4-methoxybenzophenone;Methanone,(2-hydroxy-4-methoxyphenyl)- phenyl- and Benzophenone, 2-hydroxy-4-methoxy-. Oxybenzone should be stored in shady and cool warehouse and mainly used as cosmetic raw materials.

2.Structure descriptors of Oxybenzone

IUPAC Name: (2-hydroxy-4-methoxyphenyl)-phenylmethanone

InChI: InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,
15H,1H3

InChIKey: DXGLGDHPHMLXJC-UHFFFAOYSA-N

Canonical SMILES : COC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
 

3.Biomedical effects of Oxybenzone

Oxybenzone is a commonly used, chemical UV-absorber. It has been used for many years to protect against UV-radiation. Previous studies have shown that BZ-3 penetrates the skin, and it can be found in urine, feces, and blood. In this study /the authors/ examined the percutaneous absorption of BZ-3. The amount of BZ-3 absorbed was measured in urine, as experimental studies in the rat have shown that urine is the major route of excretion. Eleven volunteers applied the recommended amount of a commercially available sunscreen and urine samples were collected during a 48-hr period after application. The average total amount excreted was 11 mg, median 9.8 mg, which is approximately 0.4% of the applied amount of BZ-3. Some of the volunteers still excreted BZ-3 48 hr after application. It is evident that BZ-3 undergoes conjugation in the body to make it water soluble. However, we do not know at what age the ability to conjugate is fully developed, and therefore for children physical filters such as titanium dioxide and/or zinc oxide might still be considered a more appropriate sunscreen component.

4.Toxicity data of oxybenzone

Organism Test Type Route Reported Dose (Normalized Dose) Source
mouse LD50 intraperitoneal 300mg/kg (300mg/kg) National Technical Information Service. Vol. AD277-689,
rat LD50 oral 7400mg/kg (7400mg/kg) Journal of the American College of Toxicology. Vol. 2(5), Pg. 35, 1983.