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Home > Encyclopedia > 2-Hydroxy-4-methoxy-4′-methylbenzophenone

2-Hydroxy-4-methoxy-4′-methylbenzophenone

2-Hydroxy-4-methoxy-4′-methylbenzophenone structure

2-Hydroxy-4-methoxy-4′-methylbenzophenone 

structure
  • CAS No:

    1641-17-4

  • Formula:

    C15H14O3

  • Chemical Name:

    2-Hydroxy-4-methoxy-4′-methylbenzophenone

  • Synonyms:

    Methanone,(2-hydroxy-4-methoxyphenyl)(4-methylphenyl)-;Benzophenone,2-hydroxy-4-methoxy-4′-methyl-;(2-Hydroxy-4-methoxyphenyl)(4-methylphenyl)methanone;2-Hydroxy-4-methoxy-4′-methylbenzophenone;Mexenone;Benzophenone 10;Mexenon;Uvistat 2211;Uvistat;(2-Hydroxy-4-methoxyphenyl)(p-tolyl)methanone

Description

Mexenone is a member of benzophenones.

2-Hydroxy-4-methoxy-4′-methylbenzophenone Basic Attributes

242.27

242.27

216-688-2

ET1UGF4A0B

760432

DTXSID8046242

Solid

Characteristics

46.5 Ų

log Kow = 4.07 (est)

1.1515

95 °C @ Solvent: Benzene

345.09°C (rough estimate)

1.5570 (estimate)

In water, 93.2 mg/L at 25 °C (est)

Keep container tightly closed in a dry and well-ventilated place.

3.13X10-6 mm Hg at 25 °C (est)

7.35±0.35

Henry's Law constant = 1.66X10-8 atm-cu m/mol at 25 °C (est)

log Kow = 3.573|Hydroxyl radical reaction rate constant = 2.01X10-10 cu cm/molec-sec at 25 °C (est)

Safety Information

36/37/38

26-36

Stable under recommended storage conditions.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Extinguishing media: Suitable extinguishing media. Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Special hazards arising from the substance or mixture: Carbon oxides

ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire protection.|ACCIDENTAL RELEASE MEASURES; Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Avoid breathing dust. Environmental precautions: Do not let product enter drains.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Toxicity

IDENTIFICATION AND USE: 2-Hydroxy-4-methoxy-4'-methylbenzophenone (Mexenone) belongs to the benzophenone group of sunscreens. HUMAN STUDIES: Mexenone was reported as one of the most frequent contact allergens among other sunscreen agents. The benzophenone group of sunscreens (mexenone, oxybenzone) were the most frequent sensitizers, accounting for 8 of the 27 positive patch tests observed for a sunscreen agents. It has also produced positive responses in photopatch testing. A case report described a patient with long-standing polymorphic light eruption who developed a photocontact allergy to mexenone and several contact allergies. ANIMAL STUDIES: There are no data available.

OBJECTIVE: To describe and identify the photoallergens causing photoallergic contact dermatitis in the population attending the outpatient clinic of the Centro Dermatologico Federico Lleras Acosta (CDFLLA), the National Institute of Dermatology of Colombia. MATERIALS AND METHODS: Eighty-two patients with clinical diagnosis of photoallergic contact dermatitis enter the study. These patients attended the CDFLLA between August 2001 and May 2003. Photopatch tests were performed using the standard series of sunscreens (Chemotechnique Diagnostics) and 6-methylcoumarin. Cetyl alcohol, phenoxyethanol, methylparabene, propylene glycol, triethanolamine, propylparabene, trichlorocarbanilide and dichromate were also included. The allergens were applied in duplicate on the healthy skin of the back and covered with opaque tape withdrawn 24 hr later, the panel on the right was irradiated with an ultraviolet A dose of 5 J/cm(2). The tests were read 24 h after the application of the allergens, 24 and 72 hr post-irradiation. The readings were assessed according to the visual scoring system recommended by the International Contact Dermatitis Research Group. RESULTS: Twenty-six patients (31.7%) showed positive photopatch test responses to one or several allergens. Four of them showed positive results to three components of the series and four patients to two components. Thirty-eight photoallergic and 18 allergic reactions were observed. Ultraviolet filters were the substances which more frequently produced positive photopatch test responses (30.5%). The most common ultraviolet filter photoallergen was benzophenone-3 with 22/82 positive results (26.8%), followed by octyl methoxycinnamate (8/82), benzophenone-4 and mexenone (2/82), phenylbenzimidazole sulphonic acid, methylbenziliden camphor and octyl dimethyl PABA (1/82). One patient showed a photoallergic response to 6-methylcoumarin. There was a concordance between the allergen which elicited the positive response and the use of different substances which contained that molecule among its compounds in 17 patients (65.3%). 19.5% of the patients (16/82) showed positive results to one or several allergens in the irradiated panel as well as in the unirradiated control site. These cases were diagnosed as contact allergy, probably caused by aeroallergens, presenting a natural history and a clinical picture similar to photocontact allergy. The most common allergen was dichromate with 10 positive results. CONCLUSIONS: The results of this study confirm that sunscreens are the more frequently involved substances in photoallergic contact dermatitis in our population. Identification of the photoallergen is the key element for adequate disease control and patient education.|INTRODUCTION: Between September 1994 and September 1999, we observed 19 cases of photoaggraved contact allergy or contact photoallergy to ketoprofen (non steroidal anti-inflammatory derived from arylpropionic acid). We present a clinical and photobiological retrospective study of these 19 cases with investigation of cross-reactivity between benzophenone-containing molecules. PATIENTS AND METHODS: On clinical level, we investigated the type of eruption, the delay of appearance, the initial area of eruption and areas of diffusion. Phototesting included patchtests and photopatchtests performed with the gel containing ketoprofen (17 patients), ketoprofen 2 p. 100 petrolatum (14 patients), fenofibrate 10 p. 100 petrolatum and 10 p. 100 water (15 patients), 3 benzophenones (19 patients): oxybenzone 10 p. 100 petrolatum, mexenone 2 p. 100 petrolatum, sulisobenzone 10 p. 100 petrolatum and the other arylpropionic derivatives (4 patients). Three identical series were applied: one was irradiated with 3/4 polychromatic minimal erythematosus dose, a second was irradiated with UVA 13 J/cm2 until January 1997, then 5 J/cm2, the third series was not irradiated (control series). RESULTS: Patients were 9 men and 10 women with an average age of 41.2 years. The type of eruption was an eczema. The delay of appearance of the eruption was one day to 3 months. For 10 patients, the delay was between 4 and 18 days. The eruption was localized to the application area in 1 case, to the application area then to the same contralateral area in 3 cases, to the application area then to all photoexposed areas in 13 cases, to the application area then to the photoexposed areas and then to non-sun-exposed areas in 2 cases. Evolution showed prolonged photosensitivity in 3 cases after withdrawal of the contact and the contact photoallergy to ketoprofen was severe. Gel-containing ketoprofen photopatchtests showed 9 photoaggravated contact allergy, 6 contact photoallergy and 2 contact allergy. Ketoprofen photopatchtests showed 12 contact photoallergy and 2 photoaggraved contact allergy. Tiaprofenic acid photopatchtests were positive in all performed cases (4/4), but photopatchtests with the other arylpropionic derivatives, without benzophenone structure, were negative. Fenofibrate photopatchtests were always positive (15/15). Benzophenones photopatchtests only showed 4 cases of contact photoallergy to oxybenzone (4/19). In 68 p. 100 of cases, patients presented a contact allergy or photoallergy to fragrances. CONCLUSIONS: This study shows the actual frequency of contact allergy and contact photoallergy to ketoprofen with a higher frequency of contact photoallergy. Thus, photopatchtesting is essential. In cases of contact photoallergy to ketoprofen, ketoprofen, tiaprofenic acid but not the other arylpropionic derivatives, fenofibrate and benzophenones have to be withdrawn.

2-Hydroxy-4-methoxy-4'methylbenzophenone's production and use as a ultraviolet light absorber(1) may result in its release to the environment through various waste streams(SRC).

Drug Information

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ The patients sensitized to sunscreen agents who attended our Contact Dermatitis Clinic between February 1985 to March 1987 have been reviewed. 15 (5%) of 280 patients tested with sunscreens had positive reactions; 3 of them were allergic to more than one agent. The most frequent contact allergens were hydroxy methoxy methyl benzophenone (Mexenone) [6], followed by isopropyl dibenzoylmethane (Eusolex 8020/8021) [5], octyl dimethyl para-aminobenzoate (Escalol 507) [2], and one reaction each to butyl methoxy dibenzoylmethane (Parsol 1789), amyl dimethyl para-aminobenzoate (Escalol 506), and ethoxy ethyl-p-methoxy cinnamate (Givtan F). Positive photopatch tests were seen with isopropyl dibenzoylmethane, butyl methoxy dibenzoylmethane, para-aminobenzoate (PABA) and ethoxy ethyl-p-methoxy cinnamate, one reaction each.|/HUMAN EXPOSURE STUDIES/ From 1989-1991, 214 patients (45 PD/AR, 54 PLE, 115 controls) were patch tested to a sunscreen series containing 9 constituents. 16/214 (7.5%) patients reacted to one or more sunscreens, with allergy being significantly more common in PD/AR /photosensitivity dermatitis/actinic reticuloid syndrome/ patients (10/45 versus 2/54 PLE /polymorphic light eruption/ and 4/115 contact dermatitis clinic controls). The benzophenone group of sunscreens (mexenone, oxybenzone) were the most frequent sensitizers, accounting for 8 of the 27 positive patch tests observed. Clinicians should consider contact allergy to sunscreens in PD/AR patients as an explanation for exposed-site dermatitis episodes.|/HUMAN EXPOSURE STUDIES/ Photopatch testing, although widely used in the diagnosis of photosensitivity disorders, is not standardized. We performed this study to determine the threshold ultraviolet light A (UV-A) dose required to elicit photopatch test responses. 4 patients with previously positive tests were reexposed to the offending allergen, using an incremental dosage regime. Isopropyl dibenzoylmethane (Eusolex 8020), mexenone (benzophenone-10) and oxybenzone (benzophenone-3) produced positive responses at 1.0, 1.0 and 0.7 J/sq cm, respectively. Responses to phenothiazines were deemed phototoxic. These results demonstrate that high doses of UV-A (e.g., 10-15 J/sq cm) are unnecessary, and that 5 J/sq cm should become the current standard.|/HUMAN EXPOSURE STUDIES/ INTRODUCTION: Between September 1994 and September 1999, we observed 19 cases of photoaggraved contact allergy or contact photoallergy to ketoprofen (non steroidal anti-inflammatory derived from arylpropionic acid). We present a clinical and photobiological retrospective study of these 19 cases with investigation of cross-reactivity between benzophenone-containing molecules. PATIENTS AND METHODS: On clinical level, we investigated the type of eruption, the delay of appearance, the initial area of eruption and areas of diffusion. Phototesting included patchtests and photopatchtests performed with the gel containing ketoprofen (17 patients), ketoprofen 2 p. 100 petrolatum (14 patients), fenofibrate 10 p. 100 petrolatum and 10 p. 100 water (15 patients), 3 benzophenones (19 patients): oxybenzone 10 p. 100 petrolatum, mexenone 2 p. 100 petrolatum, sulisobenzone 10 p. 100 petrolatum and the other arylpropionic derivatives (4 patients). Three identical series were applied: one was irradiated with 3/4 polychromatic minimal erythematosus dose, a second was irradiated with UVA 13 J/cm2 until January 1997, then 5 J/cm2, the third series was not irradiated (control series). RESULTS: Patients were 9 men and 10 women with an average age of 41.2 years. The type of eruption was an eczema. The delay of appearance of the eruption was one day to 3 months. For 10 patients, the delay was between 4 and 18 days. The eruption was localized to the application area in 1 case, to the application area then to the same contralateral area in 3 cases, to the application area then to all photoexposed areas in 13 cases, to the application area then to the photoexposed areas and then to non-sun-exposed areas in 2 cases. Evolution showed prolonged photosensitivity in 3 cases after withdrawal of the contact and the contact photoallergy to ketoprofen was severe. Gel-containing ketoprofen photopatchtests showed 9 photoaggravated contact allergy, 6 contact photoallergy and 2 contact allergy. Ketoprofen photopatchtests showed 12 contact photoallergy and 2 photoaggraved contact allergy. Tiaprofenic acid photopatchtests were positive in all performed cases (4/4), but photopatchtests with the other arylpropionic derivatives, without benzophenone structure, were negative. Fenofibrate photopatchtests were always positive (15/15). Benzophenones photopatchtests only showed 4 cases of contact photoallergy to oxybenzone (4/19). In 68 p. 100 of cases, patients presented a contact allergy or photoallergy to fragrances. CONCLUSIONS: This study shows the actual frequency of contact allergy and contact photoallergy to ketoprofen with a higher frequency of contact photoallergy. Thus, photopatchtesting is essential. In cases of contact photoallergy to ketoprofen, ketoprofen, tiaprofenic acid but not the other arylpropionic derivatives, fenofibrate and benzophenones have to be withdrawn.|For more Human Toxicity Excerpts (Complete) data for 2-Hydroxy-4-methoxy-4'-methylbenzophenone (7 total), please visit the HSDB record page.

2-hydroxy-4-methoxy-4'-methylbenzophenone

2-Hydroxy-4-methoxy-4′-methylbenzophenone Use and Manufacturing

Methods of Manufacturing

p-Toluoyl chloride is the starting material. To this is added chlorobenzene and 1,3-dimethoxybenzene. The reaction mixture is cooled to 12°C in an ice bath and aluminum chloride is added gradually, keeping the reaction below 30°C. The reaction is then gradually heated to 115°C with the evolution of hydrogen chloride gas. As the temperature increases, the reaction mixture becomes thicker. At 105°C, dimethyl formamide is added slowly. The reaction is heated at 115°C for a short time and is then poured into concentrated hydrochloric acid. The reaction mixture pours very easily and very cleanly. The acid mixture is heated with steam to dissolve all the material which had not hydrolyzed and the mixture is filtered. The red chlorobenzene layer is separated and washed twice with hot water. To the chlorobenzene solution is then added sodium hydroxide dissolved in water and the chlorobenzene is removed by a steam distillation. After all of the chlorobenzene is removed, the precipitate which forms during the distillation is removed by filtration and discarded. The solution is cooled and acidified with hydrochloric acid, precipitating a tan solid. This is removed by filtration and washed acid-free. It is then treated with sodium bicarbonate solution to remove any acid present and is then washed with water to remove all traces of bicarbonate. After drying approximately a 75% yield of mexenone is obtained.

Uses

2-Hydroxy-4-methoxy-4'-methyl-benzophenone is an UV absorbing agent in sunscreen cosmetic creams, lotions, lipstieks, sun oils, etc.

Reverse phase HPLC determination.

Cosmetics -> Uv absorber

Computed Properties

Molecular Weight:242.27
XLogP3:4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:242.094294304
Monoisotopic Mass:242.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:18
Complexity:282
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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