302776-68-7

Usage

Uses

Used in Cosmetic Industry:
Diethylamino hydroxybenzoyl hexyl benzoate is used as a UV filter for cosmetic emulsions with UV protection. It is an oil-soluble UV filter that may be incorporated in the oil phase of emulsions, providing high absorption in the UV-A range. This helps in minimizing the overexposure of human skin to ultraviolet radiation that may lead to acute and chronic photodamage.
Used in Sunscreen Products:
Diethylamino hydroxybenzoyl hexyl benzoate is used as a UV filter in sunscreen products, either alone or in combination with other UV absorbers. It is approved for use in concentrations up to 10% and has been approved in Europe since 2005. It is also marketed in the U.S., South America, Mexico, Japan, and Taiwan.
Used in Research and Development:
Hexyl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate may be used as a test material in investigating the structural elucidation of its transformation products in chlorinated water using liquid chromatography coupled to mass spectrometry. This application is particularly relevant in the field of environmental chemistry and toxicology, where understanding the behavior and breakdown of chemicals in water systems is crucial for assessing their environmental impact and potential health risks.

Flammability and Explosibility

Nonflammable

Synthesis

Expose 3 mL of a 0.018 mg/mL solution of 3-diethylaminophenyl 2-hexanoxycarbonylbenzoate in methanol to UV-B radiation in a Luzchem LZC-4 photoreactor equipped with 16 broad band UV-B lamps (LES-UVB-01) at 35 °C to obtain Diethylamino hydroxybenzoyl hexyl benzoate.

in vitro

Diethylamino hydroxybenzoyl hexyl benzoate (DHHB) absorbs UV-A radiation with a peak at 354 nm. The molar absorption coefficient of Diethylamino hydroxybenzoyl hexyl benzoate in EtOH at 25°C is obtained to be 39 000 mol/dm 3 /cm at 354 nm. The emission spectrum of Diethylamino hydroxybenzoyl hexyl benzoate in EtOH is dependent on the excitation wavelength.

InChI:InChI=1/C24H31NO4/c1-4-7-8-11-16-29-24(28)20-13-10-9-12-19(20)23(27)21-15-14-18(17-22(21)26)25(5-2)6-3/h9-10,12-15,17,26H,4-8,11,16H2,1-3H3

Synthetic route

mono-n-hexyl phthalate (24539-57-9) + 3-diethylaminophenol (91-68-9) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With zinc(II) chloride; trichlorophosphate In dimethyl sulfoxide at 20 - 50℃; for 5h; Solvent; Temperature;	95%

1-Chlorohexane (544-10-5) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 4h; Large scale;	86%

dihexyl sulfite (6257-44-9) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 4h; Large scale;	80%

dihexyl sulfate (7722-57-8) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 4h; Large scale;	78%

1-bromo-hexane (111-25-1) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 4h; Large scale;	65%

n-hexyl methanesulfonate (16156-50-6) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 4h; Large scale;	52.4%

4-methylbenzenesulfonic acid n-hexylester (3839-35-8) + 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon (5809-23-4) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃; for 4h; Large scale;	47.6%

3-diethylaminophenol (91-68-9) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 2 h / 110 - 115 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 2 h / 110 - 115 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 2 h / 110 - 115 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme

phthalic anhydride (85-44-9) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 2 h / 110 - 115 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 2 h / 110 - 115 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 2 h / 110 - 115 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme

hexan-1-ol (111-27-3) → n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 3 h / 10 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 6 h / 10 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 5 h / 30 - 90 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 8 h / 30 - 40 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: phosphorus tribromide / tetrahydrofuran / 3 h / 10 °C / Large scale 2: potassium carbonate / N,N-dimethyl-formamide / 4 h / 100 - 110 °C / Large scale View Scheme

n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7) → hexyl 2-(3-chloro-4-diethylamino-2-hydroxybenzoyl)benzoate + hexyl 2-(5-chloro-4-diethylamino-2-hydroxybenzoyl)benzoate

Conditions	Yield
With hydrogenchloride; sodium hypochlorite; sodium hydrogencarbonate; acetic acid In water; acetonitrile at 20℃; for 1h; pH=8;

n-hexyl 2-(4-diethylamino-2-hydroxybenzoyl)benzoate (302776-68-7) → C24H29Cl2NO4

Conditions	Yield
With hydrogenchloride; sodium hypochlorite; sodium hydrogencarbonate; acetic acid In water; acetonitrile at 20℃; pH=8;

Upstream product

• 24539-57-9 mono-n-hexyl phthalate 
• 91-68-9 3-diethylaminophenol 
• 111-27-3 hexan-1-ol 
• 85-44-9 phthalic anhydride 
• 111-25-1 1-bromo-hexane 
• 5809-23-4 2'-Carboxy-4-diethylamino-2-hydroxybenzophenon 
• 544-10-5 1-Chlorohexane 
• 7722-57-8 dihexyl sulfate 
• 6257-44-9 dihexyl sulfite 
• 3839-35-8 4-methylbenzenesulfonic acid n-hexylester 
• 16156-50-6 n-hexyl methanesulfonate 

Relevant academic research and scientific papers

Synthesis method of ultraviolet absorber UVA Plus

The invention discloses a synthesis method of an ultraviolet absorber UVA Plus. The method comprises the following steps: step 1, carrying out esterification reaction on phthalic anhydride and n-hexanol to obtain an intermediate monohexyl phthalate without other solvents, enabling the yield to reach over 99%, and enabling the intermediate to be directly subjected to the next step of reaction without refining; step 2, performing an acylation reaction on 3-hydroxy-N, N-diethylaniline and the intermediate monohexyl phthalate under the catalysis of a composite catalyst to prepare an ultraviolet absorber UVA Plus product, enabling the yield to be over 90%. The synthesis method has the advantages of easily available raw materials, easy refining and purification of the product, high yield, low production cost, and suitableness for industrial production.

A preparing method of diethylamino hydroxybenzoyl hexylbenzoate

The present invention relates to a method for the preparation of diethylamino hydroxybenzoyl hexyl benzoate. Specifically, the present invention relates to a method for preparing diethylamino hydroxybenzoyl hexyl benzoate which is easy to manufacture and commercially available in mass production, and diethylamino hydroxybenzoyl hexyl benzoate crystalline particles prepared thereby. According to the present invention, diethylamino hydroxybenzoyl hexyl benzoate crystalline particles having excellent UV blocking effect can be obtained in a stable and high yield.COPYRIGHT KIPO 2020

COSMETIC COMPOSITIONS COMPRISING AN ESTER DERIVED FROM 4-CARBOXY-2-PYRROLIDINONE AND A MEROCYANIN SCREENING AGENT; USE OF SAID DERIVATIVE AS A SOLVENT FOR A MEROCYANIN SCREENING AGENT

The present invention relates to a composition comprising, in a cosmetically acceptable medium, at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I) below: in which: R1 denotes a linear or branched C1-C20 alkyl radical,R2 denotes a linear or branched C1-C20 alkyl radical that may contain a C5-C6 ring, the phenyl radical, the benzyl radical or the phenethyl radical,and at least one merocyanin-type UV screening agent. The present invention also relates to the use of at least one ester derived from 4-carboxy-2-pyrrolidinone, of formula (I), as defined above, in a composition comprising, in a cosmetically acceptable medium, at least one merocyanin-type UV screening agent, as a solvent for said merocyanin screening agent, in and/or as an agent for improving the solubility of said merocyanin screening agent in said composition or with the aim of improving the sun protection factor.

COSMETIC TREATMENT METHOD USING A COMPOUND THAT CAN BE CONDENSED IN SITU AND A UV-RADIATION-FILTERING AGENT

The present invention relates to a method for the cosmetic treatment of the skin, comprising the application, to the skin: of a compound or group of compounds A capable of condensing in situ and exhibiting at least one reactive functional group FA which is free after condensation; and of a screening agent C which screens out UV radiation, comprising a reactive functional group FC capable of forming a covalent bond or a physical (ionic, hydrogen) bond by reaction with the functional group FA.

ALPHA-AMINO ACID DERIVATIVES FOR IMPROVING SOLUBILITY

The invention relates to the use of α-amino acid derivatives for improving the solubility of poorly soluble substances in water or aqueous solutions and to mixtures and preferred preparations.

USE OF CHROMAN-4-ONE DERIVATIVES

The invention relates to the use of compounds of the formula (I) or of a composition comprising at least one compound of the formula (I), containing radicals as described in the claims, for the care, preservation or improvement of the general state of the skin or hair.

Method of Increasing the Tanning Effect of Self-tanning Substances

The invention relates to a method for enhancing the tanning action of at least one self-tanner substance by reducing or eliminating the presence of oxygen.

Cosmetic/sunscreen compositions containing dibenzoylmethane compounds and dithiolane compound photostabilizers therefor

Cosmetic/sunscreen compositions contain a combination of at least one dibenzoylmethane sunscreen compound and a photostabilizing amount of at least one dithiolane compound of formula (I) below:

Cosmetic compositions comprising photostabilized dibenzoylmethane compounds and 2-pyrrolidinone-4- carboxy esters

Photostable cosmetic compositions contain, formulated into a cosmetically acceptable vehicle, at least one UV-screening system that includes: (a) at least one dibenzoylmethane compound, and(b) at least one 2-pyrrolidinone-4-carboxy ester compound having the following formula (I): in which: R1 is a linear or branched C1-C20 alkyl radical, andR2 is a linear or branched C1-C20 alkyl radical which optionally includes a C5-C6 ring member, the phenyl radical, the benzyl radical or the phenethyl radical.

Cosmetic compositions comprising 4-carboxy-2-pyrrolidinone esters and triazine lipophilic UV-screening agents

UV-screening compositions, formulated into a cosmetically acceptable medium, contain at least one ester solvent derived from 4-carboxy-2-pyrrolidinone, of formula (I) below: in which: R1 is a linear or branched C1-C20 alkyl radical,R2 is a linear or branched C1-C20 alkyl radical that may contain a C5-C6 ring member, the phenyl radical, the benzyl radical or the phenethyl radical, and at least one triazine-type lipophilic UV-screening agent.