Avobenzone

Base Information

• Chemical Name: Avobenzone
• CAS No.: 70356-09-1
• Deprecated CAS: 87075-14-7,185160-18-3,112725-59-4,112725-59-4,185160-18-3
• Molecular Formula: C20H22O3
• Molecular Weight: 310.393
• Hs Code.: 29145000
• European Community (EC) Number: 274-581-6
• NSC Number: 758680
• UNII: G63QQF2NOX
• DSSTox Substance ID: DTXSID9044829
• Nikkaji Number: J149.841J
• Wikipedia: Avobenzone
• Wikidata: Q2775914
• NCI Thesaurus Code: C47406
• RXCUI: 45045
• Pharos Ligand ID: Q93RBW2JTAV4
• Metabolomics Workbench ID: 71539
• ChEMBL ID: CHEMBL1200522
• Mol file: 70356-09-1.mol

Synonyms:4-tert-butyl-4'-methoxydibenzoylmethane;avobenzone;BMDBM cpd;butyl-methoxydibenzoylmethane;parsol 1789;parsol-1789

Chemical Property of Avobenzone

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.21E-08mmHg at 25°C
• Melting Point: 81-84 °C
• Refractive Index: 1.546
• Boiling Point: 463.6 °C at 760 mmHg
• PKA: 9.74±0.13(Predicted)
• Flash Point: 203.1 °C
• PSA: 43.37000
• Density: 1.079 g/cm³
• LogP: 4.44840
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• Water Solubility.: 27μg/L at 20℃
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 310.15689456
• Heavy Atom Count: 23
• Complexity: 405

Purity/Quality:

99.9% ^*data from raw suppliers

Avobenzone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Sunscreens
• Canonical SMILES: CC(C)(C)C1=CC=C(C=C1)C(=O)CC(=O)C2=CC=C(C=C2)OC
• Description: Avobenzone is a full-spectrum ultraviolet A (UVA) blocker. It inhibits UVA-induced increases in melanin levels and tyrosinase activity in B16/F10 melanoma cells (IC30s = 21.94 and 24.25 μM, respectively). Avobenzone (30 μM) also inhibits UVA-induced production of reactive oxygen species (ROS) and 8-hydroxy-2''-deoxyguanosine (8-OH-dG; ), as well as inhibits UVA-induced depletion of glutathione (GSH; ), in B16/F10 cells. It increases nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2) and upregulates the antioxidant response element (ARE) in UVA-irradiated B16/F10 cells when used at at a concentration of 30 μM. Formulations containing avobenzone have been used as a sun protectant in sunscreen products.
• Uses: sedative, neurosedative A component of sunscreen that absorbs the full spectrum of UVA rays. avobenzone (BMDM, butyl methoxydibenzoylmethane) is a sun-A screen chemical that offers broad-range protection against uVA rays. It is associated with some photoinstability, which can be overcome in the overall sunscreen formulation. It is approved for use up to 3 percent in the united States and 5 percent in the european union. Avobenzone is noted to rarely be photosensitizing. Avobenzone provides strong absorption through a large portion of the UVA spectrum including the majority of the UVA I range with peak absorption at 360 nm. Photostability refers to the ability of a molecule to remain intact with irradiation. It is potentially a problem with all UV filters, but particularly with the use of avobenzone. This effect may degrade other sunscreens in a formulation including octyl methoxycinnamate. Octocrylene and some of the newer sunscreens including BEMT stabilized avobenzone. Non-UV filters such as diethylhexyl 2,6 naphthalate may also be used. These molecules function as triplet–triplet quenchers. Overall formulation with avobenzone is therefore particularly critical.

Technology Process of Avobenzone

There total 19 articles about Avobenzone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

methyl 4-tert-butylbenzoate (26537-19-9) + 1-(4-methoxyphenyl)ethanone (100-06-1) → 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione (70356-09-1,87075-14-7)

Guidance literature:

With potassium methanolate; In toluene; at 110 ℃; for 2h; under 750.075 Torr; Product distribution / selectivity;

Reference yield: 94.0%

→ 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione (70356-09-1,87075-14-7)

Guidance literature:

Reference yield: 91.0%

tert-butyl 4-(tert-butyl)benzoate (92279-83-9) + 1-(4-methoxyphenyl)ethanone (100-06-1) → 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1,3-dione (70356-09-1,87075-14-7)

Guidance literature:

With potassium methanolate; In toluene; for 1.75h; under 750.075 Torr; Product distribution / selectivity; Heating;

upstream raw materials:

(Z)-1-(4-tert-Butyl-phenyl)-3-hydroxy-3-(4-methoxy-phenyl)-propenone

methyl 4-tert-butylbenzoate

1-(4-methoxyphenyl)ethanone

1,1-(4-tert-butyl-benzoyl)(4'-methoxybenzoyl)butane

Downstream raw materials:

1-(4-tert-butylphenyl)-2-decanyl-3-(4-methoxyphenyl)propane-1,3-dione

(Z)-1-(4-tert-Butyl-phenyl)-3-hydroxy-3-(4-methoxy-phenyl)-propenone

difluoroboron avobenzone

1,1-(4-tert-butyl-benzoyl)(4'-methoxybenzoyl)butane

Refernces

• 1、 Carola, Christophe,Keck, Cornelia M.,Salazar, Andrew,Termer, Michael,von Hagen, Joerg. "Methoxy-monobenzoylmethane protects human skin against uv-induced damage by conversion to avobenzone and radical scavenging". . . Retrieved 2021/10/20.
• 2、 -. "ONE-STEP, FAST, 18F-19F ISOTOPIC EXCHANGE RADIOLABELING OF DIFLUORO-DIOXABORININS AND USE OF SUCH COMPOUNDS IN TREATMENT". Paragraph 0019; 0206-0207. . Retrieved 2019/12/15.