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

• ChemBase ID: 73310
• Molecular Formular: C20H22O3
• Molecular Mass: 310.38688
• Monoisotopic Mass: 310.15689456
• SMILES: c1c(ccc(c1)C(=O)CC(=O)c1ccc(cc1)C(C)(C)C)OC
• Canonical SMILES: COc1ccc(cc1)C(=O)CC(=O)c1ccc(cc1)C(C)(C)C
• InChI: InChI=1S/C20H22O3/c1-20(2,3)16-9-5-14(6-10-16)18(21)13-19(22)15-7-11-17(23-4)12-8-15/h5-12H,13H2,1-4H3
• InChIKey: XNEFYCZVKIDDMS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-tert-butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione
• IUPAC Traditional name: avobenzone
• Synonyms: Eusolex 9020; Escalol 517; Parsol 1789; Avobenzone(Parsol 1789); Avobenzone; 1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)-1,3-propanedione; Butyl methoxydibenzoylmethane; Avobenzone; 1-[4-(1,1-Dimethylethyl)phenyl]-3-(4-methoxyphenyl)-1,3-propanedione; 1-(4-tert-Butylphenyl)-3-(4-methoxyphenyl)propane-1,3-dione; butylmethoxydibenzoylmethane; 4-tert-butyl-4'-methoxydibenzoylmethane; Avobenzone; 1-(4-甲氧苯基)-3-(4-叔丁基苯基)-1,3-丙二酮

Database IDs

• CAS Number: 70356-09-1
• EC Number: 274-581-6
• MDL Number: MFCD00210252
• PubChem SID: 162038230
• PubChem CID: 51040
• CHEMBL: 1200522
• Chemspider ID: 46261
• KEGG ID: D03015
• Unique Ingredient Identifier: G63QQF2NOX
• Wikipedia Title: Avobenzone

CALCULATED PROPERTIES

• Acid pKa: 9.877099
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.564728
• LogD (pH = 7.4): 4.5633016
• Log P: 4.564746
• Molar Refractivity: 91.7511 cm^3
• Polarizability: 35.35992 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colorless crystal
• Melting Point: 81-84 °C

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61; R
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• Personal Protective Equipment: Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: ≥99.0% (GC)
• Grade: analytical standard
• Salt Data: Free Base
• Pharmacopeia Traceability: traceable to USP 1045337
• Empirical Formula (Hill Notation): C20H22O3

DETAILS

Selleck Chemicals - S1904

Research Area: Cancer
Biological Activity:
Avobenzone(Parsol 1789) is an oil soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays and a dibenzoylmethane derivative. [1] It can degrade faster in light in combination with mineral UV absorbers like zinc oxide and titanium dioxide, though with the right coating of the mineral particles this reaction can be reduced. A manganese doped titanium dioxide may be better than undoped titanium dioxide to improve avobenzone’s stability. It reacts with minerals to form colored complexes. Manufacturers of avobenzone, like DSM recommend to include a chelator to prevent this from happening. They also recommend to avoid the inclusion of iron and ferric salts, heavy metals, formaldehyde donors and PABA and PABA esters. [2]

Toronto Research Chemicals - A794690

A component of sunscreen that absorbs the full spectrum of UVA rays.

REFERENCES

• Wakefield G et al. Photochem Photobiol Sci. 2004 Jul; 3(7):648-52.
• Leal, L., et al.: Environ. Sci. Technol., 44, 6835 (2010)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010)