Octinoxate

Base Information

• Chemical Name: Octinoxate
• CAS No.: 5466-77-3
• Molecular Formula: C18H26O3
• Molecular Weight: 290.403
• Hs Code.: 29189090
• European Community (EC) Number: 629-661-9,226-775-7
• NSC Number: 26466
• UNII: 4Y5P7MUD51
• DSSTox Substance ID: DTXSID9047205
• Nikkaji Number: J184.019C,J210.537C
• Wikipedia: Octyl_methoxycinnamate
• Wikidata: Q739648
• NCI Thesaurus Code: C66252
• RXCUI: 13369
• Metabolomics Workbench ID: 122707
• ChEMBL ID: CHEMBL1200608
• Mol file: 5466-77-3.mol

Synonyms:2-ethylhexyl-4-methoxycinnamate;2-ethylhexyl-p-methoxycinnamate;escalol 557;Heliopan New;octinoxate;octyl-methoxycinnamate;octylmethoxycinnamate;OMC cinnamate;Parsol MCX

Chemical Property of Octinoxate

Chemical Property:

• Appearance/Colour: colourless or pale yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: <-25℃
• Refractive Index: 1.543-1.547
• Boiling Point: 405.3 °C at 760 mmHg
• Flash Point: 171.6 °C
• PSA: 35.53000
• Density: 1 g/cm³
• LogP: 4.46800
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 27℃
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 290.18819469
• Heavy Atom Count: 21
• Complexity: 304

Purity/Quality:

99.0%min ^*data from raw suppliers

Octinoxate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Sunscreens
• Canonical SMILES: CCCCC(CC)COC(=O)C=CC1=CC=C(C=C1)OC
• Isomeric SMILES: CCCCC(CC)COC(=O)/C=C/C1=CC=C(C=C1)OC
• Uses: 2-Ethylhexyl 4-Methoxycinnamate is an UV induced cyclobutane pyrimidine dimer (CDP) formation inhibitior. octinoxate is the drug name for the sunscreen chemical generally known as octyl methoxycinnamate and ethylhexyl methoxycinnamate. 2-Ethylhexyl-4-methoxy-cinnamate is used as UV-B-absorbing agent in sunscreens and cosmetic creams, lotions, lipsticks, sun oils, etc.

Technology Process of Octinoxate

There total 42 articles about Octinoxate 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: 98.0%

diazo-acetic acid-(2-ethyl-hexyl ester) + 4-methoxy-benzaldehyde (123-11-5) → 2-ethylhexyl methoxycinnamate (5466-77-3,83834-59-7)

Guidance literature:

With Fe(TCP)Cl; polyethylene supported arsine; polymethylhydrosiloxane; In toluene; at 110 ℃; for 20h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c1cc16747b

Reference yield: 97.0%

2-Ethylhexyl acrylate (103-11-7) + para-iodoanisole (696-62-8) → 2-ethylhexyl methoxycinnamate (5466-77-3,83834-59-7)

Guidance literature:

With tetrabutylammomium bromide; C₃₂H₂₆Cl₂N₈O₄Pd₂; potassium carbonate; In methanol; water; for 0.416667h; Reflux;

DOI:10.1021/acs.inorgchem.0c01035

Reference yield: 96.0%

2-Ethylhexyl acrylate (103-11-7) + 4-methoxybenzenediazonium tetrafluoroborate (459-64-3) → 2-ethylhexyl methoxycinnamate (5466-77-3,83834-59-7)

Guidance literature:

[(1,3-dimesitylimidazol-2-ylidene)(benzoquinone)Pd⁽⁰⁾]2; In methanol; at 50 ℃; for 1h;

DOI:10.1002/1521-3765(20020902)8:17<3901::AID-CHEM3901>3.0.CO;2-E

upstream raw materials:

1-bromo-4-methoxy-benzene

2-Ethylhexyl acrylate

4-methoxybenzenediazonium tetrafluoroborate

4-chloromethoxybenzene

Downstream raw materials:

2-Ethylhexyl alcohol

n-tetradecyl 4-methoxycinnamate

n-hexadecyl 4-methoxycinnamate

3-(4-methoxy-phenyl)-propionic acid 2-ethyl-hexyl ester

Refernces

• 1、 Swart, Marthinus R.,Twigge, Linette,Erasmus, Elizabeth,Marais, Charlene,Bezuidenhoudt, Barend C. B.. "Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces". supporting information. p. 1752 - 1762. Retrieved 2021/05/06.
• 2、 Bumagin, Nikolay A.,Dikusar, Evgenij A.,Ivashkevich, Ludmila S.,Kletskov, Alexey V.,Kolesnik, Iryna A.,Lyakhov, Alexander S.,Petkevich, Sergey K.,Potkin, Vladimir I.. "Mimics of Pincer Ligands: An Accessible Phosphine-Free N-(Pyrimidin-2-yl)-1,2-azole-3-carboxamide Framework for Binuclear Pd(II) Complexes and High-Turnover Catalysis in Water". supporting information. . Retrieved 2020/08/12.