Octinoxate

Structural formula
Structural formula without stereochemistry in the side chain - 1: 1 mixture ( racemate )
General
Non-proprietary name	Octinoxate
other names	( EZ , RS ) -4-methoxycinnamic acid-2-ethylhexyl ester ETHYLHEXYL METHOXYCINNAMATE ( INCI ) Octyl methoxycinnamate
Molecular formula	C 18 H 26 O 3
Brief description	clear liquid
External identifiers / databases
CAS number 5466-77-3 [racemate, ( EZ ) mixture] 83834-59-7 [racemate, ( E ) isomer] EC number 629-661-9 ECHA InfoCard 100.157.824 PubChem 5355130 ChemSpider 4511170 Wikidata Q739648
properties
Molar mass	290.40 g mol −1
Physical state	liquid
Melting point	−25 ° C
boiling point	198-200 ° C
solubility	insoluble in water
Refractive index	1.545
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: 413 P: no P-phrases
Toxicological data	980 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Octinoxate is a substance that is used as a UV filter in sunscreens.

Chemically, it is a mixture of at least two isomeric chemical compounds from the group of cinnamic acid esters . Octinoxat offers protection against UVB radiation with wavelengths of 280 to 320 nanometers . Octinoxate is controversial because of its effects as an endocrine disruptor on the estrogenic hormonal system .

Extraction and presentation

Octynoxate can be produced starting from p -bromanisole by a Heck reaction via the intermediate stage 4-methoxycinnamic acid and subsequent esterification of the carboxylic acid.

Stereochemistry

Octinoxate contains a stereocenter and a double bond. Sunlight can isomerize the ( E ) form to the ( Z ) form. The esterification to octynoxate requires 2-ethylhexanol, which can be prepared as a racematic mixture [a 1: 1 mixture of ( R ) - and ( S ) form]. Therefore octynoxate could consist of the following four stereoisomers:

Isomers of octinoxate
	( R ) shapes	( S ) shapes
( E ) shapes
( Z ) shapes

safety instructions

The effects of octinoxate on human health and the environment have been examined under REACH since 2016 as part of the substance assessment by Great Britain.

Trade names

• Tinosorb OMC
• Eusolex 2292

Admission

According to Regulation (EC) No. 1223/2009 on cosmetic products , octinoxate is permitted as a UV filter up to a maximum content of 10% (calculated as acid) in the ready-to-use preparation.

A law in the US state of Hawaii will prohibit the sale of sunscreens that contain octinoxate or oxybenzone from January 2021 . Both substances have a harmful effect on corals and the genetic make-up of fish. In the South Sea state of Palau , octinoxate has been banned in sun creams since January 2020.

Individual evidence

1. ↑ Entry on ETHYLHEXYL METHOXYCINNAMATE in the CosIng database of the EU Commission, accessed on February 16, 2020.
2. ↑ ^{a b c d} Datasheet Octyl methoxycinnamate at chemicalland21.com, accessed on October 31, 2017.
3. ↑ ^{a b c} Data sheet 2-Ethylhexyl 4-methoxycinnamate, 98% from Sigma-Aldrich , accessed on February 17, 2014 ( PDF ).
4. ↑ Data sheet at Clearsynth ( Memento from March 28, 2014 in the Internet Archive )
5. ↑ smartskincare.com: Chemical UVB sunscreen / sunblock: octyl methoxycinnamate (octinoxate) , accessed October 31, 2017.
6. ↑ ToxFox - The cosmetic check. Association for the Environment and Nature Conservation Germany 
7. ↑ Dirk Steinborn: Fundamentals of organometallic complex catalysis . 2nd Edition. Vieweg + Teubner, 2009, ISBN 978-3-8348-0581-2 ( page 251 in the Google book search).
8. ↑ S. Pattanaargson, T. Munhapol, P. Hirunsupachot, P. Luangthongaram (eds.): Photoisomerization of octyl methoxycinnamate. In: Journal of Photochemistry and Photobiology A: Chemistry , Elsevier Verlag, Volume 161, No. 2-3, January 30, 2004, pp. 269-274.
9. ↑ Process for the production of 2-ethylhexanol: DE 3530839 A1 , August 29, 1985; EP 0216151 B1 , August 20, 1986.
10. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 2-Ethylhexyl-trans-4-methoxycinnamate , accessed on October 31, 2017.
11. ↑ Entry on octinoxate in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on October 31, 2017.
12. ↑ REGULATION (EC) No. 1123/2009 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 30 November 2009 on cosmetic products (PDF), accessed on 14 March 2018.
13. ↑ Hawaii Bans Certain Sunscreens , aerzteblatt, July 26, 2018.
14. ^ The Republic of Palau Bans Sunscreen Chemicals to Protect its Coral Reefs and UNESCO World Heritage site - International Coral Reef Initiative. In: icriforum.org. November 4, 2018, accessed February 20, 2020 .