Homo salad

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Structural formula
Structural formula of homosalate
Simplified structural formula without stereochemistry
General
Surname Homo salad
other names
  • Salicylic acid 3,3,5-trimethylcyclohexyl ester
  • 3,3,5-trimethylcyclohexyl-2-hydroxybenzoate
  • (1 R * , 5 R * ) -3,3,5-trimethylcyclohexyl-2-hydroxybenzoate
  • (1 R * , 5 S * ) -3,3,5-trimethylcyclohexyl-2-hydroxybenzoate
  • Homomenthyl salicylate
Molecular formula C 16 H 22 O 3
Brief description

colorless liquid

External identifiers / databases
CAS number
  • 118-56-9 (mixture of four stereoisomers)
  • 1834605-04-7 ( cis form, racemate)
  • 1834605-05-8 ( trans form, racemate)
EC number 204-260-8
ECHA InfoCard 100,003,874
PubChem 8362
Wikidata Q2260189
properties
Molar mass 262.34 g mol −1
Physical state

liquid

density

1.05 g cm −3

boiling point

165 (0.5 kPa)

solubility
  • practically insoluble in water and propylene glycol
  • miscible with paraffin oil, isopropyl myristate and ethanol
Refractive index

1.516-1.519

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 5000 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

Homosalate (of homo menthyl sal ICYL at ) is an organic compound which in some sunscreens is used. It is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol (homomenthol). It is used as a chemical UV filter in a concentration of up to 10%. The salicylic acid part of the molecule absorbs UV light with a wavelength of 295 nm to 315 nm. The hydrophobic cyclohexanol part prevents it from dissolving in water.

Homosalate is a chiral compound with two stereocenters and thus a mixture of four stereoisomers. The trans - diastereomer [(1 R * , 5 R * ) form] predominates in the products used , whereby there are two homosalate isomer mixtures: normally a mixture of 15% cis and 85% trans form and one of 40% cis and 60% of the trans form. However, isomer mixtures with 85% or more of the cis form [(1 R * , 5S * ) form] can also be prepared.

Extraction and presentation

Homosalate can be prepared by a transesterification of methyl salicylate are shown with 3,3,5-trimethylcyclohexanol.

safety instructions

As with other UV filter compounds, more homosalate is absorbed into the epidermis of the face (25%) more than that of the back. Homosalate was found to have an antiandrogen effect in vitro , and at the same time estrogenic activity on estrogen receptors , and general in vitro estrogenic activity . Homosalat shows the ability to couple to androgen and estrogen receptors in vitro . There is also evidence that homosalate can break down into toxic products.

Individual evidence

  1. ↑ a b c d e f Entry on 3,3,5-Trimethylcyclohexyl Salicylate (cis- and trans- mixture) at TCI Europe, accessed on August 14, 2018.
  2. ↑ a b c d e Scientific Committee on Consumer Products: OPINION ON HOMOSALATE , March 21, 2007, accessed on August 14, 2018.
  3. ↑ Entry on homosalate in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on August 14, 2018.
  4. ↑ Belma Imamović, Snezana Trifunovic, Ervina Becic, Mirza Dedic, Miroslav Šober: Study of homosalate stability in chlorinated water and identification chalogenated by-products by gas chromatography-mass spectrometry. In: Research Journal of Pharmaceutical, Biological and Chemical Sciences. Volume 6, number 1, 2015, pp. 990–1000.
  5. ↑ a b Patent CN105085273A Method for preparing homosalate , accessed August 11, 2018.
  6. ^ A. Rougier, D. Dupuis, C. Lotte, R. Roguet, RC Wester, HI Maibach: Regional variation in percutaneous absorption in man: measurement by the stripping method . In: Arch. Dermatol. Res. Band 278 , no. 6 , 1986, pp. 465-469 , doi : 10.1007 / bf00455165 , PMID 3789805 .
  7. ↑ HA Benson, V. Sarveiya, S. Risk, MS Roberts: Influence of anatomical site and topical formulation on skin penetration of sunscreens . In: Ther Clin Risk Manag . tape 1 , no. 3 , September 2005, pp. 209-218 , PMID 18360561 , PMC 1661631 (free full text).
  8. ^ R. Ma: UV Filters with Antagonistic Action at Androgen Receptors in the MDA-kb2 Cell Transcriptional-Activation Assay . In: Toxicological Sciences . tape 74 , no. 1 , 2003, p. 43-50 , doi : 10.1093 / toxsci / kfg102 .
  9. ↑ E. Gomez, A. Pillon, H. Fenet, D. Rosain, MJ Duchesne, JC Nicolas, P. Balaguer, C. Casellas: Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens, and musks . In: J Toxicol Environ Health A . tape 68 , no. 4 , February 2005, p. 239-251 , doi : 10.1080 / 15287390590895054 , PMID 15799449 .
  10. ↑ M. Schlumpf, P. Schmid, S. Durrer, M. Conscience, K. Maerkel, M. Henseler, M. Gruetter, I. Herzog, S. Reolon, R. Ceccatelli, O. Faass, E. Stutz, H Jarry, W. Wuttke, W. Lichtensteiger: Endocrine activity and developmental toxicity of cosmetic UV filters - an update . In: Toxicology . tape 205 , no. 1-2 , December 2004, pp. 113-122 , doi : 10.1016 / j.tox.2004.06.043 , PMID 15458796 .
  11. ↑ RH Schreurs, E. Sonneveld, JH Jansen, W. Seinen, B. van der Burg: Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays . In: Toxicol. Sci. tape 83 , February 2005, p. 264-272 , doi : 10.1093 / toxsci / kfi035 , PMID 15537743 .
  12. ↑ Z. Klimová, J. Hojerová, S. Pažoureková: Current problems in the use of organic UV filters to protect skin from excessive sun exposure . In: Acta Chimica Slovaca . tape 6 , no. 1 , 2013, p. 82–88 , doi : 10.2478 / acs-2013-0014 ( stuba.sk [PDF]).