# Homosalate

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Homosalate[1] Names IUPAC name 3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate Other names Homosalate Identifiers CAS Number 118-56-9 Y 3D model (JSmol) Interactive image ChemSpider 8059 Y ECHA InfoCard 100.003.874 KEGG D04450 Y PubChem CID 8362 UNII V06SV4M95S Y CompTox Dashboard (EPA) DTXSID1026241 InChI InChI=1S/C16H22O3/c1-11-8-12(10-16(2,3)9-11)19-15(18)13-6-4-5-7-14(13)17/h4-7,11-12,17H,8-10H2,1-3H3 Y Key: WSSJONWNBBTCMG-UHFFFAOYSA-N Y InChI=1/C16H22O3/c1-11-8-12(10-16(2,3)9-11)19-15(18)13-6-4-5-7-14(13)17/h4-7,11-12,17H,8-10H2,1-3H3 Key: WSSJONWNBBTCMG-UHFFFAOYAJ SMILES O=C(OC1CC(CC(C1)(C)C)C)c2ccccc2O Properties Chemical formula C16H22O3 Molar mass 262.349 g·mol−1 Density 1.05 g/cm3 (20 °C)[2] Melting point < −20 °C[2] Boiling point 181–185 °C (358–365 °F; 454–458 K)[2] Solubility in water 0.4 mg/L Hazards Flash point 171 °C (340 °F; 444 K)[2] Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

**Homosalate** is an [organic compound](/source/Organic_compound) used in some [sunscreens](/source/Sunscreen). It is made by the [Fischer–Speier esterification](/source/Fischer%E2%80%93Speier_esterification) of [salicylic acid](/source/Salicylic_acid) and [3,3,5-trimethylcyclohexanol](/source/3%2C3%2C5-Trimethylcyclohexanol), the latter being a [hydrogenated](/source/Hydrogenated) derivative of [isophorone](/source/Isophorone). Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter.[3] The salicylic acid portion of the molecule absorbs [ultraviolet](/source/Ultraviolet) rays with a wavelength from 295 nm to 315 nm, protecting the skin from sun damage. The [hydrophobic](/source/Hydrophobic) trimethyl cyclohexyl group provides greasiness that prevents it from dissolving in water.

## Safety

Homosalate was identified in a court case brought by German chemical company [Symrise](/source/Symrise) who claimed that the ingredient used in sunscreen did not require animal testing.

Symrise lost the appeal against a European Chemicals Agency (ECHA) decision that requires the German manufacturer to test sunscreen ingredients on animals.[4]

The Court of Justice of the European Union (CJEU) decision applies to two formerly approved ingredients used exclusively in sunscreens — UV filter homosalate and [2-ethylhexyl salicylate](/source/2-ethylhexyl_salicylate).[5][6]

Similar to other UV filter compounds,[7] more homosalate is absorbed into the uppermost stratum corneum (*ie, the stratum disjunctum*) of the face (25% of applied dose) versus back of volunteers. This amounted to approximately two to three times the amount of sunscreen that was present in the superficial [stratum corneum](/source/Stratum_corneum) layers of the face compared with the back. There was no homosalate detected in the urine samples or [blood plasma](/source/Blood_plasma) samples of the volunteers in this study.[8][9]

Homosalate has been identified as an [antiandrogen](/source/Antiandrogen) (testosterone blocker) *in vitro*,[10] as well as having estrogenic activity toward estrogen receptors α,[11] and general *in vitro* estrogenic activity.[12] Homosalate has been shown to be an antagonist toward [androgen](/source/Androgen) and [estrogen](/source/Estrogen) receptors *[in vitro](/source/In_vitro)*.[13] Some work has shown that organic UV filters in general can present concerns.[14]

There is no *[in vivo](/source/In_vivo)* evidence of toxicity, endocrine dysfunction or adverse effects; and none of these adverse events have ever been reported to occur in humans.

An *in vivo* study involving repeated [subcutaneous injections](/source/Subcutaneous_injection) of homosalate at dose levels up to 1000mg/kg of body weight to juvenile female [Wistar rats](/source/Wistar_rats) over three consecutive days revealed no estrogenic potential in the [uterotrophic](/source/Uterotrophic) assay. Another study on immature [Long–Evans rats](/source/Long%E2%80%93Evans_rat) receiving up to 892 mg/kg of body weight of homosalate in their daily diet found no estrogenic effects in vivo. Research on [zebra fish](/source/Zebra_fish) also found no estrogenic effects after being continuously exposed to homosalate for 96 hours straight. The [SCCS](/source/Scientific_Committee_on_Consumer_Safety) has declared there is no sufficient evidence that identifies pure homosalate as an endocrine disruptor in humans and further declared that *in vivo* research has confirmed that homosalate has no [genotoxic](/source/Genotoxic), [phototoxic](/source/Phototoxic) or [photosensitive](/source/Photosensitivity_in_humans) effects when applied topically.[9]

## References

1. **[^](#cite_ref-1)** [Homosalate](https://www.rsc.org/Merck-Index/monograph/MONO1500004777), *[Merck Index](/source/Merck_Index)*, 11th Edition, **4660**.

1. ^ [***a***](#cite_ref-GESTIS_2-0) [***b***](#cite_ref-GESTIS_2-1) [***c***](#cite_ref-GESTIS_2-2) [***d***](#cite_ref-GESTIS_2-3) [Record](https://gestis.dguv.de/data?name=101950&lang=en) in the [GESTIS Substance Database](/source/GESTIS_Substance_Database) of the [Institute for Occupational Safety and Health](/source/Institute_for_Occupational_Safety_and_Health_of_the_German_Social_Accident_Insurance)

1. **[^](#cite_ref-3)** [Homosalate](https://pubchem.ncbi.nlm.nih.gov/#tab/sidsrcname=ChemIDplus&query=118-56-9&input_type=text), ChemIDplus.

1. **[^](#cite_ref-4)** ["Animal tests for makeup ingredients allowed"](https://www.bbc.co.uk/news/science-environment-65484552). *BBC News*. 5 May 2023.

1. **[^](#cite_ref-5)** ["CURIA - Documents"](https://curia.europa.eu/juris/document/document.jsf?text=&docid=286802&pageIndex=0&doclang=en&mode=lst&dir=&occ=first&part=1&cid=6696644).

1. **[^](#cite_ref-6)** ["CURIA - Documents"](https://curia.europa.eu/juris/document/document.jsf;jsessionid=13FF5B0EB4FF44663026FDE8D390B8ED?text=&docid=244529&pageIndex=0&doclang=en&mode=lst&dir=&occ=first&part=1&cid=6696105).

1. **[^](#cite_ref-7)** Rougier A, Dupuis D, Lotte C, Roguet R, Wester RC, Maibach HI (1986). "Regional variation in percutaneous absorption in man: measurement by the stripping method". *Arch. Dermatol. Res*. **278** (6): 465–469. [doi](/source/Doi_(identifier)):[10.1007/bf00455165](https://doi.org/10.1007%2Fbf00455165). [PMID](/source/PMID_(identifier)) [3789805](https://pubmed.ncbi.nlm.nih.gov/3789805). [S2CID](/source/S2CID_(identifier)) [24610879](https://api.semanticscholar.org/CorpusID:24610879).

1. **[^](#cite_ref-8)** Benson HA, Sarveiya V, Risk S, Roberts MS (2005). ["Influence of anatomical site and topical formulation on skin penetration of sunscreens"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1661631). *Ther Clin Risk Manag*. **1** (3): 209–218. [PMC](/source/PMC_(identifier)) [1661631](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1661631). [PMID](/source/PMID_(identifier)) [18360561](https://pubmed.ncbi.nlm.nih.gov/18360561).

1. ^ [***a***](#cite_ref-auto_9-0) [***b***](#cite_ref-auto_9-1) ["OPINION on Homosalate"](https://ec.europa.eu/health/sites/default/files/scientific_committees/consumer_safety/docs/sccs_o_244.pdf) (PDF). Scientific Committee on Consumer Safety. June 2021.

1. **[^](#cite_ref-10)** Ma, R.; Cotton, B.; Lichtensteiger, W.; Schlumpf, M. (2003). ["UV Filters with Antagonistic Action at Androgen Receptors in the MDA-kb2 Cell Transcriptional-Activation Assay"](https://doi.org/10.1093%2Ftoxsci%2Fkfg102). *Toxicological Sciences*. **74** (1): 43–50. [doi](/source/Doi_(identifier)):[10.1093/toxsci/kfg102](https://doi.org/10.1093%2Ftoxsci%2Fkfg102). [PMID](/source/PMID_(identifier)) [12730620](https://pubmed.ncbi.nlm.nih.gov/12730620).

1. **[^](#cite_ref-11)** Gomez E, Pillon A, Fenet H, Rosain D, Duchesne MJ, Nicolas JC, Balaguer P, Casellas C (2005). "Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens, and musks". *J Toxicol Environ Health A*. **68** (4): 239–251. [Bibcode](/source/Bibcode_(identifier)):[2005JTEHA..68..239G](https://ui.adsabs.harvard.edu/abs/2005JTEHA..68..239G). [doi](/source/Doi_(identifier)):[10.1080/15287390590895054](https://doi.org/10.1080%2F15287390590895054). [PMID](/source/PMID_(identifier)) [15799449](https://pubmed.ncbi.nlm.nih.gov/15799449). [S2CID](/source/S2CID_(identifier)) [41796996](https://api.semanticscholar.org/CorpusID:41796996).

1. **[^](#cite_ref-12)** Schlumpf M, Schmid P, Durrer S, Conscience M, Maerkel K, Henseler M, Gruetter M, Herzog I, Reolon S, Ceccatelli R, Faass O, Stutz E, Jarry H, Wuttke W, Lichtensteiger W (2004). "Endocrine activity and developmental toxicity of cosmetic UV filters--an update". *Toxicology*. **205** (1–2): 113–122. [Bibcode](/source/Bibcode_(identifier)):[2004Toxgy.205..113S](https://ui.adsabs.harvard.edu/abs/2004Toxgy.205..113S). [doi](/source/Doi_(identifier)):[10.1016/j.tox.2004.06.043](https://doi.org/10.1016%2Fj.tox.2004.06.043). [PMID](/source/PMID_(identifier)) [15458796](https://pubmed.ncbi.nlm.nih.gov/15458796).

1. **[^](#cite_ref-13)** Schreurs RH, Sonneveld E, Jansen JH, Seinen W, van der Burg B (February 2005). ["Interaction of polycyclic musks and UV filters with the estrogen receptor (ER), androgen receptor (AR), and progesterone receptor (PR) in reporter gene bioassays"](https://doi.org/10.1093%2Ftoxsci%2Fkfi035). *Toxicol. Sci*. **83** (2): 264–272. [doi](/source/Doi_(identifier)):[10.1093/toxsci/kfi035](https://doi.org/10.1093%2Ftoxsci%2Fkfi035). [PMID](/source/PMID_(identifier)) [15537743](https://pubmed.ncbi.nlm.nih.gov/15537743).

1. **[^](#cite_ref-14)** Klimova, et al. (2013). ["Current problems in the use of organic UV filters to protect skin from excessive sun exposure"](http://www.acs.chtf.stuba.sk/papers/acs_0149.pdf) (PDF). *Acta Chimica Slovaca*. **6** (1): 82–88. [doi](/source/Doi_(identifier)):[10.2478/acs-2013-0014](https://doi.org/10.2478%2Facs-2013-0014). [S2CID](/source/S2CID_(identifier)) [42677951](https://api.semanticscholar.org/CorpusID:42677951).

v t e Sunscreening agents currently approved by one or more agencies (e.g. US FDA, SCCS, TGA) UVA: 400–315 nm UVB: 315–290 nm UVA filters Avobenzone Bis-(Diethylaminohydroxybenzoyl Benzoyl) Piperazine (HAA299) Bisdisulizole disodium Diethylamino hydroxybenzoyl hexyl benzoate Ecamsule Menthyl anthranilate Methoxypropylamino cyclohexenylidene ethoxyethylcyanoacetate UVB filters Amiloxate 4-Aminobenzoic acid (PABA) Cinoxate Ethylhexyl triazone Homosalate Enzacamene Octyl methoxycinnamate (Octinoxate) Ethylhexyl salicylate (Octisalate) Padimate O Phenylbenzimidazole sulfonic acid (Ensulizole) Polysilicone-15 Trolamine salicylate UVA+UVB filters Bemotrizinol Benzophenones 1–12 Bisoctrizole Dioxybenzone Drometrizole trisiloxane Iscotrizinol Octocrylene Oxybenzone Phenylene bis-diphenyltriazine Sulisobenzone Titanium dioxide Tris-biphenyl triazine Zinc oxide See also: Photoprotection, Sun protective clothing, Sun tanning, and Sunburn

v t e Salicylates Salicylic acid Aspirin Aloxiprin Methyl salicylate Magnesium salicylate Ethyl salicylate Isopropyl salicylate Bismuth subsalicylate Sodium salicylate Salicylamide Salicin Benorilate Salsalate Ethenzamide Diflunisal Trolamine salicylate Homosalate Salicylmethylecgonine 2-Ethylhexyl salicylate Aluminon Lithium salicylate Lithium cocrystal Benzyl salicylate Copper aspirinate Potassium salicylate

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Adapted from the Wikipedia article [Homosalate](https://en.wikipedia.org/wiki/Homosalate) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Homosalate?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.