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Hydrotrope
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<h2 id="applications">Applications</h2> <p>Hydrotropes are in use industrially and commercially in cleaning and personal care product formulations to allow more concentrated formulations of surfactants. About 29,000 metric tons are produced (i.e., manufactured and imported) annually in the US.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> Annual production (plus importation) in Europe and Australia is approximately 17,000 and 1,100 metric tons, respectively.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a><a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> </p><p> Common products containing hydrotropes include laundry detergents, surface cleaners, dishwashing detergents, liquid soaps, shampoos and conditioners.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> They are coupling agents, used at concentrations from 0.1 to 15% to stabilize the formula, modify viscosity and cloud-point, reduce phase separation in low temperatures, and limit foaming.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a></p> Examples of hydrotropes used for industrial and commercial purposes<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a><a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a><table><tbody><tr><th>Chemical</th><th>CAS#</th></tr><tr><td>Toluene sulfonic acid, Na salt</td><td>12068-03-0</td></tr><tr><td>Toluene sulfonic acid, K salt</td><td>16106-44-8<p>30526-22-8</p></td></tr><tr><td>Xylene sulfonic acid, Na salt</td><td>1300-72-7<p>827-21-4</p></td></tr><tr><td>Xylene sulfonic acid, ammonium salt</td><td>26447-10-9</td></tr><tr><td>Xylene sulfonic acid, K salt</td><td>30346-73-7</td></tr><tr><td>Xylene sulfonic acid, Ca salt</td><td>28088-63-3</td></tr><tr><td>Cumene sulfonic acid, Na salt</td><td>28348-53-0<p>32073-22-6</p></td></tr><tr><td>Cumene sulfonic acid, ammonium salt</td><td>37475-88-0</td></tr></tbody></table> <p><a href="/facts/Adenosine_triphosphate/nB9bwgcU">Adenosine triphosphate</a> (ATP) has been shown to prevent aggregation of proteins at normal physiologic concentrations and to be approximately an order of magnitude more effective than sodium xylene sulfonate in a classic hydrotrope assay.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> The hydrotrope activity of ATP was shown to be independent of its activity as an "energy currency" in <a href="/facts/Cell_(biology)/bLM9UQvy">cells.</a><a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> Additionally, ATP function as biological hydrotope has been shown proteome-wide under near native conditions.<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> In a recent study, however, the hydrotropic capabilities of ATP have been questioned as it has severe salting-out characteristics due to its triphosphate moiety.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> </p> <h2 id="environmental-considerations">Environmental considerations</h2> <p>Hydrotropes have a low <a href="/facts/Bioaccumulation/KaHzFKnL">bioaccumulation</a> potential, as the <a href="/facts/Octanol-water_partition_coefficient/9nM3FzBf">octanol-water partition coefficient</a> is <1.0.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> Studies have found hydrotopes to be very slightly volatile, with vapor pressures <2.0x10-5 Pa.<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> They are aerobically biodegradable. Removal via the secondary wastewater treatment process of activated sludge is >94%.<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a> Acute toxicity studies on fish show an LC50 >400 mg active ingredient (a.i.)/L. For Daphnia, the EC50 is >318 mg a.i./L. The most sensitive species is green algae with EC50 values in the range of 230–236 mg a.i./ L and No Observed Effect Concentrations (NOEC) in the range of 31–75 mg a.i./L.<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a> The aquatic Predicted No Effect Concentration (PNEC) was found to be 0.23 mg a.i./L.<a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> The Predicted Environmental Concentration (PEC)/PNEC ratio has been determined to be < 1 and, therefore, hydrotropes in household laundry and cleaning products have been determined to not be an environmental concern.<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a><a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> </p> <h2 id="human-health">Human health</h2> <p>Aggregate exposures to consumers (direct and indirect dermal contact, ingestion, and inhalation) have been estimated to be 1.42 ug/Kg bw/day.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> Calcium xylene sulfonate and sodium cumene sulfonate have been shown to cause temporary, slight eye irritation in animals.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> Studies have not found hydrotropes to be mutagenic, carcinogenic or have reproductive toxicity.<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Neuberg, C (1916). "Hydrotropic phenomena. I". Biochem. Z. 76: 107–76. <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Mehringer, Johannes; Kunz, Werner (August 2021). "Carl Neuberg's hydrotropic appearances (1916)". Advances in Colloid and Interface Science. 294: 102476. doi:10.1016/j.cis.2021.102476. PMID 34229180. S2CID 235757195. <a href="https://linkinghub.elsevier.com/retrieve/pii/S0001868621001172" target="_blank">https://linkinghub.elsevier.com/retrieve/pii/S0001868621001172</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Neuberg, C (1916). "Hydrotropic phenomena. I". Biochem. Z. 76: 107–76. <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Evstigneev, M.P.; Evstigneev, V.P.; Hernandez Santiago, A.A.; Davies, David B. (2006). "Effect of a mixture of caffeine and nicotinamide on the solubility of vitamin (B2) in aqueous solution" (PDF). European Journal of Pharmaceutical Sciences. 28 (1–2): 59–66. doi:10.1016/j.ejps.2005.12.010. PMID 16483751. S2CID 24920111. <a href="https://eprints.bbk.ac.uk/382/1/Binder1.pdf" target="_blank">https://eprints.bbk.ac.uk/382/1/Binder1.pdf</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Suzuki, H.; Sunada, H. (1998). "Mechanistic studies on hydrotropic solubilization of nifedipine in nicotinamide solution". Chemical & Pharmaceutical Bulletin. 46 (1): 125–130. doi:10.1248/cpb.46.125. PMID 9468644. <a href="https://doi.org/10.1248%2Fcpb.46.125" target="_blank">https://doi.org/10.1248%2Fcpb.46.125</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Da Silva, R.C.; Spitzer, M.; Da Silva, L.H.M.; Loh, W. (1999). "Investigations on the mechanism of aqueous solubility increase caused by some hydrotropes". Thermochimica Acta. 328 (1–2): 161–167. doi:10.1016/s0040-6031(98)00637-6. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>Singhai, A., 1992. Studies on solubilization, formulation and evaluation of some drugs, Dept. of Pharm. Sci. Dr. H. S. Gaur vishwavidhyalaya., Sagar, 10. <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Human & Environmental Risk Assessment on ingredients of household cleaning products (HERA) (2005). "Hydrotropes" (PDF). Risk Assessment. <a href="http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf" target="_blank">http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Hydrotropes Consortium (2005). "SIDS Initial Assessment Report for SIAM 21 Hydrotropes" (PDF). Archived from the original (PDF) on 2013-04-02. <a href="https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf" target="_blank">https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>Hydrotropes Consortium (2005). "SIDS Initial Assessment Report for SIAM 21 Hydrotropes" (PDF). Archived from the original (PDF) on 2013-04-02. <a href="https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf" target="_blank">https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>Human & Environmental Risk Assessment on ingredients of household cleaning products (HERA) (2005). "Hydrotropes" (PDF). Risk Assessment. <a href="http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf" target="_blank">http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Patel, Avinash; Malinovska, Liliana; Saha, Shambaditya; Wang, Jie; Alberti, Simon; Krishnan, Yamuna; Hyman, Anthony A. (2017). "ATP as a biological hydrotrope". Science. 356 (6339): 753–756. Bibcode:2017Sci...356..753P. doi:10.1126/science.aaf6846. ISSN 0036-8075. PMID 28522535. S2CID 24622983. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>Patel, Avinash; Malinovska, Liliana; Saha, Shambaditya; Wang, Jie; Alberti, Simon; Krishnan, Yamuna; Hyman, Anthony A. (2017). "ATP as a biological hydrotrope". Science. 356 (6339): 753–756. Bibcode:2017Sci...356..753P. doi:10.1126/science.aaf6846. ISSN 0036-8075. PMID 28522535. S2CID 24622983. <a href="/wiki/Bibcode_(identifier)" target="_blank">/wiki/Bibcode_(identifier)</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></p></li> <li id="fn:18"><p>Savitski, Mikhail M.; Bantscheff, Marcus; Huber, Wolfgang; Dominic Helm; Günthner, Ina; Werner, Thilo; Kurzawa, Nils; Sridharan, Sindhuja (2019-03-11). "Proteome-wide solubility and thermal stability profiling reveals distinct regulatory roles for ATP". Nature Communications. 10 (1): 1155. Bibcode:2019NatCo..10.1155S. doi:10.1038/s41467-019-09107-y. ISSN 2041-1723. PMC 6411743. PMID 30858367. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6411743" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6411743</a> <a href="#fnref:18" class="footnote-back-ref">↩</a></p></li> <li id="fn:19"><p>Mehringer, Johannes; Do, Tuan-Minh; Touraud, Didier; Hohenschutz, Max; Khoshsima, Ali; Horinek, Dominik; Kunz, Werner (February 2021). "Hofmeister versus Neuberg: is ATP really a biological hydrotrope?". Cell Reports Physical Science. 2 (2): 100343. doi:10.1016/j.xcrp.2021.100343. ISSN 2666-3864. <a href="https://doi.org/10.1016%2Fj.xcrp.2021.100343" target="_blank">https://doi.org/10.1016%2Fj.xcrp.2021.100343</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></p></li> <li id="fn:20"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></p></li> <li id="fn:21"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:21" class="footnote-back-ref">↩</a></p></li> <li id="fn:22"><p>Hydrotropes Consortium (2005). "SIDS Initial Assessment Report for SIAM 21 Hydrotropes" (PDF). Archived from the original (PDF) on 2013-04-02. <a href="https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf" target="_blank">https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf</a> <a href="#fnref:22" class="footnote-back-ref">↩</a></p></li> <li id="fn:23"><p>Hydrotropes Consortium (2005). "SIDS Initial Assessment Report for SIAM 21 Hydrotropes" (PDF). Archived from the original (PDF) on 2013-04-02. <a href="https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf" target="_blank">https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf</a> <a href="#fnref:23" class="footnote-back-ref">↩</a></p></li> <li id="fn:24"><p>Human & Environmental Risk Assessment on ingredients of household cleaning products (HERA) (2005). "Hydrotropes" (PDF). Risk Assessment. <a href="http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf" target="_blank">http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf</a> <a href="#fnref:24" class="footnote-back-ref">↩</a></p></li> <li id="fn:25"><p>Stanton, Kathleen; Caritas Tibazarwa; Hans Certa; William Greggs; Donna Hillebold; Lela Jovanovich; Daniel Woltering; Richard Sedlak (2010). "Environmental Risk Assessment of Hydrotropes in the United States, Europe, and Australia". Integrated Environmental Assessment and Management. 6 (1): 155–163. doi:10.1897/IEAM_2009-019.1. PMID 19558203. S2CID 11467860. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:25" class="footnote-back-ref">↩</a></p></li> <li id="fn:26"><p>Human & Environmental Risk Assessment on ingredients of household cleaning products (HERA) (2005). "Hydrotropes" (PDF). Risk Assessment. <a href="http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf" target="_blank">http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf</a> <a href="#fnref:26" class="footnote-back-ref">↩</a></p></li> <li id="fn:27"><p>Human & Environmental Risk Assessment on ingredients of household cleaning products (HERA) (2005). "Hydrotropes" (PDF). Risk Assessment. <a href="http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf" target="_blank">http://www.heraproject.com/files/24-F-HERA%20Hydrotropes%20Sept%202005.pdf</a> <a href="#fnref:27" class="footnote-back-ref">↩</a></p></li> <li id="fn:28"><p>Hydrotropes Consortium (2005). "SIDS Initial Assessment Report for SIAM 21 Hydrotropes" (PDF). Archived from the original (PDF) on 2013-04-02. <a href="https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf" target="_blank">https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf</a> <a href="#fnref:28" class="footnote-back-ref">↩</a></p></li> <li id="fn:29"><p>Hydrotropes Consortium (2005). "SIDS Initial Assessment Report for SIAM 21 Hydrotropes" (PDF). Archived from the original (PDF) on 2013-04-02. <a href="https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf" target="_blank">https://web.archive.org/web/20130402032100/http://www.chem.unep.ch/irptc/sids/OECDSIDS/Hydrotropes.pdf</a> <a href="#fnref:29" class="footnote-back-ref">↩</a></p></li> </ol>