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{{Short description|Chemical compound}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox
| verifiedrevid = 443857623
| IUPAC_name = 4-hexylbenzene-1,3-diol
| image = 4-Hexylresorcinol.svg
| image2 = 4-Hexylresorcinol-3D-balls.png
<!--Clinical data-->
| tradename = S.T.37, Crystoids<ref>{{cite web |title=Hexylresorcinol |url=https://webbook.nist.gov/cgi/cbook.cgi?ID=136-77-6 |website=NIST Chemistry WebBook, SRD 69 |publisher=NIST |access-date=19 April 2024}}</ref>
| Drugs.com = {{drugs.com|international|hexylresorcinol}}
| pregnancy_category =
| legal_status =
| routes_of_administration =
<!--Pharmacokinetic data-->
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'''4-Hexylresorcinol''' is an [[organic compound]] with [[local anaesthetic]], [[antiseptic]], and [[anthelmintic]] properties.<ref>{{cite book | vauthors = Gisvold O | year = 1966 | title = Textbook of Organic Medicinal and Pharmaceutical Chemistry | edition = 5th | veditors = Wilson CO, Gisvold O, Doerge RF | pages = 237–262 | location = Philadelphia | publisher = Lippincott}}</ref>
As an [[anthelmintic]], 4-hexylresorcinol was sold under the brand Crystoids.<ref>{{cite web |title=Anthelmintic Crystoids |url=https://americanhistory.si.edu/collections/nmah_212530 |publisher=National Museum of American History |access-date=19 April 2024 | id = ID number 1985.0481.142 |format=Object in collection}}</ref>
A study published in ''[[Chemical Research in Toxicology]]'' <ref>{{cite journal | vauthors = Amadasi A, Mozzarelli A, Meda C, Maggi A, Cozzini P | title = Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach | journal = Chemical Research in Toxicology | volume = 22 | issue = 1 | pages = 52–63 | date = January 2009 | pmid = 19063592 | pmc = 2758355 | doi = 10.1021/tx800048m }}</ref> shows that 4-hexylresorcinol used as a [[food additive]] (E-586) exhibits some estrogenic activity, i.e. resembles action of the female sex hormone [[estrogen]]. However, recent study published in ''[[Applied Sciences]]'' <ref>{{cite journal | vauthors = Kang YJ, Oh JH, Seok H, Jo YY, Kim DW, Garagiola U, Choi JY, Kim SG | journal = Applied Sciences| year = 2020 | volume = 10 | issue = 5 | pages = 1737 | doi = 10.3390/app10051737 | title = 4-Hexylresorcinol Exhibits Different Characteristics to Estrogen| doi-access = free }}</ref> shows that 4-hexylresorcinol did not change the expression of estrogen receptor-α, -β, or p-ERK1/2 in MCF-7 cells. In an ovariectomized animal model, the 4HR group showed similar levels of ERα, ERβ, and prolactin expression in the pituitary gland compared to the solvent only group, while the estradiol group showed higher levels. Serum prolactin levels were similar between the 4HR and solvent only groups.{{cn}}▼
Sytheon Ltd., USA markets 4-hexylresorcinol (trade named Synovea HR).
[[Johnson & Johnson]] uses 4-hexylresorcinol in its [[Neutrogena]], Aveno, and RoC skincare products as an [[anti-aging cream]]. 4-Hexylresorcinol has been used commercially by many cosmetic and personal care companies, such as [[Mary Kay]], [[Clarins]], [[Unilever]], [[Murad]], [[Facetheory]], [[Arbonne]], and many small and large companies.
▲A study published in ''[[Chemical Research in Toxicology]]'' <ref>{{cite journal | vauthors = Amadasi A, Mozzarelli A, Meda C, Maggi A, Cozzini P | title = Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach | journal = Chemical Research in Toxicology | volume = 22 | issue = 1 | pages = 52–63 | date = January 2009 | pmid = 19063592 | pmc = 2758355 | doi = 10.1021/tx800048m }}</ref> shows that 4-hexylresorcinol used as a [[food additive]] (E-586) exhibits some estrogenic activity, i.e. resembles action of the female sex hormone [[estrogen]]. However, a recent study published in ''[[Applied Sciences]]'' <ref name=":0">{{cite journal | vauthors = Kang YJ, Oh JH, Seok H, Jo YY, Kim DW, Garagiola U, Choi JY, Kim SG | journal = Applied Sciences| year = 2020 | volume = 10 | issue = 5 | pages = 1737 | doi = 10.3390/app10051737 | title = 4-Hexylresorcinol Exhibits Different Characteristics to Estrogen| doi-access = free | hdl = 2434/962276 | hdl-access = free }}</ref> shows that 4-hexylresorcinol did not change the expression of estrogen receptor-α, -β, or p-ERK1/2 in MCF-7 cells. In an ovariectomized animal model, the 4HR group showed similar levels of ERα, ERβ, and prolactin expression in the pituitary gland compared to the solvent only group, while the estradiol group showed higher levels. Serum prolactin levels were similar between the 4HR and solvent only groups.
In one study, 4-hexylresorcinol increased the [[shelf life]] of [[shrimp]] by reducing [[melanosis]] (black spots).<ref>{{cite journal | journal=Journal of Food Science | year=2006 | vauthors = Montero P | title=Effectiveness of Onboard Application of 4-Hexylresorcinol in Inhibiting Melanosis in Shrimp (''{{Interlanguage link multi|Parapenaeus longirostris|es}}'') | doi=10.1111/j.1365-2621.2004.tb09913.x | volume=69 | pages=C643–C647}}</ref>
In mice with cancer, 4-hexylresorcinol inhibited [[NF-κB]] and extended their survival rate.<ref>{{cite journal | vauthors = Kim SG, Lee SW, Park YW, Jeong JH, Choi JY | title = 4-hexylresorcinol inhibits NF-κB phosphorylation and has a synergistic effect with cisplatin in KB cells | journal = Oncology Reports | volume = 26 | issue = 6 | pages = 1527–32 | date = December 2011 | pmid = 21874263 | doi = 10.3892/or.2011.1436 | doi-access = free }}</ref>
4-Hexylresorcinol can be used in the synthesis of [[tetrahydrocannabihexol]]<ref>{{cite journal | doi = 10.1021/ja01255a061 | title = Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII<sup>1</sup> | date = 1942 | vauthors = Adams R, Loewe S, Smith CM, McPhee WD | journal = Journal of the American Chemical Society | volume = 64 | issue = 3 | pages = 694–697 }}</ref>
== References ==
{{Reflist}}
{{Throat preparations}}
{{Anthelmintics}}
{{DEFAULTSORT:hexylresorcinol}}
[[Category:Antiseptics]]
[[Category:Local anesthetics]]
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