4-Hexylresorcinol: Difference between revisions

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			{{Short description\|Chemical compound}}
⚫	~~{{Drugbox~~\| verifiedrevid = ~~415527556~~
			{{cs1 config \|name-list-style=vanc \|display-authors=6}}
	\|used in strepsils
			{{Drugbox
⚫	\|IUPAC_name = 4-hexylbenzene-1,3-diol
		⚫	\| verifiedrevid = 443857623
⚫	\| image=Hexylresorcinol.svg
		⚫	\| IUPAC_name = 4-hexylbenzene-1,3-diol
⚫	\| image2=Hexylresorcinol-3D-balls.png
		⚫	\| 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-->
		⚫	\| bioavailability =
		⚫	\| metabolism =
		⚫	\| excretion =

			<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|correct\|??}}
		⚫	\| CAS_number = 136-77-6
		⚫	\| ATC_prefix = R02
		⚫	\| ATC_suffix = AA12
		⚫	\| PubChem = 3610
			\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| ChemSpiderID = 21106121
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = R9QTB5E82N
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D04441		\| KEGG = D04441
	\| InChI = 1/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3
	\| InChIKey = WFJIVOKAWHGMBH-UHFFFAOYAH
⚫	\| smiles = Oc1cc(O)ccc1CCCCCC
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 443605		\| ChEMBL = 443605

			<!--Chemical data-->
		⚫	\| C=12 \| H=18 \| O=2
			\| melting_point = 68
			\| melting_high = 69
			\| boiling_point = 333
			\| boiling_high = 335
		⚫	\| smiles = Oc1cc(O)ccc1CCCCCC
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3		\| StdInChI = 1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = WFJIVOKAWHGMBH-UHFFFAOYSA-N		\| StdInChIKey = WFJIVOKAWHGMBH-UHFFFAOYSA-N
⚫	\| CAS_number=136-77-6
⚫	\| ATC_prefix=R02
⚫	\| ATC_suffix=~~AA12~~
	\| ATC_supplemental=
⚫	\| PubChem=3610
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| ChemSpiderID=~~21106121~~
	\| DrugBank=
⚫	\| C=12 \| H=18 \| O=2
	\| molecular_weight = 194.27
⚫	\| bioavailability=
⚫	\| metabolism =
	\| elimination_half-life=
⚫	\| excretion =
⚫	\| pregnancy_category =
⚫	\| legal_status =
⚫	\| routes_of_administration=
	}}		}}
	'''Hexylresorcinol''' is a chemical compound with ], ] and ] properties.

			'''4-Hexylresorcinol''' is an ] with ], ], and ] 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>
	It can be used topically on small ]s, or as an ingredient in ]s. In vivo studies conducted on Synovea HR Hexylresorcinol by Sytheon in January 2007 have shown that it has the same lightening effect as 2% ] over an 8 week period.

			As an ], it is marketed as '''S.T.37''' by Numark Laboratories, Inc. (in a 0.1% solution) for oral pain relief and as a topical antiseptic. It is available for use topically on small ]s or as an ingredient in ]s.
	An ingredient in ] Extra (but not Strepsils Original) and, as a 0,1% solution, it is the active ingredient in S.T.37, Topical Antiseptic/Oral Pain Reliever.

			As an ], 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 in March 2009<ref>Chem. Res. Toxicol., 2009, 22 (1), pp 52–63</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 ].
			Sytheon Ltd., USA markets 4-hexylresorcinol (trade named Synovea HR).

			] uses 4-hexylresorcinol in its ], Aveno, and RoC skincare products as an ]. 4-Hexylresorcinol has been used commercially by many cosmetic and personal care companies, such as ], ], ], ], ], ], and many small and large companies.

			A study published in '']'' <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 ] (E-586) exhibits some estrogenic activity, i.e. resembles action of the female sex hormone ]. However, a recent study published in '']'' <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.<ref name=":0" />

			In one study, 4-hexylresorcinol increased the ] of ] by reducing ] (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 ] 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 ]<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 ==		== References ==
			{{Reflist}}
	<references />

	{{Throat preparations}}		{{Throat preparations}}
			{{Anthelmintics}}
⚫	]

		⚫	{{DEFAULTSORT:hexylresorcinol}}
	]		]
	]		]
	]		]
	]		]
			]

		⚫	]
	{{respiratory-system-drug-stub}}
	{{nervous-system-drug-stub}}

	]
⚫	]
	]

Latest revision as of 14:35, 22 September 2024

Chemical compound

Pharmaceutical compound

4-Hexylresorcinol
Clinical data


Trade names	S.T.37, Crystoids
AHFS/Drugs.com	International Drug Names
ATC code	R02AA12 (WHO)
Identifiers
IUPAC name 4-hexylbenzene-1,3-diol
CAS Number	136-77-6
PubChem CID	3610
ChemSpider	21106121
UNII	R9QTB5E82N
KEGG	D04441
ChEMBL	ChEMBL443605
CompTox Dashboard (EPA)	DTXSID1020699
ECHA InfoCard	100.004.780
Chemical and physical data
Formula	C₁₂H₁₈O₂
Molar mass	194.274 g·mol
3D model (JSmol)	Interactive image
Melting point	68 to 69 °C (154 to 156 °F)
Boiling point	333 to 335 °C (631 to 635 °F)
SMILES Oc1cc(O)ccc1CCCCCC
InChI InChI=1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3 Key:WFJIVOKAWHGMBH-UHFFFAOYSA-N
(verify)

4-Hexylresorcinol is an organic compound with local anaesthetic, antiseptic, and anthelmintic properties.

As an antiseptic, it is marketed as S.T.37 by Numark Laboratories, Inc. (in a 0.1% solution) for oral pain relief and as a topical antiseptic. It is available for use topically on small skin infections or as an ingredient in throat lozenges.

As an anthelmintic, 4-hexylresorcinol was sold under the brand Crystoids. 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 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 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).

In mice with cancer, 4-hexylresorcinol inhibited NF-κB and extended their survival rate.

4-Hexylresorcinol can be used in the synthesis of tetrahydrocannabihexol

References

"Hexylresorcinol". NIST Chemistry WebBook, SRD 69. NIST. Retrieved 19 April 2024.
Gisvold O (1966). Wilson CO, Gisvold O, Doerge RF (eds.). Textbook of Organic Medicinal and Pharmaceutical Chemistry (5th ed.). Philadelphia: Lippincott. pp. 237–262.
"Anthelmintic Crystoids" (Object in collection). National Museum of American History. ID number 1985.0481.142. Retrieved 19 April 2024.
Amadasi A, Mozzarelli A, Meda C, Maggi A, Cozzini P (January 2009). "Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach". Chemical Research in Toxicology. 22 (1): 52–63. doi:10.1021/tx800048m. PMC 2758355. PMID 19063592.
^ Kang YJ, Oh JH, Seok H, Jo YY, Kim DW, Garagiola U, et al. (2020). "4-Hexylresorcinol Exhibits Different Characteristics to Estrogen". Applied Sciences. 10 (5): 1737. doi:10.3390/app10051737. hdl:2434/962276.
Montero P (2006). "Effectiveness of Onboard Application of 4-Hexylresorcinol in Inhibiting Melanosis in Shrimp (Parapenaeus longirostris [es])". Journal of Food Science. 69: C643 – C647. doi:10.1111/j.1365-2621.2004.tb09913.x.
Kim SG, Lee SW, Park YW, Jeong JH, Choi JY (December 2011). "4-hexylresorcinol inhibits NF-κB phosphorylation and has a synergistic effect with cisplatin in KB cells". Oncology Reports. 26 (6): 1527–32. doi:10.3892/or.2011.1436. PMID 21874263.
Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.

v t e Throat preparations (R02)
Antiseptics	Acriflavinium chloride Ambazone Amylmetacresol Benzalkonium Benzethonium Cetrimonium (bromide/chloride) Cetylpyridinium Chlorhexidine Chlorquinaldol Dequalinium Dichlorobenzyl alcohol Hexamidine Hexetidine Hexylresorcinol Myristyl-benzalkonium Oxyquinoline Phenol Povidone-iodine
Antibiotics	Bacitracin Fusafungine Gramicidin Neomycin Tyrothricin
Local anesthetics	Benzocaine Cocaine Dyclonine Lidocaine
Other	Flurbiprofen

Antiparasitics – Anthelmintics (P02) and endectocides (QP54)

Antiplatyhelmintic agents

Antitrematodals
(schistosomicides)

Binds tubulin	benzimidazole Triclabendazole
AChE inhibitor	phosphonic acid Metrifonate
Other/unknown	quinoline Arpraziquantel Praziquantel (+esafoxolaner/eprinomectin) Oxamniquine phenol Bithionol thiazole Niridazole thioxanthone Hycanthone Lucanthone antimony compounds Stibophen Tartar emetic

Anticestodals
(taeniacides)

Binds tubulin	benzimidazole Albendazole
Other/unknown	quinoline Praziquantel (+esafoxolaner/eprinomectin) salicylanilide Niclosamide aminoacridine Quinacrine butyrophenone Desaspidin chlorophenol Dichlorophen

Antinematodal agents
(including
macrofilaricides)

Binds tubulin	benzimidazole Mebendazole Albendazole Tiabendazole Fenbendazole Ciclobendazole Flubendazole
Glutamate-gated chloride channel, GABA receptor	avermectins Abamectin Doramectin Emamectin Eprinomectin (+esafoxolaner/praziquantel) Ivermectin Selamectin milbemycins Moxidectin (+fluralaner) Milbemycin oxime
NMDA	tetrahydropyrimidine Pyrantel pyrantel pamoate Oxantel Morantel Carbantel Febantel (aka felsantel)
Other/unknown	piperazine Piperazine Diethylcarbamazine thiazole Levamisole quinolinium Pyrvinium benzylammonium Bephenium naphthalenesulfonate Suramin Ascaridole Hexylresorcinol Santonin Tribendimidine Tetrachloroethylene

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Categories: