4-Hexylresorcinol

4-Hexylresorcinol is an organic compound with local anaesthetic, antiseptic, and anthelmintic properties.[1]

4-Hexylresorcinol
Clinical data
Trade namesS.T.37, Crystoids
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 4-hexylbenzene-1,3-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.780
Chemical and physical data
FormulaC12H18O2
Molar mass194.274 g·mol−1
3D model (JSmol)
Melting point68 to 69 °C (154 to 156 °F)
Boiling point333 to 335 °C (631 to 635 °F)
  • Oc1cc(O)ccc1CCCCCC
  • 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 checkY
  • Key:WFJIVOKAWHGMBH-UHFFFAOYSA-N checkY
  (verify)

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 [2] 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 [3] 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.[3]

In one study, 4-hexylresorcinol increased the shelf life of shrimp by reducing melanosis (black spots).[4]

In mice with cancer, 4-hexylresorcinol inhibited NF-κB and extended their survival rate.[5]

4-Hexylresorcinol can be used in the synthesis of Tetrahydrocannabihexol.

References
  1. Gisvold O (1966). Wilson CO, Gisvold O, Doerge RF (eds.). Textbook of Organic Medicinal and Pharmaceutical Chemistry (5th ed.). Philadelphia: Lippincott. pp. 237–262.
  2. 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.
  3. Kang YJ, Oh JH, Seok H, Jo YY, Kim DW, Garagiola U, Choi JY, Kim SG (2020). "4-Hexylresorcinol Exhibits Different Characteristics to Estrogen". Applied Sciences. 10 (5): 1737. doi:10.3390/app10051737.
  4. Montero P (2006). "Effectiveness of Onboard Application of 4-Hexylresorcinol in Inhibiting Melanosis in Shrimp (Parapenaeus longirostris)". Journal of Food Science. 69: C643–C647. doi:10.1111/j.1365-2621.2004.tb09913.x.
  5. 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.
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