4-Butylresorcinol

Last updated
4-Butylresorcinol
Rucinol Structural Formulae V.1.svg
Names
Preferred IUPAC name
4-Butylbenzene-1,3-diol
Other names
Rucinol, 4-n-Butylresorcinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.126.948 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 606-191-2
KEGG
PubChem CID
UNII
  • InChI=1S/C10H14O2/c1-2-3-4-8-5-6-9(11)7-10(8)12/h5-7,11-12H,2-4H2,1H3
    Key: CSHZYWUPJWVTMQ-UHFFFAOYSA-N
  • CCCCC1=C(C=C(C=C1)O)O
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H315, H319, H400
P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P391, P501
Lethal dose or concentration (LD, LC):
500mg/kg (rat) [1]
Safety data sheet (SDS) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Butylresorcinol, sometimes called 4-n-butylresorcinol, is a chemical used to treat hyperpigmentation of the epidermis. Hyperpigmentation is believed to be related to the enzyme tyrosinase which produces melanin. Among several chemicals known to inhibit tyrosinase production, such as hydroquinone, arbutin, and kojic acid, 4-butylresorcinol has been found to be the most powerful inhibitor by a wide margin. [3] 4-Butylresorcinol can be used in the synthesis of tetrahydrocannabutol.

Tyrosinase inhibition assay in μmol/L [4]
compoundin vitro IC50in vivo
arbutin> 5000
hydroquinone> 1000< 40
kojic acid500
4-n-butylresorcinol2113.5

References

  1. ↑ "SAFETY DATA SHEET" (PDF). datasheets.scbt.com.
  2. ↑ "Safety Data Sheet" (PDF). static.cymitquimica.com.
  3. ↑ "Hydroquinones". Phenols—Advances in Research and Application: 2013 Edition. Scholastic. 2013. p. 76.
  4. ↑ Kolbe, L.; Mann, T.; Gerwat, W.; Batzer, J.; Ahlheit, S.; Scherner, C.; Wenck, H.; Stäb, F. (January 2013). "4-n-butylresorcinol, a highly effective tyrosinase inhibitor for the topical treatment of hyperpigmentation". Journal of the European Academy of Dermatology and Venereology. 27 Suppl 1: 19–23. doi:10.1111/jdv.12051. ISSN   1468-3083. PMID   23205541.
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