4-Butylresorcinol

4-Butylresorcinol
Names
	Preferred IUPAC name 4-Butylbenzene-1,3-diol
	Other names Rucinol, 4-n-Butylresorcinol
Identifiers
CAS Number	18979-61-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:81689;
ChEMBL	ChEMBL450195;
ChemSpider	178414;
ECHA InfoCard	100.126.948
EC Number	606-191-2;
KEGG	C18343;
PubChem CID	205912;
UNII	2IK4UQ3ZGA;
CompTox Dashboard (EPA)	DTXSID50172403 ;
	InChI 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;
	SMILES CCCCC1=C(C=C(C=C1)O)O;
Properties
Chemical formula	C10H14O2
Molar mass	166.220 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H400
Precautionary statements	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):
LD50 (median dose)	500mg/kg (rat)
Safety data sheet (SDS)	[1]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[2] 4-Butylresorcinol can be used in the synthesis of Tetrahydrocannabutol.

Tyrosinase inhibition assay in μmol/L ^[3]
compound	in vitro IC50	in vivo
arbutin	> 5000
hydroquinone	> 1000	< 40
kojic acid	500
4-n-butylresorcinol	21	13.5

4-Butylresorcinol has been shown to have potential as an hypocholesterolaemic agent, due to anti-HMG-CoA reductase inhibition activity, as an anti-urease agent which prevents urea loss in agriculture and subsequent ammonia emission. Ureases also cause the formation of kidney stones and infections, as well as hepatic coma. The compound was tested on cancer cell lines, and it exhibited little toxicity on the normal cell line.^[4]

IC₅₀ Values of 4-Butylresorcinol Against Various Enzymes and Cell Lines
Enzyme or Cell Line	IC₅₀
HMG-CoA reductase	182.04 μM
urease	91.44 μM
HUVEC	> 1000 μg/mL (IC₅₀ not reached)
KASUMI-1	143 ± 0 μg/mLᵃ
HL-60	230 ± 0 μg/mLᵇ
THP-1	161 ± 0 μg/mLᵃ
K-562	214 ± 0 μg/mLᵇ
RS4;11	159 ± 0 μg/mLᵃ
MOLT-4	218 ± 0 μg/mLᵇ
DPPH free radicals	95 μg/ml	4-Butylresorcinol as an anti-oxidant. For reference, vitamin C has IC50 of 6.1 μg/ml

References

^ https://datasheets.scbt.com/sds/aghs/en/sc-485061.pdf
^ "Hydroquinones". Phenols—Advances in Research and Application: 2013 Edition. Scholastic. 2013. p. 76.
^ 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: JEADV. 27 Suppl 1: 19–23. doi:10.1111/jdv.12051. ISSN 1468-3083. PMID 23205541.
^ Yu, Yanli; Wang, JianJun (2022-12-31). "Anti-HMG-CoA reductase, antioxidant, anti-urease potentials, and anti-leukemia properties of 4-Butylresorcinol as a potential treatment for hypercholesterolemia". International Journal of Food Properties. 25 (1): 1974–1986. doi:10.1080/10942912.2022.2115062. ISSN 1094-2912.

[1] ttps://datasheets.scbt.com/sds/aghs/en/sc-485061.pdf

[2] "Hydroquinones". Phenols—Advances in Research and Application: 2013 Edition. Scholastic. 2013. p. 76.

[3] 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: JEADV. 27 Suppl 1: 19–23. doi:10.1111/jdv.12051. ISSN 1468-3083. PMID 23205541.

[4] Yu, Yanli; Wang, JianJun (2022-12-31). "Anti-HMG-CoA reductase, antioxidant, anti-urease potentials, and anti-leukemia properties of 4-Butylresorcinol as a potential treatment for hypercholesterolemia". International Journal of Food Properties. 25 (1): 1974–1986. doi:10.1080/10942912.2022.2115062. ISSN 1094-2912.

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