4-Butylresorcinol

Names

[ Name ]:
4-Butylresorcinol

[Synonym ]:
4-n-Butylresorcinol
4-Butyl-1,3-benzenediol
4-Butylresorcin
Butylresorcinol
1-butyl-2,4-dihydroxybenzene
1,3-Benzenediol, 4-butyl-
2,4-Dihydroxy-n-butyl benzen
4-Butylbenzene-1,3-diol
N-butylresorcinol
MFCD01684800
4-Butylresorcinol
Resorcinol,4-butyl
4-butyl-resorcinol

Biological Activity

[Description]:

4-Butylresorcinol is a phenol derivative which can inhibit tyrosinase with IC50 of 11.27 μM.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

Research Areas >> Others

[Target]

IC50: 11.27 μM (4-Butylresorcinol)[1]

[In Vitro]

It shows that 4-Butylresorcinol (4-n-butylresorcinol) significantly inhibits melanin synthesis in a concentration-dependent manner. In addition, it is also found to inhibit the activity of tyrosinase, the rate-limiting melanogenic enzyme. 4-Butylresorcinol does not induce ERK, Akt activation, or MITF degradation, and has no effect on cAMP response element binding protein (CREB) phosphorylation, which stimulates MITF expression. 4-Butylresorcinol strongly reduces tyrosinase activity in a cell-free system. Moreover, 4-Butylresorcinol shows an additive effect in combination with hinokitiol, which reduces MITF expression[2].

[Kinase Assay]

Briefly, Mel-Ab cells are cultured in 60 mm dishes. After incubating with test substances (including 4-Butylresorcinol) in DMEM containing 2% FBS for 4d, the cells are washed with ice-cold PBS and lysed with phosphate buffer (pH 6.8) containing 1% Triton X-100. The cells are then disrupted by freeze-thawing, and lysates are clarified by centrifuging at 10000×g for 5 min. After quantifying protein levels and adjusting concentrations with lysis buffer, 90 μL of each lysate, is placed in a well of a 96-well plate, and 10 μL of 10 mM L-DOPA is then added. Control wells contain 90 μL of lysis buffer and 10 μL of 10mM L-DOPA[2].

[Cell Assay]

Mel-Ab cell line is a mouse-derived spontaneously immortalized melanocyte cell line that produces large amounts of melanin. Mel-Ab cells are incubated in DMEM supplementing with 10% fetal bovine serum (FBS), 100 nM TPA, 1 nM CT, 50 μg/mL streptomycin, and 50 U/mL penicillin at 37 °C in 5% CO2. Cell viability is determined using a crystal violet assay. After incubating cells with test substances for 24 h, the medium is removed and stained with 0.1% crystal violet in 10% ethanol for 5 min at room temperature and then rinsed four times with distilled water[2].

[References]

[1]. Jiang Y, et al. Synthesis and biological evaluation of unsymmetrical curcumin analogues as tyrosinaseinhibitors. Molecules. 2013 Apr 3;18(4):3948-61.

[2]. Kim DS, et al. Inhibitory effects of 4-n-butylresorcinol on tyrosinase activity and melanin synthesis. Biol Pharm Bull. 2005 Dec;28(12):2216-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
300.7±12.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₄O₂

[ Molecular Weight ]:
166.217

[ Flash Point ]:
144.5±14.2 °C

[ Exact Mass ]:
166.099380

[ PSA ]:
40.46000

[ LogP ]:
2.82

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.555

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VH0420000

CHEMICAL NAME :: Resorcinol, 4-butyl-

CAS REGISTRY NUMBER :: 18979-61-8

BEILSTEIN REFERENCE NO. :: 1942645

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H14-O2

MOLECULAR WEIGHT :: 166.24

WISWESSER LINE NOTATION :: QR EQ B4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 32,592,1935

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H400

[ Precautionary Statements ]:
P273-P280-P301 + P312 + P330-P305 + P351 + P338-P337 + P313-P391

[ Hazard Codes ]:
Xi

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
2907299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2907299090

[ Summary ]:
2907299090 polyphenols; phenol-alcohols。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:5.5%。general tariff:30.0%