4-Butylresorcinol

Modify Date: 2024-01-02 09:35:05

4-Butylresorcinol Structure
4-Butylresorcinol structure
Common Name 4-Butylresorcinol
CAS Number 18979-61-8 Molecular Weight 166.217
Density 1.1±0.1 g/cm3 Boiling Point 300.7±12.0 °C at 760 mmHg
Molecular Formula C10H14O2 Melting Point N/A
MSDS Chinese USA Flash Point 144.5±14.2 °C
Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning

 Use of 4-Butylresorcinol


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

 Names

Name 4-butylbenzene-1,3-diol
Synonym More Synonyms

 4-Butylresorcinol Biological Activity

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

 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

 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
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

~65%

4-Butylresorcinol Structure

4-Butylresorcinol

CAS#:18979-61-8

Literature: Mizobuchi, Shigeyuki; Sato, Yuko Agricultural and Biological Chemistry, 1985 , vol. 49, # 5 p. 1327 - 1334

~%

4-Butylresorcinol Structure

4-Butylresorcinol

CAS#:18979-61-8

Literature: DE489117 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2867

~%

4-Butylresorcinol Structure

4-Butylresorcinol

CAS#:18979-61-8

Literature: Arzneimittel-Forschung/Drug Research, , vol. 23, # 12 p. 1745 - 1758

~%

4-Butylresorcinol Structure

4-Butylresorcinol

CAS#:18979-61-8

Literature: DE489117 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 2867 Journal of the American Chemical Society, , vol. 43, p. 357

~%

4-Butylresorcinol Structure

4-Butylresorcinol

CAS#:18979-61-8

Literature: Arzneimittel-Forschung/Drug Research, , vol. 23, # 12 p. 1745 - 1758

~%

4-Butylresorcinol Structure

4-Butylresorcinol

CAS#:18979-61-8

Literature: Arzneimittel-Forschung/Drug Research, , vol. 23, # 12 p. 1745 - 1758

 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%

 Synonyms

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
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