resorcinol derivative History Uses tyrosinase inhibitor
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4-Butylresorcinol

resorcinol derivative History Uses tyrosinase inhibitor
Product Name
4-Butylresorcinol
CAS No.
18979-61-8
Chemical Name
4-Butylresorcinol
Synonyms
Butylresorcinol;4-N-BUTYLRESORCINOL;4-Butylbenzene-1,3-diol;2,4-DIHYDROXY-N-BUTYL BENZEN;Rucinol;N-BUTYLRESEOCINOL;4-Butylresorcinol;Serine Impurity 12;Resorcinol, 4-butyl-;4-Butylresorcinol >
CBNumber
CB9361328
Molecular Formula
C10H14O2
Formula Weight
166.22
MOL File
18979-61-8.mol
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4-Butylresorcinol Property

Melting point:
50.0 to 55.0 °C
Boiling point:
166°C/7mmHg(lit.)
Density 
1.092±0.06 g/cm3(Predicted)
vapor pressure 
0.041Pa at 25℃
storage temp. 
Inert atmosphere,Room Temperature
solubility 
DMSO : 150 mg/mL (902.42 mM)
form 
Powder
pka
9.95±0.18(Predicted)
color 
white to pale yellow powder
Odor
Characteristic
InChI
InChI=1S/C10H14O2/c1-2-3-4-8-5-6-9(11)7-10(8)12/h5-7,11-12H,2-4H2,1H3
InChIKey
CSHZYWUPJWVTMQ-UHFFFAOYSA-N
SMILES
C1(O)=CC=C(CCCC)C(O)=C1
LogP
2.8 at 24℃ and pH7
Surface tension
17.8mN/m at 1g/L and 20℃
CAS DataBase Reference
18979-61-8(CAS DataBase Reference)
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Safety

RTECS 
VH0420000
HS Code 
2907290090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TCI Chemical
Product number
B3773
Product name
4-Butylresorcinol
Purity
>98.0%(GC)
Packaging
1g
Price
$357
Updated
2024/03/01
TRC
Product number
B809320
Product name
4-Butylresorcinol
Packaging
500mg
Price
$170
Updated
2021/12/16
TRC
Product number
B809320
Product name
4-Butylresorcinol
Packaging
1g
Price
$235
Updated
2021/12/16
Biosynth Carbosynth
Product number
FB168030
Product name
4-n-Butylresorcinol
Packaging
2g
Price
$280
Updated
2021/12/16
Apolloscientific
Product number
OR936805
Product name
4-Butylresorcinol
Purity
95%
Packaging
250mg
Price
$218
Updated
2021/12/16
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4-Butylresorcinol Chemical Properties,Usage,Production

resorcinol derivative

4-n-Butylresorcinol is a resorcinol derivative that inhibits both tyrosinase and tyrosinase-related protein-1 (TRP-1). It may be used to decrease skin irritation and is also known to inhibit melanin production. Its hypopigmenting action was first reported in 1995, and many following studies have documented its efficacy and safety in melasma treatment with the 0.1% cream, but there is paucity of clinical studies that used the 0.3% cream. The biochemical assay on inhibition of human tyrosinase activity has revealed the superiority of 4-n-butylresorcinol over other hypopigmenting agents. Many studies show good efficacy and safety in treating melisma.

4-n-Butylresorcinol may be used to produce a safe cosmetic agent, with the clinical efficacy required of a pharmacological agent. Furthermore, 4-n-butylresorcinol acts mainly by inhibition of tyrosinase activity and has no effect on MITF. 4-n-butylresorcinol showed an additive effect in combination with hinokitiol, which reduces MITF expression.

History

4-n-Butylresorcinol (Rucinol® ) (Obtained by POLA in 1998) was selected by screening synthetic resorcinol derivatives that can elicit strong competitive inhibition of tyrosinase activity. Melanin synthesis is catalyzed by tyrosinase, together with tyrosinase-related proteins (TRP) -1 and -2, and Rucinol® has been shown to inhibit melanin synthesis in cultured mouse melanocytes via direct inhibition not only of tyrosinase activity, but also of TRP-1 activity. A 0.3% Rucinol® -containing lotion was shown to be effective for treating hyperpigmentary disorders, such as melasma.

Uses

4-Butylresorcinol(18979-61-8) is considered a potential Cytochrome P450 inhibitor. It can cause hypopigmentation due to its direct inhibition of tyrosinase.

tyrosinase inhibitor

4-butylresorcinol(18979-61-8) is use as an effective treatment option for topical hyperpigmentation management. Similar to hydroquinone, 4-n-butylresorcinol is also a tyrosinase inhibitor. It has been characterized as a strong tyrosinase25 and TRP‐126 inhibitor. We measured an IC50 in the human tyrosinase assay of 21μmol/L for 4‐butylresorcinol compared with 94 and 131?μmol/L for 4‐hexylresorcinol and 4‐phenylethylresorcinol respectively. Also on skin models, 4‐butylresorcinol was most effective of all tested substances with an IC50 of 13.5 μmol/L. Therefore, 4‐butylresorcinol was selected for several clinical studies to prove in vivo efficacy. In comparison with 4‐hexylresorcinol and 4‐phenylethylresorcinol, 4‐butylresorcinol treated age spots showed a faster onset of improvement and also a higher degree of lightening after 12 weeks of treatment.

Description

4-n-butylresorcinol is a derivative of resorcinol and a potent human tyrosinase inhibitor. It may be used to decrease skin irritation and is also known to inhibit melanin production.

Uses

4-Butylresorcinol is considered a potential Cytochrome P450 inhibitor. It can cause hypopigmentation due to its direct inhibition of tyrosinase.

Definition

ChEBI: 4-n-Butylresorcinol is a member of resorcinols.

Application

Glycerol is used both in sample preparation and gel formation for polyacrylamide gel electrophoresis. Glycerol (5-10%) increases the density of a sample so that the sample will layer at the bottom of a gel′s sample well. Glycerol is also used to aid in casting gradient gels and as a protein stabilizer and storage buffer component.

Biological Activity

Glutathione reductase IGR) is a crucial flavoenzyme in the antioxidant defense system. Reduced glutathione (GSH) is used by glutathione peroxidase to detoxify hydrogen peroxide and in the process is converted to oxidized glutathione (GSSG). The GSSG is then recycled back to GSH by glutathione reductase (GR) using NADPH that is then converted to NADP+. The regenerated GSH is then available to detoxify more hydrogen peroxide. The enzyme uses FAD as a cofactor. GR and glutathione peroxidase may inhibit lipid peroxidation by functioning as antioxidant enzymes in sperm. Glutathione reductase shares a structural motif with a number of other proteins including aspartyl proteases, citrate synthase, EF hands, hemoglobins, lipocalins, and α/β hydrolases. GR is stimulated by melatonin and is reportedly irreversibly inhibited by a number of oxygen radical generating systems.A sweet tastant for mammals. A glycerol taste receptor binding site specific for glucose has been proposed in drosophila.

Mechanism of action

The mechanism of action of 4-butylresorcinol depigmentation is through inhibition of tyrosinase and tyrosinase-related protein-1 (TRP-1)[1].

Synthesis


Under the protection of nitrogen, 110 g (1 mol) of resorcinol and 220 g of n-heptane were mixed in the reaction flask, heated and dissolved, and the temperature was lowered to 10 ?? C. A turbid solution of 40.8 g (1.02 mol) of sodium hydroxide and 100 g of n-butanol was added in portions. , And control the temperature of 10 to 15 , after TLC (EA developing agent) detection of almost no remaining raw materials, add n-butanol (2.5mol), tris (pentafluorobenzene) borane 17.5g (0.1mol) and calcium chloride 1.1 g, raise the temperature to 40-45 ?? C for 1 hour, then raise the temperature to 98 ?? C for reflux and water separation. After 8 hours of water separation, take a sample and quench the GC to detect resorcinol <1%, cool to room temperature, add a small amount of water to quench It is extinguished, and then dilute sulfuric acid is added to adjust the pH = 1-2. The insoluble solids are filtered through diatomaceous earth, and the organic phase is concentrated to a stagnant liquid. Water is added for replacement, and then 660 g of water, 2.2 g of sodium thiosulfate, and 5.5 g are added. Activated carbon was heated to reflux for 1 hour, and was hot-filtered to obtain a pale yellow solution. Then, flaky crystals were precipitated by cooling, and 151 g of 4-n-butylresorcinol was obtained by filtration, GC: 99.3%, and yield: 90.9%.

References

[1] D. RESENDE. Skin Depigmenting Agents in Anti-Aging Cosmetics: A Medicinal Perspective on Emerging Ingredients[J]. Applied Sciences-Basel, 2022. DOI:10.3390/app12020775.

4-Butylresorcinol Preparation Products And Raw materials

Raw materials

Preparation Products

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4-Butylresorcinol Suppliers

LoongZe (NanJing) Medicine Chemical Industry CO.,LTD
Tel
025-025-58168368-12-12 13817339189
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13817339189@163.com
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China
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Taizhou Ruishinuo Pharmaceutical Technology Co., Ltd.
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0523-86848872 19952992164
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0523-86848872
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725236090@qq.com
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China
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Hubei YiKangYuan Chemical Co., Ltd.
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027-87182908 18064088908
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027-87182900
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65824125@qq.com
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Hangzhou Linran Biotechnology Co. LTD
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0571-18067987-92 18067987892
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0571-88772395
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2543558860@qq.com
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Beri Pharma Co., Ltd.
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13427714006
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sales@zhberi.com
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China
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Lanzhou Zhongchuan Xuentian Tech.Co. LTD
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18661722072
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mk@xuentian.cn
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China
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Nanjing XiLang Chemical Products Co., Ltd.
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chemxilang@163.com
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Shanghai Qingyunqi Daily Chemical Technology Co., Ltd
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021-17396836079 17396836079
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1514012023@qq.com
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China
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Ningbo jinuo chemical co., LTD
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0574-87314919 057487319282
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info@nbinno.com
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China
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7028
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J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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View Lastest Price from 4-Butylresorcinol manufacturers

Hebei Longbang Technology Co., Ltd
Product
4-Butylresorcinol 18979-61-8
Price
US $6.00/kg
Min. Order
1kg
Purity
More than 99%
Supply Ability
2000KG/Month
Release date
2024-05-08
Hebei Jingbo New Material Technology Co., Ltd
Product
4-Butylresorcinol 18979-61-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000000
Release date
2023-11-15
HebeiShuoshengImportandExportco.,Ltd
Product
4-Butylresorcinol 18979-61-8
Price
US $6.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000KG/Month
Release date
2024-08-07

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