Deoxyarbutin
- Product Name
- Deoxyarbutin
- CAS No.
- 53936-56-4
- Chemical Name
- Deoxyarbutin
- Synonyms
- Tetrahydropyranyloxyphenol;Dexyarbutin;Deoxyarbutin;LGB-D ARBUTIN;Deoxyarbutin, 96%;Deoxyarbutin, 98%+;Deoxyarbutin 53936-56-4;Tranexamic acid 701-54-2;Pure Deoxyarbutin Powder;Deoxyarbutin, 10 mM in DMSO
- CBNumber
- CB32473685
- Molecular Formula
- C11H14O3
- Formula Weight
- 194.23
- MOL File
- 53936-56-4.mol
Deoxyarbutin Property
- Melting point:
- 88-89 °C(Solv: ligroine (8032-32-4))
- Boiling point:
- 349.8±32.0 °C(Predicted)
- Density
- 1.174
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
- pka
- 10.10±0.15(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability:
- Hygroscopic
- InChI
- InChI=1S/C11H14O3/c12-9-4-6-10(7-5-9)14-11-3-1-2-8-13-11/h4-7,11-12H,1-3,8H2
- InChIKey
- GFBCWCDNXDKFRH-UHFFFAOYSA-N
- SMILES
- C1(O)=CC=C(OC2OCCCC2)C=C1
Safety
- HS Code
- 2932990090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 21077
- Product name
- Deoxyarbutin
- Packaging
- 10g
- Price
- $49
- Updated
- 2024/03/01
- Product number
- 21077
- Product name
- Deoxyarbutin
- Packaging
- 250g
- Price
- $593
- Updated
- 2024/03/01
- Product number
- 21077
- Product name
- Deoxyarbutin
- Packaging
- 50g
- Price
- $216
- Updated
- 2024/03/01
- Product number
- 21077
- Product name
- Deoxyarbutin
- Packaging
- 100g
- Price
- $263
- Updated
- 2024/03/01
- Product number
- D232105
- Product name
- Deoxyarbutin
- Packaging
- 50mg
- Price
- $105
- Updated
- 2021/12/16
Deoxyarbutin Chemical Properties,Usage,Production
Description
Deoxyarbutin is a tyrosinase inhibitor (IC50 = 17.5 μM for mushroom tyrosinase). It reduces melanin content in isolated dark human melanocytes when used at a concentration of 1.56 μM. Topical administration of deoxyarbutin (5%) induces skin lightening in human skin mouse xenograft models. Deoxyarbutin also inhibits proliferation of B16/F10 murine melanoma cells (EC50 = 39.56 μM). It induces apoptosis and halts the cell cycle at the S phase in B16/F10 cells when used at a concentration of 50 μM. Deoxyarbutin (50 mg/kg) reduces tumor growth in a B16/F10 murine melanoma model.
Uses
Deoxyarbutin acts as a skin whitening agent through the inhibition of tyrosinase. A safer alternative to the use of hydroquinone and arbutin.
Preparation
Deoxyarbutin is a derivative of ?-arbutin, obtained by removal of hydroxyl groups from the glucose side-chain of ?-arbutin.
Synthesis
110-87-2
123-31-9
53936-56-4
Under nitrogen protection, 3,4-dihydro-2H-pyran (19.1 g, 227.0 mmol) was dissolved in a solution of dichloromethane (200 ml) containing pyridinium p-toluenesulfonate (PPTS) (5.7 g, 22.7 mmol). After cooling the reaction system to 10°C, a solution of hydroquinone (25.0 g, 227.0 mmol) in dichloromethane (100 ml) was added slowly and dropwise. Subsequently, the reaction mixture was gradually warmed to 25°C and stirred continuously for 16 hours. After completion of the reaction, the mixture was poured into water (500 ml) and the aqueous layer was extracted with dichloromethane. The organic layers were combined and washed sequentially with saturated aqueous sodium chloride solution and saturated aqueous sodium bicarbonate solution, then dried with anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=5:1, v/v) to afford 4-((tetrahydro-2H-pyran-2-yl)oxy)phenol (23.2 g, 119.7 mmol, 52.7% yield).
References
[1] Canadian Journal of Chemistry, 2006, vol. 84, # 9, p. 1174 - 1179
[2] Patent: JP5978938, 2016, B2. Location in patent: Paragraph 0149; 0154
[3] Journal of Materials Chemistry, 2012, vol. 22, # 48, p. 25011 - 25018
[4] Patent: US2009/326186, 2009, A1. Location in patent: Page/Page column 64
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 16, p. 4356 - 4360
Deoxyarbutin Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Deoxyarbutin manufacturers
- Product
- Deoxyarbutin 53936-56-4
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1
- Release date
- 2025-09-08
- Product
- Deoxyarbutin 53936-56-4
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 2000KG
- Release date
- 2025-08-30
- Product
- Deoxyarbutin 53936-56-4
- Price
- US $0.00/Kg/Bag
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 3500kg/month
- Release date
- 2021-06-04