Deoxyarbutin

Base Information

• Chemical Name: Deoxyarbutin
• CAS No.: 53936-56-4
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Hs Code.: 2938909090
• Mol file: 53936-56-4.mol

Synonyms:4-(Tetrahydro-2H-pyran-2-yloxy)phenol;

Chemical Property of Deoxyarbutin

Chemical Property:

• Melting Point: 83-88℃
• Boiling Point: 349.779 °C at 760 mmHg
• PKA: 10.10±0.15(Predicted)
• Flash Point: 165.341 °C
• PSA: 38.69000
• Density: 1.174 g/cm³
• LogP: 2.29760
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)

Purity/Quality:

99% ^*data from raw suppliers

Deoxyarbutin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of Deoxyarbutin

There total 9 articles about Deoxyarbutin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

4-benzyloxyphenyl 2-tetrahydropyranyl ether (53936-79-1) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 20 ℃; for 3h; under 3000.3 Torr; Autoclave;

Reference yield: 84.0%

2-(4-Acetoxyphenoxy)tetrahydropyran (134142-87-3) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Guidance literature:

With sodium perborate; In methanol; at 25 ℃; for 0.25h;

DOI:10.1039/b203766c

Reference yield: 72.0%

3,4-dihydro-2H-pyran (110-87-2) + hydroquinone (123-31-9,8027-02-9) → 4-(tetrahydro-2H-2-pyranyloxy)phenol (53936-56-4)

Guidance literature:

With ruthenium(III) acetate; at 20 ℃; for 12h;

DOI:10.1139/V06-137

upstream raw materials:

2-(4-Acetoxyphenoxy)tetrahydropyran

3,4-dihydro-2H-pyran

hydroquinone

4-benzyloxyphenyl 2-tetrahydropyranyl ether

Downstream raw materials:

2-{4-[4-(oxetan-3-yloxy)-butoxy]-phenoxy}-tetrahydro-pyran

6-[(4-hydroxyphenyl)oxy]hexyl acrylate

C₂₀H₂₈O₅

C₁₅H₁₆O₇

Refernces

• 1、 -. "POLYMERIZABLE CINNAMATE ESTER DERIVATIVE MANUFACTURING METHOD". Paragraph 0121-0122; 0127. . Retrieved 2020/08/15.
• 2、 -. "Method for producing 2-hydrazinobenzothiazole derivative also providing a polymerizable composition which is useful for producing a film-like polymer". Paragraph 0150; 0152; 0161. . Retrieved 2019/09/04.