Raspberryketone glucoside

Base Information

• Chemical Name: Raspberryketone glucoside
• CAS No.: 38963-94-9
• Molecular Formula: C16H22O7
• Molecular Weight: 326.346
• UNII: W3LCK69N6O
• DSSTox Substance ID: DTXSID80192255
• Nikkaji Number: J748.292B
• Wikidata: Q21547195
• ChEMBL ID: CHEMBL4211137
• Mol file: 38963-94-9.mol

Synonyms:Raspberry ketone glucoside;38963-94-9;Raspberryketone glucoside;Oristar RKG;Raspberryketone glucoside TH;Raspberryketone glucoside [INCI];4-(4-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)butan-2-one;UNII-W3LCK69N6O;W3LCK69N6O;(4-Hydroxyphenyl)-2-butanone beta-d-glucoside;Raspberry ketone beta-d-glucoside;2-Butanone, 4-[4-(b-D-glucopyranosyloxy)phenyl]-;4-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]butan-2-one;Raspberry ketone beta-d-glucopyranoside;4-(4'-Hydroxylphenyl)-2-butanone 4'-O-glucopyranoside;4-(4-Hydroxyphenyl)-2-butanone beta-D-glucoside;4-(P-hydroxyphenyl)-2-butanone beta-D-glucoside;2-Butanone, 4-(4-(beta-d-glucopyranosyloxy)phenyl)-;MEGxp0_000222;SCHEMBL8976171;CHEMBL4211137;DTXSID80192255;HY-N6069;MFCD09838679;s3222;AKOS022174882;RASPBERRY KETONE GLUCOSIDE [MI];AS-15354;RASPBERRY KETONE .BETA.-D-GLUCOSIDE;4-(3-Oxobutyl)phenyl beta-D-glucopyranoside;CS-0032306;RASPBERRY KETONE .BETA.-D-GLUCOPYRANOSIDE;A873739;4-(p-Hydroxyphenyl)-2-butanone-beta-D-glucopyranoside;Q21547195;(4-HYDROXYPHENYL)-2-BUTANONE .BETA.-D-GLUCOSIDE;4-(4-HYDROXYPHENYL)-2-BUTANONE .BETA.-D-GLUCOSIDE;4-(P-HYDROXYPHENYL)-2-BUTANONE .BETA.-D-GLUCOSIDE;2-BUTANONE, 4-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)PHENYL)-;(4-Hydroxyphenyl)-2-butanone beta-D-glucoside;4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone;4-(4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)butan-2-one

Chemical Property of Raspberryketone glucoside

Chemical Property:

• Boiling Point: 553.8±50.0 °C(Predicted)
• PKA: 12.83±0.70(Predicted)
• PSA: 116.45000
• Density: 1.362 g/cm³
• LogP: -0.61310
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 13 g/L at 25 ºC
• XLogP3: 0
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 326.13655304
• Heavy Atom Count: 23
• Complexity: 381

Purity/Quality:

99% ^*data from raw suppliers

Raspberry ketone glucoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CCC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: CC(=O)CCC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
• Uses: 4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone has good anti-aging, whitening, brightening and skin conditioning effects,and it is widely used in skin care products.

Technology Process of Raspberryketone glucoside

There total 11 articles about Raspberryketone glucoside 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: 94.0%

4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7) → 4-(4’-hydroxyphenyl)-2-butanone-4’-O-β-D-glucopyranoside (38963-94-9)

Guidance literature:

With calcium hydroxide; In water; at 20 ℃; for 1h;

DOI:10.1038/s41557-018-0041-8

Reference yield:

4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2-O-galloyl)-glycopyranoside (87075-18-1) → 4-(4’-hydroxyphenyl)-2-butanone-4’-O-β-D-glucopyranoside (38963-94-9)

Guidance literature:

With tannase; In water; at 37 ℃; for 0.166667h;

Reference yield:

raspberry ketone tetra-O-acetyl-β-D-glucopyranoside (38963-96-1) → 4-(4’-hydroxyphenyl)-2-butanone-4’-O-β-D-glucopyranoside (38963-94-9)

Guidance literature:

With potassium hydroxide; In methanol; for 24h;

DOI:10.1016/0031-9422(90)85346-H

upstream raw materials:

4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2,6-di-O-galloyl)glucopyranoside

4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2-O-galloyl)-glycopyranoside

raspberry ketone tetra-O-acetyl-β-D-glucopyranoside

4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2-O-galloyl-6-O-cinnamoyl)glucopyranoside

Refernces

• 1、 Wadzinski, Tyler J.,Steinauer, Angela,Hie, Liana,Pelletier, Guillaume,Schepartz, Alanna,Miller, Scott J.. "Rapid phenolic O-glycosylation of small molecules and complex unprotected peptides in aqueous solvent". . p. 644 - 652. Retrieved 2018/05/04.
• 2、 Kashiwada,Nonaka,Nishioka. "Tannins and related compounds. XLVII. Rhubarb. (6). Isolation and characterization of new p-hydroxyphenylbutanones, stilbenes and gallic acid glucosides". . p. 3237 - 3243. Retrieved 2007/10/02.