38963-94-9

Basic information

• Product Name: 4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone
• Synonyms: RASPBERRY KETONE β-D-GLUCOSIDE;Raspberry ketone beta-D-glucoside;Brillian-MB280;4-(4-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)butan-2-one;4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone;(4-hydroxyphenyl)-2-butanone beta-d-glucoside;raspberry ketone glucoside
• CAS NO: 38963-94-9
• Molecular Formula: C₁₆H₂₂O₇
• Molecular Weight: 326.34168
• EINECS: 1806241-263-5
• Mol File: 38963-94-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 553.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.362
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.83±0.70(Predicted)
• Water Solubility: 13 g/L at 25 ºC
• CAS DataBase Reference: 4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone(38963-94-9)
• EPA Substance Registry System: 4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone(38963-94-9)

Safety Data

• Hazardous Substances Data: 38963-94-9(Hazardous Substances Data)

Usage

Description

4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone is a white or off-white crystalline powder that is easily soluble in water and soluble in polar organic solvents such as ethanol. It is known for its good anti-aging, whitening, brightening, and skin conditioning effects, making it a valuable compound in the cosmetics and skincare industry.

Uses

Used in Skin Care Products:
4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone is used as an active ingredient for its anti-aging, whitening, brightening, and skin conditioning effects. It is widely utilized in various skincare products to improve the overall appearance and health of the skin.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, due to its chemical properties and solubility, 4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone could potentially be used in the pharmaceutical industry for the development of drugs that require water and polar organic solvent solubility, as well as for applications in drug delivery systems where its skin conditioning properties could be beneficial.
Used in Cosmetics Industry:
4-[4-(beta-D-Glucopyranosyloxy)phenyl]-2-butanone is used as a key component in the formulation of cosmetics, particularly those aimed at enhancing skin quality and appearance. Its properties make it suitable for inclusion in a range of products such as creams, lotions, and serums that target skin aging, pigmentation, and overall skin health.

Upstream product

• 105274-14-4 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2,6-di-O-galloyl)glucopyranoside 
• 5471-51-2 4-(4-hydroxyphenyl)-2-oxobutane 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 2106-10-7 1-deoxy-1-fluoro-α-D-glucose 
• 105274-15-5 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2-O-galloyl-6-O-cinnamoyl)glucopyranoside 
• 38963-96-1 raspberry ketone tetra-O-acetyl-β-D-glucopyranoside 
• 87075-18-1 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2-O-galloyl)-glycopyranoside 
• 105274-16-6 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2-O-galloyl-6-O-p-coumaroyl)glucopyranoside 

Relevant articles and documents

Glycosidically Bound Norisoprenoids from Vitis vinifera Cv. Riesling Leaves

HRGC and HRGC-MS identifications of glycosidically bound Riesling leaf constituents were achieved after extraction with MeOH, Amberlite XAD-2 adsorption, and subsequent enzymatic hydrolysis of the glycoconjugates.Among the enzymatically liberated aglycons 23 bound C13 norisoprenoids were identified.With the aid of multilayer coil countercurrent chromatography (MLCCC) five major C13 glycosides were purified, and their structures were elucidated by high-field NMR, i.e., the β-D-glucopyranosides of vomifoliol, 4,5-dihydrovomifoliol, 3-hydroxy-5,6-epoxy-β-ionone, grasshopper ketone, and 3-oxo-megastigman-9-ol.The latter glucoside with a saturated megastigmane skeleton is reported here for the first time.In addition, the β-D-glucopyranosides of benzyl alcohol and raspberry ketone have been isolated.

PHENYLBUTAN-2-ONE β-D-GLUCOSIDES FROM RASPBERRY FRUIT

From a methanolic extract of raspberry fruit, the 4'-O-β-D-glucopyranoside of 4-(4'-hydroxyphenyl)butan-2-one (raspberry ketone) and the 3'-O-β-D-glucopyranoside of 4-(3',4'-dihydroxyphenyl)butan-2-one were isolated by liquid chromatography on XAD-2, Sephadex LH-20 and RP-18 as well as by HPLC on a diol phase.Identifications were carried out by 1H and 13C NMR spectroscopy, using synthetic reference compounds.Assignment of the carbon resonances was made by DEPT and INADEQUATE experiments.The effects of glucosylation on the 13C NMR spectra of phenylbutanone derivatives are discussed.

Tannins and Related Compounds. X. Rhubarb (2): Isolation and Structures of a Glycerol Gallate, Gallic Acid Glucoside Gallates, Galloylglucoses and Isolindleyin

Six tannin-related compounds (I-VI) have been isolated from commercial rhubarb, and their structures have been established on the basis of chemical and spectroscopic data to be 1-O-galloylglycerol (I), gallic acid 3-O-β-D-(6'-O-galloyl)-glucopyranoside (II), gallic acid 4-O-β-D-(6'-O-galloyl)-glucopyranoside (III), 1,6-di-O-galloyl-β-D-glucose (IV), 6-O-galloylglucose (V) and 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-(2"-O-galloyl)-glucopyranoside (VI, named isolindleyin).Keywords - rhubarb; Polygonaceae; glycerol gallate; gallic acid glucoside gallate; galloylglucose; isolindleyin; tannin-related compound