10588-30-4

Basic information

• Product Name: 2-(β-D-Glucopyranosyloxy)-1,3-propanediol
• Synonyms: 2-(β-D-Glucopyranosyloxy)-1,3-propanediol;2-Hydroxy-1-(hydroxymethyl)ethyl β-D-glucopyranoside;Lilioside B;2-(β-Glucosyl)glycerol;2-(b-Glucosyl)glycerol
• CAS NO: 10588-30-4
• Molecular Formula: C₉H₁₈O₈
• Molecular Weight: 254.23442
• Product Categories: Carbohydrates & Derivatives
• Mol File: 10588-30-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 130-135 °C
• Boiling Point: 606.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.58±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: 12.85±0.70(Predicted)
• Stability: Very Hygroscopic
• CAS DataBase Reference: 2-(β-D-Glucopyranosyloxy)-1,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(β-D-Glucopyranosyloxy)-1,3-propanediol(10588-30-4)
• EPA Substance Registry System: 2-(β-D-Glucopyranosyloxy)-1,3-propanediol(10588-30-4)

Safety Data

• Hazardous Substances Data: 10588-30-4(Hazardous Substances Data)

Usage

Description

2-(β-D-Glucopyranosyloxy)-1,3-propanediol is a naturally occurring glycosylglycerol compound characterized by an off-white solid appearance. It features a unique structure where a β-D-glucopyranosyloxy group is attached to a 1,3-propanediol moiety, endowing it with distinct chemical properties and potential applications across various industries.

Uses

Used in Cosmetic Formulation:
2-(β-D-Glucopyranosyloxy)-1,3-propanediol is used as an active ingredient in cosmetic formulations for its beneficial properties to the skin. Its presence in these products is attributed to its potential to improve skin health and provide nourishment.
Used in Cancer Chemoprevention:
In the field of cancer chemoprevention, 2-(β-D-Glucopyranosyloxy)-1,3-propanediol, particularly its diesters, is utilized for its activity in preventing the onset of cancer. 2-(β-D-Glucopyranosyloxy)-1,3-propanediol's unique structure allows it to potentially modulate cellular processes and pathways that contribute to the development of cancer, thus serving as a preventative measure.
These applications highlight the versatility of 2-(β-D-Glucopyranosyloxy)-1,3-propanediol, showcasing its potential in both personal care and healthcare industries. Further research and development could unlock additional uses and enhance its effectiveness in these areas.

Upstream product

• 76222-77-0 2-O-(β-D-glucopyranosyl)-1,3-O-benzylideneglycerol 
• 67-56-1 methanol 
• 120601-64-1 regaloside G 
• 131831-31-7 2-O-β-D-glucopyranosyl-D-glyceraldehyde 
• 131831-29-3 2-O-β-D-glucopyranosyl-L-glyceraldehyde 
• 157024-67-4 (β,β'-dihydroxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 157024-66-3 1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 
• 76222-76-9 (ξ-2-phenyl-[1,3]dioxan-5-yl)-[tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 584-30-5 laminaribiose 
• 10159-52-1 2-O-β-D-glucopyranosyl-D-arabinitol 
• 86049-24-3 2-O-β-D-glucopyranosyl-D-arabinose 
• 10547-04-3 2-O-β-D-glucopyranosyl-D-erythritol 

Downstream Products

• 36722-53-9 (β,β'-bis-benzoyloxy-isopropyl)-(tetra-O-benzoyl-β-D-glucopyranoside) 
• 113134-96-6 (β,β'-dimethoxy-isopropyl)-(tetra-O-methyl-β-D-glucopyranoside) 
• 158110-30-6 (2R)-1-O-acetyl-2-O-(β-D-glucopyranosyl)glycerol 
• 131831-28-2 (2S)-1-O-acetyl-2-O-β-D-glucopyranosyl-sn-glycerol 
• 176966-03-3 1-O-butanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 
• 176966-04-4 1-O-decanoyl-2-O-β-D-glucopyranosyl-sn-glycerol 

Relevant articles and documents

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Synthesis of glycosyl glycerols and related glycolipids

Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the α-anomer preferentially. The 2-O-(tetra-O-acetyl-β-glycopyranosyl)-sn-glycerols and 2-O-(β-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding α-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-β-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding α-derivative of D-mannose were synthesized.

LILIOSIDE A FROM LILIUM LONGIFLORUM: SYNTHESIS AND ABSOLUTE CONFIGURATION

The absolute configuration of lilioside A, previously isolated from Lilium longiflorum, has been established as 2R by the syntheses of lilioside A and its diastereoisomer from laminaribiose and cellobiose, respectively.