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

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

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

• 56-81-5 glycerol 
• 59-56-3 α-D-glucopyranosyl-1-phosphate 
• 10547-04-3 2-O-β-D-glucopyranosyl-D-erythritol 
• 86049-24-3 2-O-β-D-glucopyranosyl-D-arabinose 
• 10159-52-1 2-O-β-D-glucopyranosyl-D-arabinitol 
• 584-30-5 laminaribiose 
• 604-69-3 β-D-glucose pentaacetate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 76222-76-9 (ξ-2-phenyl-[1,3]dioxan-5-yl)-[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 
• 157024-67-4 (β,β'-dihydroxy-isopropyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 120601-64-1 regaloside G 
• 131831-29-3 2-O-β-D-glucopyranosyl-L-glyceraldehyde 
• 131831-31-7 2-O-β-D-glucopyranosyl-D-glyceraldehyde 

Downstream Products

• 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

Small-molecule glucosylation by sucrose phosphorylase: Structure-activity relationships for acceptor substrates revisited

Sucrose phosphorylase catalyzes the O-glucosylation of awide range of acceptor substrates. Acceptors presenting a suitable 1,2-diol moiety are glucosylated exclusively at the secondary hydroxyl. Production of the naturally occurring compatible solute, 2-O-α-D-glucopyranosyl-sn-glycerol, from sucrose and glycerol is a notable industrial realization of the regio-and stereoselective biotransformation promoted by sucrose phosphorylase. The acceptor substrate specificity of sucrose phosphorylase was analyzed on the basis of recent high-resolution crystal structures of the enzyme. Interactions at the acceptor binding site, observed in the crystal (D-fructosyl) and suggested by results of docking experiments (glycerol), are used to rationalize experimentally determined efficiencies and regioselectivities of enzymatic glucosyl transfer.

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.

New Phenylpropanoid Glycerol Glucosides from the Bulbs of Lilium Species

The fresh bulbs of the genus Lilium have yielded new phenylpropanoid glycerol glucosides, epi-regaloside A (6b), epi-regaloside C (7b) and epi-regaloside F (10b), as mixtures with the corresponding (2S)-regalosides (6a, 7a and 10a), and regaloside G (11).Compounds 6b and 7b have been obtained from Lilium pardarinum, and 6b, 10b and 11 from L. auratum.The spectroscopic data and chemical evidence have allowed us to assign the structures of 6b, 7b, 10b and 11 as (2R)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylglycerol, (2R)-1-O-caffeoyl-3-O-β-D-glucopyranosylglycerol, (2R)-1-O-feruloyl-3-O-β-D-glucopyranosylglycerol and (2S)-1-O-feruloyl-2-O- β-D-glucopyranosylglycerol, respectively.In addition, jatropham and its glucoside have been detected in the fresh bulbs of L. medeoloides.Several previously reported compounds have also been obtained and identified.Keywords - Lilium pardarinum; Lilium auratum; Lilium medeoloides; Liliaceae; phenolic glycerol glucoside; epi-regaloside A; epi-regaloside C; epi-regaloside F; regaloside G; jatropham

REGALOSIDE A AND B, ACYLATED GLYCEROL GLUCOSIDES FROM LILIUM REGALE

Novel acylated glycerol glucosides, regaloside A and B, both bitter to the taste, have been isolated from the fresh bulbs of Lilium regale.Their structures have been shown by the spectral and chemical evidence to be (2S)-1-O-p-coumaroyl-3-O-β-D-glucopyranosylglycerol and (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, respectively.Key Word Index - Lilium regale; Liliaceae; acylated glycerol glucosides; p-coumaric acid esters; regaloside A; regaloside B; bitter principles; stereochemistry.