499-23-0

Basic information

• Product Name: B,B-TREHALOSE
• Synonyms: B,B-TREHALOSE;BETA,BETATREHALOSE;SS,SSTREHALOSE;Isotrehalose, β-D-Glucopyranosyl β-D-glucopyranoside
• CAS NO: 499-23-0
• Molecular Formula: C₁₂H₂₂O₁₁
• Molecular Weight: 342.295
• Mol File: 499-23-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 130-135 °C
• Boiling Point: 675.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.76±0.1 g/cm3(Predicted)
• PKA: 12.53±0.70(Predicted)
• CAS DataBase Reference: B,B-TREHALOSE(CAS DataBase Reference)
• NIST Chemistry Reference: B,B-TREHALOSE(499-23-0)
• EPA Substance Registry System: B,B-TREHALOSE(499-23-0)

Safety Data

• Hazardous Substances Data: 499-23-0(Hazardous Substances Data)

Usage

Description

B,B-Trehalose, also known as β,β-trehalose, is a disaccharide composed of two α-glucose units. It is a naturally occurring sugar that can be found in various organisms, including bacteria, fungi, and some plants. Due to its unique properties, B,B-trehalose has a wide range of applications in different industries.

Uses

Used in Pharmaceutical Industry:
B,B-Trehalose is used as a stabilizing agent for proteins and other biological molecules, which is crucial for the development and formulation of various pharmaceutical products. Its ability to protect proteins from denaturation and aggregation makes it an essential component in the production of certain drugs and vaccines.
Used in Cosmetics Industry:
In the cosmetics industry, B,B-trehalose is used as a humectant and moisturizing agent. Its ability to retain moisture and maintain the skin's hydration levels makes it a popular ingredient in various skincare products, such as creams, lotions, and serums.
Used in Food Industry:
B,B-Trehalose is used as a natural sweetener in the food industry. It has a lower glycemic index compared to other sugars, making it a suitable alternative for people with diabetes or those looking to reduce their sugar intake. Additionally, its non-crystallizing properties make it an ideal ingredient for certain confectionery products.
Used in Chemical Synthesis:
B,B-Trehalose is used in the synthesis of water-soluble bisphosphinite chiral ligands, which can be used as asymmetrical hydrogenation catalysts for dehydroamino acids and their esters. This application is particularly relevant in the development of new pharmaceuticals and other chemical products.

Upstream product

• 25018-28-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 55676-46-5 2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 502-73-8 palmitone 
• 76054-91-6 Hexadecanoic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 55676-46-5 2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside 
• 108811-30-9 6-O-(triphenylmethyl)-β-D-glucopyranosyl-6'-O-(triphenylmethyl)-β-D-glucopyranoside 

Relevant articles and documents

Novel Water-Soluble Bisphosphinite Chiral Ligands Derived from α,α- And β,β-Trehalose. Application to Asymmetric Hydrogenation of Dehydroamino Acids and Their Esters in Water or an Aqueous/ Organic Biphasic Medium

Novel 2,3:4,6-di-O-isopropylidene-α-D-glucopyranosyl-(1,1)-4,6-O-isopropylidene- 2,3-di-O-diphenylphosphino-α-D-glucopyranoside (2), 2,3:4,6-di-O-cyclohexylidene-α-D-glucopyranosyl-(1,1)-4,6-O- cyclohexylidene-2,3-di-O-diphenylphosphino-α-D-glucopyranoside (4), and 2,3:4,6-di-O-cyclohexylidene-β-D-glucopyranosyl-(1,1)-4,6-O- cyclohexylidene-2,3-di-O-diphenylphosphino-β-D-glucopyranoside (11) were prepared from the corresponding α,α- or β,β-trehalose. The ligands were transformed into cationic Rh complexes, such as [Rh(α-D-glucopyranosyl-(1,1)-2,3-di-O-diphenylphosphino-α-D- glucopyranoside)(cod)]BF4 (3) and [Rh(β-D-glucopyranosyl-(1,1)-2,3-di-O-diphenylphosphino-β-D- glucopyranoside)(cod)]BF4 (12) bearing free hydroxy groups. These complexes were soluble in water and were efficient catalysts for the asymmetric hydrogenation of dehydroamino acids and their esters in water or an aqueous/organic biphasic medium with high enantioselectivity (up to 99.9% ee). Aqueous biphasic systems offer an easy separation of the aqueous catalyst phase from the product phase and allow recycling of the catalyst phase without the loss of enantioselectivity.

Synthesis and glycosylation shift of 1,1'-disaccharides

Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.

A NOVEL OBSERVATION ON KOENIGS-KNORR CONDENSATION OF 2,3,4,6-TETRA-O-ACETYL-α-D-GLUCOPYRANOSYL BROMIDE WITH METHYL 4,6-O-BENZYLIDENE-α-D-GLUCOPYRANOSIDE

As a result of condensation between methyl 4,6-O-benzylidene-α-D-glucopyranoside and bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose in 1,2-dichloroethane in presence of silver carbonate, after removal of functional groups, the following substances were ob