4144-94-9

Basic information

• Product Name: (2R,3S)-butane-1,2,3-triol
• CAS NO: 4144-94-9
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.1204
• Mol File: 4144-94-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 281.8°C at 760 mmHg
• Flash Point: 145.8°C
• Density: 1.208g/cm³
• Vapor Pressure: 0.000412mmHg at 25°C
• Refractive Index: 1.483
• CAS DataBase Reference: (2R,3S)-butane-1,2,3-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-butane-1,2,3-triol(4144-94-9)
• EPA Substance Registry System: (2R,3S)-butane-1,2,3-triol(4144-94-9)

Safety Data

• Hazardous Substances Data: 4144-94-9(Hazardous Substances Data)

Usage

Description

(2R,3S)-butane-1,2,3-triol, also known as erythritol, is a sugar alcohol that is naturally occurring and found in fruits and fermented foods. It is a low-calorie sweetener that is used in a variety of products, including sugar-free gum, beverages, and baked goods.

Uses

Used in Food and Beverage Industry:
(2R,3S)-butane-1,2,3-triol is used as a low-calorie sweetener for its natural occurrence and versatility in various products such as sugar-free gum, beverages, and baked goods. It is considered safe for consumption and is often used as a sugar substitute for those looking to reduce their calorie and sugar intake.
Used in Sugar-Free Products:
(2R,3S)-butane-1,2,3-triol is used as a sugar substitute in sugar-free products due to its low-calorie content and ability to provide sweetness without significantly increasing blood sugar levels.
Used in Health-Conscious Applications:
(2R,3S)-butane-1,2,3-triol is used as a sweetener in health-conscious applications because of its digestive tolerance, as it is not fully absorbed by the body and does not cause a significant increase in blood sugar levels. This makes it a popular choice for those looking to manage their sugar intake for health reasons.

Upstream product

• 909878-64-4 meso-erythritol 
• 14694-95-2 Wilkinson's catalyst 
• 6347-01-9 fructopyranose 
• 57-48-7 sorbose 
• 64039-44-7 (R)-1-Phenoxy-butane-2,3-diol 

Downstream Products

• 33581-76-9 trimethylsilyl ether of 1-deoxyerythritol 

Relevant articles and documents

Hydrodeoxygenation of C4-C6 sugar alcohols to diols or mono-alcohols with the retention of the carbon chain over a silica-supported tungsten oxide-modified platinum catalyst

The hydrodeoxygenation of erythritol, xylitol, and sorbitol was investigated over a Pt-WOx/SiO2 (4 wt% Pt, W/Pt = 0.25, molar ratio) catalyst. 1,4-Butanediol can be selectively produced with 51% yield (carbon based) by erythritol hydrodeoxygenation at 413 K, based on the selectivity over this catalyst toward the regioselective removal of the C-O bond in the -O-C-CH2OH structure. Because the catalyst is also active in the hydrodeoxygenation of other polyols to some extent but much less active in that of mono-alcohols, at higher temperature (453 K), mono-alcohols can be produced from sugar alcohols. A good total yield (59%) of pentanols can be obtained from xylitol, which is mainly converted to C2 + C3 products in the literature hydrogenolysis systems. It can be applied to the hydrodeoxygenation of other sugar alcohols to mono-alcohols with high yields as well, such as erythritol to butanols (74%) and sorbitol to hexanols (59%) with very small amounts of C-C bond cleavage products. The active site is suggested to be the Pt-WOx interfacial site, which is supported by the reaction and characterization results (TEM and XAFS). WOx/SiO2 selectively catalyzed the dehydration of xylitol to 1,4-anhydroxylitol, whereas Pt-WOx/SiO2 promoted the transformation of xylitol to pentanols with 1,3,5-pentanetriol as the main intermediate. Pre-calcination of the reused catalyst at 573 K is important to prevent coke formation and to improve the reusability.

Metal-mediated decarbonylation and dehydration of ketose sugars

Ketose sugars can be decarbonylated and/or dehydrated by the action of certain metal complexes. Fructose reacts with 1 equiv of RhCl(PPh3)3 (1) in N-methyl-2-pyrrolidinone (NMP) at 130°C to give furfuryl alcohol, Rh(CO)Cl(PPh3)2 (2), and a small amount of 1-deoxyerythritol. 1,3-Dihydroxyacetone consumes 2 equiv of 1, giving methane and ca. 2 mol of 2. With manno-2-heptulose the primary product is 2,7-anhydromanno-2-heptulopyranose. The mechanisms of these unusual reactions have been studied by using 13C-labeling experiments and model reactions employing Pd(II) and HCl. Attempts to make the reactions catalytic using [Rh(Ph2PCH2CH2CH2PPh 2)2]+[BF4]- in place of 1 were not successful. The use of NMP as a solvent offers some advantages in the acid-catalyzed synthesis of certain carbohydrate dehydration products, as exemplified by the conversion of manno-2-heptulose to its 2,7-anhydride and of 2-deoxyglucose to 1-(2-furanyl)-1,2-ethanediol.