22554-74-1

Basic information

• Product Name: (-)-1,4-ANHYDRO-L-THREITOL
• Synonyms: ERYTHRITAN;L-THREITAN;(-)-1,4-ANHYDRO-L-THREITOL;(3S,4S)-TETRAHYDRO-FURAN-3,4-DIOL;Tetrahydro-3,4-furandiol;trans-tetrahydrofuran-3,4-diol;trans-3,4-Dihydroxytetrahydrofuran;Trans-3,4-Dihydroxy-THF
• CAS NO: 22554-74-1
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.1
• EINECS: 245-074-7
• Mol File: 22554-74-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 221.8°Cat760mmHg
• Flash Point: 104°C
• Appearance: /
• Density: 1.411g/cm³
• Vapor Pressure: 0.0216mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: (-)-1,4-ANHYDRO-L-THREITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-1,4-ANHYDRO-L-THREITOL(22554-74-1)
• EPA Substance Registry System: (-)-1,4-ANHYDRO-L-THREITOL(22554-74-1)

Safety Data

• Hazardous Substances Data: 22554-74-1(Hazardous Substances Data)

Usage

General Description

(-)-1,4-ANHYDRO-L-THREITOL (also known as L-erythritol) is a sugar alcohol compound commonly used as a sweetener in low-calorie and sugar-free products. It is a white, crystalline powder with a sweet taste, approximately 70% as sweet as sucrose. L-erythritol is naturally occurring in some fruits and fermented foods, and it is also produced through the fermentation of glucose by certain microorganisms. Unlike other sugar alcohols, L-erythritol is absorbed into the bloodstream and excreted unchanged in the urine, leading to minimal caloric impact and a low glycemic index. It is considered safe for consumption and is approved for use in food and beverages by regulatory agencies around the world. Additionally, it has been studied for potential health benefits, such as dental health and antioxidant properties.

InChI:InChI=1/C4H8O3/c5-3-1-7-2-4(3)6/h3-6H,1-2H2/t3-,4-/m0/s1

Upstream product

• 285-69-8 3,4-epoxytetrahydrofuran 
• 6117-80-2 1,4-butenediol 
• 6968-16-7 rac-threitol 
• 285-69-8 (1R,5S)-3,6-dioxabicyclo[3.1.0]hexane 
• 497-06-3 3,4-butenediol 
• 909878-64-4 meso-erythritol 
• 1708-29-8 2,5-dihydrofuran 

Downstream Products

• 85386-39-6 1,4-anhydro-DL-threitol 2,3-diacetate 

Relevant articles and documents

The solvent-free thermal dehydration of tetritols on zeolites

A new alditol dehydration method at high temperatures, in the presence of molecular sieves without solvent in an argon atmosphere, is described. Investigations on tetritols have been carried out. Products arising after the intramolecular and intermolecular elimination of water, with retention or inversion of the configuration of asymmetric carbon atoms, were observed. Complete analytical separation of reaction products was achieved by means of GLC. The chemical structures of the compounds obtained were assigned using co-injection with standards, GLC-CIMS and GLC-EIMS analyses. Two intermolecular dehydration products of tetritols were isolated by HPLC and identified by 1H and 13C NMR spectroscopy. Copyright (C) 2000 Elsevier Science Ltd.

N,N,O-Coordinated tricarbonylrhenium precatalysts for the aerobic deoxydehydration of diols and polyols

Rhenium complexes are well known catalysts for the deoxydehydration (DODH) of vicinal diols (glycols). In this work, we report on the DODH of diols and biomass-derived polyols using L4Re(CO)3as precatalyst (L4Re(CO)3= tricarbonylrhenium 2,4-di-tert-butyl-6-(((2-(dimethylamino)ethyl)(methyl)amino)methyl)phenolate). The DODH reaction was optimized using 2 mol% of L4Re(CO)3as precatalyst and 3-octanol as both reductant and solvent under aerobic conditions, generating the active high-valent rhenium speciesin situ. Both diol and biomass-based polyol substrates could be applied in this system to form the corresponding olefins with moderate to high yield. Typical features of this aerobic DODH system include a low tendency for the isomerization of aliphatic external olefin products to internal olefins, a high butadiene selectivity in the DODH of erythritol, the preferential formation of 2-vinylfuran from sugar substrates, and an overall low precatalyst loading. Several of these features indicate the formation of an active species that is different from the species formed in DODH by rhenium-trioxo catalysts. Overall, the bench-top stable and synthetically easily accessible, low-valent NNO-rhenium complex L4Re(CO)3represents an interesting alternative to high-valent rhenium catalysts in DODH chemistry.

Epoxide hydrolase-catalyzed enantioselective synthesis of chiral 1,2-diols via desymmetrization of meso-epoxides

The discovery, from nature, of a diverse set of microbial epoxide hydrolases is reported. The utility of a library of epoxide hydrolases in the synthesis of chiral 1,2-diols via desymmetrization of a wide range of meso-epoxides, including cyclic as well as acyclic alkyl- and aryl-substituted substrates, is demonstrated. The chiral (R,R)-diols were furnished with high ee's and yields. The discovery of the first microbial epoxide hydrolases providing access to complementary (S,S)-diols is also described. Copyright