(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

Base Information

• Chemical Name: (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
• CAS No.: 87-81-0
• Deprecated CAS: 73952-11-1
• Molecular Formula: C6H12O6
• Molecular Weight: 180.158
• Hs Code.: 29400000
• UNII: T7A20Y888Y
• Nikkaji Number: J9.874D
• Wikidata: Q414089
• Metabolomics Workbench ID: 38325
• ChEMBL ID: CHEMBL1236183
• Mol file: 87-81-0.mol

Synonyms:D-tagatose;tagatose;tagatose, (alpha-D)-isomer;tagatose, (beta-D)-isomer;tagatose, (D)-isomer;tagatose, (DL)-isomer

Chemical Property of (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 4.23E-08mmHg at 25°C
• Melting Point: 130-136 °C
• Refractive Index: -5.5 ° (C=1, H2O)
• Boiling Point: 551.7 °C at 760 mmHg
• PKA: 11.86±0.20(Predicted)
• Flash Point: 301.5 °C
• PSA: 118.22000
• Density: 1.589 g/cm³
• LogP: -3.37720
• Storage Temp.: Refrigerator
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 180.06338810
• Heavy Atom Count: 12
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

D-Tagatose 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C(=O)CO)O)O)O)O
• Isomeric SMILES: C([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O
• Description: D-tagatose is a carbohydrate occurring in small amounts in several foods. The solubility in water is approximately 580 g/L at room temperature. As a ketohexose, tagatose reacts in foods in browning reactions like other ketohexoses, for example, fructose. Tagatose is, depending on the concentration, approximately 92 % as sweet as sucrose and noncariogenic. The caloric value of tagatose is generally set to 1.5 kcal/g. In the European Union, tagatose is approved as a novel food. In the United States, tagatose has GRAS status and it is also approved in many other countries.
• Uses: A monosaccharide (hexose) that can be used as a low-calorie sweetener, as an intermediate for synthesis of other optically active compounds, and as an additive in detergent, cosmetic, and pharmaceutical formulation. D-(-)-Tagatose has been used as a carbohydrates for fermentation. It has also been used as one of the standards to confirm the identity of majority of the metabolites selected by least absolute shrinkage and selection operator (LASSO). D-tagatose is a compound useful in organic synthesis.

Technology Process of (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

There total 121 articles about (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

dihydroxyacetone (96-26-4,26776-70-5) + Glyceraldehyde (56-82-6,367-47-5,26793-98-6) → D-Glyceraldehyde (453-17-8,367-47-5,26793-98-6) + L-fructose (57-48-7,87-79-6,87-81-0,551-68-8,3615-39-2,3615-56-3,6035-50-3,7776-48-9,16354-64-6,17598-81-1,17598-82-2,23140-52-5,30237-26-4,65732-90-3,73952-10-0,73952-11-1,139686-85-4,18875-34-8)

Guidance literature:

With E_. coli BL₂₁ (DE₃) cells harboring pETDRhaD aldolase; sodium borate buffer; In water; toluene; at 37 ℃; for 16h; pH=7.6;

DOI:10.1002/adsc.200600356

Reference yield: 29.0%

D-Galactose (59-23-4) → D-Fructose (57-48-7,18875-34-8) + D-tagatose (87-81-0,18875-34-8)

Guidance literature:

With water; In ethanol; at 200 ℃; under 75007.5 Torr; Supercritical conditions;

DOI:10.1080/09168451.2015.1127135

Reference yield: 29.0%

D-glucose (50-99-7) → D-Fructose (57-48-7,18875-34-8) + D-tagatose (87-81-0,18875-34-8)

Guidance literature:

With water; In ethanol; at 200 ℃; under 75007.5 Torr; Supercritical conditions;

DOI:10.1080/09168451.2015.1127135

upstream raw materials:

D-talitol

D-Galactose

D-talose

alpha-lactose monohydrate

Downstream raw materials:

lyxo-2-hexulose

2-amino-D-2-deoxy-talose

D-galactosamine

2-amino-2-deoxy-α-D-talopyranose; hydrochloride

Refernces

Fluorogenic stereochemical probes for transaldolases

10.1002/chem.200390110

The study focuses on the development and application of fluorogenic stereochemical probes for transaldolases, enzymes that catalyze the transfer of dihydroxyacetone between sugar phosphates. The researchers synthesized two probes, 6-O-coumarinyl-fructose (1) and its 5-deoxy derivative (2), which are designed to measure the stereoselectivity of transaldolases. These probes work by undergoing a retro-aldolization reaction catalyzed by transaldolases, producing a primary product that further reacts to release a strongly fluorescent product, umbelliferone, upon elimination in the presence of bovine serum albumin (BSA). The study also involved the synthesis of a stereoisomer related to tagatose (3), which serves as a control to assess the stereoselectivity of the enzymes. The purpose of these chemicals is to provide a fluorogenic assay system for transaldolases, suitable for high-throughput screening of enzyme libraries, particularly for directed evolution experiments aiming to alter enzyme stereoselectivity. The study includes the use of various other chemicals, such as erythrose 4-phosphate as a natural acceptor to shift the reaction equilibrium, and a range of solvents and reagents in the synthesis and purification processes.