1758-51-6

Basic information

• Product Name: (2R,3R)-2,3,4-trihydroxybutanal
• Synonyms: (2R,3R)-2,3,4-trihydroxybutanal;(R*,R*)-2,3,4-Trihydroxybutanal;Butanal, 2,3,4-trihydroxy-, (R*,R*)-
• CAS NO: 1758-51-6
• Molecular Formula: C₄H₈O₄
• Molecular Weight: 120.12
• Mol File: 1758-51-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 144.07°C (rough estimate)
• Appearance: /
• Density: 1.0500 (rough estimate)
• Refractive Index: 1.4502 (estimate)
• PKA: 12.49±0.20(Predicted)
• CAS DataBase Reference: (2R,3R)-2,3,4-trihydroxybutanal(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2,3,4-trihydroxybutanal(1758-51-6)
• EPA Substance Registry System: (2R,3R)-2,3,4-trihydroxybutanal(1758-51-6)

Safety Data

• Hazardous Substances Data: 1758-51-6(Hazardous Substances Data)

Usage

General Description

(2R,3R)-2,3,4-trihydroxybutanal is a compound with the chemical formula C4H8O4. It is a trihydroxy aldehyde, meaning it contains three hydroxyl groups and an aldehyde functional group. (2R,3R)-2,3,4-trihydroxybutanal is also known as erythrulose and is commonly found in fruits such as grapes and raspberries. Erythrulose is used in the cosmetic industry as a self-tanning agent due to its ability to react with amino acids in the outer layer of the skin and produce a brown color, similar to the natural tanning process. It is also used as a precursor in the synthesis of various pharmaceuticals and other organic compounds.

InChI:InChI=1/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1

Upstream product

• 96-26-4 dihydroxyacetone 
• 141-46-8 Glycolaldehyde 
• 50-00-0 formaldehyd 
• 23147-58-2 glycolaldehyde dimer 
• 14694-95-2 Wilkinson's catalyst 
• 533-50-6 L-erythrulose 
• 909878-64-4 meso-erythritol 
• 608-66-2 D-galactitol 
• 7732-18-5 water 

Downstream Products

• 18952-67-5 Erythrose-methylphenylalkazon; Tetraoxo-butan-tetrakis-(1-methyl-1-phenyl-hydrazon) 
• 781577-54-6 calcium(II) oxalate 
• 5892-21-7 calcium mesotartrate*3H₂O 
• 2319-57-5 1,2,3,4-butanetetrol 
• 57-48-7 sorbose 
• 3154-37-8 3,4-dihydroxy-2-phenylhydrazono-butyraldehyde phenylhydrazone 

Relevant articles and documents

Selective Reductive Dimerization of CO2into Glycolaldehyde

The selective dimerization of CO2 into glycolaldehyde is achieved in a one-pot two-step process via formaldehyde as a key intermediate. The first step concerns the iron-catalyzed selective reduction of CO2 into formaldehyde via formation and controlled hydrolysis of a bis(boryl)acetal compound. The second step concerns the carbene-catalyzed C-C bond formation to afford glycolaldehyde. Both carbon atoms of glycolaldehyde arise from CO2 as proven by the labeling experiment with 13CO2. This hybrid organometallic/organic catalytic system employs mild conditions (1 atm of CO2, 25 to 80 °C in less than 3 h) and low catalytic loadings (1 and 2.5%, respectively). Glycolaldehyde is obtained in 53% overall yield. The appealing reactivity of glycolaldehyde is exemplified (i) in a dimerization process leading to C4 aldose compounds and (ii) in a tri-component Petasis-Borono-Mannich reaction generating C-N and C-C bonds in one process.

Catalytic effect of aluminium chloride on the example of the conversion of sugar model compounds

Abstract In this work, the catalytic effect of the Bronsted acid hydrochloric acid, the Bronsted base sodium hydroxide and the Lewis acid AlCl3 on the conversion of biomass derived carbohydrates is investigated. On the example of the glycolaldehyde conversion, it is shown that the Lewis acid catalyses the ketol-endiol-tautomerism, the dehydration, the retro-aldol-reaction and the benzilic-acid-rearrangement. The main products are C4- and C6-carbohydrates as well as their secondary products 2-hydroxybut-3-enoic acid 1 and several furans. Under the same reaction conditions hydrochloric acid catalyzes mainly the dehydration and sodium hydroxide the tautomerism and subsequent aldolization.

Methods for the electrolytic production of erythrose or erythritol

Methods for the production of erythrose and/or erythritol are provided herein. Preferably, the methods include the step of electrolytic decarboxylation of a ribonic acid or arabinonic acid reactant to produce erythrose. Optionally, the reactant can be obtained from a suitable hexose sugar, such as allose, altrose, glucose, fructose or mannose. The erythrose product can be hydrogenated to produce erythritol.