3946-09-6

Basic information

• Product Name: (2R)-hydroxypropanal
• Synonyms: (2R)-hydroxypropanal;D-Lactaldehyde;(2R)-2-Hydroxypropanal;(R)-2-Hydroxypropanal;[R,(-)]-2-Hydroxypropionaldehyde;R-Lactaldehyde
• CAS NO: 3946-09-6
• Molecular Formula: C₃H₆O₂
• Molecular Weight: 74.04
• Mol File: 3946-09-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 121.9 °C at 760 mmHg
• Flash Point: 36.8 °C
• Appearance: /
• Density: 1.011 g/cm³
• PKA: 13.41±0.20(Predicted)
• CAS DataBase Reference: (2R)-hydroxypropanal(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-hydroxypropanal(3946-09-6)
• EPA Substance Registry System: (2R)-hydroxypropanal(3946-09-6)

Safety Data

• Hazardous Substances Data: 3946-09-6(Hazardous Substances Data)

Usage

Description

(2R)-hydroxypropanal, also known as L-glyceraldehyde, is a chiral sugar-derived aldehyde with the molecular formula C3H6O2. It plays a crucial role as an intermediate in various biochemical pathways, such as glucose metabolism and energy production in cells. Furthermore, it serves as a key precursor in the synthesis of amino acids and nucleotides, which are vital for the formation of proteins and DNA.

Uses

Used in Pharmaceutical and Fine Chemical Production:
(2R)-hydroxypropanal is used as a starting material for the synthesis of pharmaceuticals and fine chemicals due to its versatile reactivity and ability to serve as a building block in the creation of complex organic molecules.
Used in Biochemical Research:
As an important intermediate in biochemical pathways, (2R)-hydroxypropanal is utilized in research to study the mechanisms of glucose metabolism, energy production, and the synthesis of essential biomolecules like amino acids and nucleotides.
Used in Industrial Processes:
(2R)-hydroxypropanal finds applications in various industrial processes, where it is employed as a key component in the production of different chemical compounds and materials, contributing to the development of new products and technologies.

Upstream product

• 72-19-5 L-threonine 
• 42919-42-6 (S)-1,1-dimethoxy-2-hydroxypropane 
• 4254-14-2 (2R)-propane-1,2-diol 
• 129172-95-8 methyl 6-deoxy-α/β-D-galactopyranoside 
• 74262-56-9 (2R)-2-(tert-butyldimethylsilyloxy)propanal 
• 17392-83-5 (R)-Methyl lactate 
• 75-07-0 acetaldehyde 

Downstream Products

• 103866-63-3 6-deoxy-D-fructose-1-phosphate disodium salt 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 40560-98-3 (1S,2R)-1-phenylpropane-1,2-diol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 

Relevant articles and documents

Stereostructure of komodoquinone A, a neuritogenic anthracycline, from marine Streptomyces sp. KS3

The absolute stereostructure of komodoquinone A (1), a neuritogenic anthracycline, which was isolated from a cultured marine Streptomyces sp. KS3, has been determined on the basis of chemical derivatization. Komodoquinone A (1) induces neuronal cell differentiation in the neuroblastoma cell line, Neuro 2A and arrests the cell cycle at the G1 phase. The effect of a solid-state medium on the production of 1 and its aglycone, komodoquinone B (2), was examined.

Biocatalytic Construction of Quaternary Centers by Aldol Addition of 3,3-Disubstituted 2-Oxoacid Derivatives to Aldehydes

The congested nature of quaternary carbons hinders their preparation, most notably when stereocontrol is required. Here we report a biocatalytic method for the creation of quaternary carbon centers with broad substrate scope, leading to different compound classes bearing this structural feature. The key step comprises the aldol addition of 3,3-disubstituted 2-oxoacids to aldehydes catalyzed by metal dependent 3-methyl-2-oxobutanoate hydroxymethyltransferase from E. coli (KPHMT) and variants thereof. The 3,3,3-trisubstituted 2-oxoacids thus produced were converted into 2-oxolactones and 3-hydroxy acids and directly to ulosonic acid derivatives, all bearing gem-dialkyl, gem-cycloalkyl, and spirocyclic quaternary centers. In addition, some of these reactions use a single enantiomer from racemic nucleophiles to afford stereopure quaternary carbons. The notable substrate tolerance and stereocontrol of these enzymes are indicative of their potential for the synthesis of structurally intricate molecules.

The first practical approach to optically pure cyclopropanes derived from trans γ-hydroxy enones

The optically pure cyclopropanes derived from trans γ-hydroxy enones were discussed. The trans γ-hydroxy enones were found to be prepared from reaction of stabilized ketoylides on optically pure α hydroxy aldehydes. The analysis showed that the use of light and a triplet sensitizer lead to a dramatic increase in reaction rate and isolated yield.