7306-96-9

Basic information

• Product Name: L-Threonic Acid
• Synonyms: (2R,3S)-2,3,4-trihydroxybutanoic acid;L-Threonic Acid;L-Threonate
• CAS NO: 7306-96-9
• Molecular Formula: C₄H₈O₅
• Molecular Weight: 136.10332
• Mol File: 7306-96-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 518.9°Cat760mmHg
• Flash Point: 281.7°C
• Appearance: /
• Density: 1.65g/cm³
• Vapor Pressure: 6.17E-13mmHg at 25°C
• Refractive Index: 1.56
• PKA: 3.47±0.17(Predicted)
• CAS DataBase Reference: L-Threonic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-Threonic Acid(7306-96-9)
• EPA Substance Registry System: L-Threonic Acid(7306-96-9)

Safety Data

• Hazardous Substances Data: 7306-96-9(Hazardous Substances Data)

Usage

General Description

L-Threonic Acid is a type of sugar acid that is derived from ascorbic acid or vitamin C. It is a chiral molecule and appears in the L-form, a type of stereoisomer. This monosaccharide substance has four carbon atoms and is the product of the enzymatic breakdown of vitamin C. L-Threonic Acid has been studied for its role in metabolizing and enhancing the biological activity of certain drugs in the body. It is not naturally found in high quantities, but can be synthesized in the laboratory for various biological and pharmacological research.

InChI:InChI=1/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1

Upstream product

• 67-56-1 methanol 
• 50-81-7 ascorbic acid 
• 87-79-6 L-sorbose 
• 490-83-5 L-dehydroascorbic acid 
• 3458-28-4 D-Mannose 
• 5328-37-0 L-arabinose 
• 24587-49-3 (2E)-4-hydroxybut-2-enoic acid 
• 909878-64-4 meso-erythritol 
• 7697-37-2 nitric acid 
• 2319-57-5 1,2,3,4-butanetetrol 
• 600-17-9 vinyl glycolic acid 
• 7732-18-5 water 
• 50-99-7 D-glucose 
• 62842-54-0 DL-erythro-pentyne-⁽¹⁾-triol-(3.4.5) 

Downstream Products

• 56-82-6 Glyceraldehyde 
• 13092-55-2 γ lacton-of dl-erythronic acid 
• 133-37-9 DL-tartaric acid 
• 144-62-7 oxalic acid 
• 64-18-6 formic acid 
• 849585-22-4 LACTIC ACID 
• 64-19-7 acetic acid 
• 40837-73-8 L-threonic acid-(N'-phenyl-hydrazide) 
• 40837-73-8 DL-threonic acid-(N'-phenyl-hydrazide) 
• 40837-73-8 erythronic acid-(N'-phenyl-hydrazide) 
• 28617-15-4 O²,O³-dibenzoyl-DL-threonic acid-lactone 

Relevant articles and documents

Iron-mediated cleavage of C-C bonds in vicinal tricarbonyl compounds in water

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Kinetic study of iridium(III) catalyzed oxidation of D-mannitol and erythritol by N-bromosuccinimide in acidic medium

Kinetic investigations on iridium trichloride catalyzed oxidation of D-mannitol and erythritol by acidic solution of N-bromosuccinimide (NBS) in the presence of mercuric acetate as a scavenger for Br- have been carried out in the temperature range 30-45 °C. The reactions follow identical kinetics. The rate shows a first-order dependence on [NBS] in lower concentration range which tends to zero-order at its higher concentrations. A first-order dependence on [IrIII] is also observed. Negligible effect of [substrate], [Hg(OAc)2] and ionic strength have been observed. Addition of [H+], [Cl-] and succinimide shows a negative effect. Activation parameters have been computed and a suitable mechanism conforming to above results has been proposed.

Autoxidation Reaction Mechanism for L-Ascorbic Acid in Methanol without Metal Ion Catalysis

The autoxidation reaction of L-ascorbic acid (ASA) in methanol without metal ion catalysis was studied. Besides L-threonolactone (THL) and oxalic acid (OXA), methyl L-threonate, and threonic acid were identified as initial autoxidation products of ASA, which were the C(2)-C(3) fission product via the C(2) oxygen adduct of ASA. This pathway is different from the one via dehydro-L-ASA (DASA), which has long been believed to be the only oxidation pathway of ASA. It was confirmed that this reaction also occurred in both water and other polar solvents, including methanol. It was clarified that mono-dissociated ASA was more reactive than the non-dissociated ASA in this pathway, and that the main reaction products formed from these two forms of ASA were also somewhat different. Determination of the amount of remaining ASA and the yields of THL and OXA, C(2)-C(3) fission products, and of DASA were carried out doing the autoxidation of ASA under various reaction conditions.