21730-93-8

Basic information

• Product Name: L-Threonolactone
• Synonyms: 3,4-bis(trimethylsilyloxy)oxolan-2-one;Threonolactone;L-Threonic acid-1,4-lactone;(3R,4S)-3,4-Dihydroxydihydrofuran-2(3H)-one;L-Threonic acid γ-lactone
• CAS NO: 21730-93-8
• Molecular Formula: C₄H₆O₄
• Molecular Weight: 118.09
• Mol File: 21730-93-8.mol

Chemical Properties

• Melting Point: 74-75 °C
• Boiling Point: 277.8°Cat760mmHg
• Flash Point: 101.3°C
• Appearance: /
• Density: 0.99g/cm³
• Vapor Pressure: 0.00443mmHg at 25°C
• Refractive Index: 1.437
• PKA: 12.34±0.40(Predicted)
• BRN: 81074
• CAS DataBase Reference: L-Threonolactone(CAS DataBase Reference)
• NIST Chemistry Reference: L-Threonolactone(21730-93-8)
• EPA Substance Registry System: L-Threonolactone(21730-93-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 21730-93-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Threonolactone is used as a pharmaceutical compound for its potential therapeutic applications. It is derived from L-Ascorbic acid, which is essential for numerous enzymatic reactions in the body and has antioxidant properties that protect cells from oxidative damage.
Used in Antioxidant Applications:
L-Threonolactone is used as an antioxidant agent due to its connection with L-Ascorbic acid, which is known for scavenging free radicals and preventing oxidative damage to cells. This property makes L-Threonolactone a valuable component in the development of antioxidant therapies and products.
Used in Enzymatic Reactions:
L-Threonolactone is used as a component in various enzymatic reactions within the body, as it is formed during the autoxidation of L-Ascorbic acid. This involvement in enzymatic processes highlights its importance in maintaining proper cellular function and overall health.
Used in Research and Development:
L-Threonolactone is used as a research compound for studying the autoxidation process of L-Ascorbic acid and its effects on cellular processes. This research can lead to a better understanding of the role of L-Ascorbic acid and L-Threonolactone in cellular health and the development of new therapeutic strategies.

InChI:InChI=1/C10H22O4Si2/c1-15(2,3)13-8-7-12-10(11)9(8)14-16(4,5)6/h8-9H,7H2,1-6H3

Upstream product

• 67-56-1 methanol 
• 146-75-8 sodium L-ascorbate 
• 50-81-7 ascorbic acid 
• 7732-18-5 water 
• 490-83-5 L-dehydroascorbic acid 
• 488-16-4 (+/-)-erythronic acid 
• 909878-64-4 meso-erythritol 
• 89-65-6 isoascorbic acid 
• 2418-52-2 D-threitol 

Downstream Products

• 538368-86-4 2′,3′-di-O-benzoyl-L-threonolactone 
• 40837-73-8 L-threonic acid-(N'-phenyl-hydrazide) 
• 40837-73-8 erythronic acid-(N'-phenyl-hydrazide) 
• 74421-65-1 L-threonamide 
• 1021178-08-4 C₃₀H₂₆O₄ 
• 91345-19-6 2′-O-benzoyl-L-threonolactone 
• 150575-74-9 (3R,4S)-3,4-bis(benzyloxy)dihydrofuran-2(3H)-one 
• 909878-64-4 meso-erythritol 
• 87-69-4 tartaric acid 
• 28617-15-4 O²,O³-dibenzoyl-DL-threonic acid-lactone 

Relevant articles and documents

Substrate-like water soluble lipase inhibitors from Filipendula kamtschatica

Filipendula kamtschatica is a plant utilized as a traditional medicine by Ainu people in Japan, but its chemical constituents are not much studied. Pancreatic lipase inhibitors are a promising tool for the treatment of obesity. We searched for natural lipase inhibitors from F. kamtschatica and two new compounds were isolated along with the known flavonoid glycoside. The structure elucidation of new compounds revealed these two to be 2-O-caffeoyl-4-O-galloyl- l-threonic acid and 3-O-caffeoyl-4-O-galloyl-l-threonic acid, which can be recognized as a pancreatic lipase's substrate-like structure. The isolated compounds all showed an inhibitory activity against porcine pancreatic lipase and one of the isomer, 3-O-caffeoyl-4-O-galloyl-l-threonic acid, possessed the most potent activity with IC50 value showing an order lower value compared to others. The substrate-like structure of the new compounds seemed to be important for their activity.

A new efficient access to glycono-1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system

Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.

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

The autoxidation mechanism for L-ascorbic acid (ASA)-related compounds such as D-arabo-ascorbic acid (= erythorbic acid; ERA) and triose reductone (TR) in methanol without metal ion catalysis was studied.The oxidation reaction of these ASA-related compounds seems to proceed via the C(2) oxygen adduct of ERA (or TR) by a similar reaction mechanism to that of ASA. - Keywords: L-ascorbic acid; autoxidation; D-erythorbic acid; triose reductone; C(2) oxygen adduct

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.