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
• Article Data: 4

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

L-Threonolactone is formed in the autoxidation of L-Ascorbic acid (A786990), a compound that is essential for numerous enzymatic reactions in the body and is also responsible for scavenging free radicals to prevent oxidative damage to cells.

Definition

ChEBI: A butan-4-olide that is dihydrofuran-2-one substituted at C-3 and C-4 by hydroxy groups (the 3R,4S-diastereomer).

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

Downstream Products

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

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.

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