D-Isoascorbic acid

Base Information

• Chemical Name: D-Isoascorbic acid
• CAS No.: 89-65-6
• Molecular Formula: C6H8O6
• Molecular Weight: 176.126
• Hs Code.: 29329990
• Mol file: 89-65-6.mol

Synonyms:D-erythro-Hexonicacid, 3-keto-, g-lactone(6CI);Erythorbic acid (7CI);Araboascorbic acid;Araboascorbic acid, D-;D-(-)-Isoascorbic acid;D-Araboascorbic acid;D-Erythorbic acid;D-arabino-Ascorbic acid;E 315;Erycorbin;Glucosaccharonic acid;Isoascorbic acid;Isovitamin C;Mercate 5;Neo-Cebicure;Saccharosonic acid;Erythorbic acid;

Chemical Property of D-Isoascorbic acid

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 3.28E-12mmHg at 25°C
• Melting Point: 169-172 °C (dec.)(lit.)
• Refractive Index: -17.5 ° (C=10, H2O)
• Boiling Point: 552.7 °C at 760 mmHg
• PKA: 4.09±0.10(Predicted)
• Flash Point: 238.2 °C
• PSA: 107.22000
• Density: 1.954 g/cm³
• LogP: -1.40740
• Storage Temp.: Store at 0-5°C
• Solubility.: H2O: 0.1 g/mL, clear, colorless to very faintly yellow
• Water Solubility.: 1g/10mL

Purity/Quality:

99.5% ^*data from raw suppliers

D(-?)?-?IsoascorbicAcid(ErythorbicAcid) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Antioxidant (industrial and food), especially in brewing industry, reducing agent in photography. Erythorbic Acid is a food preservative that is a strong reducing agent (oxygen accepting) which functions similarly to antioxidants. In the dry crystalline state it is nonreactive, but in water solutions it reacts readily with atmospheric oxygen and other oxidizing agents, making it valuable as an antioxidant. During preparation, dissolving and mixing should incorporate a minimum amount of air, and storage should be at cool temperatures. It has a solubility of 43 g/100 ml of water at 25°c. One part is equivalent to one part ascorbic acid and equivalent to one part sodium erythorbate. It is used to control oxidative color and flavor deterioration in fruits at 150–200 ppm. It is used in meat curing to speed and control the nitrite curing reaction and prolong the color of cured meat at levels of 0.05%. Erythorbic Acid is used as a food additive as an antimicrobial and antioxidative agent.

Technology Process of D-Isoascorbic acid

There total 13 articles about D-Isoascorbic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

D-arabino-[2]hexulosonic acid methyl ester (21063-40-1) → isoascorbic acid (89-65-6,98966-42-8)

Guidance literature:

With manganese; water;

Reference yield:

→ isoascorbic acid (89-65-6,98966-42-8)

Guidance literature:

With methanol; sulfuric acid; anschl. mit wss. NaHCO₃;

Reference yield:

D-erythro-pentos-2-ulose (3445-24-7) → isoascorbic acid (89-65-6,98966-42-8)

Guidance literature:

With potassium cyanide; nitrogen; water; anschl. mit wss. HCl unter Ausschluss von Luft;

DOI:10.1002/hlca.19340170157

upstream raw materials:

D-erythro-pentos-2-ulose

D-arabino-[2]hexulosonic acid methyl ester

methanol

diethylamine

Downstream raw materials:

D-erythro-2,4,5,6-tetrahydro-3-methoxy-hex-2c-enoic acid-4-lactone

D-erythro-4,5,6-trihydroxy-2,3-dimethoxy-hex-2c-enoic acid-4-lactone

6-O-palmitoyl-L-ascorbic acid

D-erythro-2,3-bis-(2,4-dinitro-phenylhydrazono)-4,5,6-trihydroxy-hexanoic acid-4-lactone

Refernces

Stereoselective total synthesis of (-)-cleistenolide

10.1016/j.tet.2011.03.107

The research describes the development of a stereoselective total synthesis route for the natural product (?)-cleistenolide, derived from D-(?)-isoascorbic acid. The purpose of this study is to develop a new synthetic strategy for (?)-cleistenolide, a compound with significant biomedical importance due to its antibacterial and antifungal activities. The key steps in this synthesis include highly diastereoselective reduction, one-pot protection of required benzoyl and acetyl groups, and a ring-closing metathesis (RCM) reaction using the Grubbs catalyst. The synthesis starts from D-(?)-isoascorbic acid, which is converted into various intermediates through a series of reactions involving reagents such as TBDMSCl for protection, DIBAL-H for reduction, and K-Selectride for selective diastereomeric reduction. The RCM reaction using the Grubbs second generation catalyst is crucial for forming the desired ring structure. The final product, (?)-cleistenolide, is obtained with an overall yield of 18% and its physical and spectroscopic data match those of the natural product. The study concludes that the developed synthetic route is highly diastereoselective and efficient, providing a valuable method for the synthesis of (?)-cleistenolide and potentially other related bioactive compounds.