(-)-Diacetone-2-keto-L-gulonic acid monohydrate, CAS No. 68539-16-2

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68539-16-2

Catalog No. EBD21666

CAS 68539-16-2

Name (-)-Diacetone-2-keto-L-gulonic acid monohydrate

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Basic Information

Synonyms: 2,3:4,6-di-O-isopropylidene-2-keto-L-gulonicacid (-)-2,3:4,6-Di-O-isopropylidene-2-keto-L-gulonicAcidMonohydrate Diisoproyplideneketogulonicacidmonohydrate (-)-2,3:4,6-Di-O-isoproyplidene-2-keto-L-gulonicacidmonohydrate Dikegulacacid (3aS,3bR,7aS,8aR)-2,2,5,5-tetramethyltetrahydro-8aH-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxine-8a-carboxylicacidhydrate(non-preferredname) (-)-Diacetone-2-keto-L-gulonicacidmonohydrate 2,3:4,6-Di-O-isopropylidene-2-keto-L-gulonicacidmonohydrate

Molecular Formula: C12H20O8

Molecular Weight: 292.28

MDL Number: MFCD00150517

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Other Pharmaceutical Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Saccharides, Nucleosides, and Nucleotides

Product Description:

2,3:4,6-Di-O-isopropylidene-2-keto-L-gulonic acid is a key protected derivative of L-ascorbic acid (Vitamin C). It is a white to off-white crystalline powder with the molecular formula C12H18O7. This compound is characterized by the presence of two isopropylidene protecting groups, which mask the hydroxyl functionalities, and a ketone group at the C2 position. Its primary and most significant application is as a crucial advanced intermediate in the industrial synthesis of L-ascorbic acid (Vitamin C) via the classic Reichstein-Grüssner process and its modern variations. The compound serves as the direct precursor for the final lactonization step to form ascorbic acid. Due to this role, it is of paramount importance in the pharmaceutical, nutraceutical, and food additive industries for the large-scale production of Vitamin C. Beyond its role as a bulk pharmaceutical intermediate, this protected keto-gulonic acid derivative is also used in organic synthesis and research as a chiral building block for the preparation of other sugar derivatives and analogs. Its defined stereochemistry makes it valuable for constructing complex molecules in medicinal chemistry.

Physical Properties

Melting Point: 88-90 °C(lit.)

Boiling Point: 445.7 °C at 760 mmHg

Flash Point: 223.3 °C

Storage: 2-8°C