4(trans)-hydroxyproline, methyl ester, CAS No. 1499-56-5

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1499-56-5

Catalog No. EBD225640

CAS 1499-56-5

Name 4(trans)-hydroxyproline, methyl ester

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Basic Information

Synonyms: 4(trans)-hydroxyproline,methylester methyl4-hydroxyprolinate (2S,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine trans-4-hydroxy-L-prolinemethylester (2S,4R)-4-hydroxyprolinemethylester (R)-4-hydroxy-L-prolineethylester 4(R)-hydroxy-L-prolinemethylester l-proline,4-hydroxy-,methylester,(4r)-(9ci) methyl(2s,4r)-4-hydroxypyrrolidine-2-carboxylate l-proline,4-hydroxy-,methylester,(4r)- (2r,4s)-methyl4-hydroxypyrrolidine-2-carboxylate Methyl(4R)-4-Hydroxy-L-Prolinate Methyl4-Hydroxy-L-Prolinate

Molecular Formula: C6H11NO3

Molecular Weight: 145.16

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Amino Acids and Derivatives

Product Description:

(2S,4R)-Methyl 4-hydroxyproline, also known as trans-4-hydroxy-L-proline methyl ester, is a derivative of the non-standard amino acid 4-hydroxyproline. It features a pyrrolidine ring with a hydroxyl group at the 4-position and a methyl ester at the carboxyl group, with defined (2S,4R) stereochemistry. This compound serves as a crucial chiral building block in pharmaceutical synthesis. Its primary application is as a key intermediate in the production of various drugs, particularly protease inhibitors and other bioactive molecules where the rigid, hydroxylated proline scaffold is essential for biological activity and target binding. The methyl ester group enhances its solubility and reactivity for further chemical modifications. As a derivative of a naturally occurring amino acid, it is also relevant in biochemical research and peptide chemistry. It is used to introduce the hydroxyproline motif into synthetic peptides to mimic collagen-like structures or to study post-translational modifications.

Physical Properties

Boiling Point: 247.177°C at 760 mmHg

Flash Point: 103.289°C

Density: 1.216g/cm3