3-Methyloxetane-3-carboxylicacid

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Cat Number

INT28562687

CAS Number

28562-68-7

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Product Detail Description Customer Q&A

CAS Number

28562-68-7

Storage

Store at -20℃

Synonyms

3-methyloxetane carboxylic acid;3-Methyl-3-oxetanecarboxylic acid

Molecular Formula

C5H8O3

Molecular Weight

116.12

Smiles

O1CC(C)(C(O)=O)C1

Appearance

White to off-white powder

Melting Point

58-60℃

Boiling Point

224℃

Relative Density

1.25

pKa

3.95

General Description

3-Methyloxetane-3-carboxylic acid is a substituted oxetane (four-membered cyclic ether) bearing both a methyl group and a carboxylic acid at the C-3 position of the ring. The oxetane ring is a four-membered saturated heterocycle containing oxygen, and the gem-disubstitution at C-3 creates a quaternary carbon that constrains the ring conformation and blocks metabolic cleavage. The carboxylic acid provides a handle for conjugation and further transformation.

Mechanism of Action

3-Methyloxetane-3-carboxylic acid functions as a conformationally constrained amino acid-like building block. The gem-dimethyl substitution at C-3 creates a sterically hindered quaternary center that resists metabolic oxidation. The oxetane ring is less lipophilic than cyclopropane but more metabolically labile, providing intermediate properties between acyclic and larger cyclic ethers. The carboxylic acid can be converted to esters, amides, or activated derivatives for peptide coupling.

Application

3-Methyloxetane-3-carboxylic acid is used as an intermediate in the synthesis of constrained amino acid derivatives and peptidomimetic pharmaceuticals. The oxetane-3-carboxylic acid motif is found in certain marketed drugs and clinical candidates, particularly in CNS programs targeting neurotransmitter receptors. The quaternary center improves the drug-like properties of peptidic leads by reducing flexibility, increasing metabolic stability, and improving membrane permeability.

What is the recommended storage condition for 3-Methyloxetane-3-carboxylicacid?

It should be stored at -20°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

What documentation is provided with each batch of 3-Methyloxetane-3-carboxylicacid?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

Is 3-Methyloxetane-3-carboxylicacid available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

Can 3-Methyloxetane-3-carboxylicacid be provided with custom specifications for synthetic applications?

Custom specifications including adjusted particle size, solvent residue limits, or additional purity testing can be arranged for qualified customers with defined requirements.

Is 3-Methyloxetane-3-carboxylicacid manufactured under GMP conditions?

It is produced in facilities operating under applicable GMP or equivalent quality standards, ensuring consistent product quality and compliance with pharmaceutical industry requirements.