Chemical Identity and Structure

2-((3-Hydroxyadamantan-1-yl)amino)acetic acid (Aladdin SKU: A734527) is a synthetic organic compound belonging to the class of adamantane-derived amino acid analogues. Its systematic name reflects two key structural features: a 3-hydroxyadamantan-1-yl group — an adamantane cage bearing a tertiary hydroxyl at the 3-position — linked via a secondary amine to an acetic acid (glycine) moiety.

The adamantane scaffold is a bridged polycyclic hydrocarbon renowned for its exceptional rigidity, lipophilicity, and metabolic stability. When functionalized with a hydroxyl group and conjugated to a glycine unit through a nitrogen bridge, the resulting compound gains both hydrogen-bond donor/acceptor capacity and a handle for further synthetic elaboration. The molecular formula is C₁₂H₁₉NO₃ with a molecular weight of approximately 225.28 g/mol.

Note: Researchers should verify exact physicochemical parameters (melting point, logP, pKa) from the current certificate of analysis (CoA) supplied with each lot, as these values are lot-dependent and subject to revision.

Research Applications and Mechanistic Context

Adamantane amino acid conjugates have attracted sustained interest in drug discovery and chemical biology for several reasons. The adamantane cage confers steric bulk and conformational rigidity that can pre-organise pharmacophoric elements, enhance binding selectivity, and resist cytochrome P450-mediated oxidation relative to flexible alkyl chains.

Compounds structurally related to 2-((3-hydroxyadamantan-1-yl)amino)acetic acid have been reported in the literature as scaffolds or intermediates relevant to:

• HIF prolyl hydroxylase (PHD) inhibitor research: Hydroxyadamantyl-glycine derivatives have been explored as mimetics of the 2-oxoglutarate co-substrate or as transition-state analogues for iron(II)/2-oxoglutarate-dependent dioxygenases, including PHD enzymes that regulate hypoxia-inducible factor (HIF) stability.
• Medicinal chemistry building blocks: The free amine and carboxylate provide orthogonal coupling handles for peptide bond formation, reductive amination, and amide library synthesis.
• Bioisostere design: The 3-hydroxyadamantyl group serves as a conformationally restricted bioisostere for certain cycloalkyl and terpene-derived motifs.

Review flag: Specific biological activity data (IC₅₀ values, selectivity profiles) for this exact compound against named targets have not been confirmed from primary sources and should be independently verified before citation in publications.

Handling, Storage, and Safety Guidelines

Although 2-((3-Hydroxyadamantan-1-yl)amino)acetic acid is not classified as acutely hazardous under standard research-reagent criteria, all laboratory chemicals should be handled with appropriate precautions in accordance with your institution's chemical safety program.

Recommended Handling Practices

• Wear appropriate personal protective equipment (PPE): nitrile gloves, laboratory coat, and safety glasses at minimum.
• Handle in a well-ventilated area or fume hood when weighing powders to minimise inhalation exposure.
• Avoid contact with eyes, skin, and mucous membranes.
• Wash hands thoroughly after handling.

Storage Conditions

• Store in a tightly sealed container in a cool (15–25 °C), dry location away from direct light and moisture.
• Keep away from strong oxidising agents and strong acids/bases.
• Confirm specific storage temperature recommendations on the product label and CoA for each lot.

Disposal

• Dispose of waste in accordance with local, national, and institutional regulations governing chemical waste.
• Do not pour down the drain without confirming compatibility with local waste-water treatment requirements.

Review flag: A full Safety Data Sheet (SDS) specific to SKU A734527 should be consulted for authoritative hazard classification, first-aid measures, and regulatory information. Contact Aladdin Scientific for the current SDS.

Preparation and Solubility Guidance

Successful use of 2-((3-Hydroxyadamantan-1-yl)amino)acetic acid in assays and synthetic reactions depends on preparing homogeneous, accurately concentrated stock solutions. The following guidance is based on general principles for zwitterionic amino acid analogues with an adamantyl substituent; lot-specific solubility data should be verified experimentally.

Predicted Solubility Profile

The compound contains both an amine (basic) and a carboxylic acid (acidic) group and is therefore amphoteric. At physiological pH it is likely to exist as a zwitterion with reduced net charge and potentially limited aqueous solubility. Solubility may be enhanced by:

• DMSO: A common co-solvent for stock preparation (typically 10–100 mM); ensure final DMSO concentration in biological assays does not exceed tolerated limits (usually ≤0.1–1% v/v).
• Aqueous base (dilute NaOH or NH₄OH): Deprotonation of the carboxylic acid can improve aqueous dissolution; adjust pH carefully to the desired assay pH after dissolution.
• Phosphate-buffered saline (PBS), pH 7.4: May offer limited direct solubility; sonication and gentle warming (≤37 °C) can assist.

Stock Solution Preparation

1. Allow the sealed vial to equilibrate to room temperature before opening to prevent moisture condensation on the solid.
2. Weigh the required amount accurately using a calibrated analytical balance.
3. Dissolve in the chosen solvent and verify clarity; if turbidity persists, filter through a 0.2 µm PTFE syringe filter.
4. Prepare aliquots to avoid repeated freeze–thaw cycles.
5. Label with compound name, lot number, concentration, solvent, and preparation date.

Review flag: Experimentally determined solubility values (mg/mL in specific solvents) for lot A734527 are not available in the current source material. Users should determine solubility empirically or contact Aladdin Scientific for available data.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 2-((3-Hydroxyadamantan-1-yl)amino)acetic acid under SKU A734527 for research use. Each lot is accompanied by a Certificate of Analysis (CoA) that documents identity confirmation, purity assessment, and appearance.

Typical Quality Attributes

• Identity: Confirmed by techniques such as NMR spectroscopy and/or mass spectrometry (refer to the CoA for lot-specific data).
• Purity: Assessed by HPLC or related chromatographic methods (specific purity threshold stated on the CoA).
• Appearance: Typically a white to off-white solid powder (verify on CoA).

Ordering

To order SKU A734527 or request a quote, visit the Aladdin Scientific website or contact your regional sales representative. Bulk quantities and custom packaging may be available upon request. For regulatory documentation, SDS, or CoA requests, contact Aladdin Scientific customer support directly.

For Research Use Only. Not for diagnostic, therapeutic, or food use.

Review flag: Specific purity percentage, available pack sizes, and pricing are not included in the current source material and should be confirmed from the live product page or by contacting Aladdin Scientific.