2-Cyclohexyl-2-hydroxyacetic Acid: Properties & Lab FAQ

2-Cyclohexyl-2-hydroxyacetic acid is an aliphatic alpha-hydroxy acid bearing a cyclohexyl substituent at the chiral alpha-carbon, widely used as a pharmaceutical intermediate and chiral building block in organic synthesis.

Chemical Name

2-Cyclohexyl-2-hydroxyacetic acid

Functional Class

Alpha-hydroxy acid (AHA); mandelic acid aliphatic analog

Key Structural Feature

Chiral alpha-carbon bearing hydroxyl, carboxyl, and cyclohexyl groups

Primary Research Use

Pharmaceutical intermediate, chiral ligand synthesis, and asymmetric synthesis building block

Aladdin SKU

C680344

Stereochemistry

Possesses one chiral center; available as racemate or enantiopure forms depending on supplier lot

Chemical Identity and Structure

2-Cyclohexyl-2-hydroxyacetic acid (CAS number should be confirmed with the certificate of analysis) is a member of the alpha-hydroxy acid family. Its structure consists of a cyclohexane ring attached to the alpha-carbon of glycolic acid, creating a sterically hindered chiral center that bears both a hydroxyl group and a carboxylic acid. This makes the compound a close aliphatic analogue of mandelic acid (2-phenyl-2-hydroxyacetic acid), with the aromatic ring replaced by a saturated cyclohexyl ring.

The presence of the bulky cyclohexyl group confers increased lipophilicity and steric differentiation at the chiral center compared with simpler alpha-hydroxy acids such as lactic or glycolic acid. These features make it a valuable scaffold for the preparation of chiral auxiliaries, resolving agents, and drug-like fragments.

Physical and Chemical Properties

2-Cyclohexyl-2-hydroxyacetic acid is expected to be a white to off-white crystalline solid at room temperature, consistent with other small-molecule alpha-hydroxy acids of similar molecular weight. The carboxylic acid and hydroxyl functionalities render the compound capable of hydrogen bonding, influencing its melting point, solubility profile, and reactivity.

Solubility: The compound is anticipated to dissolve readily in polar organic solvents such as ethanol, methanol, ethyl acetate, and DMSO, and to show limited solubility in non-polar solvents such as hexane. Aqueous solubility is expected to be moderate and pH-dependent due to the ionizable carboxylic acid group (typical pKa for aliphatic alpha-hydroxy acids is approximately 3–4).

Note: Precise values for melting point, optical rotation, and pKa are not provided in the available source material and should be confirmed from the product certificate of analysis (CoA) or peer-reviewed literature.

Handling, Storage, and Safety

As with all research reagents, standard laboratory safety precautions should be observed when working with 2-cyclohexyl-2-hydroxyacetic acid. Personnel should wear appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Avoid inhalation of dust and contact with skin and eyes.

Storage: Store in a tightly sealed container in a cool, dry, and well-ventilated location, away from incompatible materials such as strong bases and oxidizing agents. Refrigerated storage (2–8 °C) is typically recommended for long-term preservation of alpha-hydroxy acids to minimize hydrolytic or oxidative degradation.

Disposal: Dispose of in accordance with local, regional, and national regulations. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for complete hazard and disposal information before use.

Research and Synthetic Applications

2-Cyclohexyl-2-hydroxyacetic acid serves several roles in synthetic and medicinal chemistry research:

• Pharmaceutical intermediate: The compound can be used in the synthesis of active pharmaceutical ingredients (APIs) and drug candidates, particularly those requiring a chiral alpha-hydroxy acid moiety. It is structurally related to agents targeting muscarinic receptors and other pharmacological targets where alicyclic mandelic acid derivatives appear as key pharmacophores.
• Chiral building block: The alpha-hydroxy acid motif allows for further derivatization via esterification, amide coupling, or protection of the hydroxyl group, enabling incorporation into complex chiral molecules and peptidomimetics.
• Asymmetric synthesis: Enantiopure forms of the compound can serve as chiral auxiliaries or starting materials in asymmetric transformations, leveraging the stereodirecting influence of the bulky cyclohexyl group.
• Ligand and catalyst development: Alpha-hydroxy acids are frequently employed as ligands in metal-catalyzed asymmetric reactions; the cyclohexyl variant may be explored in this context.

Note: Specific published synthetic routes and biological activity data for this exact compound were not available in the source material and should be verified in primary literature.

Quality, Purity, and Ordering Information

Aladdin Scientific supplies 2-cyclohexyl-2-hydroxyacetic acid under SKU C680344. Customers should request the certificate of analysis (CoA) for each lot to confirm purity, appearance, identity (NMR, HPLC, or MS), and any stereochemical specifications prior to use in sensitive applications.

For bulk quantities, custom purity grades, or enantiopure material, contact Aladdin Scientific customer service or submit an inquiry through the product page. Volume pricing and institutional procurement options may be available.

Related reference material and additional specification data are cross-listed with Pharmablock (catalog reference PBTEN8268), which may provide supplementary characterization data useful for quality verification.

Frequently asked questions

What is 2-cyclohexyl-2-hydroxyacetic acid used for in research?

It is primarily used as a pharmaceutical intermediate and chiral building block in organic and medicinal chemistry. The alpha-hydroxy acid functionality enables esterification, amide coupling, and derivatization, while the chiral center and bulky cyclohexyl group make it valuable for asymmetric synthesis and the preparation of drug candidates with defined stereochemistry.

How should 2-cyclohexyl-2-hydroxyacetic acid be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area, away from strong bases and oxidizing agents. Refrigerated storage at 2–8 °C is generally recommended for long-term stability of alpha-hydroxy acids. Always consult the lot-specific CoA and SDS for confirmed storage conditions.

Is 2-cyclohexyl-2-hydroxyacetic acid available in enantiopure form?

The compound contains one chiral center and may be available as a racemate or in enantiopure form depending on the lot specification. Customers requiring a specific enantiomer should review the CoA for optical rotation or ee data, and contact Aladdin Scientific customer service to inquire about enantiopure material or custom synthesis options.

What solvents are suitable for dissolving 2-cyclohexyl-2-hydroxyacetic acid?

Based on its alpha-hydroxy acid structure, the compound is expected to dissolve well in polar organic solvents such as ethanol, methanol, DMSO, and ethyl acetate. Solubility in water is anticipated to be moderate and pH-dependent. Solubility in non-polar solvents such as hexane is expected to be low. Confirm solubility experimentally before use in critical applications.

How do I obtain a Safety Data Sheet (SDS) or Certificate of Analysis (CoA) for C680344?

Safety Data Sheets and Certificates of Analysis for Aladdin Scientific products, including C680344, are available through the product page on the Aladdin Scientific website or by contacting customer service directly. It is recommended to request a lot-specific CoA to verify purity and identity for your application.

References

1. Pharmablock product entry PBTEN8268: 2-Cyclohexyl-2-hydroxyacetic acid. Pharmablock Sciences (Nanjing), Inc.
2. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley-Interscience, 1992. (General reference for alpha-hydroxy acid chemistry.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.