cis-4-Hydroxycyclohexanecarboxylic Acid is an alicyclic compound built on a cyclohexane ring that carries a carboxylic acid group and a hydroxyl group at opposing positions, with the cis configuration already established. As a non-heterocyclic building block, it provides a rigid three-dimensional framework while still offering two reactive functional groups of differing character. In the laboratory, this material is widely used in medicinal chemistry to construct molecules with a specific spatial orientation, and as a difunctional linker in stepwise organic synthesis.
The principal value of this compound lies in its defined stereochemistry. The cis configuration places the hydroxyl and carboxylate groups in a particular spatial relationship that the trans isomer cannot reproduce, so that the final molecules built from it possess a predictable three-dimensional shape. In drug design, a saturated cyclohexane scaffold of this kind is valued because it increases the sp3 character of a molecule, an approach frequently associated with improved solubility and physicochemical profiles compared with fully aromatic frameworks. In addition, the two functional groups can be differentiated by reactivity, allowing them to be addressed selectively during a synthetic sequence.
In Indonesian laboratories, this building block is typically encountered in university research groups, pharmaceutical research and development units, and contract synthesis laboratories working on small-molecule preparation. It is generally ordered in research-scale quantities for route scouting, analogue preparation, and method development work, where a stereochemically defined starting material removes the need for a separate resolution or isomer separation step and shortens the overall synthetic path.
- Medicinal chemistry scaffold construction: the fixed cis relationship between the two substituents gives designers a predictable spatial arrangement when building target molecules with defined geometry.
- Difunctional linker in stepwise synthesis: the carboxylic acid and hydroxyl groups can be coupled at different stages, letting chemists extend a molecule from two independent points.
- Preparation of sp3-rich analogues: the saturated cyclohexane ring raises the three-dimensional character of a candidate series, an approach often pursued to improve solubility and physicochemical behaviour.
- Selective derivatisation studies: the differing reactivity of the acid and alcohol functions allows one group to be protected or activated while the other remains available for reaction.
- Stereochemistry-dependent structure–activity work: because the cis isomer is supplied as such, researchers can compare geometric isomers without performing their own separation or resolution step.
| Brand | TCI |
|---|---|
| CAS number | 3685-22-1 |
| Molecular formula | — |
| Purity | — |
| Category | Chemistry > Building Blocks > Non-Heterocyclic Building Blocks |
| Pack sizes | research-scale packs as listed by the manufacturer for this catalogue number |
| Physical form | — |
| Storage | keep in the tightly closed original container as indicated on the manufacturer's label |
- Catalogue number: H0980
Store the material in its tightly closed original container, in a cool, dry and well-ventilated area away from moisture and direct sunlight, following the storage conditions stated on the manufacturer's label and safety data sheet. Glass containers with chemically resistant closures are suitable for any transfer or subdivision. Handle the compound in a fume hood, wearing safety glasses, gloves and a laboratory coat, and avoid generating dust during weighing. Keep the container closed when not in use, label all subdivided portions clearly, and review the safety data sheet before first use and before disposal.
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