Some advances in chemistry come from careful patience more than game-changing discoveries. You can trace the road to (4S)-4-Cyclohexyl-L-Proline back to early work on amino acids in peptide engineering. Once researchers started to adjust Proline’s structure by swapping its cyclic ring for something bulkier, such as a cyclohexyl group, things opened up for custom peptide synthesis. This progress didn’t spring from nowhere. Before 1980, organic chemists were working to coax higher selectivity and rigidity out of designer amino acids for better pharmaceutical leads. Efforts in the late 20th century nailed down efficient routes to these non-natural amino acids, laying the groundwork for products that go beyond the usual L-Proline. By the early 2000s, demand grew for tools that let chemists fine-tune protein conformations and block unwanted side reactions, especially in drug design. (4S)-4-Cyclohexyl-L-Proline walked onto the stage for these roles, hand in hand with improvements in asymmetric synthesis.
You can pick up (4S)-4-Cyclohexyl-L-Proline as a solid white or off-white powder, usually pure enough for biochemistry work. Built off the classic L-Proline core, this version swaps the hydrogen at the fourth carbon for a cyclohexyl group, adding both girth and hydrophobicity. A chemist friends the rigid, puckered ring; an engineer notes the boost in solubility profiles. Folks working in peptide synthesis value this compound for what it delivers — stubborn resistance to unwanted backbone flexibility, which lets you build peptides with just the right kinks. Researchers have logged solid performance both in academic settings and industrial builds, finding a fit for this molecule wherever classic amino acids fall short.
(4S)-4-Cyclohexyl-L-Proline lands with a molecular formula of C12H21NO2, massing in at a neat 211.30 g/mol. Pure samples come as crystalline powders, stable under ambient air for months if kept dry. The compound resists high heat, holding shape until above 200°C (melting point varies slightly depending on hydration). Water solubility sits at moderate levels, but organic solvents — methanol, ethanol, DMF — chew it up quickly, making it workable for peptide couplings. The cyclohexyl ring at position 4 imparts higher lipophilicity versus standard Proline, showing up in altered chromatographic retention times and improved compatibility with hydrophobic environments. This altered side chain also reshapes the pKa values for both the amino and carboxyl groups, something to remember when designing experiments or scale-up processes.
Lab supply firms ship this amino acid with tight purity specs — 98% or better, measured by HPLC. Labels call out stereochemistry (4S), usually referencing its optical rotation for confirmation. CAS number 124059-19-0 appears on every drum and vial. Companies follow GHS guidance, printing hazard codes and recommended PPE. Bulk packaging comes in nitrogen-purged bottles to avoid moisture uptake, and each lot carries certificates for heavy metals, enantiomeric excess, and trace residues. That’s become standard, with pharmaceutical buyers pushing for full transparency as part of GMP supply chains. Batch traceability draws on both production logs and chromatographic fingerprints, letting users backtrack if troubles show up downstream.
The world of synthetic amino acid production keeps most details tight, yet the general approach for (4S)-4-Cyclohexyl-L-Proline relies on two maneuvers — chiral pool synthesis and asymmetric catalysis. One common starting point uses L-Proline itself or a protected L-hydroxyproline. Chemists run alkylation reactions with cyclohexyl derivatives under base and phase-transfer conditions, guided by protecting groups to steer the cyclohexyl group onto the right carbon, all set by the (S) configuration. Another well-used play calls for chiral auxiliary-directed alkylation, then removal of the auxiliary to restore free amino acid. Purification leans on repeated extraction and crystallization cycles, with fine-tuning at the end by flash chromatography. Quality control screens for regioisomeric and enantiomeric impurities; high-end users add mass spectrometry checks.
Once you’ve got this molecule in hand, it plays well in standard peptide coupling reactions, joining other amino acids using EDC, HATU, or DCC protocols. Both acid and amine functionalities remain open for typical protection and deprotection strategies. This variant shows less reactivity toward epimerization than native Proline under strong coupling conditions, making it easier to hold onto stereochemical integrity through multiple reaction steps. Side-chain manipulation stays limited by the cyclohexyl’s stubborn inertness, but selective hydrogenation or bromination offers some routes to diversifying the core. Researchers push further using fluorination at the cyclohexyl ring, looking for improved metabolic stability or altered binding in protein matrices. The compound withstands moderate acid and base strengths, so standard SPPS (solid phase peptide synthesis) protocols run smoothly.
Depending on the supplier or catalog, (4S)-4-Cyclohexyl-L-Proline carries different handles: 4-Cyclohexylproline, 4-CHP, or even Cx-Pro for short. Some academic papers use ‘L-4-cyclohexylproline’ or ‘(S)-4-cyclohexylproline’ to mark stereochemistry. You’ll also find the chemical name as (2S,4S)-4-Cyclohexylpyrrolidine-2-carboxylic acid in more technical databases. Each name pays tribute to the backbone (Pyrrolidine ring) with a nod to proline’s placement in peptide chains.
Working with amino acids like this one calls for respect, though you won’t face the hazards linked to many industrial chemicals. Glove use, eye protection, and lab coats form the norm against mild irritancy. Safety data sheets say the compound may irritate skin, eyes, or mucus membranes if you go splashing it around. Accidental inhalation seems rare given its low vapor pressure, but any solid dust can be trouble in an open flask — ventilation helps. Disposal routes mirror those for amino acids in general, running through non-hazardous waste with documentation. Spill controls and cleanup follow standard operating procedures for organic solids with water solubility. Storage out of direct sunlight, dry and cool, prevents hydrolysis or slow oxidative side reactions, preserving shelf life.
Peptide synthesis shops lean hard on (4S)-4-Cyclohexyl-L-Proline for making constrained peptides that resist enzymatic chop-down inside living bodies. Pharmaceutical R&D teams use these building blocks to block kinks and control protein folding in drug candidates — especially those that go after protein–protein interaction sites in diseases like cancer and autoimmune conditions. Medicinal chemists see value in improved serum half-life and lower off-target degradation. Outside pharma, researchers also test this amino acid in designer enzyme catalysts, where its hydrophobic side chain shapes the microenvironment around the active site. Studies keep branching into creating biosensors and smart materials that need sturdy peptide backbones to withstand industrial processing.
Research on (4S)-4-Cyclohexyl-L-Proline has explored many angles: structure–activity relationships in peptides, ribosomal incorporation in synthetic biology, and tuning the compound’s electronic effects through fluorination or aryl substitution. In big pharma, programs run screens on libraries of modified peptides to pick out promising hits for resistant infections or novel pain pathways. Academic groups tweak the side chain to understand its effects on helical propensity and β-turn formation. Publications map out its influence on target selectivity and probe its resistance to enzymatic hydrolysis. Research consortia try to link up these findings so improved amino acids can transition from benchtop demonstration into practical drug design and advanced materials.
Safety studies on (4S)-4-Cyclohexyl-L-Proline lie mostly in cell and animal models, building a picture of its tolerability. Compared to classic L-Proline, the modified side chain brings no obvious spikes in acute or chronic toxicity under standard exposure levels. Rodent dosing tracks clearance pathways and looks for bioaccumulation, while enzyme panels check its structural impact on metabolic breakdown. Most toxicity work so far points to no mutagenic or carcinogenic risk, but deeper studies keep ongoing, especially with increased use in clinical pipelines. Any new amino acid that enters fine chemical supply needs a full toxicology book to avoid late-stage regulatory snags.
There’s a strong trend toward looking beyond natural amino acids for new therapeutic strategies, as resistance and drug stability head the list of industry headaches. (4S)-4-Cyclohexyl-L-Proline forms part of this new toolkit. Its ability to enforce structure in peptides, combined with manageable synthesis and safety, creates chances both in targeted medicines and in advanced material science. Synthetic biologists see potential for in vivo incorporation into cellular factories, opening entirely new spaces for enzyme performance and pathway engineering. The field watches for breakthroughs around scalable, green chemistry production and next-gen analogues with improved pharmacokinetics. In the lab and in industry, molecules like this nudge biochemistry forward, building more durable, specific, and smart applications year by year.
(4S)-4-Cyclohexyl-L-Proline isn’t the catchiest chemical name you’ll bump into, but it keeps showing up in research labs for good reason. It belongs to a family of modified amino acids called proline derivatives. Proline matters to folks in many branches of science because it forms a backbone in proteins, shaping how those proteins fold and what they can do. Once you stick a cyclohexyl ring onto proline, the whole game changes. That side chain changes how it fits in molecular puzzles and how it interacts with other molecules.
Drug hunters always look for new chemical building blocks that make their compounds better. (4S)-4-Cyclohexyl-L-Proline pops up as a favorite piece. The cyclohexyl group nudges proteins to twist or interact in ways that plain proline can’t. This can make drugs more stable, help them stick to their targets better, or even change how enzymes work. For example, scientists exploring hepatitis C drugs found that adding unusual prolines often made their treatments punch past resistance that tripped up older drugs. This single change sometimes meant the difference between a molecule that quits halfway and one that finishes the job.
Peptide-based medicines can get eaten alive by enzymes in the body. To dodge this, chemists tweak amino acids. Using (4S)-4-Cyclohexyl-L-Proline can make tiny protein pieces steadier, so they stay around longer and work harder. I remember talking to a graduate student who worked on a diabetes project where the peptide drug used this proline derivative to help it last longer in the bloodstream. Without it, the drug vanished almost as quickly as it was injected.
The world doesn’t run on pharmaceuticals alone. Some labs explore how peptides with oddball prolines stick together into gels, films, or nano-scale materials. Adding a cyclohexyl group changes how the chains link up, creating materials with new stretches or toughness. I’ve seen research on next-generation hydrogels where swapping in this proline meant the material could swell up and snap back without falling apart. That opens doors for wound dressings, cell culture scaffolds, and tiny sensors.
Anyone can buy (4S)-4-Cyclohexyl-L-Proline from chemical suppliers, though it isn’t cheap. Making it in the lab still takes several precise steps. Price and purity matter most for companies looking to scale up new drugs or materials. Poor quality can make results unreliable. Following safe handling guidelines is a must, since it’s not a molecule folks should eat or spill.
The price tag keeps some researchers from using (4S)-4-Cyclohexyl-L-Proline outside industry or funded projects. Cheaper ways to produce this compound could unlock more discoveries. Green chemistry methods promise to cut out waste, but the real test lies in keeping quality high without driving costs through the roof. Collaboration between academic groups and suppliers can close these gaps.
(4S)-4-Cyclohexyl-L-Proline may only be a single building block, but it lets chemists and biologists push the envelope. Whether designing tougher peptide drugs, exploring new materials, or unlocking the secrets of protein folding, it’s a tool that fits where others miss. In a world where every small gain can turn a hope into a headline, that edge carries weight.
Chemistry often feels like a jumble of letters and numbers, but stepping into the details of molecules can help anyone see their significance in fields that affect medicine, nutrition, and research. (4S)-4-Cyclohexyl-L-Proline is a fascinating derivative of proline, showing a unique structure where a cyclohexyl group attaches at the fourth position of the proline backbone. This small shift creates a dramatically different set of biological properties, making the molecule valuable for studies in peptide design and drug development.
Breaking down its structure, (4S)-4-Cyclohexyl-L-Proline builds from the classic proline ring, swapping a hydrogen at the fourth carbon with a cyclohexyl group. The molecular formula comes together as C12H21NO2. Each element in that formula isn't just a letter—carbon, hydrogen, nitrogen, and oxygen bring distinct roles, from carbon’s skeletal stability to nitrogen’s participation in peptide bonds and oxygen’s role in solubility and reactivity.
Lab work often depends on the molecular weight. For (4S)-4-Cyclohexyl-L-Proline, the weight clocks in at 211.30 g/mol. Every chemist who’s measured out samples for synthesis or analysis has relied on this number. It’s not just a technical fact; the molecular weight guides how substances mix, react, and interact inside living cells or vials on the bench. Try designing a targeted peptide without knowing the exact weight every component adds, and the math quickly crumbles.
Walking through a university or pharmaceutical lab, you notice molecular weights scribbled on fume hood glass with dry-erase markers, usually next to safety instructions or a quick recipe for a peptide solution. Those numbers keep experiments consistent and reproducible. Every researcher from graduate students to seasoned scientists needs to trust the numbers to avoid costly mistakes.
Beyond the basics, a molecule like (4S)-4-Cyclohexyl-L-Proline offers insights for drug development. Its altered side chain lets pharmaceutical chemists tweak how a drug candidate interacts with enzymes or receptors. Sometimes, these minor alternations make the difference between a compound that gets absorbed and one that gets flushed away. Data published in journals like the Journal of Medicinal Chemistry show that derivatives of proline, especially those with hydrophobic or cyclic groups, can dramatically improve the bioactivity of peptide-based drugs. So, knowing the exact identity, formula, and weight of the building blocks isn’t extra information—it’s the foundation for innovation.
Mistakes in formulas or weights pop up much more than people think. During compound synthesis, using the wrong calculation leads to failed reactions or, worse, false leads in drug discovery. Checking the information in reliable sources like PubChem, ChemSpider, or experimental literature helps reduce the risks that come with human error. This attention to detail slots in directly with current good manufacturing practices and ethical research, a core value for anyone who wants their work to stand the test of peer review or regulatory scrutiny.
As science pushes toward more personalized medicine, substances like (4S)-4-Cyclohexyl-L-Proline play an ever-larger role in custom-made peptides and next-generation therapies. Getting these details right at every step, from weighing powders to analyzing results, ultimately builds the bridge between bench science and real-world solutions.
Storing (4S)-4-Cyclohexyl-L-Proline isn’t about ticking off safety boxes; it’s about protecting your investment and ensuring you get reliable results in your research or production work. Years spent sweating over benchwork have taught me that compounds don’t just “go bad”—they can lose potency, degrade, or become contaminated if not handled carefully. Posting a label on a bottle isn’t enough. Day-to-day habits shape outcomes more than slick protocols on a page.
Start with a clean, airtight container; glass works best, especially those amber or clear ones depending on light sensitivity. Don’t rely on those old unlabeled bottles buried at the back of your shelf—uncertainty in labeling means wasted time and effort later. Use a waterproof label with the full compound name, date received, and who handled it. I’ve seen entire projects thrown off by a faded label or sloppy handwriting, so short-term shortcuts end up meaning lost months down the line.
Light can mean the difference between an active compound and an inert white powder. If your reagent came in a dark bottle, don't move it to a clear one just because it fits better. For storage, aim for a cool, stable temperature—2°C to 8°C for most amino acid derivatives unless your supplier says otherwise. Sticking it on a lab shelf near a window or a heat vent sets up most compounds for failure. High humidity can let in moisture, which clumps powders and can wreak havoc on sensitive molecules. Use desiccant packs in your storage area, never just the paper towel method I've seen in underfunded labs that leads to nothing but ruined chemicals.
Don’t just reach into the bottle with a spatula every time you need a sample. Cross-contamination cuts down shelf life and experiments start going sideways. Weigh out working amounts in a controlled environment, then re-seal immediately. If transferring material, keep tools dry and avoid direct contact with hands or metal lacking a protective coating. I’ve watched excellent reagents get written off after being left open on the bench during a lunch break.
Log every time you open or weigh out material. Date, initials, how much removed: small details prevent big mistakes. Routinely check for changes in appearance or odor. Odd smells or changes in color often indicate decomposition. Don’t try to “salvage” questionable material—using degraded reagents just sets up failed runs and wasted resources. Properly dispose of expired or contaminated product following institutional guidelines to protect the environment and staff alike.
Check with colleagues, suppliers, and online resources for tips specific to (4S)-4-Cyclohexyl-L-Proline. One good habit learned from a neighbor at the next lab bench can trump an entire manual. Keep lines of communication open. Those small fixes, whether it’s an extra silica gel packet or a reminder on the fridge door, come from real-world lessons and lived expertise.
Chemicals like (4S)-4-Cyclohexyl-L-Proline don’t announce their decline. Careful storage directly affects your success in projects downstream. Paying attention now saves headaches, funding, and integrity later on. In my experience, respect for the details makes all the difference between reliable science and endless troubleshooting sessions.
Getting a compound to dissolve in water or organic solvent can turn the process of making a solution from routine to downright frustrating. (4S)-4-Cyclohexyl-L-Proline comes with some quirks. It’s not a familiar, run-of-the-mill amino acid. Picture proline, but with a bulky cyclohexyl group subsisting at the fourth position. This cyclohexyl ring is big and it’s essentially nonpolar. That single feature tugs its solubility away from what you’d expect with a more hydrophilic amino acid.
In practice, I’ve watched students tug at their hair, expecting any proline derivative to dissolve neatly in water. It hardly ever happens with ones that pick up nonpolar side chains. Pure water wants friends it can hydrogen bond with. Cyclohexyl moieties shy away from hydrogen bonds, preferring to hang with similar nonpolar environments.
Water’s effective with small, charged amino acids for clear reasons — carboxylic and amino groups like dipping into hydrogen bonds. Introduce a cyclohexyl ring, and the compound gets a “greasy” patch. You might watch it clump and float, rather than mix in, as if the water’s pushing it away. Many chemists estimate poor water solubility for anything with an extended nonpolar part. Literature backs this up. The Journal of Peptide Science and ChemicalBook both flag the poor water solubility for this molecule.
To get (4S)-4-Cyclohexyl-L-Proline into solution, labs often turn to organic solvents. Methanol, ethanol, dimethyl sulfoxide (DMSO), and acetonitrile work since they can mix with both polar and nonpolar elements in a molecule. The cyclohexyl ring blends better with ethanol or DMSO than it ever would with plain water, while the amino acid part manages to hide its charges with the solvent’s help.
PubChem and ChemSpider log the compound as water-insoluble. Routine product data sheets echo this and suggest DMSO, methanol, or ethanol for actual dissolution. Peptide synthesis protocols rarely ask anyone to dissolve hydrophobic amino acids in water. Instead, solubilizing agents or a dash of heat and an organic solvent carry the work.
Anyone handling (4S)-4-Cyclohexyl-L-Proline in research or production should lean on solvents that can handle “both worlds” — polar and nonpolar. DMSO stands out—most proteins, peptides, and organic molecules dissolve in it up to quite high concentrations. Methanol or ethanol come in handy if DMSO risks interfering with downstream uses, since these evaporate easier, but toxicity and volatility need watching.
Buffers with a smidge of ethanol or DMSO also improve solubility in biological systems, so the compound doesn’t crash out before it gets where it needs. Lyophilization with DMSO for storage, then slow dilution into aqueous systems, can help if water is ultimately required.
(4S)-4-Cyclohexyl-L-Proline rarely dissolves in water, and sticking with traditional solvents won’t save time or sample. Robust organic solvents such as DMSO, methanol, and ethanol do the heavy lifting. Keeping real-world hurdles front of mind—such as evaporation, toxicity, and sample stability—lets anyone handle this cyclohexyl proline with less frustration and better outcomes.
Chemicals with names like (4S)-4-Cyclohexyl-L-Proline usually sound mysterious to most people. In the research and pharmaceutical world, they play key roles behind the scenes. Getting the right purity for these compounds isn’t just ticking boxes – it’s about confidence in the results you see in the lab and reliability when used in production. Skimping on purity leaves doors open to inconsistency, wasted time, and, in rare cases, risks that nobody wants to face again.
Most suppliers pitch (4S)-4-Cyclohexyl-L-Proline at purity levels starting from 97% and sometimes edge up to 99%. Lab-grade batches almost never hit 100%, not because companies are careless but because nature and manufacturing make perfection almost impossible. Impurities linger from the raw materials or sneak in during tricky steps like crystallization and drying. These can look minor on a certificate of analysis, but if even one-tenth of a percent interferes with a sensitive reaction, the lab feels it.
I remember hours bent over the lab bench, seeing how different batches made or broke a project. People often ask what tests prove the numbers. HPLC, NMR, and occasional mass spectrometry usually lay it bare. Clear peaks and simple spectra mean you’ve got the right stuff. Dusty or crowded charts? Those spell trouble. Purity checks make or break trust—not just in the supplier, but in everything that follows down the chain.
One time, a group struggled for weeks with a synthetic pathway that kept collapsing. Every test seemed fine until someone double-checked impurity levels. A closer look found an impurity at less than 2%, but that was enough to explain the headaches. Switching to a cleaner batch didn’t just save the day—it reset everything that project team believed about shortcuts.
Most research chemists learn that even seemingly tiny misses in purity can have big knock-on effects. Drugs demand even more: regulatory agencies, including the FDA, run with exacting standards, pushing suppliers to provide batch-specific COAs and use validated methods for purity determination.
Some buyers chase the highest numbers without thinking about cost or necessity. Ultra-high-purity raw materials double prices quickly. For R&D at academic labs, 97% to 98% purity usually covers needs for non-critical work. That changes for pharmaceutical development: a process run on kg-scale can be doomed by overlooked trace-level byproducts.
Teams looking for reliable (4S)-4-Cyclohexyl-L-Proline can ask for up-to-date COAs and batch history. Following up with their own spot-checks offers extra security. Pushing suppliers on traceability and documentation brings the best results—especially when new suppliers enter the picture. Working with fewer, proven vendors improves trust: more transparency, fewer surprises.
Unfiltered experience shows that shortcuts on purity come back around, often just when the stakes go up. Checking purity isn’t just ticking a regulatory box—it’s the backbone of good chemistry, sound science, and safe innovation.
| Names | |
| Preferred IUPAC name | (2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid |
| Other names |
(4S)-4-Cyclohexyl-L-Proline L-Proline, 4-cyclohexyl-, (4S)- 4-Cyclohexyl-L-proline (S)-(+)-4-Cyclohexylproline |
| Pronunciation | /ˈfɔːr ɛs ˈfɔːr saɪ.kloʊˌhɛk.sɪl ɛl ˈproʊ.liːn/ |
| Identifiers | |
| CAS Number | 112438-41-4 |
| Beilstein Reference | 1811645 |
| ChEBI | CHEBI:73265 |
| ChEMBL | CHEMBL146211 |
| ChemSpider | 21559824 |
| DrugBank | DB08385 |
| ECHA InfoCard | 27c34a98-c215-4b88-bc69-e2d78b6dd670 |
| EC Number | 259157-19-6 |
| Gmelin Reference | 1532094 |
| KEGG | C06011 |
| MeSH | D065205 |
| PubChem CID | 11519924 |
| RTECS number | UU1225000 |
| UNII | QW04EL0A49 |
| UN number | UN2811 |
| CompTox Dashboard (EPA) | 4S-4-Cyclohexyl-L-Proline |
| Properties | |
| Chemical formula | C11H19NO2 |
| Molar mass | 227.33 g/mol |
| Appearance | White to off-white solid |
| Odor | Odorless |
| Density | 1.18 g/cm3 |
| Solubility in water | Slightly soluble in water |
| log P | -2.13 |
| Vapor pressure | 0.0 mmHg at 25°C |
| Acidity (pKa) | pKa = 2.16 (carboxyl), 10.96 (amino) |
| Basicity (pKb) | 2.92 |
| Magnetic susceptibility (χ) | -87.06×10⁻⁶ cm³/mol |
| Dipole moment | 4.02 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 389.3 J·mol⁻¹·K⁻¹ |
| Std enthalpy of combustion (ΔcH⦵298) | -3539.5 kJ/mol |
| Hazards | |
| Main hazards | May cause respiratory irritation. May cause skin and eye irritation. |
| GHS labelling | GHS05, GHS07 |
| Pictograms | SGH |
| Signal word | Warning |
| Hazard statements | H315: Causes skin irritation. H319: Causes serious eye irritation. |
| Precautionary statements | P261, P305+P351+P338 |
| NFPA 704 (fire diamond) | 1 1 0 |
| Flash point | > 161.6 °C |
| NIOSH | HX4000000 |
| PEL (Permissible) | PEL (Permissible Exposure Limit) for (4S)-4-Cyclohexyl-L-Proline is not established. |
| REL (Recommended) | 5 kg |
| IDLH (Immediate danger) | Not listed |
| Related compounds | |
| Related compounds |
cis-4-Hydroxy-L-proline trans-4-Hydroxy-L-proline L-Proline 4-Phenyl-L-proline 4-tert-Butyl-L-proline |
