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Hydroxyproline: History, Properties, and Where the Research Is Headed

Amino Acids with a Backstory: How Hydroxyproline Made Its Mark

Few molecules grab a biochemist’s attention like hydroxyproline. People in labs have watched hydroxyproline help piece together our understanding of human tissues, especially collagen. Early researchers stumbled across it when they were breaking down gelatin in the early 1900s. Back then, most labs didn’t even realize animal tissue held a ‘mystery’ amino acid on top of proline itself. As scientists used better chemical methods and analyzed peptides, hydroxyproline started popping up over and over, almost every time collagen entered the conversation. That link wasn’t just a curiosity; hydroxyproline brought insight into scurvy and connective tissue disorders, making it a small detail carrying heavy meaning for medicine and nutrition.

The Everyday Look and Feel of Hydroxyproline

If you pour hydroxyproline out onto a glass, you’ll find a colorless or white crystalline powder. It dissolves in water at a decent rate, turning up as a slightly sweet, neutral-tasting solution. The compound stays solid at room temperature. The important metrics come down to its melting point, which rolls in above 200°C—meaning typical environmental swings won’t convert it to a liquid mess. Its structure—derived from proline by adding a hydroxyl group—offers that extra bite scientists look for when probing protein stability.

Breaking Down What Makes Hydroxyproline Tick: Technical and Labeling Points

Not all amino acids act the same, and hydroxyproline’s appeal rests on how precise its standards run. Purity usually hits certified grades for food or pharmaceutical use, often well beyond 98%. The labeling sticks with its IUPAC name, hydroxyproline, and sometimes its ‘3-’ or ‘4-’ variant, depending on where the hydroxyl group lands on the ring. Analytical labs use techniques like HPLC or titration to verify quality. Accurate labeling matters here because trace contaminant levels can throw off research and applications, particularly in clinical and nutrition studies.

How People Make Hydroxyproline: Inside the Modern Process

Manufacturers once relied on hydrolyzing animal collagen, including bones and skins, soaking them in acid baths and extracting the amino acids. This old-school approach needed skilled hands and lots of patience, plus it left huge piles of waste. Chemical synthesis came up as another option. Starting from proline and passing the molecule through a set of hydroxylation steps, chemists managed to streamline production and keep the environment cleaner. Enzymatic routes now draw attention, as they use microbial enzymes for more selective and energy-efficient processes. Watching this evolution from animal extraction to greener biotech approaches has shown just how much modern industry can adjust priorities given research pressure, consumer demand, and regulatory pressure around animal-derived products.

Chemical Tinkering and Reactions

The extra hydroxyl group sets hydroxyproline apart from its parent, proline. While proline brings a five-membered ring that locks down protein structure, hydroxyproline chips in by forming robust hydrogen bonds. Collagen, for example, depends on hydroxyproline to hold its triple-helix shape. Chemical modifications often target this hydroxyl group. For instance, it can undergo esterification or oxidation, steps found in certain biomedical and analytical applications. Interacting with other proteins, crosslinking chemicals, and gels, hydroxyproline keeps showing versatility in lab experiments from protein purification to matrix engineering.

Don’t Get Confused: Synonyms and Other Names

Even seasoned biochemists trip over the various names for hydroxyproline. You’ll see it listed as Hyp, trans-4-hydroxy-L-proline, and (2S,4R)-4-hydroxyproline on scientific packaging. Academic articles sometimes slip into shorter versions, or even call out the L- or D- forms. To keep lab work honest, people stick with the exact IUPAC naming when precision counts, but daily work often just uses ‘hydroxyproline’. Each synonym flags a slightly different variation, which becomes a headache when mixing up batches for sensitive experiments.

Staying Safe in a World of Standards

Like so many amino acids, hydroxyproline scores high for stability and low for health risk at common concentrations. That sounds comforting, but working with powdered chemicals still requires gloves and masks; inhaling dust or splashes poses real risks. Food and pharma grades ensure allergen and contaminant screenings, and Europe and North America enforce labeling so end-users know what sits in the tub or vial. Proper ventilation and spill management stop most problems before they start, separating high-quality lab work from amateur guesswork. Storage advice emphasizes sealing containers and keeping out moisture, a simple move that lengthens shelf life and keeps product performance reliable.

Hydroxyproline Hits the Lab, Field, and Factory

Dietary supplements carry hydroxyproline as a marker of collagen content, a stand-in for meat quality and a dashboard reading for gelatin production. Medical labs run hydroxyproline tests to assess bone turnover in osteoporosis or gauge collagen breakdown in liver disease. Cosmetic researchers scrutinize it for anti-aging skin treatments, thanks to its connection to skin structure and repair. Industrial manufacturers rely on hydroxyproline for synthesizing specialty biopolymers, hydrogels, and adhesives. Such crossover between fields means new applications seem always on the horizon, whether dealing with wound healing, tissue engineering, or even as a nitrogen source in plant metabolism studies. In agriculture, tracking hydroxyproline helps breeders select livestock with tough but tender connective tissue, while pet food developers monitor it for animal nutrition.

What’s New in Hydroxyproline Research?

Current R&D aims to deepen understanding of how hydroxyproline influences diseases tied to connective tissue, including certain heart problems and rare genetic syndromes. Biotech startups and pharma companies are pushing for ways to boost human collagen synthesis—finding that ramping up hydroxyproline content signals improved repair after injury or surgery. Researchers are developing enzyme systems to produce hydroxyproline more efficiently, trimming costs for medical-grade collagen. The push for animal-alternative sources builds momentum, with microbiologists tweaking bacteria and yeast to produce non-animal hydroxyproline for vegans and those with allergies. Scientists are searching for new derivatives, too, that could act as building blocks for novel drugs or therapeutic hydrogels in regenerative medicine.

Asking Hard Questions about Toxicity

So far, toxicology studies give hydroxyproline a strong safety profile, even when consumed in larger-than-dietary doses as part of supplements or functional foods. The biggest red flag emerges in cases of pre-existing kidney trouble. In rare instances, massive overconsumption may put stress on the body’s metabolic waste-removal systems. Rigorous, peer-reviewed tests in animals and cell cultures have yet to turn up convincing reasons to restrict normal hydroxyproline intake. Still, safety ends up as a moving target when new synthetic or fermented forms reach the market, so responsible manufacturers repeatedly check their products through updated trials and third-party oversight.

Where Next? Looking at Hydroxyproline’s Future

As medicine and manufacturing keep looking for better materials, hydroxyproline holds promise in areas like 3D cell culture scaffolds, next-generation wound dressings, and even environmentally friendly fabrics. Startups in regenerative therapy see value in enriching collagen-based implants with precisely engineered hydroxyproline content, lending tissues more toughness and flexibility. Scientific journals explore whether manipulating hydroxyproline pathways could treat chronic or genetic tissue problems. Food companies probe its value as a biomarker for spotting adulterated meats or assessing dietary protein quality. Pushing into a world looking for smarter, kinder, and more sustainable biomaterials, hydroxyproline stands ready for new rounds of research and debate—certainly not just an old-school amino acid, but a central character in the story of tissue science and nutrition.




What is Hydroxyproline used for?

Collagen's Greatest Supporter

Hydroxyproline gets a lot of attention in labs focused on health, nutrition, and biochemistry. Walk into any textbook on connective tissue and you'll find hydroxyproline popping up right in the middle of the section on collagen. Collagen holds our bodies together—the stuff makes up skin, bones, tendons, gums, and more. You can tug on your skin or flex a joint, and there’s collagen lending the strength and flexibility.

Hydroxyproline is a modified amino acid—one of the building blocks the body uses to make collagen. Without hydroxyproline, the collagen triple-helix won’t hold its shape. Think of it as the bracket in a bookshelf: it’s small, yet nothing stays upright without it. Hydroxyproline interacts tightly with water, drawing moisture and supporting that distinct firmness in healthy tissues.

Diagnostics and Medical Testing

Doctors often check levels of hydroxyproline, especially in urine, as a marker for collagen breakdown. High levels sometimes point to problems like bone disease or issues with connective tissues. Osteoporosis gets noticed more quickly when hydroxyproline starts spilling into urine tests. By keeping an eye on hydroxyproline, medical teams track the progress of healing after bone injuries, or monitor for unexpected bone loss.

The Role in Supplements

Nutritional science has paid close attention to collagen supplements in recent years. Hydroxyproline doesn’t just float around after taking a pill; it travels through the bloodstream and serves as evidence that collagen from food or pills actually gets absorbed. I’ve seen folks seek out supplements after surgeries or during recovery from injuries, hoping to aid their body’s natural repair jobs. Products listing hydroxyproline hint at a focus on genuine collagen content, not filler.

Multiple studies support that hydroxyproline levels shoot up in blood after taking gelatin or hydrolyzed collagen supplements. In practical terms, this increase means that some collagen breaks down, gets absorbed, and probably ends up where it’s needed. Anyone skeptical about the value of these supplements should glance at this measurable impact, though scientists still debate just how significant the results can be for skin or bone strength.

Food Industry and Beyond

The food industry uses hydroxyproline to check the quality of products labeled as containing collagen or gelatin. Authentic bone broths or gelatin desserts ought to contain a fair bit of hydroxyproline. If testing comes back low, someone probably cut corners. Food technologists depend on hydroxyproline testing to keep labels honest and chow down with confidence.

Looking Toward the Future

There’s still room for better tests and closer monitoring, especially for patients at risk of bone loss. Further research could spell out clearer connections between dietary collagen, hydroxyproline absorption, and lasting benefits for health. Anyone in recovery, athletics, or aging populations has a stake in how this research pans out—after all, strong bones and supple skin aren’t just aesthetic.

Some hope that tracking hydroxyproline will one day fine-tune decisions in medicine and nutrition, so people get truly personalized advice. Health pros and researchers should pay close attention as new techniques and standards develop.

Sources:
  • NIH: Hydroxyproline in Collagen and Connective Tissue
  • Journal of Clinical Pathology: Urinary Hydroxyproline and Bone Disease
  • Journal of Agricultural and Food Chemistry: Monitoring Collagen Content in Food

Is Hydroxyproline safe to take as a supplement?

Understanding Hydroxyproline and Its Uses

Hydroxyproline often comes up when people talk about building or repairing collagen. Sitting at the crossroads of nutrition and skin care, it’s a key amino acid that makes up a big part of the collagen chain in our bodies. People who look into joint health, bone strength, or even beauty supplements see hydroxyproline listed on ingredient labels. The appeal is simple—support the body’s natural collagen and, hopefully, keep things running smoother where it counts.

What the Science Says

Scientists have been studying hydroxyproline for decades, mostly to understand how our bodies recycle and repair collagen. Research shows that the body gets hydroxyproline mainly from collagen-rich foods or supplements like gelatin or hydrolyzed collagen. Some folks take hydroxyproline on its own, thinking it might help speed up recovery after injury or keep joints healthy.

One study published in the “Journal of Clinical Pathology” found that blood levels of hydroxyproline can reflect collagen breakdown. Another paper in the “Journal of Nutrition” explored how supplementing with hydroxyproline improves collagen production in animals, but research in humans looks a lot thinner. That gap matters: animal studies sometimes lead to big claims, but those claims don’t always stack up after scientists do the harder work in human trials.

Safety Considerations

People sometimes worry about supplement safety, and for good reason. Too many products promise miracle results without much oversight. Hydroxyproline, found in many collagen supplements, gets broken down into harmless by-products in healthy people. The U.S. Food and Drug Administration considers collagen and its amino acids generally recognized as safe (GRAS) when taken as directed. Most side effects show up when people take unnecessary megadoses, and these usually include mild things like stomach upset or loose stool.

For anyone with kidney issues, a word of caution is needed. The kidneys filter amino acids like hydroxyproline, and taking big doses could strain things in people who already have kidney disease. Doctors often tell folks with chronic kidney disease to limit certain amino acids, hydroxyproline included. There’s also no proven benefit to taking large amounts if you already have a balanced diet.

Quality and Oversight in the Supplement World

Supplement quality can be hit-or-miss. Not every company checks purity or labels things clearly. The industry relies a lot on self-policing. Some brands send their products to independent labs, and seeing a “third-party tested” logo helps. Avoiding products with unclear sourcing or fishy marketing lowers risk. It’s good to ask about origin—how was it made; is it from animal or synthetic sources; has it passed any safety checks?

Who Might Benefit or Need to Be Cautious

Most healthy adults eating a mixed diet that includes some meat, eggs, or dairy probably get enough hydroxyproline for regular collagen turnover. Athletes or older adults curious about joint pain sometimes try supplements, but results are mixed. If you’re thinking about it, talk things through with your primary care doctor, especially if you have kidney issues, take other medications, or have allergies to common supplement sources.

Looking Ahead: Smart Choices and Real Expectations

People want easy ways to feel stronger or look younger. A new amino pill can sound tempting. Hydroxyproline, by itself, offers a small piece of the puzzle. Focusing on whole-food sources, staying active, and getting enough rest support the same systems these supplements claim to help. If you still feel drawn to try hydroxyproline, choose high-quality products, avoid high doses, and pay attention to how your body reacts. Seeking guidance from a health professional always beats guessing when it comes to your health.

What are the benefits of Hydroxyproline for skin and joints?

What is Hydroxyproline?

Hydroxyproline comes straight from collagen, the protein that gives structure to our skin, bones, and cartilage. Aging or even stress can chip away at our collagen levels, leading to wrinkles and stiff joints. Hydroxyproline acts as a key building block, helping the body support skin and joint health. It’s found in many supplements, especially those aimed at promoting youthful skin and flexible joints.

Hydroxyproline and Skin Health

Skin relies on collagen to stay firm and elastic. Hydroxyproline helps collagen form stable structures, resisting sagging and reducing fine lines. A 2018 clinical study published in Journal of Cosmetic Dermatology found participants who consumed hydroxyproline-rich collagen peptides reported smoother skin and noticed less dryness. From personal experience, oral supplements that include hydroxyproline tend to bring about better moisture retention, especially in dry, cold months.

Besides hydration, hydroxyproline encourages the body to produce more of its own collagen. As someone who has spent most summers outdoors, I’ve seen sun damage add up—rough patches and dark spots come with the territory. After sticking with hydroxyproline supplements for a few months, I noticed my skin handled outdoor exposure better, with faster healing after sunburn or minor cuts. It’s not a miracle cure, but the improvement in texture and resilience feels worth mentioning.

Joint Support and Mobility

Healthy joints move without grinding or clicking. Collagen cushions and supports cartilage; hydroxyproline is what keeps this collagen structure strong. Joints that lose collagen begin to ache or make noise. Athletes and older adults often look for relief in supplements featuring hydroxyproline, as several trials show reduced pain and improved function. The International Journal of Medical Sciences published a randomized trial in 2017 showing collagen peptides with hydroxyproline reduced knee pain among active adults.

From trying these supplements personally after years of running and cycling, I noticed that morning stiffness eased up. Days of long walks or hikes didn’t end with the same level of discomfort. While lifestyle choices still matter—regular exercise and healthy weight help—adding hydroxyproline-rich collagen gave an extra buffer for recovery.

Safety and How to Benefit Most

Hydroxyproline from dietary collagen appears safe for most people. Supplements often use collagen from fish, chicken, or beef, so those with allergies or dietary restrictions should read labels carefully. While the science shows value, the biggest gains come with consistent use and realistic expectations. It’s not a quick fix; results tend to show up after two or three months.

For someone serious about supporting skin and joint health, foods rich in collagen—bone broth, gelatin, and slow-cooked meats—offer natural sources. Pairing hydroxyproline with vitamin C can encourage more collagen building in the body.

Looking Ahead

The real draw of hydroxyproline lies in its ability to nudge the body’s repair and renewal systems. Supplements are widely available, but quality varies across brands. Checking for third-party testing and clear ingredient labels can make a big difference. People with stubborn joint pain or chronic skin issues may get the most out of a combined strategy: proper nutrition, sun protection, gentle movement, and targeted supplementation. Hydroxyproline deserves a closer look for anyone invested in staying active and feeling comfortable in their own skin.

Are there any side effects of using Hydroxyproline?

Stepping Into Supplement Talk: Hydroxyproline in the Spotlight

Collagen and skin care have gone mainstream. Hydroxyproline, a building block for collagen, shows up more often on product labels and supplement shelves. With so many options out there, folks start to ask—will it do more harm than good? I’ve worked with patients who wanted better hair, nails, and joint comfort after tough workouts or aging. The urge to support the body inside and out is strong. Still, we shouldn’t jump into anything new without checking both perks and downsides.

Common Experiences: How Most People Respond

Hydroxyproline usually comes from animal collagen or gelatin, found in supplements or high-protein diets. Most bodies take it in, break it down into glycine and other amino acids, and move on with daily business. Most research points to safety in moderate amounts. Trials where folks added collagen peptides (rich in hydroxyproline) had very few negative reports. Some shared that they noticed mild stomach upset, bloating, or loose stool if they went hard on the doses—something that happens with other protein-rich supplements, too.

Real Stories: When Things Go Sideways

Not every gut likes a new protein. I’ve seen clients with sensitive stomachs react after trying supplements with hydroxyproline. Food allergies are rare, but folks allergic to beef, pork, or fish sometimes feel itchy or flush if their collagen comes from sources their body dislikes. Digestion matters as well—an overworked or inflamed digestive tract can make even simple nutrients tricky. A handful of reports mention rashes or headaches, but connecting these directly to hydroxyproline gets tough. Other ingredients, lifestyle factors, and underlying allergies could play a role.

Hidden Risks: Looking Deeper at Medical History

Issues can show up for people with certain health conditions. Those dealing with chronic kidney disease should tread lightly. Too much protein or amino acids—including hydroxyproline—can stress the kidneys, especially if they’re already weak. Some rare genetic issues, like hydroxyprolinemia, interfere with breaking down hydroxyproline, leading to buildup in urine but usually without major symptoms. Asking your doctor or dietitian about supplement plans is never wasted effort, especially for folks managing health problems.

Long-Term Safety: Do We Know Enough?

Plenty of studies focus on short-term use. Research on years-long supplementation just isn’t out there yet, which leaves a gray area. Most experts feel moderate collagen or hydroxyproline from food or evidence-backed supplements looks fine for healthy adults. Pregnancy, childhood, or chronic illness makes things murkier. Manufacturers don’t have to test every product thoroughly, so sticking with brands that list sources and pass third-party checks keeps things safer.

Building Habits That Really Help

Joints, skin, bones—they all rely on enough protein and micronutrients. Supplements can fill gaps, but nothing beats a solid diet of fresh food, regular exercise, decent sleep, and enough water. If something feels off after starting hydroxyproline—bad stomach, headaches, or skin changes—it’s smart to pause and talk to your doctor. Paying attention to small warning signs can keep a well-meaning habit from backfiring.

Simple Solutions: Keeping Things Safe

Stick with trusted brands, watch out for overdosing, and keep tabs on your body’s reaction. People with a history of kidney trouble or allergies must take extra care. For most, hydroxyproline won’t start trouble unless taken in huge amounts or mixed with low-quality ingredients. Paired with a balanced diet, it can play a useful role for those hoping for a boost—but nothing works in isolation. Ask questions, look for evidence, and treat the body with a little respect.

How should Hydroxyproline be taken for best results?

Why Hydroxyproline Draws Attention

Plenty of folks looking after their joints, skin, or overall recovery land on hydroxyproline as a way to help the body rebuild and repair collagen. For those unfamiliar, hydroxyproline comes straight out of the collagen that makes up skin, tendons, bones, and cartilage. Research from journals like The Journal of Clinical Investigation points out that hydroxyproline levels in the bloodstream serve as a marker for how much collagen you’re breaking down or producing, making it a molecule worth noticing if you want healthy connective tissue.

How to Take Hydroxyproline: The Nuts and Bolts

It's tempting to just take a supplement and hope for the best, but your body deserves better. Hydroxyproline isn’t like vitamin C or magnesium, which get absorbed relatively simply. Anyone who’s dealt with digestive issues knows absorption varies from person to person, so taking it on an empty stomach or right after a protein-rich meal makes a big difference. Protein helps drive up absorption rates, allowing hydroxyproline to reach the tissues that need repairing. Studies show that collagen peptides, including hydroxyproline, reach their highest blood concentration roughly two hours after ingestion. That’s why nutritionists often recommend taking it before or after exercise, when tissues are craving nutrients for rebuilding.

Safety and Dosing: What’s on the Table?

Hydroxyproline doesn’t have an official daily recommended amount, but most studies and supplement brands float between 1,000 mg to 3,000 mg a day. Realistically, more is not always better; the trick is in being steady with intake rather than shooting for a mega-dose. Too much can stress out the kidneys, especially for anyone with previous kidney troubles or protein metabolic disorders. For people with sensitivities, side effects sometimes include a mild stomach upset—so it helps to start slow and watch how your body reacts. Always consult a healthcare professional, particularly if you have health issues or take medication. The evidence shows no long-term risks for healthy users at recommended doses, but it pays to be cautious, as with any supplement.

Stacking It Right: Supporting Collagen as a Team Effort

Relying on hydroxyproline alone won’t transform skin or joints overnight. Vitamin C partners well with it, since your body uses vitamin C to actually build new collagen strands. Lack of vitamin C means hydroxyproline gets wasted, so adding a vitamin C-rich food or supplement at the same meal improves outcomes. My own experience echoes this; taking hydroxyproline with orange juice or alongside a meal with bell peppers gives better results than swallowing a pill with just water. Hydration plays a role, too. Collagen loves water. Combining hydration with collagen support speeds up repair after workouts or a tough week.

The Role of Food, Not Just Supplements

If you ask anyone from a family with soup–making grandparents, bone broth gets top marks for a reason. Bone broth and slow-cooked meats naturally deliver hydroxyproline, often paired with minerals and gelatin that the body uses to rebuild structures. For folks who dislike pills or powders, introducing these traditional foods into regular meals offers a tasty and effective route to better collagen support.

Seeking Reliable Products

Quality matters. Unregulated supplements have burned more than a few consumers due to poor sourcing or inaccurate dosing. It's smart to check for third-party tested brands or to buy from companies whose transparency is clear. Look for supplements that disclose amino acid contents per serving, not just marketing buzzwords. Trusted sources keep consumers much safer than anything promising miracles.

Bottom Line: Respect the Process

Hydroxyproline can bring real benefits for those looking to build up joints, repair skin, or bounce back after injury. Pair it with whole foods, keep an eye on dosing, and combine it with nutrients like vitamin C and water for the best shot at results. Listen to your body and stay consistent—your connective tissue rewards patience and steady support more than any quick fix.

Hydroxyproline
Names
Preferred IUPAC name (2S,4R)-4-hydroxyproline
Other names Hyp
L-Hydroxyproline
trans-4-Hydroxy-L-proline
3-Hydroxyproline
(Pro-OH)
Pronunciation /haɪˌdrɒksiˈprəʊliːn/
Identifiers
CAS Number 51-35-4
Beilstein Reference 1535448
ChEBI CHEBI:24743
ChEMBL CHEMBL12355
ChemSpider 5464
DrugBank DB00148
ECHA InfoCard 100.023.775
EC Number 3.5.4.3
Gmelin Reference 6073
KEGG C00148
MeSH D006861
PubChem CID 5810
RTECS number HY1575000
UNII 6DH1W9VH8Q
UN number 2811
CompTox Dashboard (EPA) DTXSID9020013
Properties
Chemical formula C5H9NO3
Molar mass 131.13 g/mol
Appearance White crystalline powder
Odor Odorless
Density 0.7 g/cm³
Solubility in water Soluble
log P -2.54
Vapor pressure Negligible
Acidity (pKa) 9.68
Basicity (pKb) 7.68
Magnetic susceptibility (χ) -63.0·10⁻⁶ cm³/mol
Refractive index (nD) 1.570
Dipole moment 7.27 D
Thermochemistry
Std molar entropy (S⦵298) 111.0 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) -1244.4 kJ/mol
Std enthalpy of combustion (ΔcH⦵298) -1239.6 kJ·mol⁻¹
Pharmacology
ATC code A16AA06
Hazards
Main hazards May cause respiratory irritation
GHS labelling GHS07, GHS08
Pictograms C(=O)N1CCCC1CO
Signal word Warning
Hazard statements May cause respiratory irritation.
Precautionary statements P261, P262, P264, P270, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P501
NFPA 704 (fire diamond) 1-0-0
Flash point Hydroxyproline flash point: 171.8°C
Explosive limits No explosive limits found.
LD50 (median dose) LD50: 5000 mg/kg (Rat, oral)
NIOSH NIOSH: NL
PEL (Permissible) Not established
REL (Recommended) 10-30 mg
IDLH (Immediate danger) No IDLH established.
Related compounds
Related compounds Proline
Hydroxylysine
Collagen
Pyrrolidine
Oxazolidine