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Send EmailCitrulline, L-Citrulline, Stimol, 372-75-8
L-CITRULLINE – L-SİTRÜLİN
CAS Number: 372-75-8
EC Number (EINECS): 206-759-6
Molecular Formula: C₆H₁₃N₃O₃
Molecular Weight: 175.19 g/mol
Chemical Class: Amino acid (non-essential, conditionally essential)
SECTION 1: CHEMICAL IDENTITY AND DEFINITION
| Parameter | Information |
|---|---|
| Chemical Name (IUPAC) | (2S)-2-Amino-5-(carbamoylamino)pentanoic acid |
| Other Names | L-Citrulline, Citrulline, Watermelon Amino Acid, Stimol |
| Chemical Formula | C₆H₁₃N₃O₃ |
| Molecular Weight | 175.19 g/mol |
| CAS Number | 372-75-8 |
| EC Number (EINECS) | 206-759-6 |
| Chemical Class | Amino acid (non-essential, conditionally essential) |
| Appearance | White crystalline powder |
| Odor | Odorless |
| Taste | Slightly bitter |
| Physical State (20°C) | Solid (crystalline powder) |
| Optical Activity | L-form (natural, biologically active) |
SECTION 2: PHYSICAL PROPERTIES
| Property | Value |
|---|---|
| Appearance | White crystalline powder |
| Odor | Odorless |
| Taste | Slightly bitter |
| Molecular Weight | 175.19 g/mol |
| Melting Point | 210 – 214 °C (decomposes) |
| Density | ~1.5 g/cm³ |
| Solubility in Water (20°C) | Soluble (~200 g/L) |
| Solubility in Ethanol | Slightly soluble |
| pH (1% solution) | 5.5 – 7.0 |
| Specific Rotation [α]D²⁰ | +24.5° to +26.5° |
| pKa₁ (COOH) | 2.45 |
| pKa₂ (NH₃⁺) | 9.00 |
| pKa₃ (Guanidino) | 12.48 |
SECTION 3: CHEMICAL PROPERTIES
| Property | Information |
|---|---|
| Chemical Formula | C₆H₁₃N₃O₃ |
| Molecular Weight | 175.19 g/mol |
| Chemical Class | Amino acid (non-essential, conditionally essential) |
| Functional Groups | Amino (-NH₂), carboxyl (-COOH), ureido (-NH-CO-NH₂) |
| Structure | α-amino acid; ornithine derivative |
| SMILES | C(CC(C(=O)O)N)CNC(=O)N |
| InChI Key | RHGKLRLOHDJJDR-UHFFFAOYSA-N |
| Optical Activity | L-form (natural, biologically active) |
| Stability | Stable under normal storage conditions |
| Hygroscopicity | Low to medium |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
Chemical Structure:
NH₂
|
HOOC-CH-(CH₂)₃-NH-CO-NH₂
(L-Citrulline / 2-Amino-5-(carbamoylamino)pentanoic acid)
SECTION 4: BIOLOGICAL MECHANISM AND FUNCTION
| Parameter | Description |
|---|---|
| Primary Function | Nitric oxide (NO) precursor; urea cycle intermediate |
| Urea Cycle | Plays role in ammonia detoxification; intermediate between ornithine and arginine |
| Nitric Oxide Production | Serves as substrate for L-arginine → Nitric oxide conversion |
| Vasodilation | Dilates blood vessels through nitric oxide production; improves blood flow |
| Metabolism | Converted to arginine in kidneys; participates in urea cycle in liver |
| Energy Metabolism | Supports energy production during exercise; reduces muscle fatigue |
SECTION 5: HEALTH BENEFITS
| Benefit | Description |
|---|---|
| Improved Blood Flow | Dilates blood vessels through nitric oxide production; increases blood flow |
| Heart Health | Supports cardiovascular health; regulates blood pressure |
| Exercise Performance | Reduces muscle fatigue; increases endurance |
| Muscle Recovery | Accelerates post-exercise recovery |
| Detoxification | Helps remove ammonia from the body through urea cycle |
| Immune Support | Supports immune system functions |
| Erectile Function | Supports erectile function through improved blood flow |
| Muscle Mass | Supports protein synthesis; preserves muscle mass |
SECTION 6: NATURAL SOURCES
| Source | Content (mg/100g) |
|---|---|
| Watermelon | 200-300 |
| Cucumber | 10-20 |
| Pumpkin | 10-15 |
| Melon | 5-10 |
| Soybean | 50-100 |
| Nuts | 10-30 |
| Meat | 10-20 |
| Fish | 10-20 |
| Eggs | 5-10 |
| Dairy Products | 5-10 |
SECTION 7: DIETARY SUPPLEMENT APPLICATIONS
| Application | Function |
|---|---|
| Sports Nutrition | Exercise performance; muscle recovery; endurance |
| Cardiovascular Support | Blood flow; heart health; blood pressure |
| Pre-Workout Formulations | Vasodilation; pump effect |
| Post-Workout Formulations | Muscle recovery; ammonia clearance |
| Healthy Aging | Blood flow; heart health; muscle preservation |
| Sexual Health | Erectile function support |
SECTION 8: TYPICAL DOSAGE
| Application | Recommended Daily Dose |
|---|---|
| Sports Performance | 3-6 g/day |
| Cardiovascular Health | 2-5 g/day |
| Erectile Function | 3-6 g/day |
| Muscle Recovery | 2-5 g/day |
| General Health | 1-3 g/day |
SECTION 9: CITRULLINE MALATE COMPARISON
| Parameter | L-Citrulline | Citrulline Malate |
|---|---|---|
| Form | Pure amino acid | Citrulline + Malic acid (2:1) |
| Molecular Weight | 175.19 g/mol | ~345 g/mol |
| Absorption | Good | Good |
| Energy Support | Moderate | High (due to malate) |
| Fatigue Reduction | Good | Better |
| Cost | Lower | Higher |
| Use | General supplementation | Sports performance |
SECTION 10: QUALITY SPECIFICATIONS
| Parameter | Specification (USP / FCC) |
|---|---|
| Appearance | White crystalline powder |
| Identification | Positive (IR, HPLC) |
| Assay (on dried basis) | 98.0 – 101.0% |
| Specific Rotation [α]D²⁰ | +24.5° to +26.5° |
| Loss on Drying | ≤ 0.5% |
| Residue on Ignition | ≤ 0.1% |
| pH (1% solution) | 5.5 – 7.0 |
| Chlorides (Cl) | ≤ 0.02% |
| Sulfates (SO₄) | ≤ 0.02% |
| Heavy Metals (as Pb) | ≤ 10 ppm |
| Lead (Pb) | ≤ 2 ppm |
| Arsenic (As) | ≤ 3 ppm |
| Mercury (Hg) | ≤ 1 ppm |
| Cadmium (Cd) | ≤ 1 ppm |
| Ammonium (NH₄) | ≤ 0.1% |
| Other Amino Acids | ≤ 0.5% |
| Chiral Purity (HPLC) | ≥ 99.0% |
SECTION 11: MICROBIOLOGICAL SPECIFICATIONS
| Parameter | Specification |
|---|---|
| Total Aerobic Mesophilic Bacteria | ≤ 1,000 CFU/g |
| Yeast and Mold | ≤ 100 CFU/g |
| Salmonella spp. | Negative in 25g |
| Escherichia coli | Negative in 10g |
| Staphylococcus aureus | Negative in 1g |
| Pseudomonas aeruginosa | Negative in 1g |
SECTION 12: STORAGE AND SHELF LIFE
| Parameter | Information |
|---|---|
| Storage Conditions | Cool (15-25°C), dry, well-ventilated area |
| Container Requirements | Tightly closed, original packaging |
| Protect From | Moisture, strong oxidizing agents, strong acids, strong bases |
| Shelf Life | 24-48 months (unopened original packaging) |
SECTION 13: PACKAGING OPTIONS
| Packaging Type | Quantity | Material |
|---|---|---|
| Aluminum foil bag | 1-5 kg | Laminated aluminum |
| PE-lined kraft paper bag | 25 kg | Kraft paper + PE |
| Plastic pail | 20-25 kg | HDPE |
| Fiber drum | 25-50 kg | HDPE + PE |
| Big-Bag | 500-1000 kg | Polypropylene (with PE liner) |
SECTION 14: SAFETY AND HEALTH INFORMATION
GHS Classification (Bulk Powder)
| Hazard Class | Category |
|---|---|
| Not classified as hazardous | - |
Hazard Statements
| Code | Statement |
|---|---|
| None | Not classified as hazardous |
Precautionary Statements
| Code | Statement |
|---|---|
| P261 | Avoid breathing dust |
| P280 | Wear protective gloves/eye protection |
| P305+P351+P338 | IF IN EYES: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing |
SECTION 15: TOXICOLOGICAL INFORMATION
| Parameter | Value |
|---|---|
| Oral LD50 (Rat) | > 5,000 mg/kg |
| GRAS Status | Considered GRAS by FDA |
| Carcinogenicity | Not classified |
| Mutagenicity | Negative in standard tests |
| Reproductive Toxicity | No evidence of adverse effects |
| Side Effects | Mild gastrointestinal discomfort at high doses |
| Safety Profile | Excellent safety profile |
SECTION 16: FIRST AID MEASURES
| Exposure Route | Action |
|---|---|
| Inhalation | Move to fresh air. If respiratory irritation persists, seek medical attention. |
| Skin Contact | Wash with plenty of soap and water. |
| Eye Contact | Rinse immediately with plenty of water for at least 15 minutes. Seek medical attention. |
| Ingestion | Rinse mouth. Drink plenty of water. Seek medical attention. |
SECTION 17: REGULATORY STATUS
| Region / Authority | Status |
|---|---|
| European Union | Approved as food supplement |
| USA (FDA) | GRAS (Generally Recognized as Safe) |
| Turkey | Approved as food supplement |
| EFSA | Approved; safety assessment completed |
| JECFA | Approved |
SECTION 18: TRANSPORT INFORMATION
| Parameter | Information |
|---|---|
| UN Number | Not regulated (not dangerous goods) |
| Hazard Class | Not applicable |
| Packing Group | Not applicable |
| ADR/RID | Not regulated |
| IMDG Code | Not regulated |
| IATA (Air) | Not regulated |
| Marine Pollutant | No |
SECTION 19: FIRE-FIGHTING MEASURES
| Parameter | Information |
|---|---|
| Fire Hazard | Combustible organic solid |
| Suitable Extinguishing Media | Water spray (mist), CO₂, dry chemical powder |
| Specific Hazards | When heated, emits CO, CO₂, nitrogen oxides |
| Decomposition Products | CO, CO₂, NOx |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
SECTION 20: ACCIDENTAL SPILLAGE AND CLEANUP
| Parameter | Information |
|---|---|
| Personal Protection | Nitrile gloves, protective goggles, dust mask (N95) |
| Cleaning Methods | Collect mechanically (sweep or spatula) |
| Environmental Precautions | Prevent entry into drains, soil, and surface waters |
| Waste Disposal | According to local regulations; landfilling at licensed facilities |
SECTION 21: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| Turkish Names | L-Sitrülin, Sitrülin, Karpuz Amino Asidi |
| English Names | L-Citrulline, Citrulline, Watermelon Amino Acid |
| Chemical Names | (2S)-2-Amino-5-(carbamoylamino)pentanoic acid |
| Trade Names | Stimol®, L-Citrulline Malate |
| CAS Number | 372-75-8 |
| EC Number | 206-759-6 |
| INCI | Citrulline |
SECTION 22: SUMMARY AND CRITICAL NOTES
Product Summary
| Parameter | Value |
|---|---|
| Product | L-Citrulline |
| CAS Number | 372-75-8 |
| Appearance | White crystalline powder |
| Molecular Weight | 175.19 g/mol |
| Primary Function | Nitric oxide precursor, urea cycle intermediate |
| GRAS | Yes |
Critical Notes
-
Nitric Oxide Precursor: L-citrulline is converted to arginine in the body, increasing nitric oxide production; improves blood flow and vasodilation.
-
Urea Cycle: Plays a critical role in ammonia detoxification; reduces ammonia accumulation during exercise.
-
Natural Source: The richest natural source is watermelon; also known as "watermelon amino acid."
-
Sports Performance: Reduces muscle fatigue; increases endurance; accelerates post-exercise recovery.
-
Citrulline Malate: Combination with malic acid further enhances energy production.
-
Safety: Excellent safety profile; considered GRAS by FDA.
-
Bioavailability: Well-absorbed orally; effectively increases blood levels.
-
Dosage: Typical usage doses range from 3-6 grams per day.
-
Medical Applications: Used in treatment of certain genetic disorders, heart disease, and erectile dysfunction.
-
Regulatory Status: Approved as food supplement in USA, EU, and Turkey.
IMPORTANT DECLARATION: This Technical Data Sheet (TDS) is for informational purposes only and has been prepared based on available technical data. The user is responsible for determining the product's suitability for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, use, transport, waste, and regulatory compliance information, refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. This document does not replace medical advice.
