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L-Hydroxyproline

CAS No.: 51-35-4
Formula: C5H9NO3
Molecular Weight: 131.13
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What is L-Hydroxyproline

**Introduction to 4-Hydroxy-L-Proline** 4-Hydroxy-L-proline (Hyp) is a modified amino acid derived from L-proline, featuring a hydroxyl group at the fourth carbon position. It is a key component of collagen and elastin, playing a vital role in stabilizing their triple-helix structures and ensuring tissue integrity. Found abundantly in connective tissues, Hyp contributes to skin elasticity, wound healing, and joint health. Beyond its biological significance, it is widely used in pharmaceuticals, cosmetics, and nutritional supplements for its collagen-boosting properties. Additionally, 4-hydroxy-L-proline serves as a chiral building block in organic synthesis and drug development. Its versatility makes it valuable in both biomedical research and industrial applications.

Preparation Process: 4-Hydroxy-L-proline can be prepared via the hydroxylation of L-proline using a suitable oxidizing agent. One common method involves treating L-proline with hydrogen peroxide (H₂O₂) in the presence of a metal catalyst, such as ferrous sulfate (FeSO₄), under mild acidic conditions. The reaction is typically carried out at room temperature or slightly elevated temperatures (30–50°C) for several hours. After completion, the mixture is neutralized, and the product is purified by recrystallization or chromatography. Alternatively, enzymatic hydroxylation using prolyl hydroxylase can also yield 4-hydroxy-L-proline with high specificity. The final product is characterized by NMR and HPLC.

Usage Scenarios: 4-Hydroxy-L-proline is a modified amino acid primarily used in biomedical research and pharmaceutical applications. It serves as a key component in collagen synthesis, playing a critical role in stabilizing collagen’s triple-helix structure. In medicine, it aids in wound healing and tissue repair. The compound is also utilized as a chiral building block in peptide synthesis and drug development. Additionally, it acts as a biomarker for collagen degradation in diseases like fibrosis and osteoarthritis. In biotechnology, 4-hydroxy-L-proline is employed in protein engineering to enhance stability and functionality. Its applications extend to cosmetics, where it supports skin hydration and anti-aging formulations.

L-Hydroxyproline Basic Info
Chemical Name L-Hydroxyproline
Synonyms TRANS-4-HYDROXY-L-PROLINE;HYDROXYPROLINE;(2S,4R)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;Hyp;4-Hydroxyproline;4-HYDROXY-L-PROLINE;H-HYP-OH;4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID;HYDROXY-L-PROLINE;4R-4-hydroxyproline
CAS No. 51-35-4
Molecular Formula C5H9NO3
Molecular Weight 131.13
PSA 69.56000
LogP -0.350 (est)
Safely Info
RTECS TW3586500
Hazard Class IRRITANT
Safety Statements 24/25-36/37/39-27-26
HS Code 29339990
WGK Germany 3
Packing Group -
RIDADR -
Risk Statements 36/37/38-22
Hazard Codes Xi,Xn
Caution Statement P261-P271-P280
Hazard Declaration H315-H319-H335
Symbol GHS07
Signal Word Warning
L-Hydroxyproline Price
United States: $50-$100
China: $30-$60
Russia: $40-$80
Germany: $60-$120
India: $20-$40
Japan: $70-$130
Brazil: $45-$90
South Korea: $35-$70
Philippines: No results
United Kingdom: $55-$110
France: $65-$130
Mexico: $25-$50
Canada: $50-$100
South Africa: $30-$60
Egypt: $35-$70
Turkey: $40-$80
Thailand: $30-$60
Indonesia: $25-$50
MSDS
MSDS
Name: L-Hydroxyproline Material Safety Data Sheet
Synonym: Trans-4-hydroxy-L-prolin
CAS: 51-35-4
Section 1 - Chemical Product   MSDS Name:L-Hydroxyproline Material Safety Data Sheet
Synonym:Trans-4-hydroxy-L-prolin

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
51-35-4 L-Hydroxyproline 100 % 200-091-9
Hazard Symbols: None Listed.
Risk Phrases: None Listed.

Section 3 - HAZARDS IDENTIFICATION
  EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
  Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
  General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
  General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Reduce airborne dust and prevent scattering by moistening with water. Clean up spills immediately, observing precautions in the Protective Equipment section.

Section 7 - HANDLING and STORAGE
  Handling:
Wash thoroughly after handling. Wash hands before eating. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
  Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 51-35-4: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES
 
Physical State: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 273 deg C (decomposes)
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Soluble in water.
Specific Gravity/Density: Not available.
Molecular Formula: C5H9NO3
Molecular Weight: 131.0679

Section 10 - STABILITY AND REACTIVITY
  Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
  RTECS#:
CAS# 51-35-4: TW3586500 LD50/LC50:
Not available.
Carcinogenicity:
L-Hydroxyproline - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION
 

Section 13 - DISPOSAL CONSIDERATIONS
  Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

Section 14 - TRANSPORT INFORMATION
 
IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

Section 15 - REGULATORY INFORMATION
 
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
WGK (Water Danger/Protection)
CAS# 51-35-4: 0
Canada
CAS# 51-35-4 is listed on Canada's DSL List.
CAS# 51-35-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 51-35-4 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A
SDS 1.0
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