L-PROLINE-(4-3H(N)) Chemical Properties

storage temp. 

2-8°C

form 

aqueous ethanol solution

InChI

InChI=1/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/s3

InChIKey

ONIBWKKTOPOVIA-UFLUHPNLNA-N

SMILES

N1CCC[C@H]1C(O)=O |&1:4,r|

Safety Information

Hazard Codes 

R

RIDADR 

UN 2910 7

WGK Germany 

3

L-PROLINE-(4-3H(N)) Usage And Synthesis

Application

1. Pharmaceutical Applications: Amino acid drugs. One of the raw materials for compound amino acid large-volume parenteral solutions. Used for malnutrition, protein deficiency, severe gastrointestinal diseases, and protein supplementation after burns and surgery. No obvious toxic side effects. 2. Improving Plant Cold Resistance: Proline (Pro) is a component of plant proteins and can exist widely in a free state in plants. Under stress conditions such as drought and salinity, many plants accumulate large amounts of proline. Besides acting as an osmotic regulator in plant cytoplasm, accumulated proline plays an important role in stabilizing the structure of biological macromolecules, reducing cell acidity, detoxifying ammonia, and regulating cellular redox potential as an energy reservoir. Under adverse conditions (drought, salinity, heat, cold, freezing), the proline content in plants increases significantly. The proline content in plants reflects their stress resistance to a certain extent; drought-resistant varieties often accumulate more proline. Therefore, measuring proline content can be used as a physiological indicator for drought-resistant breeding. In addition, due to its strong hydrophilicity, proline can stabilize protoplasmic colloids and metabolic processes within tissues, thus lowering the freezing point and preventing cell dehydration. Under low-temperature conditions, increased proline in plant tissues can improve cold resistance, and therefore can also be used as a physiological indicator for cold-resistant breeding.
3. In Vivo Functions
In vivo, proline is not only an ideal osmotic regulator, but also a protective substance for membranes and enzymes, as well as a free radical scavenger, thus protecting plant growth under osmotic stress. Proline also plays a role in regulating cytoplasmic osmotic balance regarding the accumulation of potassium ions, another important osmotic regulator in vacuoles.
4. Industrial Applications
In the synthetic industry, proline can participate in inducing asymmetric reactions and can be used as a catalyst for hydrogenation, polymerization, and aqueous reactions. When used as a catalyst for these reactions, it exhibits high activity and good stereospecificity.
5. Other Applications
5.1 Proline and its derivatives are commonly used as symmetrical catalysts in organic reactions; the reduction of CBS and the catalytic aldol condensation reaction of proline are prominent examples.
5.2 During brewing, proteins rich in proline bound to polyphenols can produce haze (turbidity).
5.3 Raw material for the synthesis of cholesterol ester inhibitors.
5.4 Flavoring agent; when heated with sugar, it undergoes an amino-hydroxyl reaction to generate substances with special aromas.

Definition

ChEBI: L-proline is pyrrolidine in which the pro-S hydrogen at position 2 is substituted by a carboxylic acid group. L-Proline is the only one of the twenty DNA-encoded amino acids which has a secondary amino group alpha to the carboxyl group. It is an essential component of collagen and is important for proper functioning of joints and tendons. It also helps maintain and strengthen heart muscles. It has a role as a micronutrient, a nutraceutical, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite, a mouse metabolite and a member of compatible osmolytes. It is a glutamine family amino acid, a proteinogenic amino acid, a proline and a L-alpha-amino acid. It is a conjugate base of a L-prolinium. It is a conjugate acid of a L-prolinate. It is an enantiomer of a D-proline. It is a tautomer of a L-proline zwitterion.

L-PROLINE-(4-3H(N))(37159-97-0)Related Product Information

• L-Ornithine
• Valine
• Glycine