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Proline

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Identification
Molecular formula
C5H9NO2
CAS number
147-85-3
IUPAC name
(2R)-pyrrolidine-2-carboxylic acid
State
State

At room temperature, Proline is a solid.

Melting point (Celsius)
220.00
Melting point (Kelvin)
493.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
115.13g/mol
Molar mass
115.1310g/mol
Density
1.3500g/cm3
Appearence

Proline is a white to off-white crystalline powder. It is odorless and has a slightly sweet taste.

Comment on solubility

Solubility of (2R)-pyrrolidine-2-carboxylic acid

(2R)-pyrrolidine-2-carboxylic acid, commonly referred to as proline, exhibits interesting solubility characteristics that make it significant in various chemical and biological applications. This compound is characterized as follows:

  • Solvent Interaction: Proline is readily soluble in water due to its polar carboxylic acid group, which enhances hydrogen bonding with water molecules.
  • Saturation Point: Its solubility increases at elevated temperatures, showcasing the typical behavior of many amino acids which dissolve better in warmer conditions.
  • Organic Solvents: While proline is highly soluble in polar solvents like methanol and ethanol, it exhibits poor solubility in non-polar organic solvents.

This solubility behavior is crucial, especially in biochemical contexts, where proline acts as a building block for proteins. As a result:

  • Biological Relevance: Its solubility allows it to participate effectively in enzymatic reactions and serve as a structural component in peptides.
  • Pharmaceutical Applications: The favorable solubility profile contributes to its utility in drug formulation and delivery systems.

In summary, the solubility of (2R)-pyrrolidine-2-carboxylic acid is influenced by its chemical structure, showcasing a distinct ability to dissolve in water and polar solvents while remaining insoluble in non-polar environments. This property underscores its importance across various scientific domains.

Interesting facts

Interesting Facts about (2R)-Pyrrolidine-2-carboxylic Acid

(2R)-Pyrrolidine-2-carboxylic acid, commonly known as proline, is a fascinating amino acid with unique properties and applications. Here are some interesting facts about this intriguing compound:

  • Cyclic Structure: Proline is notable for being a cyclic amino acid, as it has a five-membered ring structure formed by the connection of the amino group and the side chain. This ring plays a crucial role in protein folding and stability.
  • Protein Synthesis: As one of the 20 standard amino acids, proline is a building block of proteins and is frequently found in collagen, the most abundant protein in animals. Its unique structure allows for flexibility in the protein chain.
  • Role in Metabolism: Proline is involved in various metabolic pathways, including the synthesis of other amino acids and glucose, highlighting its importance in energy production and nutrition.
  • Biological Functions: It serves several biological roles, such as:
    • Helping to stabilize protein structures.
    • Acting as a precursor for the synthesis of certain hormones.
  • Medicinal Applications: Proline has been researched for its potential therapeutic use, including its effects on wound healing and its impact on conditions like neurodegenerative diseases.
  • Natural Occurrence: Found in numerous food sources, such as dairy products, meat, and some plant-based proteins, proline is vital for human health. Your body can also synthesize it, but dietary intake is crucial during periods of stress or injury.

To sum up, (2R)-pyrrolidine-2-carboxylic acid is more than just a simple amino acid; it is a compound with significant biological implications and a wide range of applications in both science and health. As part of the natural world, proline continues to be a subject of study for its diverse roles in life processes.

Synonyms
D-proline
344-25-2
(2R)-pyrrolidine-2-carboxylic acid
(R)-pyrrolidine-2-carboxylic acid
H-D-Pro-OH
D-Prolin
D-(+)-Proline
R-Proline
(R)-PROLINE
(R)-2-CARBOXYPYRROLIDINE
D-Pro
MFCD00064317
CHEBI:16313
EINECS 206-452-7
L01Q4LGZ5L
PROLINE, D-
1331908-17-8
(+)-(R)-PROLINE
DTXSID70883367
(2R)-pyrrolidin-1-ium-2-carboxylate
(2R)-pyrrolidine-2-carboxylate
d-2-pyrrolidinecarboxylic acid
H-Pros-OH
H-DPro-OH
(D)-proline
D-D-Pro-OH
starbld0002768
R)-2-Carboxypyrrolidine
UNII-L01Q4LGZ5L
NCIStruc1_001918
NCIStruc2_000132
SCHEMBL65555
CHEMBL80257
(R)-pyrrolidine-2-carboxylate
GTPL4676
DTXCID801022904
pyrrolidine-2-(R)-carboxylic acid
NCI97923
BDBM50357224
CCG-37784
s6016
AKOS015923206
D-Proline, ReagentPlus(R), >=99%
CS-W020557
DB02853
FP12674
NCGC00163339-01
NCGC00163339-02
AC-24083
HY-75087
TS-01590
D-Proline, Vetec(TM) reagent grade, 98%
NS00079485
P0994
EN300-60161
C00763
Q20035962
F1905-6974
Z933632584
D2735F99-0D23-48C4-B266-5C7A7DA319A4