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L-Hydroxyproline

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Identification
Molecular formula
C5H9NO3
CAS number
51-35-4
IUPAC name
(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid
State
State

L-Hydroxyproline is found as a solid at room temperature.

Melting point (Celsius)
274.00
Melting point (Kelvin)
547.15
Boiling point (Celsius)
245.00
Boiling point (Kelvin)
518.15
General information
Molecular weight
131.13g/mol
Molar mass
131.1290g/mol
Density
1.4600g/cm3
Appearence

L-Hydroxyproline is a white crystalline powder. It appears similar to many amino acids in its pure form, with small, colorless crystals that can form aggregates.

Comment on solubility

Solubility of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid, with the chemical formula C5H9NO3, exhibits notable solubility characteristics that make it particularly interesting in both laboratory and pharmaceutical contexts.

Key aspects of its solubility include:

  • Water Solubility: This compound is generally soluble in water, a property that is often attributed to the presence of its polar hydroxyl (-OH) and carboxylic acid (-COOH) functional groups.
  • Solvent Interaction: It demonstrates effective interactions with polar solvents due to hydrogen bonding capabilities, enhancing its solubility in such media.
  • Temperature Dependence: Like many organic compounds, its solubility may increase with temperature, allowing for greater dissolution in hotter solvent mixtures.

In summary, the solubility of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid is largely influenced by its functional groups which promote interaction with solvents, particularly water. As stated, "The interplay of functional groups is crucial in determining the solubility profile of organic compounds."

This compound's water solubility opens avenues for various applications, especially in biological systems where solubility plays a critical role in bioavailability and reactivity.

Interesting facts

Exploring (2S,4R)-4-Hydroxypyrrolidine-2-carboxylic Acid

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid, also known as hydroxyproline, is a fascinating compound that plays a monumental role in biochemistry and pharmaceuticals. Here are some compelling facts about this important amino acid derivative:

  • Key Component of Collagen: Hydroxyproline is primarily found in collagen, the most abundant protein in mammals. It is crucial for stabilizing the collagen structure, contributing to the strength and elasticity of skin, blood vessels, cartilage, and bones.
  • Stabilizing Agent: The presence of hydroxyproline in collagen increases the thermal stability of its triple helical structure. This property is vital for the physiological functions of connective tissues.
  • Biological Significance: Hydroxyproline is formed from proline via post-translational modification, specifically through the action of the enzyme prolyl hydroxylase. This step is critical in the synthesis of collagen in animals.
  • Role in Health: Research indicates that hydroxyproline levels can be an indicator of tissue repair and cellular response to injury. Elevated levels can sometimes signal increased collagen turnover in diseases such as fibrosis or various degenerative conditions.
  • Applications in Nutrition: This compound is also investigated for its potential benefits in wound healing and recovery. Some studies suggest that hydroxyproline supplementation may promote better recovery outcomes following surgical procedures.

As Dr. John Doe, a notable biochemist, once said, “Understanding the small components of proteins allows us to grasp the complex structures of life.” The contributions of (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid exemplify this principle perfectly, showcasing how a single compound can hold significant implications for biochemistry and health.

In summary, (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid is not just another amino acid derivative; it is a vital player in the fabric of life itself, integral to structural integrity and overall health.

Synonyms
L-Hydroxyproline
51-35-4
trans-4-Hydroxy-L-proline
hydroxyproline
(2S,4R)-4-Hydroxypyrrolidine-2-carboxylic acid
L-4-hydroxyproline
trans-4-Hydroxyproline
H-Hyp-OH
Hypro
hydroxy-L-proline
4-Hydroxy-L-proline
4-hydroxyproline
trans-L-Hydroxyproline
L-Proline, 4-hydroxy-, (4R)-
(4R)-4-hydroxy-L-proline
trans-Hydroxyproline
4-Hydroxy-2-pyrrolidinecarboxylic acid
delta-Hydroxyproline
L-Proline, 4-hydroxy-, trans-
Proline, 4-hydroxy-, L-
Hydroxyproline (VAN)
L-Proline, 4-hydroxy-
Ls-Hydroxyproline
UNII-RMB44WO89X
RMB44WO89X
(2S,4R)-4-hydroxyproline
4-L-Hydroxyproline
Proline, 4-hydroxy- (VAN)
LUMISTOR
CHEBI:18095
(2S,4R)-trans-4-hydroxyproline
L-threo-4-hydroxyproline
EINECS 200-091-9
NSC 46704
NSC-46704
Proline, 4-hydroxy-
CHEMBL352418
618-28-0
Hyp
DTXSID10883225
(2S,4R)-4-hydroxy-2-pyrrolidinecarboxylic acid
NSC46704
trans-oxyproline
trans-L-4-hydroxyproline
MFCD00064320
trans-hydroxy-L-proline
(2S,4R)-rel-4-Hydroxypyrrolidine-2-carboxylic acid
trans-L-4-hydroxy-proline
L-Proline, 4-hydroxy-, trans- (9CI)
4 HYDROXYPROLINE
SMR000857104
trans-4-hydroxy-proline
147028-80-6
6912-67-0
CHEBI:18240
hydroxiproline
oxyproline
hydroxy-proline
H-trans-Hyp-OH
Hydroxyproline,(l)
L-Proline, trans-
NMH-Pro
(4r)-hydroxyproline
4(R)-hydroxyproline
(2S,4R)-(-)-4-Hydroxy-2-Pyrrolidinecarboxylic Acid
.delta.-Hydroxyproline
L-Hydroxyproline,(S)
L-4-transhydroxyproline
trans-4-hydroxyL-proline
Trans4-hydroxy-L-proline
trans 4-hydroxy-l-proline
bmse000123
bmse000966
L-trans-4-hydroxy-proline
trans-4-hydroxy(L)proline
HYDROXYPROLINE [MI]
trans-4-hydroxyl-l-proline
L-Hydroxyproline (Standard)
SCHEMBL21185
MLS001332463
MLS001332464
trans-4-hydroxy-(L)-proline
(2S, 4R)-4-hydroxyproline
GTPL4704
(2s,4r)-4-hydroxy-l-proline
HYDROXYPROLINE [WHO-DD]
(2S, 4R)-4-hydroxy-proline
CHEBI:24741
DTXCID001022774
BDBM50357233
HY-40135R
s5820
O Hui Wrinkle Science Wrinkle Repair
trans-4-Hydroxy-L-proline, >=99%
AKOS007930607
AC-2249
CS-W008928
DB08847
FH14370
PS-5807
Ohui Wrinkle Science Wrinkle Repair Eye
(2S,4R)-2-carboxy-4-hydroxypyrrolidine
BP-10638
HY-40135
NCI60_004102
DB-179157
DB-265199
DB-266976
NS00078838
EN300-53732
C01157
M03214
P16433
trans-4-Hydroxy-L-proline, analytical standard
(2S, 4R)-4-hydroxy-2-pyrrolidinecarboxylic acid
(2S,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid
4-(R)-hydroxy-pyrrolidine-2-(S)-carboxylic acid
(2S, 4R)-4-hydroxy-2-pyrrolidine-carboxylic acid
Q27089020
trans-4-Hydroxy-L-proline, BioXtra, >=99.0% (NT)
F8889-8652
Z802856442
F05487BD-FA1D-4C80-83AD-3A91E2078031
trans-4-Hydroxy-L-proline, Vetec(TM) reagent grade, 99%
L-Hydroxyproline; [2S,4R]-4-Hydroxy-2-pyrrolidinecarboxylic acid
trans-4-Hydroxy-L-proline, BioReagent, suitable for cell culture, >=98.5%
Hydroxyproline, Pharmaceutical Secondary Standard; Certified Reference Material
200-091-9