Hydroxyproline

Base Information

• Chemical Name: Hydroxyproline
• CAS No.: 51-35-4
• Deprecated CAS: 138-46-5,17210-41-2,21105-75-9,24784-87-0,54733-36-7
• Molecular Formula: C5H9NO3
• Molecular Weight: 131.131
• Hs Code.: 29339990
• European Community (EC) Number: 200-091-9
• NSC Number: 46704
• UNII: RMB44WO89X
• DSSTox Substance ID: DTXSID10883225
• Nikkaji Number: J148.015D
• Wikipedia: Hydroxyproline
• Wikidata: Q12460151
• NCI Thesaurus Code: C76144
• RXCUI: 1311548
• Metabolomics Workbench ID: 73611
• ChEMBL ID: CHEMBL352418
• Mol file: 51-35-4.mol

Synonyms:N-methyl-trans-4-hydroxy-L-proline;NMH-Pro;trans-4-hydroxy-L-proline

Chemical Property of Hydroxyproline

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 273 °C (dec.)(lit.)
• Refractive Index: -75.5 ° (C=4, H2O)
• Boiling Point: 355.2 °C at 760 mmHg
• PKA: 1.82, 9.66(at 25℃)
• Flash Point: 168.6 °C
• PSA: 69.56000
• Density: 1.395 g/cm³
• LogP: -0.87740
• Storage Temp.: Store at RT.
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: 357.8 g/L (20 º C)
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 131.058243149
• Heavy Atom Count: 9
• Complexity: 125

Purity/Quality:

98.5% ^*data from raw suppliers

Trans-4-Hydroxy-L-Proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 24/25-36/37/39-27-26

MSDS Files:

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1C(CNC1C(=O)O)O
• Isomeric SMILES: C1[C@H](CN[C@@H]1C(=O)O)O
• Role in Collagen Synthesis: Hydroxyproline is a non-proteinogenic amino acid formed by the hydroxylation of proline. It plays a pivotal role in stabilizing the helical structure of collagen fibers, contributing to the structural integrity of connective tissues.
• Role in Disease Pathophysiology: Abnormalities in hydroxyproline metabolism are implicated in various diseases, including graft versus host disease, keloids, and vitiligo. Elevated levels of hydroxyproline are observed in these disorders, while decreased levels indicate poor wound healing.
• Significance in Liver Health: In liver fibrosis, hydroxyproline levels in tissues, serum, and urine serve as important indicators of fibrogenesis rates and disease progression. Its presence in the extracellular matrix (ECM) produced by hepatic stellate cells (HSCs) helps preserve liver cell integrity and function.
• Diagnostic Marker: Hydroxyproline estimation is utilized as a marker for diagnosing liver fibrosis and evaluating the anti-fibrotic effects of therapeutic interventions, including herbal and non-herbal medicines. It serves as a noninvasive biomarker for detecting severe fibrosis in chronic liver diseases.
• Biochemical Properties: Hydroxyproline, along with proline, constitutes about one-third of the amino acids in collagen synthesis.; The presence of 伪-amino groups in proline and hydroxyproline classifies them as 伪-amino acids. Hydroxyproline contributes to the stability of collagen proteins, essential for maintaining the structure and function of connective tissues.
• Enzymatic Hydroxylation: Hydroxyproline formation involves the catalytic hydroxylation of proline units by proline hydroxylase enzyme, utilizing ascorbic acid and oxygen as cofactors.

Technology Process of Hydroxyproline

There total 78 articles about Hydroxyproline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

→ 2-Benzyloxycarbonylamino-4-iodobutyric acid tert-butyl ester + 3-hydroxy-dl-proline (51-35-4,30724-02-8)

Guidance literature:

Reference yield: 48.0%

→ 3-hydroxy-dl-proline (51-35-4,30724-02-8)

Guidance literature:

Reference yield:

type I collagen from Bester sturgeon scales → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + L-serin (56-45-1,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + L-methionine (63-68-3,26062-47-5,58576-49-1) + L-lysine (56-87-1,3506-25-0) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + (5R)-5-hydroxy-L-lysine (504-91-6,1190-94-9,3506-26-1,6000-08-4,18899-29-1,18899-30-4,18899-31-5,52153-41-0,78088-29-6,28902-93-4) + L-arginine (74-79-3,25212-18-4) + S,S-cystine (349-46-2) + L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) + glycine (56-40-6,18875-39-3,25718-94-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) + 4R-4-hydroxyproline (51-35-4,30724-02-8) + L-histidine (71-00-1)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1016/j.foodchem.2014.03.075

upstream raw materials:

4(R)-hydroxyproline methyl ester

N-nitrosohydroxyproline

water

rac-Pro-OH

Downstream raw materials:

trans-4-hydroxy-1-[1-(toluene-4-sulfonyl)-L-prolyl]-L-proline

(R)-4-hydroxy-L-proline ethyl ester

Betonicine

(2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester

Refernces

• 1、 Dussauge, Solene,Moore, Charles,Snajdrova, Radka,Tassano, Erika,Vargas, Alexandra. "Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of l-Proline". supporting information. . Retrieved 2022/02/09.
• 2、 Cai, Weijing,Matthew, Susan,Chen, Qi-Yin,Paul, Valerie J.,Luesch, Hendrik. "Discovery of new A- and B-type laxaphycins with synergistic anticancer activity". . p. 2310 - 2319. Retrieved 2018/04/02.