Chondroitin 4-sulfate

Base Information

• Chemical Name: Chondroitin 4-sulfate
• CAS No.: 9007-28-7
• Deprecated CAS: 42615-52-1,9045-60-7,49718-76-5
• Molecular Weight: 463.36854
• Hs Code.: 39139000
• European Community (EC) Number: 232-696-9,246-844-5,609-686-1,618-658-8
• DSSTox Substance ID: DTXSID601017238
• Wikidata: Q76001893
• NCI Thesaurus Code: C28141
• Metabolomics Workbench ID: 37319
• Mol file: 9007-28-7.mol

Synonyms:Blutal;Chondroitin 4 Sulfate;Chondroitin 4 Sulfate, Aluminum Salt;Chondroitin 4 Sulfate, Potassium Salt;Chondroitin 4-Sulfate;Chondroitin 4-Sulfate, Aluminum Salt;Chondroitin 4-Sulfate, Potassium Salt;Chondroitin 6 Sulfate;Chondroitin 6 Sulfate, Potassium Salt;Chondroitin 6 Sulfate, Sodium Salt;Chondroitin 6-Sulfate;Chondroitin 6-Sulfate, Potassium Salt;Chondroitin 6-Sulfate, Sodium Salt;Chondroitin Sulfate;Chondroitin Sulfate 4 Sulfate, Sodium Salt;Chondroitin Sulfate 4-Sulfate, Sodium Salt;Chondroitin Sulfate A;Chondroitin Sulfate C;Chondroitin Sulfate, Calcium Salt;Chondroitin Sulfate, Iron (+3) Salt;Chondroitin Sulfate, Iron Salt;Chondroitin Sulfate, Potassium Salt;Chondroitin Sulfate, Sodium;Chondroitin Sulfate, Sodium Salt;Chondroitin Sulfate, Zinc Salt;Chondroitin Sulfates;Chonsurid;Sodium Chondroitin Sulfate;Sulfate, Chondroitin;Sulfate, Sodium Chondroitin;Sulfates, Chondroitin;Translagen

Chemical Property of Chondroitin 4-sulfate

Chemical Property:

• Appearance/Colour: white or light yellow amorphous powder
• PSA: 287.45000
• LogP: -3.73080
• Storage Temp.: Store at RT.
• Water Solubility.: Soluble in water.
• XLogP3: -4.8
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 463.06319014
• Heavy Atom Count: 30
• Complexity: 739

Purity/Quality:

99%, ^*data from raw suppliers

ChondroitinSulfate,BovineTrachea ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1O)OS(=O)(=O)O)O)OC2C(C(C(C(O2)C(=O)O)O)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O)OS(=O)(=O)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O)O)O
• Recent ClinicalTrials: Effects of Glucosamine and Chondroitin Sulfate Supplementation in Addition to Resistance Exercise Training and Manual Therapy in Patients With Knee Osteoarthritis
• Recent EU Clinical Trials: Double-Blind, Randomised, Placebo-Controlled Clinical Trial to Evaluate the Efficacy and Safety of the Combination of Chondroitin Sulphate and Glucosamine Hydrochloride in Patients with Hand Osteoarthritis
• Chemical Composition and Structure: Chondroitin 4-sulfate (C4S) is a glycosaminoglycan (GAG) composed of repetitive disaccharide units, consisting of an amino sugar (GalNAc) and uronic acid (GlcA) with a sulfate group at the 4-position of the GalNAc residue. It is a major component of chondroitin sulfate proteoglycans (CSPGs) found in various tissues.
• Mechanism of Action: Chondroitin 4-sulfate is naturally present in the extracellular matrix of tissues such as cartilage, where it imparts gel-like properties and contributes to lubrication, water retention, and resistance.; In cancer development, C4S has been implicated in promoting cell viability, migration, and invasion, particularly in gliomas. It interacts with the PI3K/AKT signaling pathway to enhance epithelial-to-mesenchymal transition and expression of MMP-2, facilitating tumor progression. In the nervous system, C4S inhibits axonal regrowth/sprouting and synaptic rearrangements after spinal cord injury, mainly through its glycosaminoglycan chains.
• Uses in Medical Applications: Chondroitin 4-sulfate has potential therapeutic applications in glioma therapy, where it may serve as a target for intervention. Peptides binding to C4S have shown promise in neutralizing CSPG-mediated inhibition, suggesting a role in repairing nervous system injuries. Additionally, C4S influences collagen fibril functionality, affecting cell adhesion, migration, proliferation, differentiation, and growth factor stability in bone and cartilage tissues.
• Production Methods: Chondroitin 4-sulfate can be obtained from natural sources such as cartilage through extraction and purification processes. Industrial production methods may involve chemical modification or synthesis to produce specific forms or derivatives of chondroitin sulfate for various applications.

Technology Process of Chondroitin 4-sulfate

There total 1 articles about Chondroitin 4-sulfate 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:

methacrylated chondroitin sulfate → chondroitin sulfate (24967-93-9,9007-28-7)

Guidance literature:

With (2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone); sodium chloride; for 0.0833333h; UV-irradiation;

DOI:10.1039/c5ra15376j

Reference yield:

chondroitin sulfate (24967-93-9,9007-28-7) → D-Galactose (10257-28-0) + 2-deoxy-2-amino glucose (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) + D-glucuronic acid (6556-12-3,489-91-8,528-16-5,552-12-5,577-46-8,643-33-4,2240-07-5,6294-16-2,10133-02-5,18402-78-3,18968-14-4,21179-08-8,23018-83-9,33599-45-0,33599-46-1,46171-67-9,46171-69-1,46172-26-3,70021-34-0,71031-08-8,104195-06-4,106499-29-0,124817-72-7) + chondrosine (112464-83-2,140866-46-2,143521-24-8) + D-galactosamine (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8)

Guidance literature:

With trifluoroacetic acid; at 110 ℃; for 3h;

DOI:10.1016/j.ab.2014.07.021

Reference yield:

chondroitin sulfate (24967-93-9,9007-28-7) → C46H60N6O23 + C46H60N6O23 + C32H39N5O12 + C34H41N5O13 + C32H39N5O15S + C32H39N5O15S + C34H41N5O16S + C38H47N5O18 + C40H49N5O19 + C40H49N5O22S + C44H58N6O22

Guidance literature:

With trifluoroacetic acid; at 100 ℃; for 1h; Sealed tube;

DOI:10.1016/j.carres.2017.07.009

Downstream raw materials:

D-Galactose

2-deoxy-2-amino glucose

D-glucuronic acid

chondrosine

Refernces