Chondroitin 4-sulfate Chemical Properties

alpha 

D -28 to -32°

storage temp. 

2-8°C

solubility 

H₂O: 0.1 g/mL, slightly hazy, faintly yellow

Safety Information

WGK Germany 

3

F 

3-10

Toxicity

mouse,LD,oral,> 15gm/kg (15000mg/kg),Zhonghua Yixue Zazhi. Chinese Medical Journal. Vol. 58, Pg. 739, 1978.

MSDS

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Chondroitin 4-sulfate Usage And Synthesis

Description

Chondroitin 4-sulfate is a natural polymer of a disaccharide consisting of glucuronic acid and N-acetyl glucosamine which is sulfated either in the 4 or 6 position. It is a glycosaminoglycan considered as a symptomatic slow-acting drug for osteoarthritis (SYSADOA).

Chemical Properties

White or yellowish amorphous powder. Tasteless, odorless, hygroscopic, soluble in water, insoluble in organic solvents such as ethanol, acetone, ether, etc. Optical rotation -25°-+35°(c=1, H2O). There are characteristic absorption peaks at 725cm-1, 852cm-1 and 930cm-1 by infrared spectroscopy.

Uses

sodium chondroitin sulfate is described as a skin-conditioning agent, with possible anti-inflammatory properties. It can be found in such products as moisturizers and night skin care preparations. It is a derivative of natural mucopolysaccharides. Chondroitin 4-sulfate is an important structural component of cartilage and has been used as a dietary supplement to treat symptoms of joint discomfort.

Preparation

Chondroitin 4-sulfate can be extracted using the following method:
Weigh pig throat and nasal cartilage and put it into a solution of 20g/L (2%) sodium hydroxide, using a ratio of 5 times the weight of the cartilage.
Soak the cartilage in the sodium hydroxide solution and stir it intermittently.
Filter the solution when the leachate reaches 5.5°Be.
Extract the residue left on the filter by adding it to the sodium hydroxide solution again and combining the filtrate.
To remove impurities such as protein, hydrolyze the solution with crude trypsin at 50°C.
Filter the solution until it becomes clear.
Adjust the pH of the solution to 6.
Add ethanol to the solution until the alcohol content reaches 75%.
Let the solution stand overnight to allow precipitation.
Centrifuge the solution to separate the precipitate.
Wash the precipitate with absolute ethanol.
Dry the precipitate at 60°C to obtain crude chondroitin sulfate.

Definition

ChEBI: Chondroitin 4'-sulfate is a chondroitin sulfate in which the site of sulfation is carbon 4 of the N-acetylgalactosamine (GalNAc) sugar. It has a role as a mouse metabolite. It is a conjugate acid of a chondroitin 4'-sulfate anion.

References

1. Inhibition of Spiral Growth and Dissolution at the Brushite (010) Interface by Chondroitin 4-Sulfate. DOI:10.1021/acs.jpcb.8b11531
2. Evaluation of Chitosan-Based Films Containing Gelatin, Chondroitin 4-Sulfate and ZnO for Wound Healing. DOI:10.1007/s12010-017-2462-z
3. Expression and function of chondroitin 4‐sulfate and chondroitin 6‐sulfate in human glioma. DOI:10.1096/fj.201901621RRR
4. https://pubchem.ncbi.nlm.nih.gov/compound/70678540

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