| Name: | (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid |
| CAS Number: | 9007-28-7 |  3D/inchi
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| Other(deleted CASRN): | 11120-14-2 |
| ECHA EINECS - REACH Pre-Reg: | 232-696-9 |
| FDA UNII: | 6IC1M3OG5Z |
| XlogP3-AA: | -4.80 (est) |
| Molecular Weight: | 463.37037000 |
| Formula: | C13 H21 N O15 S |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:food additive, dietary supplements
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Flash Point: | 32.00 °F. TCC ( 0.00 °C. ) (est)
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| logP (o/w): | -2.177 (est) |
| Soluble in: |
| | water, 1e+006 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
intravenous-mouse LD50 2340 mg/kg
Kiso to Rinsho. Clinical Report. Vol. 6, Pg. 506, 1972.
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | food additive, dietary supplements |
| Recommendation for chondroitin sulfates usage levels up to: | | | not for fragrance use.
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| |
| Recommendation for chondroitin sulfates flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: View |
| ClinicalTrials.gov:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):9007-28-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :24766 |
| National Institute of Allergy and Infectious Diseases:Data |
| (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid |
| Chemidplus:0009007287 |
References:
| | (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 24766 |
| Pubchem (sid): | 134989364 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3- | acetamido-2,5-bis(oxidanyl)-6-sulfooxy-oxan-4-yl]oxy-3,4,5-tris(oxidanyl)oxane-2-carboxylic acid | | (2S,3S,4S,5R,6R)-6-[[(2R,3R,4R,5R,6R)-3- | acetamido-2,5-dihydroxy-6-sulfooxy-4-oxanyl]oxy]-3,4,5-trihydroxy-2-oxanecarboxylic acid | | (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3- | acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid | | (2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3- | acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylicacid | | | blutal | | | chondroitin sodium sulfate | | | chondroitin sulfate C | | | chondroitin sulfate from swine | | | chondroitin sulfuric acids | | | chondroitin sulphate | | | chondroitinsulfate C | | | chondroitinsulfurate | | | chonsurid | | | translagen |
Articles:
| PubMed:Polypyrrole coating on poly-(lactide/glycolide)-β-tricalcium phosphate screws enhances new bone formation in rabbits. |
| PubMed:Arresting progressive atherosclerosis by immunization with an anti-glycosaminoglycan monoclonal antibody in apolipoprotein E-deficient mice. |
| PubMed:Synthesis and detection of N-sulfonated oversulfated chondroitin sulfate in marketplace heparin. |
| PubMed:One-hour screening of adulterated heparin by simplified peroxide digestion and fast RPIP-LC-MS(2). |
| PubMed:The Anticancer Role of Capsaicin in Experimentallyinduced Lung Carcinogenesis. |
| PubMed:Characterization of acidic polysaccharides from the mollusks through acid hydrolysis. |
| PubMed:Isolation and characterization of monoclonal antibodies specific for chondroitin sulfate E. |
| PubMed:Chondroitin Lyase from a Marine Arthrobacter sp. MAT3885 for the Production of Chondroitin Sulfate Disaccharides. |
| PubMed:Stable nanoparticles prepared by heating electrostatic complexes of whey protein isolate-dextran conjugate and chondroitin sulfate. |
| PubMed:Chemical characteristics and antithrombotic effect of chondroitin sulfates from sturgeon skull and sturgeon backbone. |
| PubMed:Composition of glycosaminoglycans in elasmobranchs including several deep-sea sharks: identification of chondroitin/dermatan sulfate from the dried fins of Isurus oxyrinchus and Prionace glauca. |
| PubMed:Comparative efficacy of chloramphenicol loaded chondroitin sulfate and dextran sulfate nanoparticles to treat intracellular Salmonella infections. |
| PubMed:Production of chondroitin in metabolically engineered E. coli. |
| PubMed:Glycosaminoglycans analogs from marine invertebrates: structure, biological effects, and potential as new therapeutics. |
| PubMed:Chitin and chitosan composites for bone tissue regeneration. |
| PubMed:Defining the role of common variation in the genomic and biological architecture of adult human height. |
| PubMed:Fucosylated chondroitin sulfate from sea cucumber improves insulin sensitivity via activation of PI3K/PKB pathway. |
| PubMed:Optimisation extraction of chondroitin sulfate from fish bone by high intensity pulsed electric fields. |
| PubMed:Inhibitory effect of fucosylated chondroitin sulfate from the sea cucumber Acaudina molpadioides on adipogenesis is dependent on Wnt/β-catenin pathway. |
| PubMed:Effect of swimming on clinical functional parameters and serum biomarkers in healthy and osteoarthritic dogs. |
| PubMed:Fucosylated chondroitin sulfate from sea cucumber improves glucose metabolism and activates insulin signaling in the liver of insulin-resistant mice. |
| PubMed:Extraction of aggrecan-peptide from cartilage by tissue autolysis. |
| PubMed:Green synthesis of chondroitin sulfate-capped silver nanoparticles: characterization and surface modification. |
| PubMed:Deer bone extract suppresses articular cartilage damage induced by monosodium iodoacetate in osteoarthritic rats: an in vivo micro-computed tomography study. |
| PubMed:Increased expression of colonic Wnt9A through Sp1-mediated transcriptional effects involving arylsulfatase B, chondroitin 4-sulfate, and galectin-3. |
| PubMed:KfoE encodes a fructosyltransferase involved in capsular polysaccharide biosynthesis in Escherichia coli K4. |
| PubMed:Oversulfated chondroitin sulfate binds to chemokines and inhibits stromal cell-derived factor-1 mediated signaling in activated T cells. |
| PubMed:Biochemical and atomic force microscopic characterization of salmon nasal cartilage proteoglycan. |
| PubMed:Enzymatic and regulatory properties of the trehalose-6-phosphate synthase from the thermoacidophilic archaeon Thermoplasma acidophilum. |
| PubMed:Method to detect contaminants in heparin using radical depolymerization and liquid chromatography-mass spectrometry. |
| PubMed:Detection of keratan sulfate by immunological methods in commercial chondroitin sulfate preparations. |
| PubMed:Luminescence response of an osmium(II) complex to macromolecular polyanions for the detection of heparin and chondroitin sulfate in biomedical preparations. |
| PubMed:Melamine nanosensing with chondroitin sulfate-reduced gold nanoparticles. |
| PubMed:Fucosylated chondroitin sulfate from sea cucumber in combination with rosiglitazone improved glucose metabolism in the liver of the insulin-resistant mice. |
| PubMed:Homogalacturonans from preinfused green tea: structural characterization and anticomplementary activity of their sulfated derivatives. |
| PubMed:Fucosylated chondroitin sulfate from Acaudina molpadioides improves hyperglycemia via activation of PKB/GLUT4 signaling in skeletal muscle of insulin resistant mice. |
| PubMed:[Determination of chondroitin sulfate in food supplements by capillary zone electrophoresis]. |
| PubMed:Characterization of currently marketed heparin products: key tests for LMWH quality assurance. |
| PubMed:High-throughput differentiation of heparin from other glycosaminoglycans by pyrolysis mass spectrometry. |
| PubMed:Ex vivo porcine model to measure pH dependence of chemical exchange saturation transfer effect of glycosaminoglycan in the intervertebral disc. |
| PubMed:Transcriptional engineering of Escherichia coli K4 for fructosylated chondroitin production. |
| PubMed:ROS-major mediators of extracellular matrix remodeling during tumor progression. |
| PubMed:Dietary interventions for atopic disorders. |
| PubMed:Depolymerization of fucosylated chondroitin sulfate from sea cucumber, Pearsonothuria graeffei, via 60Co irradiation. |
| PubMed:Chondroitin sulfate, hyaluronic acid and chitin/chitosan production using marine waste sources: characteristics, applications and eco-friendly processes: a review. |
| PubMed:[Microbial production of chondroitin sulfate: a review]. |
| PubMed:Mass preparation of oligosaccharides by the hydrolysis of chondroitin sulfate polysaccharides with a subcritical water microreaction system. |
| PubMed:Sequence analysis and domain motifs in the porcine skin decorin glycosaminoglycan chain. |
| PubMed:The treatment with an anti-glycosaminoglycan antibody reduces aortic oxidative stress in a rabbit model of atherosclerosis. |
| PubMed:Sulfation pattern of the fucose branch is important for the anticoagulant and antithrombotic activities of fucosylated chondroitin sulfates. |
| PubMed:Extraction, purification and characterisation of chondroitin sulfate in Chinese sturgeon cartilage. |
| PubMed:Symptom and structure modification in osteoarthritis with pharmaceutical-grade chondroitin sulfate: what's the evidence? |
| PubMed:Oversulfated chondroitin sulfate inhibits the complement classical pathway by potentiating C1 inhibitor. |
| PubMed:Capillary electrophoresis methods for the analysis of antimalarials. Part I. Chiral separation methods. |
| PubMed:The heparin recall of 2008. |
| PubMed:Chondroitin sulfate based nanocomplex for enhancing the stability and activity of anthocyanin. |
| PubMed:Characterization of currently marketed heparin products: adverse event relevant bioassays. |
| PubMed:Nutritional management of osteoarthritis. |
| PubMed:Melatonin combined with exercise cannot alleviate cerebral injury in a rat model of focal cerebral ischemia/reperfusion injury. |
| PubMed:Cell-Based Microscale Isolation of Glycoaminoglycans for Glycomics Study. |
| PubMed:Complement C1 esterase inhibitor levels linked to infections and contaminated heparin-associated adverse events. |
| PubMed:Sequence determination and anticoagulant and antithrombotic activities of a novel sulfated fucan isolated from the sea cucumber Isostichopus badionotus. |
| PubMed:Erythrocytes express chondroitin sulphate/dermatan sulphate, which undergoes quantitative changes during diabetes and mediate erythrocyte adhesion to extracellular matrix components. |
| PubMed:Exposure to common food additive carrageenan leads to reduced sulfatase activity and increase in sulfated glycosaminoglycans in human epithelial cells. |
| PubMed:Ablation of NG2 proteoglycan leads to deficits in brown fat function and to adult onset obesity. |
| PubMed:Lumican is a major small leucine-rich proteoglycan (SLRP) in Atlantic cod (Gadus morhua L.) skeletal muscle. |
| PubMed:Concerted and adaptive alignment of decorin dermatan sulfate filaments in the graded organization of collagen fibrils in the equine superficial digital flexor tendon. |
| PubMed:Effect of a dietary supplement containing glucosamine hydrochloride, chondroitin sulfate and quercetin glycosides on symptomatic knee osteoarthritis: a randomized, double-blind, placebo-controlled study. |
| PubMed:Detection of possible economically motivated adulterants in heparin sodium and low molecular weight heparins with a colorimetric microplate based assay. |
| PubMed:Sensitive detection of oversulfated chondroitin sulfate in heparin sodium or crude heparin with a colorimetric microplate based assay. |
| PubMed:Diabetes results in structural alteration of chondroitin sulfate/dermatan sulfate in the rat kidney: effects on the binding to extracellular matrix components. |
| PubMed:New and generic anticoagulants and biosimilars: safety considerations. |
| PubMed:Characterization of currently marketed heparin products: reversed-phase ion-pairing liquid chromatography mass spectrometry of heparin digests. |
| PubMed:Characterization of currently marketed heparin products: key tests for quality assurance. |
| PubMed:Description of hypersensitivity adverse events following administration of heparin that was potentially contaminated with oversulfated chondroitin sulfate in early 2008. |
| PubMed:Extraction, isolation and analysis of chondroitin sulfate glycosaminoglycans. |
| PubMed:Bradykinin forming capacity of oversulfated chondroitin sulfate contaminated heparin in vitro. |
| PubMed:Composition of OSCS-contaminated heparin occurring in 2008 in batches on the German market. |
| PubMed:Assay of possible economically motivated additives or native impurities levels in heparin by 1H NMR, SAX-HPLC, and anticoagulation time approaches. |
| PubMed:Synergistic chondroprotective effect of alpha-tocopherol, ascorbic acid, and selenium as well as glucosamine and chondroitin on oxidant induced cell death and inhibition of matrix metalloproteinase-3--studies in cultured chondrocytes. |
| PubMed:Analysis of crude heparin by (1)H NMR, capillary electrophoresis, and strong-anion-exchange-HPLC for contamination by over sulfated chondroitin sulfate. |
| PubMed:Quality of different chondroitin sulfate preparations in relation to their therapeutic activity. |
| PubMed:The proteoglycan bamacan is a host cellular ligand of vaccinia virus neurovirulence factor N1L. |
| PubMed:Evaluation and comparison of the antioxidative potency of various carbohydrates using different methods. |
| PubMed:Determination of oversulfated chondroitin sulfate and dermatan sulfate impurities in heparin by capillary electrophoresis. |
| PubMed:Lessons learned from the contamination of heparin. |
| PubMed:Analysis of heparin sodium by SAX/HPLC for contaminants and impurities. |
| PubMed:Screening of heparin API by near infrared reflectance and Raman spectroscopy. |
| PubMed:Inhibition of Taq polymerase as a method for screening heparin for oversulfated contaminants. |
| PubMed:Chondroitin sulfate extracted from ascidian tunic inhibits phorbol ester-induced expression of Inflammatory factors VCAM-1 and COX-2 by blocking NF-kappaB activation in mouse skin. |
| PubMed:Quality assessment of unfractionated heparin using 1H nuclear magnetic resonance spectroscopy. |
| PubMed:[Safety of health foods and importance of their origin]. |
| PubMed:Contaminated heparin associated with adverse clinical events and activation of the contact system. |
| PubMed:Potential glucosamine-warfarin interaction resulting in increased international normalized ratio: case report and review of the literature and MedWatch database. |
| PubMed:Characterization and purification of glycosaminoglycans from crude biological samples. |
| PubMed:EDC/NHS-crosslinked type II collagen-chondroitin sulfate scaffold: characterization and in vitro evaluation. |
| PubMed:Thermal and storage stability of nutraceuticals in a milk beverage dietary supplement. |
| PubMed:Glucosamine and chondroitin sulfate as therapeutic agents for knee and hip osteoarthritis. |
| PubMed:Chitosan based hydrogel microspheres as drug carriers. |
| PubMed:Nonheme iron absorption in young women is not influenced by purified sulfated and unsulfated glycosaminoglycans. |
| PubMed:The utility of nutraceuticals in the treatment of osteoarthritis. |
| PubMed:Glucosamine regulates differentiation of a chondrogenic cell line, ATDC5. |
| PubMed:Identification of the origin of chondroitin sulfate in "health foods". |
| PubMed:Acute and subchronic oral toxicity studies in rats of a hydrolyzed chicken sternal cartilage preparation. |
| PubMed:Crystal structure of unsaturated glucuronyl hydrolase complexed with substrate: molecular insights into its catalytic reaction mechanism. |
| PubMed:Osteoarthritis and nutrition. From nutraceuticals to functional foods: a systematic review of the scientific evidence. |
| PubMed:Randomised double-blind, positive-controlled trial to assess the efficacy of glucosamine/chondroitin sulfate for the treatment of dogs with osteoarthritis. |
| PubMed:Effect of bitter gourd and spent turmeric on constituents of glycosaminoglycans in different tissues in streptozotocin induced diabetic rats. |
| PubMed:Sulfated polysaccharides derived from dietary seaweeds increase the esterase activity of a lymphocyte tryptase, granzyme A. |
| PubMed:The efficacy of glucosamine and chondroitin sulfate in the treatment of osteoarthritis: are these saccharides drugs or nutraceuticals? |
| PubMed:Sulfated glycosaminoglycans in the extracellular matrix of muscle tissue in Atlantic cod (Gadus morhua) and Spotted wolffish (Anarhichas minor). |
| PubMed:Potentiation of T cell function by a marine algae-derived sulfated polymannuroguluronate: in vitro analysis of novel mechanisms. |
| PubMed:Chronic barium intoxication disrupts sulphated proteoglycan synthesis: a hypothesis for the origins of multiple sclerosis. |
| PubMed:Role of mast cells in gastrointestinal mucosal defense. |
| PubMed:Naturocetic (glucosamine and chondroitin sulfate) compounds as structure-modifying drugs in the treatment of osteoarthritis. |
| PubMed:Glucosamine and chondroitin sulfate supplementation to treat symptomatic disc degeneration: biochemical rationale and case report. |
| PubMed:A size-exclusion HPLC method for the determination of sodium chondroitin sulfate in pharmaceutical preparations. |
| PubMed:The bioavailability and pharmacokinetics of glucosamine hydrochloride and low molecular weight chondroitin sulfate after single and multiple doses to beagle dogs. |
| PubMed:Galactosaminoglycan composition in chicken eggshell. |
| PubMed:Extraction of glycosaminoglycans from chicken eggshell. |
| PubMed:Extraction of Glycosaminoglycan Peptide from Bovine Nasal Cartilage with 0.1 M Sodium Acetate. |
| PubMed:Argument against use of food additives for osteoarthritis of the hip. |
| PubMed:Evidence of nutriceutical effectiveness in the treatment of osteoarthritis. |
| PubMed:Sulfated glycosaminoglycans and collagen in two bovine muscles (M. Semitendinosus and M. Psoas major) differing in texture. |
| PubMed:Nutraceuticals as therapeutic agents in osteoarthritis. The role of glucosamine, chondroitin sulfate, and collagen hydrolysate. |
| PubMed:Infectious laryngotracheitis virus, an alpha herpesvirus that does not interact with cell surface heparan sulfate. |
| PubMed:Isolation and characterization of proteoglycans from growing antlers of wapiti (Cervus elaphus). |
| PubMed:Effects of dietary manganese on arterial glycosaminoglycan metabolism in Sprague-Dawley rats. |
| PubMed:Isolation, characterization and localization of glycosaminoglycans in growing antlers of wapiti (Cervus elaphus). |
| PubMed:Regulation of anti-HIV-1 activity of RANTES by heparan sulfate proteoglycans. |
| PubMed:[The coronary artery structure and early atherosclerotic lesions of 80 young adults cases in the Ningbo fishing region]. |
| PubMed:Heparan sulfate is essential to amphiregulin-induced mitogenic signaling by the epidermal growth factor receptor. |
| PubMed:Cell-surface heparan sulfate proteoglycan mediates HIV-1 infection of T-cell lines. |
| PubMed:Enzymatic lysis of sulfated glycosaminoglycans reduces the electrophoretic mobility of vascular endothelial cells. |
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derivatives of chondroitin which have a sulfate moiety esterified to the galactosamine moiety of chondroitin. chondroitin sulfate a, or chondroitin 4-sulfate, and chondroitin sulfate c, or chondroitin 6-sulfate, have the sulfate esterified in the 4- and 6-positions, respectively. chondroitin sulfate b (beta heparin; dermatan sulfate) is a misnomer and this compound is not a true chondroitin sulfate. Chondroitin sulfate (CS) is a linear heteropolysaccharide consisting of repeating disaccharide units of glucuronic acid and galactosamine, which is commonly sulfated at C-4 and/or C-6 of galactosamine. chondroitin sulfate (CS) is a glycosaminoglycan (GAG) covalently linked to proteins forming proteoglycans (PGs). GAGs are all anionic linear heteropolysaccharide chains of repeating disaccharide units. According to the monosaccharide types and the glycosidic bonds between them, GAGs are divided into (1) hyaluronan, (2) CS and dermatan sulfate (DS), (3) heparan sulfate and heparin, and (4) keratan sulfate. CS was isolated from cartilage in 1884, but the nature of its monosaccharides and structure was first described in 1925. On the basis of the structure of chondroitin sulfate, at least five enzyme activities could be predicted, including three transferases (EC 2.4.1.79, the initiating GalNAc transferase, EC 2.4.1.175, polymerizing GalNAc and EC 2.4.1.17, GlcA transferase) and two sulfotransferases (EC 2.8.2.5, GalNAc 4-sulfotransferase and EC 2.8.2.17, GalNAc 6-sulfotransferase). Additional enzymes exist for epimerization of GlcA, sulfation of the uronic acids, and other patterns of sulfation found in unusual species of chondroitin. chondroitin sulfate assembly can occur on virtually all proteoglycans, depending on the cell in which the core protein is expressed. chondroitin sulfates from different sources vary in the location of sulfate groups. Separation of the products reveals that many types of chondroitin sulfate exist in nature but many chains are hybrid structures containing more than one type of disaccharide. Animal cells also degrade chondroitin sulfate in lysosomes using a series of exoglycolytic activities. (PMID: 167797850) [HMDB]
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