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Glucosamine

3416-24-8

C6H13NO5

179.17

GLUCOSAMINE; D-GLUCOSAMINE; D-(+)-Glucosamine hy; SYNTHETICGLUCOSAMINE; 2-Amino-2-deoxyglucose; aldehydo-D-glucosamine; GlucosaMine(Feed grade); D-Glucosamine(HCl form); 2-amino-2-deoxy-d-glucos; 2-amino-2-deoxy-d-glucose

USP (HCL, KCL, NaCl, powder and granular)

Glucosamine
ProductSpecifications
GlucosamineHCL USP
GlucosamineKCL USP
GlucosamineNaCl USP
GlucosaminePowder USP
GlucosamineGranular USP

Glucosamine Properties

Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of the polysaccharides, chitosan, and chitin. Glucosamine is one of the most abundant monosaccharides. It is produced commercially by the hydrolysis of crustacean exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat.

Evidence for the effectiveness of glucosamine as a dietary supplement is mixed. In the United States, it is one of the most common dietary supplements used by adults that is neither a vitamin nor a mineral.

Oral glucosamine is a dietary supplement and is not a pharmaceutical drug. It is illegal in the US to market any dietary supplement as a treatment for any disease or condition.[3] Glucosamine is marketed to support the structure and function of joints, and the marketing is targeted to people suffering from osteoarthritis.

Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine hydrochloride, and N-acetylglucosamine. Of the three commonly available forms of glucosamine, only glucosamine sulfate is given a "likely effective" rating for treating osteoarthritis.[4] Glucosamine is often sold in combination with other supplements such as chondroitin sulfate and methylsulfonylmethane.

Glucosamine, along with commonly used chondroitin, is not routinely prescribed to treat people who have symptomatic osteoarthritis of the knee, as there is insufficient evidence that this treatment is helpful.[5]

As is common with heavily promoted dietary supplements, the claimed benefits of glucosamine are based principally on clinical and laboratory studies. Clinical studies are divided, with some reporting relief from arthritic pain and stiffness, while higher quality studies report no benefit above placebo.[6]

There is no evidence to date that consumption of glucosamine by sport participants will prevent or limit joint damage after injury.[7] In a randomized placebo-controlled trial, glucosamine supplementation had no additional effect on any rehabilitation outcome when given to athletes after anterior cruciate ligament (ACL) reconstruction.[8]

Adverse effects and drug interactions

One clinical study over three years showed that glucosamine in doses of 1500 mg per day is safe to use.[9]

Glucosamine with or without chondroitin elevates the international normalized ratio (INR) in individuals who are taking the blood thinner, warfarin.[4][10] It may also interfere with the efficacy of chemotherapy for treating cancer symptoms.[4]

Adverse effects may include stomach upset, constipation, diarrhea, headache, and rash.[11] There are case reports of people who have chronic liver disease and a worsening of their condition with glucosamine supplementation.[12] More high-quality clinical research is needed before recommending glucosamine in pregnancy.[4]

Since glucosamine is usually derived from the shells of shellfish, it may be unsafe for those with shellfish allergy.[13] However, many manufacturers of glucosamine derived from shellfish include a warning that those with a seafood allergy should consult a healthcare professional before taking the product.[14] Alternative, non-shellfish-derived forms of glucosamine are available.[15]

Another concern has been that the extra glucosamine could contribute to diabetes by interfering with the normal regulation of the hexosamine biosynthesis pathway,[16] but several investigations found no evidence that this occurs.[17][18] Other studies conducted in lean or obese subjects concluded that oral glucosamine at standard doses does not affect insulin resistance.[19][20]

Biochemistry

Glucosamine is naturally present in the shells of shellfish, animal bones, bone marrow, and fungi.[21] D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars.[22] Specifically in humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine—fructose-6-phosphate transaminase[23] as the first step of the hexosamine biosynthesis pathway.[24] The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc),which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.

As the formation of glucosamine-6-phosphate is the first step for the synthesis of these products, glucosamine may be important in regulating their production; however, the way that the hexosamine biosynthesis pathway is actually regulated, and whether this could be involved in contributing to human disease remains unclear.[16]

Manufacturing

Most glucosamine is manufactured by processing chitin from the shells of shellfish including shrimp, lobsters, and crabs.[25] To meet the demands of vegetarians and others with objections to shellfish, manufacturers have brought glucosamine products to market made using fungus Aspergillus niger and from fermenting corn.[15]

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