3416-24-8 Usage
Description
Glucosamine, also known as D-glucosamine, is an amino sugar that plays a crucial role in the regulation of growth factor gene transcription. It is a naturally occurring substance found in mucopolysaccharides, chitin, and mucoproteins, with glucosamine sulfate being manufactured synthetically. Glucosamine is characterized by its colorless needle-like appearance and its solubility properties, being very soluble in water and slightly soluble in methanol and ethanol, while being insoluble in ether and chloroform.
Uses
Used in Health Medicine:
Glucosamine is used as a therapeutic agent for osteoarthritis (OA), a condition characterized by the degeneration of joint cartilage and underlying bone. It helps in the management and relief of OA symptoms, providing support to the affected joints and promoting overall joint health.
Used in Pharmaceutical Aid:
Glucosamine is utilized as a pharmaceutic aid, contributing to the development and formulation of various medications. Its presence in these formulations aids in enhancing the efficacy and performance of the drugs, making it an essential component in the pharmaceutical industry.
Used in Health Food:
As a component of health food products, Glucosamine is used to support joint health and overall well-being. It is commonly found in dietary supplements and nutraceuticals, targeting individuals seeking to improve their joint function and maintain a healthy lifestyle.
Used in Cosmetics:
Glucosamine is also employed in the cosmetics industry, where it is used as an ingredient in various skincare and beauty products. Its presence in these products is aimed at promoting skin health, improving skin elasticity, and providing anti-aging benefits.
Outline
Glucosamine, also known as 2deoxy aminosamidose, is a common amino sugar and is a derivative of glucose. It is a compound formed by the substitution of hydroxyl on the second carbon atom of glucose molecule. A hydrogen atom on the amino group is often substituted by acetyl group to form N-acetylglucosamine. It rarely exists in organisms, mainly as chitin, glycoprotein and proteoglycan components.
Physicochemical properties
Its molecular formula is C6H13NO5, and its molecular weight is 179.17. Glucosamine has the property of polyhydroxylamines and exists in the cell walls of crustaceans, insects, molds and bacteria in the form of polymers or derivatives. Chitin (Nacetyl glucosamine condensate) produces amino glucosamine in water. The alpha body is crystalline and its melting point is 88 degrees, and it changes []D20100] to 47.5 degrees (30 minutes) in aqueous solution. The beta body can be obtained from methanol by acicular crystals, decomposing at 110 degrees, and changing in aqueous solution [alpha]D2028 degrees to 47.5 degrees (30 minutes). It is soluble in water, soluble in hot methanol, slightly soluble in cold methanol and ethanol, and insoluble in ethyl ether and chloroform. It exists in crustacean, mucin and mucin.
It is a trace organic component in seawater, particulates and marine sediments. The content of marine samples can be separated by hydrolysis and cation exchange column and determined by spectrophotometry.
Preparative method:dehydrated glucose and ammonia react in absolute ethanol, and then hydrolyze to produce crude glucosamine.
Natural Substance
Glucosamine hydrochloride is a natural substance that stimulates the body to make glycosaminoglycans to repair and form cartilage. Hydrochloride is a kind of easily absorbed small component, composed of amino acids such as glucose and glutamine.
Its function is to stimulate the production of synovial fluid and promote articular cartilage repair. It also strengthens the synthesis of connective tissue. Hydrochloride is a hydrophilic molecule that absorbs water into cartilage and improves cartilage elasticity. Glucosamine is an amino acid naturally occurring in the human body. Its role is to form and repair cartilage. Although glucosamine is a natural substance produced by human body, its level decreases with aging, resulting in cartilage degeneration.
Taking glucosamine as a nutritional supplement is one of the ways to help reduce the level of glucosamine in the body. Glucosamine nutritional supplement is the shell of crustacean seafood extracted from crabs, lobsters and shrimps. Crustacean seafood, like humans, naturally produces this substance. It is known that glucosamine nutritional supplements are effective for osteoarthritis. This is because glucosamine is the precursor of glycosaminoglycan, and the latter is the basic material for articular cartilage to repair cartilage tissue. The human body needs these glycosaminoglycans to make proteoglycans.
Proteoglycan is a substance similar to clay made from protein and sugar. Before collagen is deposited in the joint, it is the basic material for cartilage. The more glycosaminoglycan in articular cartilage, the higher the rate of cartilage formation. As glucosamine is the precursor of glycosaminoglycan, glucosamine supplements help to reduce inflammation and swelling of the joints and rebuild damaged cartilage, which is beneficial to the treatment of osteoarthritis. Previous studies have shown that patients with mild to moderate osteoarthritis can feel pain relieved after taking glucosamine. Its analgesic effect is similar to aspirin and Bloven (Ibuprofen) and other non steroidal anti-inflammatory drugs (NSAIDs). Other studies have shown that glucosamine may help slow down cartilage damage in osteoarthritis patients.
World Health Organization (WHO)
Glucosamine is found in chitin, mucoproteins and
mucopolysaccharides. It is used as a pharmaceutical aid. Glucosamine sulfate has
been used in the treatment of rheumatic disorders though it is not widely marketed for this purpose.
Veterinary Drugs and Treatments
These compounds may be useful in treating osteoarthritis or other
painful conditions in domestic animals, but large, well-designed
controlled clinical studies proving efficacy were not located. One
study in dogs (McCarthy, O’Donovan et al. 2007) showed some positive
effect, but this study was not placebo controlled and compared
responses versus carprofen. Another placebo-controlled, blinded
study in dogs (Moreau, Dupuis et al. 2003), did not demonstrate
statistically significant improvement after 60 days of treatment.
These compounds potentially could be of benefit in cats with
FLUTD (feline lower urinary tract disease) because of the presence
of glycosaminoglycans as part of the protective layer of the urinary
tract. Controlled studies have shown some positive effects in some
cats, but overall did not appear to make a significant difference.
Purification Methods
Crystallise the amines from MeOH. The free base has been obtained from the hydrochloride (21.5g, see below) in a mixture of Et3N (15mL) and EtOH (125mL) by shaking for 2days at room temperature, and the solid Et3N.HCl is filtered off and the process repeated with more Et3N (3-4 times) until the D-glucosamine (15g) is free from Cl ions. It has m 88o , [] D20 +100o mutarotating to +47.5o (c 1, H2O). When Et2NH is used as base, the to conversion is complete giving D-glucosamine. The pentaacetate is purified by dissolving in CHCl3, treating with charcoal, drying (MgSO4), evaporating the solvent, and adding a little dry Et2O to induce crystallisation. It has m 124-126o, [] D +113o (c 1, CHCl3) after 16hours in a desiccator. [Leaback Biochemical Preparations 10 118 1963.] The N-acetyl derivative, m 203-205o from MeOH/Et2O (dry in vacuum P2O5) has [] D +75o to +41o (c 2, H2O); this derivative can also be purified by dissolving in the minimum volume of H2O to which is added 7-8volumes of EtOH followed by Et2O until turbid and keeping at ~20o to crystallise. Wash the crystals with MeOH then Et2O and dry in vacuo over P2O5. [Horton Biochemical Preparations 11 1 1966.]
Check Digit Verification of cas no
The CAS Registry Mumber 3416-24-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,4,1 and 6 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3416-24:
(6*3)+(5*4)+(4*1)+(3*6)+(2*2)+(1*4)=68
68 % 10 = 8
So 3416-24-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6-;/m1./s1
3416-24-8Relevant articles and documents
Brasilane sesquiterpenoids and alkane derivatives from cultures of the basidiomycete Coltricia sideroides
Hu, Dong-Bao,Zhang, Shen,He, Jiang-Bo,Dong, Ze-Jun,Li, Zheng-Hui,Feng, Tao,Liu, Ji-Kai
, p. 50 - 54 (2015)
Three new brasilane-type sesquiterpenoids, brasilanes A-C (1-3), together with two new alkane derivatives, colisiderin A (4) and 7(E),9(E)-undecandiene-2,4,5-triol (5), were isolated from cultures of the basidiomycete Coltricia sideroides. Their structures were elucidated by NMR and MS data analyses. The absolute configuration of 4 was determined by TDDFT ECD calculations while brasilane-type sesquiterpenoids were isolated from cultures of mushroom for the first time. Compounds 2 and 4 showed weak cytotoxicities against HL-60 and SW480, respectively.
The structure of the O-antigen of Cronobacter sakazakii HPB 2855 isolate involved in a neonatal infection
MacLean, Leann L.,Vinogradov, Evgeny,Pagotto, Franco,Farber, Jeffrey M.,Perry, Malcolm B.
, p. 1932 - 1937 (2010)
Strains of Cronobacter sakazakii (previously known as Enterobacter sakazakii) are medically recognized important Gram-negative bacterial pathogens that cause enterocolitis, septicemia, and meningitis, with a high mortality rate in neonates. The structure of their O-antigens, that form part of their somatic lipopolysaccharide (LPS) components, is of interest for their chemical and serological identification and their relationship to virulence. The O-polysaccharide (O-PS) of C. sakazakii HPB 2855 (SK 81), a strain isolated from an infant at the Hospital for Sick Children in Toronto in 1981, was shown to be a polymer of a partially O-acetylated-repeating hexasaccharide unit composed of d-glucose, d-galacturonic acid, 2-acetamido-2-deoxy-d-galactose, and l-rhamnose (1:1:1:3). From composition and methylation analysis, and the application of 1D and 2D 1H and 13C NMR spectroscopy, the O-PS was determined to be a polymer of a repeating oligosaccharide unit having the structure: [figure persented]
Triterpenoid saponins from Piptadeniastrum africanum (Hook. f.) Brenan
Noté, Olivier Placide,Tapondjou, Azefack Léon,Mitaine-Offer, Anne-Claire,Miyamoto, Tomofumi,Pegnyemb, Dieudonné Emmanuel,Lacaille-Dubois, Marie-Aleth
, p. 505 - 510 (2013)
One new triterpenoid saponin, named piptadeniaoside (1), along with two known saponins (2-3) have been isolated from the stem bark of Piptadeniastrum africanum. After previous isolation of flavone derivatives from this plant, new phytochemical investigati
Simplified determination of the content and average degree of acetylation of chitin in crude black soldier fly larvae samples
D'Hondt, Els,Soetemans, Lise,Bastiaens, Leen,Maesen, Miranda,Jespers, Vincent,Van den Bosch, Bert,Voorspoels, Stefan,Elst, Kathy
supporting information, (2020/01/25)
Insects are considered a promising alternative protein source for food and feed, but contain significant amounts of chitin, often undesirable due to indigestibility, disagreeable texture and negative effect on nutrients intake. Fractionation strategies are thus increasingly being applied to isolate and valorize chitin separately. The analysis of chitin generally requires an intensive pretreatment to remove impurities, and derivatization to generate sufficient detector response. In this work, a liquid chromatography method, without pretreatment nor derivatization, was developed for the simultaneous determination of chitin content and degree of acetylation in non-purified samples of black soldier fly (BSF) larvae. The method is found to be more suitable, compared to traditional methods, for assessing high degrees of acetylation. For the first time, the degree of acetylation of BSF chitin (81 ± 2%) is reported. Additionally, the chitin content of BSF soft tissues is estimated at approximately 20% of the total chitin content (8.5 ± 0.1%).
Enzymatic production of fully deacetylated chitooligosaccharides and their neuroprotective and anti-inflammatory properties
Santos-Moriano,Fernandez-Arrojo,Mengibar,Belmonte-Reche,Pe?alver,Acosta,Ballesteros,Morales,Kidibule,Fernandez-Lobato,Plou, Francisco J.
, p. 57 - 67 (2017/09/30)
Among several commercial enzymes screened for chitosanolytic activity, Neutrase 0.8L (a protease from Bacillus amyloliquefaciens) was selected in order to obtain a product enriched in deacetylated chitooligosaccharides (COS). The hydrolysis of different chitosans with this enzyme was followed by size exclusion chromatography (SEC-ELSD), mass spectrometry (ESI-Q-TOF), and high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD). Neutrase 0.8L converted 10?g/L of various chitosans into mostly deacetylated oligosaccharides, yielding approximately 2.5?g/L of chitobiose, 4.5?g/L of chitotriose, and 3?g/L of chitotetraose. We found out that the neutral protease was not responsible for the chitosanolytic activity in the extract, while it could participate in the deacetylating process. The synthesized COS were tested in vitro for their neuroprotective (toward human SH-S5Y5 neurons) and anti-inflammatory (in RAW macrophages) activities, and compared with other functional ingredients, namely fructooligosaccharides.