(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Base Information

• Chemical Name: (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
• CAS No.: 3458-28-4
• Deprecated CAS: 147-74-0,50986-23-7,50986-24-8,149014-30-2,530-26-7,149014-30-2,50986-24-8
• Molecular Formula: C6H12 O6
• Molecular Weight: 180.158
• Hs Code.: 29400010
• UNII: PHA4727WTP
• DSSTox Substance ID: DTXSID5040463
• Nikkaji Number: J82.111J
• Wikidata: Q27117223
• NCI Thesaurus Code: C83903
• Metabolomics Workbench ID: 55657
• Mol file: 3458-28-4.mol

Synonyms:D Mannose;D-Mannose;Mannopyranose;Mannopyranoside;Mannose

Chemical Property of (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Chemical Property:

• Appearance/Colour: White powder
• Melting Point: 133-140ºC
• Refractive Index: 1.5730 (estimate)
• Boiling Point: 527.1 °C at 760 mmHg
• PKA: 12.08(at 25℃)
• Flash Point: 286.7 °C
• PSA: 118.22000
• Density: 1,581 g/cm³
• LogP: -3.37880
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 50 mg/mL
• Water Solubility.: 2480 g/L (17 ºC)
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 180.06338810
• Heavy Atom Count: 12
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

D-Mannose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(C(C=O)O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@@H](C=O)O)O)O)O)O
• Description: D-Mannose is a nutritional supplement that can be found in cranberries, peaches, apples, other berries, and some plants. D-mannose is a sugar that has an important role in human metabolism, especially in the glycosylation of certain proteins. D-mannose functionalizes by the inhibition of bacterial adherence to uroepithelial cells. More than 90 percent of recurrent urinary tract infections (UTIs) are caused by Escherichia coli (E. coli), which is normally found in the intestinal tract. The cell walls of each E. coli are covered with tiny fingerlike projections called fimbria. Mannose can bind to the lectin on the bacteria’s fimbria so that the bacteria can be effectively rinsed out by urination. D-Mannose is by far the most effective supplement for both treatment and prevention of UTIs. And it is used for the treating carbohydrate-deficient glycoprotein syndrome, an inherited metabolic disorder.
• Uses: D-Mannose is a carbohydrate that is important in the glycosylation of molecules in a variety of cellular processes. It is involved in N and O glycosylation of bovine why protein products, used in inf ant formulas. It is also responsible for the O-glycosylation of the T helper cell-derived cytokine interlukin-17A, an important cell-signaling molecule. It has been used in a study to assess the synthesis of a family of amphiphilic glycopolymers. It has also been used in a study to investigate the early detection of bronchiolitis obliterans after lung transplantation. D-mannose acts as an alternative energy source utilized by brain. It is used in the study of assessing the synthesis of amphiphilic glycopolymers and investigating early detection of bronchiolitis obliterans.It may be useful in the treatment of urinary tract infections (UTIs) and carbohydrate-deficient glycoprotein syndrome type 1b. It is also useful in the formation of glycan structure and glycosylation.

Technology Process of (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

There total 295 articles about (2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal 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:

dendrobium denneanum polysaccharide → D-xylose (58-86-6) + D-Mannose (3458-28-4) + D-Arabinose (10323-20-3) + D-glucose (50-99-7) + D-Galactose (59-23-4) + D-myo-inositol (87-89-8)

Guidance literature:

With trifluoroacetic acid; at 100 ℃; for 8h;

DOI:10.3390/molecules16021579

Reference yield:

β-glucan FoHA2 from fruit bodies Fomitopsis officinalis → D-xylose (58-86-6) + D-Mannose (3458-28-4) + D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + galactose (93780-23-5)

Guidance literature:

With trifluoroacetic acid; In water; at 100 ℃; for 5h;

DOI:10.1016/j.phytochem.2020.112313

Reference yield:

β-glucan FoHA4 from fruit bodies Fomitopsis officinalis → D-xylose (58-86-6) + D-Mannose (3458-28-4) + D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + galactose (93780-23-5)

Guidance literature:

With trifluoroacetic acid; In water; at 100 ℃; for 5h;

DOI:10.1016/j.phytochem.2020.112313

upstream raw materials:

pyridine

D-glucose

mannitol

2-amino-2-deoxyglucose

Downstream raw materials:

D-Fructose

d-manno-α-heptonic acid amide

2(RS)-D-manno-(1',2',3',4',5'-pentahydroxypentyl)thiazolidine-4(R)-carboxylic acid

Refernces

• 1、 Das, Asim K.,Islam, Monirul,Bayen, Ruhidas. "Studies on kinetics and mechanism of oxidation of D-sorbitol and D-mannitol by cerium (IV) in aqueous micellar sulfuric acid media". . p. 445 - 453. Retrieved 2008.
• 2、 Bjerre, Jeannette,Bols, Mikael. "Substantial spatial flexibility and hydrogen bonding within the catalysis exerted by cyclodextrin artificial glycosidases". . p. 3487 - 3500. Retrieved 2010.
• 3、 Drews. "Demonstration of sugar in the thylakoids of Rhodospirillum rubrum and Rhodopseudomonas viridis". . . Retrieved 1968.
• 4、 Shul'Tsev,Panarin. "Synthesis, structure, and properties of allylamino glycosides". . p. 510 - 519. Retrieved 2013.
• 5、 Tang, Huiling,Wei, Weikun,Wang, Wang,Zha, Zhengqi,Li, Ting,Zhang, Zhijie,Luo, Chen,Yin, Hongping,Huang, Fengjie,Wang, Ying. "Effects of cultured Cordyceps mycelia polysaccharide A on tumor neurosis factor-α induced hepatocyte injury with mitochondrial abnormality". . p. 43 - 53. Retrieved 2017.
• 6、 Wang, Shi-Jiang,Huo, Zhi-Jun,Liu, Kai,Yu, Ning,Ma, Yan,Qin, Yue-Hong,Li, Xiao-Chen,Yu, Jin-Ming,Wang, Zhi-Qi. "Ligand-conjugated pH-sensitive polymeric micelles for the targeted delivery of gefitinib in lung cancers". . p. 73184 - 73193. Retrieved 2015.
• 7、 Zheng, Wei,Zhao, Ting,Feng, Weiwei,Wang, Wei,Zou, Ye,Zheng, Daheng,Takase, Mohammed,Li, Qian,Wu, Huiyu,Yang, Liuqing,Wu, Xiangyang. "Purification, characterization and immunomodulating activity of a polysaccharide from flowers of Abelmoschus esculentus". . p. 335 - 342. Retrieved 2014.
• 8、 Golovchenko, Victoria V.,Naranmandakh, Shinen,Ganbaatar, Jamsranjav,Prilepskii, Artur Yu.,Burygin, Gennady L.,Chizhov, Alexander O.,Shashkov, Alexander S.. "Structural investigation and comparative cytotoxic activity of water-soluble polysaccharides from fruit bodies of the medicinal fungus quinine conk". . . Retrieved 2020.
• 9、 Tanase, Tomoaki,Shimizu, Fumihiko,Kuse, Manabu,Yano, Shigenobu,Yoshikawa, Sadao,Hidai, Masanobu. "C-2 Epimerization of Aldoses promoted by Combinations of Metals and Diamines involving a Novel Rearrangement of the Carbon Skeleton". . p. 659 - 661. Retrieved 1987.
• 10、 Yang, Guang,Qu, Yunhe,Meng, Yue,Wang, Yushi,Song, Chengcheng,Cheng, Hairong,Li, Xiaomeng,Sun, Lin,Zhou, Yifa. "A novel linear 3-O-methylated galactan isolated from Cantharellus cibarius activates macrophages". . p. 34 - 43. Retrieved 2019.