Pentitol

Base Information

• Chemical Name: Pentitol
• CAS No.: 87-99-0
• Deprecated CAS: 12426-00-5,37191-59-6,7313-55-5,75398-81-1,84709-42-2
• Molecular Formula: C5H12O5
• Molecular Weight: 152.147
• Hs Code.: 29054910
• NSC Number: 83253,25288,25283,16868
• DSSTox Substance ID: DTXSID7042514
• Nikkaji Number: J1.453.993J
• Wikidata: Q81977867
• Metabolomics Workbench ID: 123381
• ChEMBL ID: CHEMBL1369426
• Mol file: 87-99-0.mol

Synonyms:(+--)-arabitol;arabinitol, D-;arabinitol, L-;arabino-pentitol;arabitol;arabitol, (D)-isomer;arabitol, (L)-isomer;D-arabinitol;D-arabitol;DL-arabitol;L-arabinitol;lyxitol

Chemical Property of Pentitol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.329Pa
• Melting Point: 94-97 °C(lit.)
• Refractive Index: 1.3920 (estimate)
• Boiling Point: 494.5 °C at 760 mmHg
• PKA: 13.24±0.20(Predicted)
• Flash Point: 261.9 °C
• PSA: 101.15000
• Density: 1.525 g/cm³
• LogP: -2.94630
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: 0.1 g/mL, clear, colorless
• Water Solubility.: SOLUBLE
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 152.06847348
• Heavy Atom Count: 10
• Complexity: 76.1

Purity/Quality:

98% ^*data from raw suppliers

Xylitol ^*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

Useful:

• Canonical SMILES: C(C(C(C(CO)O)O)O)O
• Sources and Categories: Xylitol is a naturally occurring pentitol (five-carbon sugar alcohol) found in low concentrations in various edible plants, mushrooms, and in small quantities in humans and animals during glucose metabolism.
• Chemical Composition and Structure: Xylitol is a white crystalline sugar alcohol with a chemical structure of a 5-carbon sugar alcohol.
• Characteristics: Xylitol has approximately two-thirds the calories of most sugars.; It induces very little insulin release and is antiketogenic, making it suitable for low-carbohydrate diets and safe for diabetics.; Exhibits antibacterial properties and is palatable, making it popular in dental products for preventing dental caries.; Metabolism of xylitol is independent of insulin.
• Mechanism of Action: Xylitol inhibits certain bacterial growth and does not require insulin to enter cells, serving as an energy source.
• Uses: Used as a sugar substitute for patients with diabetes due to its low glycemic index and antiketogenic properties. Also employed in dental products for its antibacterial properties to prevent dental caries.; Generally recognized as safe (GRAS) by the FDA and approved for use as a food additive.
• Historical Development: Discovered in the late 19th century and widely used as a sugar substitute during World War II. Recognized as a potent sweetener after the discovery of its property of not elevating blood sugar levels. Its dental benefits became apparent in the 1970s after the "Turku Sugar Studies".
• Production Methods: Chemical Synthesis: ; Involves catalytic hydrogenation of xylose extracted from lignocellulosic biomass.; Industrial Production: ; Catalytic hydrogenation process using Raney nickel as a catalyst to convert xylose to xylitol, followed by purification and crystallization steps. Biotechnological methods involving microbial fermentation and enzyme conversion from xylose are also employed, offering a safer and more environmentally friendly alternative to chemical methods.; Xylitol production historically relied on chemical methods, which are energy-intensive and labor-intensive. Biotechnological methods are gaining interest due to their potential for lower energy consumption, environmental sustainability, and safer production processes.

Technology Process of Pentitol

There total 149 articles about Pentitol 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: 100.0%

D-xylose (58-86-6) → XYLITOL (87-99-0)

Guidance literature:

With hydrogen; In water; at 120 ℃; for 0.166667h; under 15001.5 Torr; Temperature; Pressure;

Reference yield: 99.8%

arabinose → XYLITOL (87-99-0)

Guidance literature:

With hydrogen; Ru(III) chloride, reduced with H₂, inertated with N₂, passivated with O₂; In water; at 80 - 130 ℃; under 67506.8 Torr;

Reference yield: 99.0%

C24H54O5Si3 → XYLITOL (87-99-0)

Guidance literature:

With triethylsilane; tris(pentafluorophenyl)borate; In toluene; at 25 ℃; for 48h; Glovebox; Inert atmosphere;

DOI:10.1002/anie.202007415

upstream raw materials:

D-xylose

L-xylose

D-xylono-1,4-lactone

formaldehyd

Downstream raw materials:

1,5-di-O-tritylxylitol

DL-O¹,O³;O²,O⁴-dimethanediyl-xylitol

pentakis-O-(2,4-dinitro-phenyl)-xylitol

4,5-Bis-(phenyl-hydrazono)-pentane-1,2,3-triol

Refernces

• 1、 Li, Sha,Zhang, Jinliang,Xu, Hong,Feng, Xiaohai. "Improved xylitol production from d-arabitol by enhancing the coenzyme regeneration efficiency of the pentose phosphate pathway in Gluconobacter oxydans". . p. 1144 - 1150. Retrieved 2016.
• 2、 Suzuki, Shun-ichi,Sugiyama, Masakazu,Mihara, Yasuhiro,Hashiguchi, Ken-ichi,Yokozeki, Kenzo. "Novel enzymatic method for the production of xylitol from D-arabitol by Gluconobacter oxydans.". . p. 2614 - 2620. Retrieved 2002.
• 3、 Yadav, Mithilesh,Mishra, Dinesh Kumar,Hwang, Jin-Soo. "Catalytic hydrogenation of xylose to xylitol using ruthenium catalyst on NiO modified TiO2 support". . p. 110 - 116. Retrieved 2012.
• 4、 Audemar, Ma?té,Ramdani, Wahiba,Junhui, Tang,Raluca Ifrim, Andreea,Ungureanu, Adrian,Jér?me, Fran?ois,Royer, Sébastien,de Oliveira Vigier, Karine. "Selective Hydrogenation of Xylose to Xylitol over Co/SiO2 Catalysts". . p. 1973 - 1978. Retrieved 2020.
• 5、 Sugiyama, Masakazu,Suzuki, Shun-Ichi,Tonouchi, Naoto,Yokozeki, Kenzo. "Transaldolase/glucose-6-phosphate isomerase bifunctional enzyme and ribulokinase as factors to increase xylitol production from D-arabitol in Gluconobacter oxydans". . p. 2524 - 2532. Retrieved 2003.
• 6、 Graziani, Vittoria,Esposito, Assunta,Scognamiglio, Monica,Chambery, Angela,Russo, Rosita,Ciardiello, Fortunato,Troiani, Teresa,Potenza, Nicoletta,Fiorentino, Antonio,D'Abrosca, Brigida. "Spectroscopic characterization and cytotoxicity assessment towards human colon cancer cell lines of acylated cycloartane glycosides from Astragalus boeticus L.". . . Retrieved 2019.
• 7、 Zhang, Meng,Puri, Adarsh Kumar,Wang, Zhengxiang,Singh, Suren,Permaul, Kugen. "A unique xylose reductase from Thermomyces lanuginosus: Effect of lignocellulosic substrates and inhibitors and applicability in lignocellulosic bioconversion". . p. 374 - 381. Retrieved 2019.
• 8、 Lin, Lu,Qiu, Jiarong,Sun, Yong,Tang, Xing,Zeng, Xianhai,Zhang, Liangqing. "Efficient Synthesis of Sugar Alcohols over a Synergistic and Sustainable Catalyst". . p. 2467 - 2476. Retrieved 2021/07/16.
• 9、 Fongarland, Pascal,Freitas, Victoria D. S.,Paez, Ana,Philippe, Régis,Veyre, Laurent,Vilcocq, Léa. "Unexpected reactivity related to support effects during xylose hydrogenation over ruthenium catalysts". . p. 39387 - 39398. Retrieved 2021/12/27.