Arabitol
 | |
| Names | |
|---|---|
| IUPAC name
D-Arabinitol[2] | |
| Systematic IUPAC name
(2R,4R)-Pentane-1,2,3,4,5-pentol | |
| Other names
(2R,4R)-Pentane-1,2,3,4,5-pentaol (not recommended) Arabitol | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.006.988 |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C5H12O5 | |
| Molar mass | 152.146 g·mol−1 |
| Appearance | Prismatic crystals |
| Melting point | 103 °C (217 °F; 376 K) |
| 729 g/L[3] | |
| Hazards | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Arabitol, or arabinitol, is a sugar alcohol. It can be formed by the reduction of either arabinose. Some organic acid tests check for the presence of D-arabitol, which may indicate overgrowth of intestinal microbes such as Candida albicans or other yeast/fungus species.[4]
Arabitol and lyxitol are diastereomeric pentitols, differing in the configuration of two stereocenters. Arabitol was initially produced, soon after its discovery, through the catalytic reduction of D-arabinose or D-lixose.[5] It can be obtained in two spatial forms: L-arabitol and D-arabitol.
Production
[edit]Industrial production of arabitol has traditionally relied on chemical reduction of oxidized arabinose derivatives, including lactones, arabinonic acid and lixonic acid. These processes require high temperatures (around 100 °C) and expensive catalysts, and generally involve extensive purification of the feedstock prior to catalytic reduction.[6]
Biotechnological production routes have also been developed.[7] L-Arabitol can be obtained by microbial fermentation using organisms capable of metabolizing L-arabinose, including Candida tropicalis, Pichia stipitis and Debaryomyces hansenii, as well as genetically engineered strains of Saccharomyces cerevisiae. Most reported studies have used batch cultivation with synthetic L-arabinose as substrate, although lignocellulosic hydrolysates such as sisal bagasse and soybean flour hydrolysates have also been evaluated.[8][9]
References
[edit]- ↑ Merck Index, 11th Edition, 789
- ↑ "2-Carb-19".
- ↑ Arabitol at the Human Metabolome Database
- ↑ "Candida and Yeast Overgrowth". Archived from the original on 2010-03-02. Retrieved 2010-03-16.
- ↑ Hajny, G. J. (January 1964). "D-Arabitol Production by Endomycopsis chodati". Applied Microbiology. 12 (1): 87–92. doi:10.1128/am.12.1.87-92.1964. ISSN 0003-6919. PMC 1058070. PMID 14111539.
- ↑ Kumdam, Himabindu; Narayana Murthy, Shweta; Gummadi, Sathyanarayana N (2013-05-09). "Production of ethanol and arabitol by Debaryomyces nepalensis: influence of process parameters". AMB Express. 3 (1) 23. doi:10.1186/2191-0855-3-23. ISSN 2191-0855. PMC 3671168. PMID 23659479.
- ↑ Kordowska-Wiater, M. (2015-04-08). "Production of arabitol by yeasts: current status and future prospects". Journal of Applied Microbiology. 119 (2): 303–314. doi:10.1111/jam.12807. ISSN 1364-5072. PMID 25809659.
- ↑ de Medeiros, Lorena Lucena; da Silva, Flávio Luiz Honorato; de Queiroz, Angela Lima Menêses; de Oliveira, Ysrael Simões Lins; de Souza Junior, Evanildo Francisco; Madruga, Marta Suely; da Conceição, Marta Maria (2020-07-28). "Structural-chemical characterization and potential of sisal bagasse for the production of polyols of industrial interest". Brazilian Journal of Chemical Engineering. 37 (3): 451–461. doi:10.1007/s43153-020-00049-3. ISSN 0104-6632.
- ↑ Garcia Sanchez, Rosa; Karhumaa, Kaisa; Fonseca, César; Sànchez Nogué, Violeta; Almeida, João RM; Larsson, Christer U; Bengtsson, Oskar; Bettiga, Maurizio; Hahn-Hägerdal, Bärbel; Gorwa-Grauslund, Marie F (2010-06-15). "Improved xylose and arabinose utilization by an industrial recombinant Saccharomyces cerevisiae strain using evolutionary engineering". Biotechnology for Biofuels. 3 (1) 13. Bibcode:2010BB......3...13G. doi:10.1186/1754-6834-3-13. ISSN 1754-6834. PMC 2908073. PMID 20550651.
Further reading
[edit]- Herman, Anna; Herman, Andrzej Przemysław (15 January 2022). "Could Candida Overgrowth Be Involved in the Pathophysiology of Autism?". Journal of Clinical Medicine. 11 (2): 442. doi:10.3390/jcm11020442. PMC 8778531. PMID 35054136.
External links
[edit]
Media related to Arabitol at Wikimedia Commons
