Arabitol
Chemical compound
From Wikipedia, the free encyclopedia
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]
| |
| 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 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
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]
