Arabitol

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Wikipedia

Arabitol[1]
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 Edit this at Wikidata
UNII
  • InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1 checkY
    Key: HEBKCHPVOIAQTA-QWWZWVQMSA-N checkY
  • InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1
    Key: HEBKCHPVOIAQTA-QWWZWVQMBW
  • OC[C@@H](O)C(O)[C@H](O)CO
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)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

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

  1. ↑ Merck Index, 11th Edition, 789
  2. ↑ "2-Carb-19".
  3. ↑ Arabitol at the Human Metabolome Database
  4. ↑ "Candida and Yeast Overgrowth". Archived from the original on 2010-03-02. Retrieved 2010-03-16.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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

  • Media related to Arabitol at Wikimedia Commons