{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477350323 | Reference = <ref>''Merck Index'', 11th Edition, '''789'''</ref> | ImageFile = Arabitol.svg | IUPACName = <small>D</small>-Arabinitol<ref>{{cite web | url=https://iupac.qmul.ac.uk/2carb/19.html | title=2-Carb-19 }}</ref> | SystematicName = (2''R'',4''R'')-Pentane-1,2,3,4,5-pentol | OtherNames = (2''R'',4''R'')-Pentane-1,2,3,4,5-pentaol (not recommended)<br />Arabitol | Section1 = {{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=7643-75-6 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 45Z1K06N9V | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 18333 | PubChem=94154 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 84971 | SMILES = OC[C@@H](O)C(O)[C@H](O)CO | InChI = 1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1 | InChIKey = HEBKCHPVOIAQTA-QWWZWVQMBW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HEBKCHPVOIAQTA-QWWZWVQMSA-N }} | Section2 = {{Chembox Properties | C=5 | H=12 | O=5 | Appearance=Prismatic crystals | Density= | MeltingPtC=103 | BoilingPt= | Solubility=729 g/L<ref>{{HMDB|0000568}}</ref> }} | Section3 = {{Chembox Hazards | NFPA-H = 0 | NFPA-F = 0 | NFPA-R = 0 | MainHazards= | FlashPt= | AutoignitionPt = }} }}
'''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 <small>D</small>-arabitol, which may indicate overgrowth of intestinal microbes such as ''Candida albicans'' or other yeast/fungus species.<ref>{{cite web|url=http://www.greatplainslaboratory.com/home/eng/candida.asp |title=Candida and Yeast Overgrowth |access-date=2010-03-16 |url-status=dead |archive-url=https://web.archive.org/web/20100302192738/http://www.greatplainslaboratory.com/home/eng/candida.asp |archive-date=2010-03-02 }}</ref>
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 <small>D</small>-arabinose or <small>D</small>-lixose.<ref>{{Cite journal |last=Hajny |first=G. J. |date=January 1964 |title=D-Arabitol Production by ''Endomycopsis chodati'' |url=https://doi.org/10.1128/am.12.1.87-92.1964 |journal=Applied Microbiology |volume=12 |issue=1 |pages=87–92 |doi=10.1128/am.12.1.87-92.1964 |pmid=14111539 |pmc=1058070 |issn=0003-6919}}</ref> It can be obtained in two spatial forms: <small>L</small>-arabitol and <small>D</small>-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.<ref>{{Cite journal |last1=Kumdam |first1=Himabindu |last2=Narayana Murthy |first2=Shweta |last3=Gummadi |first3=Sathyanarayana N |date=2013-05-09 |title=Production of ethanol and arabitol by Debaryomyces nepalensis: influence of process parameters |journal=AMB Express |volume=3 |issue=1 |article-number=23 |doi=10.1186/2191-0855-3-23 |doi-access=free |pmid=23659479 |issn=2191-0855|pmc=3671168 }}</ref>
Biotechnological production routes have also been developed.<ref>{{Cite journal |last=Kordowska-Wiater |first=M. |date=2015-04-08 |title=Production of arabitol by yeasts: current status and future prospects |url=https://doi.org/10.1111/jam.12807 |journal=Journal of Applied Microbiology |volume=119 |issue=2 |pages=303–314 |doi=10.1111/jam.12807 |pmid=25809659 |issn=1364-5072|url-access=subscription }}</ref> <small>L</small>-Arabitol can be obtained by microbial fermentation using organisms capable of metabolizing <small>L</small>-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 <small>L</small>-arabinose as substrate, although lignocellulosic hydrolysates such as sisal bagasse and soybean flour hydrolysates have also been evaluated.<ref>{{Cite journal |last1=de Medeiros |first1=Lorena Lucena |last2=da Silva |first2=Flávio Luiz Honorato |last3=de Queiroz |first3=Angela Lima Menêses |last4=de Oliveira |first4=Ysrael Simões Lins |last5=de Souza Junior |first5=Evanildo Francisco |last6=Madruga |first6=Marta Suely |last7=da Conceição |first7=Marta Maria |date=2020-07-28 |title=Structural-chemical characterization and potential of sisal bagasse for the production of polyols of industrial interest |url=https://doi.org/10.1007/s43153-020-00049-3 |journal=Brazilian Journal of Chemical Engineering |volume=37 |issue=3 |pages=451–461 |doi=10.1007/s43153-020-00049-3 |issn=0104-6632|url-access=subscription }}</ref><ref>{{Cite journal |last1=Garcia Sanchez |first1=Rosa |last2=Karhumaa |first2=Kaisa |last3=Fonseca |first3=César |last4=Sànchez Nogué |first4=Violeta |last5=Almeida |first5=João RM |last6=Larsson |first6=Christer U |last7=Bengtsson |first7=Oskar |last8=Bettiga |first8=Maurizio |last9=Hahn-Hägerdal |first9=Bärbel |last10=Gorwa-Grauslund |first10=Marie F |date=2010-06-15 |title=Improved xylose and arabinose utilization by an industrial recombinant Saccharomyces cerevisiae strain using evolutionary engineering |journal=Biotechnology for Biofuels |volume=3 |issue=1 |article-number=13 |doi=10.1186/1754-6834-3-13 |doi-access=free |pmid=20550651 |pmc=2908073 |bibcode=2010BB......3...13G |issn=1754-6834}}</ref>
==References== {{reflist}}
==Further reading== * {{cite journal |last1=Herman |first1=Anna |last2=Herman |first2=Andrzej Przemysław |title=Could Candida Overgrowth Be Involved in the Pathophysiology of Autism? |journal=Journal of Clinical Medicine |date=15 January 2022 |volume=11 |issue=2 |pages=442 |doi=10.3390/jcm11020442 |pmid=35054136 |pmc=8778531 |doi-access=free }}
==External links== *{{Commonscatinline}}
{{Alcohols}}
Category:Sugar alcohols