Ribitol

{{Use dmy dates|date=March 2023}} {{chembox | Watchedfields = changed | verifiedrevid = 464382143 | ImageFile = Ribitol.svg | SystematicName = (2''R'',3''S'',4''S'')-Pentane-1,2,3,4,5-pentol | IUPACName = <small>D</small>-Ribitol<ref>{{cite web | url=https://iupac.qmul.ac.uk/2carb/19.html | title=2-Carb-19 }}</ref> | OtherNames = (2''R'',3''S'',4''S'')-Pentane-1,2,3,4,5-pentaol (not recommended)<br />Adonit<br />Adonite<br />Adonitol<br />Adonitrol<br />Pentitol<br />1,2,3,4,5-Pentanepentol<br />1,2,3,4,5-Pentanol<br />Pentane-1,2,3,4,5-pentol |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 488-81-3 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 15963 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 10254628 | ChEMBL = 3137744 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 353ZQ9TVDA | PubChem = 827 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C00474 | EINECS = 207-685-7 | Beilstein = 1720524 | Gmelin = 82894 | 3DMet = | SMILES = O[C@H](CO)[C@@H](O)[C@@H](O)CO | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = HEBKCHPVOIAQTA-ZXFHETKHSA-N | InChI = 1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- }} |Section2={{Chembox Properties | C=5 | H=12 | O=5 | Appearance = | Density = | MeltingPtC = 102 | BoilingPt = | Solubility = | MagSus = −91.30·10⁻⁶ cm³/mol }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Ribitol''', or '''adonitol''', is a crystalline pentose alcohol (C₅H₁₂O₅) formed by the reduction of ribose. It occurs naturally in the plant ''Adonis vernalis''<ref>{{Cite book|url=https://books.google.com/books?id=6Gn38-UqvbwC&pg=PA170|title=Advances in Applied Microbiology|date=28 October 1997|publisher=Academic Press|isbn=9780080564586|language=en}}</ref> as well as in the cell walls of some Gram-positive bacteria, in the form of ribitol phosphate, in teichoic acids.<ref>{{Cite book|url=https://books.google.com/books?id=j637CAAAQBAJ&pg=PA134|title=The Bacterial Cell Wall|last1=Seltmann|first1=Guntram|last2=Holst|first2=Otto|date=9 March 2013|publisher=Springer Science & Business Media|isbn=9783662048788|language=en}}</ref> It also forms part of the chemical structure of riboflavin and flavin mononucleotide (FMN), which is a nucleotide coenzyme used by many enzymes, the so-called flavoproteins.<ref>{{Cite book|title=Biochemistry|author=Mathews, Christopher K.|date=2000|publisher=Benjamin Cummings|others=Van Holde, K. E. (Kensal Edward), 1928-, Ahern, Kevin G.|isbn=0805330666|edition=3rd|location=San Francisco, Calif.|pages=492|oclc=42290721}}</ref>

Ribitol is one of four stereoisomers having the formula {{chem2|C5H12O5}}: * <small>D</small>-arabitol and <small>L</small>-arabitol * Ribitol (non-chiral) * Xylitol (non-chiral)

== References == <references />

==External links== *{{Commons category-inline}} *[http://gmd.mpimp-golm.mpg.de/Spectrums/6C5A1810-9E0F-4A2D-8842-70A237692F3B.aspx GMD MS Spectrum] *[http://ptcl.chem.ox.ac.uk/MSDS/AD/adonitol.html Safety MSDS data] {{Webarchive|url=https://web.archive.org/web/20071011133424/http://ptcl.chem.ox.ac.uk/MSDS/AD/adonitol.html |date=11 October 2007 }} *[http://www.bmrb.wisc.edu/metabolomics/mol_summary/index.php?molName=adonitol&id=bmse000062&whichTab=0 Biological Magnetic Resonance Data Bank] {{Webarchive|url=https://web.archive.org/web/20200922054144/http://www.bmrb.wisc.edu/metabolomics/mol_summary/index.php?molName=adonitol&id=bmse000062&whichTab=0 |date=22 September 2020 }}

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Category:Sugar alcohols Category:Orphan drugs

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