View source for Ribitol

{{Use dmy dates|date=March 2023}}
{{chembox
| Watchedfields = changed
| verifiedrevid = 464382143
| ImageFile = Ribitol structure.png
| 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<sup>−6</sup> cm<sup>3</sup>/mol
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
  }}
}}

'''Ribitol''', or '''adonitol''', is a crystalline [[pentose]] [[Alcohol (chemistry)|alcohol]] (C<sub>5</sub>H<sub>12</sub>O<sub>5</sub>) formed by the [[reduction (chemistry)|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 [[stereoisomer]]s 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 }}

{{Alcohols}}

[[Category:Sugar alcohols]]
[[Category:Orphan drugs]]


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