Ribitol

Ribitol
Names
	IUPAC name D-ribitol
	Systematic IUPAC name (2R,3s,4S)-Pentane-1,2,3,4,5-pentol
	Other names (2R,3s,4S)-Pentane-1,2,3,4,5-pentaol (not recommended); Adonit; Adonite; Adonitol; Adonitrol; Pentitol; 1,2,3,4,5-Pentanepentol; 1,2,3,4,5-Pentanol; Pentane-1,2,3,4,5-pentol
Identifiers
CAS Number	488-81-3 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1720524
ChEBI	CHEBI:15963 ;
ChemSpider	10254628 ;
ECHA InfoCard	100.006.987
EC Number	207-685-7;
Gmelin Reference	82894
KEGG	C00474 ;
PubChem CID	827;
UNII	353ZQ9TVDA ;
	InChI InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- Key: HEBKCHPVOIAQTA-ZXFHETKHSA-N ; InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-;
	SMILES O[C@H](CO)[C@@H](O)[C@@H](O)CO;
Properties
Chemical formula	C5H12O5
Molar mass	152.146 g·mol−1
Melting point	102 °C (216 °F; 375 K)
Magnetic susceptibility (χ)	-91.30·10−6 cm3/mol
Hazards
S-phrases (outdated)	S22 S24/25
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ribitol, or adonitol, is a crystalline pentose alcohol (C₅H₁₂O₅) formed by the reduction of ribose. It occurs naturally in the plant Adonis vernalis^[1] as well as in the cell walls of some Gram-positive bacteria, in the form of ribitol phosphate, in teichoic acids.^[2] 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.^[3]

References

^ Advances in Applied Microbiology. Academic Press. 1997-10-28. ISBN 9780080564586.
^ Seltmann, Guntram; Holst, Otto (2013-03-09). The Bacterial Cell Wall. Springer Science & Business Media. ISBN 9783662048788.
^ 1937-, Mathews, Christopher K. (2000). Biochemistry. Van Holde, K. E. (Kensal Edward), 1928-, Ahern, Kevin G. (3rd ed.). San Francisco, Calif.: Benjamin Cummings. p. 492. ISBN 0805330666. OCLC 42290721.

External links

Media related to Ribitol at Wikimedia Commons
GMD MS Spectrum
Safety MSDS data
Biological Magnetic Resonance Data Bank

[1] Advances in Applied Microbiology. Academic Press. 1997-10-28. ISBN 9780080564586.

[2] Seltmann, Guntram; Holst, Otto (2013-03-09). The Bacterial Cell Wall. Springer Science & Business Media. ISBN 9783662048788.

[3] 1937-, Mathews, Christopher K. (2000). Biochemistry. Van Holde, K. E. (Kensal Edward), 1928-, Ahern, Kevin G. (3rd ed.). San Francisco, Calif.: Benjamin Cummings. p. 492. ISBN 0805330666. OCLC 42290721.

[1]

[2]

[3]

Names

IUPAC name D-ribitol
Systematic IUPAC name (2R,3s,4S)-Pentane-1,2,3,4,5-pentol
Other names (2R,3s,4S)-Pentane-1,2,3,4,5-pentaol (not recommended) Adonit Adonite Adonitol Adonitrol Pentitol 1,2,3,4,5-Pentanepentol 1,2,3,4,5-Pentanol Pentane-1,2,3,4,5-pentol
Identifiers
CAS Number	488-81-3
3D model (JSmol)	Interactive image
Beilstein Reference	1720524
ChEBI	CHEBI:15963
ChemSpider	10254628
ECHA InfoCard	100.006.987
EC Number	207-685-7
Gmelin Reference	82894
KEGG	C00474
PubChem CID	827
UNII	353ZQ9TVDA
InChI InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5- Key: HEBKCHPVOIAQTA-ZXFHETKHSA-N InChI=1/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-
SMILES O[C@H](CO)[C@@H](O)[C@@H](O)CO
Properties
Chemical formula	C₅H₁₂O₅
Molar mass	152.146 g·mol⁻¹
Melting point	102 °C (216 °F; 375 K)
Magnetic susceptibility (χ)	-91.30·10⁻⁶ cm³/mol
Hazards
S-phrases (outdated)	S22 S24/25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).