FComEx: Ribitol (PC000075)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:01 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000075

FoodDB Record

FDB022083

Chemical Information

Name

Ribitol

Description

D-Arabitol or D-arabinitol, also known as klinit or lyxitol, belongs to the class of organic compounds known as sugar alcohols, a type of polyols. These are hydrogenated forms of carbohydrates in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. A polyol is an organic compound containing many hydroxyls. D-Arabitol is neutral compound. Polyols, classified by the number of carbon atoms and include the sugar alcohols, are linked to the pentose phosphate pathway (PPP). The PPP generates, NADPH and pentoses (5-carbon sugars) as well as ribose 5-phosphate, a precursor for the synthesis of nucleotides. While the pentose phosphate pathway oxidizes glucose, its primary role is anabolic rather than catabolic. Polyols, including D-arabitol, accumulates in body fluids in individuals with two defects in PPP, involving the enzymes ribose-5-phosphate isomerase (RPI) and transaldolase (PMID: 18987987). A patient with leukoencephalopathy and peripheral neuropathy, with a strong brain-CSF-plasma gradient of C5 polyols such as D-arabitol, was identified as suffering from RPI deficiency. Another patient displaying mainly liver problems and increased concentrations of polyols, mainly D-arabitol, was diagnosed with transaldolase deficiency. However, the mechanism of pathophysiology of polyols in patients with defects in the PPP is poorly understood. It is thought that D-arabitol is a metabolic end-product in humans. The mechanisms of brain and neuronal damage in RPI deficiency may result from polyol accumulation, causing secondary brain dysfunction (PMID: 16435225). D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway. D-Arabitol accumulated in a Penicillium rubens strain deleted of four highly expressed biosynthetic gene clusters that produce penicillin, roquefortine, chrysogine and fungisporin. The transcriptome of the P. rubens strain had changed when the gene cluster was removed, resulting in increased expression of D-arabinitol 4-dehydrogenase (PMID: 32376967). D-Arabitol, a fungal metabolite, is used as a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861; PMID: 10647119). It is also a metabolite of Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659).

CAS Number

488-81-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2,3,4,5-pentanepentol	hmdb
Adonit	hmdb
Adonite	hmdb
Adonitol	hmdb
D-Adonitol	ChEBI
D-Ribitol	ChEBI
L-Ribitol	ChEBI
pentitol	hmdb
Ribitol	hmdb

Chemical Formula

C5H12O5

IUPAC name

(2R,3s,4S)-pentane-1,2,3,4,5-pentol

InChI Identifier

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-

InChI Key

HEBKCHPVOIAQTA-ZXFHETKHSA-N

Isomeric SMILES

OC[C@H](O)[C@H](O)[C@H](O)CO

Average Molecular Weight

152.1458

Monoisotopic Molecular Weight

152.068473494

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents