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Identification |
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YMDB ID | YMDB00778 |
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Name | Xylitol |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | D-Xylitol, also known as meso-xylitol or xylisorb, 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. D-Xylitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Within yeast, D-xylitol participates in a number of enzymatic reactions. In particular, D-xylitol can be converted into D-xylulose; which is catalyzed by the enzyme D-xylulose reductase. In addition, D-xylitol can be biosynthesized from D-xylose; which is mediated by the enzyme trifunctional aldehyde reductase/xylose reductase/glucose 1-dehydrogenase (nadp(+)). In yeast, D-xylitol is involved in the metabolic pathway called the xylitol degradation pathway. |
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Structure | |
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Synonyms | - (2R,3R,4S)-Pentane-1,2,3,4,5-pentaol
- D-Xylitol
- Eutrit
- Fluorette
- Klinit
- Kylit
- L-xylitol
- meso-xylitol
- Pentitol
- Wood sugar alcohol
- XLS
- Xylit
- Xylite
- Xylitol
- Xylitol C
- Xyliton
- xylo-Pentitol
- Xylisorb
- Xylisorb 300
- Xylisorb 700
- Xylitab 100
- Xylitab 300
- Xylitab DC
- Xylite (sugar)
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CAS number | 87-99-0 |
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Weight | Average: 152.1458 Monoisotopic: 152.068473494 |
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InChI Key | HEBKCHPVOIAQTA-SCDXWVJYSA-N |
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InChI | InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+ |
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IUPAC Name | (2R,4S)-pentane-1,2,3,4,5-pentol |
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Traditional IUPAC Name | (2R,4S)-pentane-1,2,3,4,5-pentol |
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Chemical Formula | C5H12O5 |
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SMILES | OC[C@H](O)[C@@H](O)[C@H](O)CO |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Sugar alcohols |
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Alternative Parents | |
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Substituents | - Sugar alcohol
- Monosaccharide
- Secondary alcohol
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | 93.5 °C |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 642 mg/mL [MERCK INDEX (1996)] | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | |
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SMPDB Pathways | |
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KEGG Pathways | Pentose and glucuronate interconversions | ec00040 |  |
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SMPDB Reactions | Not Available |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0gb9-0962000000-d64d55ac02d5d037d679 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0gb9-0962000000-d64d55ac02d5d037d679 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0gba-0941000000-0d418fcb2879fa30315e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0gba-0941000000-1842afabd092c907a920 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03dl-9100000000-738016d8bd07caed9ccc | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-0a4i-6033900000-a5ac27dc62580d112ccd | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-014i-9600000000-42440e0b7d380a297360 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-02t9-9000000000-d41bf19405e393c2be01 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-02t9-9000000000-3d14b034f5655c90b890 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-1900000000-4f856d537cc8252ecc47 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9300000000-403bacad5117a30582df | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9000000000-eb879b27e7b182cfe7c0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udu-9400000000-3db6454ab3e2315aa744 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0btl-9200000000-b84c400427c7e44eb4dd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-c37624fb31a8cb33b163 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Richard, P., Toivari, M. H., Penttila, M. (1999). "Evidence that the gene YLR070c of Saccharomyces cerevisiae encodes a xylitol dehydrogenase." FEBS Lett 457:135-138.10486580
- Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
- UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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Synthesis Reference: | Hasumi, Fumihiko; Teshima, Chitoku; Okura, Ichiro. Synthesis of xylitol by reduction of xylulose with the combination of hydrogenase and xylulose reductase. Chemistry Letters (1996), (8), 597-598. |
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