A | B | C | D | E | F | G | H | CH | I | J | K | L | M | N | O | P | Q | R | S | T | U | V | W | X | Y | Z | 0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9
Names | |
---|---|
IUPAC name
D-Threitol[2]
| |
Systematic IUPAC name
(2R,3R)-Butane-1,2,3,4-tetrol | |
Identifiers | |
3D model (JSmol)
|
|
1719752 | |
ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.150.149 |
EC Number |
|
1782960 | |
KEGG | |
PubChem CID
|
|
UNII | |
| |
| |
Properties | |
C4H10O4 | |
Molar mass | 122.12 |
Appearance | Solid |
Melting point | 88 to 90 °C (190 to 194 °F; 361 to 363 K) |
Hazards | |
GHS labelling:[3] | |
Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
|
Threitol is the chiral four-carbon sugar alcohol with the molecular formula C4H10O4. It is primarily used as an intermediate in the chemical synthesis of other compounds. It exists in the enantiomorphic forms D-threitol and L-threitol, the reduced forms of D- and L-threose. It is the diastereomer of erythritol, which is used as a sugar substitute.
In living organisms, threitol is found in the edible fungus Armillaria mellea.[4] It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetle Upis ceramboides.[5]
See also
- Antifreeze protein
- Dithiothreitol, a thiol derivative of threitol
References
- ^ Threitol at Sigma-Alrich
- ^ "2-Carb-19".
- ^ "D-Threitol". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
- ^ Elks, J.; Ganellin, C. R. (1990). Dictionary of Drugs. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7.
- ^ Walters, K. R. Jr; Pan, Q.; Serianni, A. S.; Duman, J. G. (2009). "Cryoprotectant biosynthesis and the selective accumulation of threitol in the freeze-tolerant Alaskan beetle, Upis ceramboides". Journal of Biological Chemistry. 284 (25): 16822–16831. doi:10.1074/jbc.M109.013870. PMC 2719318. PMID 19403530.
External links
- Media related to Threitol at Wikimedia Commons
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