Threitol

Threitol is a four-carbon sugar alcohol with the molecular formula C4H10O4. It is primarily used as an intermediate in the chemical synthesis of other compounds. It is the diastereomer of erythritol, which is used as a sugar substitute.

Threitol[1]
Names
Systematic IUPAC name
(2R,3R)-Butane-1,2,3,4-tetrol
Other names
(2R,3R)-Butane-1,2,3,4-tetraol (not recommended)
Identifiers
3D model (JSmol)
1719752
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.150.149
EC Number
  • 621-282-7
1782960
KEGG
UNII
  • InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1 Y
    Key: UNXHWFMMPAWVPI-QWWZWVQMSA-N Y
  • InChI=1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1
    Key: UNXHWFMMPAWVPI-QWWZWVQMBP
  • OC[C@@H](O)[C@H](O)CO
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:[2]
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 [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

In living organisms, threitol is found in the edible fungus Armillaria mellea.[3] It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetle Upis ceramboides.[4]

See also

References
  1. Threitol at Sigma-Alrich
  2. "D-Threitol". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  3. Elks, J.; Ganellin, C. R. (1990). Dictionary of Drugs. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7.
  4. 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.
  • Media related to Threitol at Wikimedia Commons


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