Threitol

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Threitol[1]
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 Edit this at Wikidata
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 checkY
    Key: UNXHWFMMPAWVPI-QWWZWVQMSA-N checkY
  • InChI=1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1
    Key: UNXHWFMMPAWVPI-QWWZWVQMBP
  • OC(O)(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:[3]
GHS07: Exclamation mark
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).
☒N verify (what is checkY☒N ?)

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

References

  1. ^ Threitol at Sigma-Alrich
  2. ^ "2-Carb-19".
  3. ^ "D-Threitol". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
  4. ^ Elks, J.; Ganellin, C. R. (1990). Dictionary of Drugs. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7.
  5. ^ 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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