Threitol

Last updated
Threitol [1]
Threitol.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 621-282-7
1782960
KEGG
PubChem CID
UNII
  • InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1 Yes check.svgY
    Key: UNXHWFMMPAWVPI-QWWZWVQMSA-N Yes check.svgY
  • 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
AppearanceSolid
Melting point 88 to 90 °C (190 to 194 °F; 361 to 363 K)
Hazards
GHS labelling: [3]
GHS-pictogram-exclam.svg
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).
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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.

Contents

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.
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