Wikipedia

Threitol

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.

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[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:[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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

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References

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  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 19403530.16822-16831&rft.date=2009&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2719318#id-name=PMC&rft_id=info:pmid/19403530&rft_id=info:doi/10.1074/jbc.M109.013870&rft.au=Walters, K. R. Jr&rft.au=Pan, Q.&rft.au=Serianni, A. S.&rft.au=Duman, J. G.&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2719318&rfr_id=info:sid/en.wikipedia.org:Threitol" class="Z3988">
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