Threitol

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
CAS Number	7493-90-5 (DL) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48300 ;
ChemSpider	147828 ;
ECHA InfoCard	100.150.149
KEGG	C16884 ;
PubChem CID	169019;
UNII	6DN82XBT5M ;
CompTox Dashboard (EPA)	DTXSID801336604 ;
	InChI InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1 Key: UNXHWFMMPAWVPI-QWWZWVQMSA-N ; InChI=1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1 Key: UNXHWFMMPAWVPI-QWWZWVQMBP;
	SMILES OC[C@@H](O)[C@H](O)CO;
Properties
Chemical formula	C4H10O4
Molar mass	122.12
Appearance	Solid
Melting point	88 to 90 °C (190 to 194 °F; 361 to 363 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Threitol is a sweet 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.

In living things, threitol is found in the edible fungus Armillaria mellea.^[2] It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetle Upis ceramboides.^[3]

References

^ Threitol at Sigma-Alrich
^ Elks, J.; Ganellin, C. R. (1990). "Dictionary of Drugs". doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7. {{cite journal}}: Cite journal requires |journal= (help)
^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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[1] Threitol at Sigma-Alrich

[ElksGanellin1990-2] Elks, J.; Ganellin, C. R. (1990). "Dictionary of Drugs". doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7. {{cite journal}}: Cite journal requires |journal= (help)

[3] 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1]

[2]

[3]

v t e Sugar alcohols
2-carbon	Ethylene glycol ^{[citation needed]}
3-carbon	Glycerol
4-carbon	Erythritol Threitol
5-carbon	Arabitol Ribitol Xylitol
6-carbon	Mannitol Sorbitol Galactitol Iditol
7-carbon	Volemitol
Deoxy sugar alcohols	Fucitol
Cyclic sugar alcohols	Inositol
Glycylglycitols	Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol

See also

References