Threitol
Names | |
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IUPAC name D-Threitol[2] | |
Systematic IUPAC name (2R,3R)-Butane-1,2,3,4-tetrol | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 1719752 |
ChEBI |
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ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.150.149 |
EC Number |
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Gmelin Reference | 1782960 |
KEGG |
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PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | 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] | |
Pictograms | |
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 |
Chemical compound
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
- Antifreeze protein
- Dithiothreitol, a thiol derivative of threitol
References
- ^ Threitol at Sigma-Alrich
- ^ "2-Carb-19".
- ^ "D-Threitol". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
- ^ Elks, J.; Ganellin, C. R. (1990). Dictionary of Drugs. doi:10.1007/978-1-4757-2085-3. ISBN 978-1-4757-2087-7.
- ^ 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.
External links
- Media related to Threitol at Wikimedia Commons
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Alcohols
Alcohols found in alcoholic drinks |
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Medical alcohol |
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Toxic alcohols |
alcohols (1°)
Methanol | |
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Ethanol |
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Butanol |
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Straight-chain saturated C1 — C9 |
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Straight-chain saturated C10 — C19 |
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Straight-chain saturated C20 — C29 |
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Straight-chain saturated C30 — C39 |
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Straight-chain saturated C40 — C49 |
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alcohols (2°)
alcohols (3°)
- 2-Methyl-2-pentanol
- 2-Methylheptan-2-ol
- 2-Methylhexan-2-ol
- 3-Methyl-3-pentanol
- 3-Methyloctan-3-ol
- Diacetone alcohol
- Ethchlorvynol
- Methylpentynol
- Nonafluoro-tert-butyl alcohol
- tert-Amyl alcohol
- tert-Butyl alcohol
- Triphenylethanol
- Triphenylmethanol
Monohydric alcohols |
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Dihydric alcohols | |
Trihydric alcohols | |
Polyhydric alcohols (sugar alcohols) |
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fatty alcohols
unsaturated
fatty alcohols
- 3-Methyl-3-pentanol
- Erucyl alcohol
- Linolenyl alcohol
- Linoleyl alcohol
- Oleyl alcohol
- Palmitoleyl alcohol
- tert-Amyl alcohol
- tert-Butyl alcohol
C1 — C7 |
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Deoxy sugar alcohols | |
Cyclic sugar alcohols | |
Glycylglycitols |
Monoterpene alcohols | |
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Sesquiterpene alcohols | |
Diterpene alcohols |
- 1,3-Difluoro-2-propanol
- 2,2,2-Trifluoroethanol
- 2-Fluoroethanol
- Nonafluoro-tert-butyl alcohol
- Trifluoromethanol
- Category
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