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Threitol information


Threitol[1]
Names
IUPAC name
D-Threitol[2]
Systematic IUPAC name
(2R,3R)-Butane-1,2,3,4-tetrol
Identifiers
CAS Number
  • 2418-52-2 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1719752
ChEBI
  • CHEBI:48300 checkY
ChemSpider
  • 147828 checkY
DrugBank
  • DB03278
ECHA InfoCard 100.150.149 Edit this at Wikidata
EC Number
  • 621-282-7
Gmelin Reference
1782960
KEGG
  • C16884 checkY
PubChem CID
  • 169019
UNII
  • 6DN82XBT5M checkY
CompTox Dashboard (EPA)
  • DTXSID801336604 Edit this at Wikidata
InChI
  • 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
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)
Hazards
GHS labelling:[3]
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
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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Infobox references

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]

  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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Threitol

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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...

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Dithiothreitol

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4-Dimercaptobutane-2,3-diol D-threo-1,4-Dimercapto-2,3-butanediol 1,4-Dithio-D-threitol Cleland's reagent Reductacryl Identifiers CAS Number 3483-12-3 Y 3D model...

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Erythritol

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is a tradename for erythritol. Erythritol tetranitrate Pentaerythritol Threitol, the diastereomer of erythritol O'Neil M, ed. (2006). The Merck Index:...

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Sugar alcohol

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Ethylene glycol (2-carbon) Glycerol (3-carbon) Erythritol (4-carbon) Threitol (4-carbon) Arabitol (5-carbon) Xylitol (5-carbon) Ribitol (5-carbon) Mannitol...

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Methanol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Beetle

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molecule consisting of a sugar bound to a fatty acid, and the sugar-alcohol, threitol. Conversely, desert dwelling beetles are adapted to tolerate high temperatures...

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Threose

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referred to as "threo", and are anti in the isomer referred to as "erythro". Threitol Threonic acid Threose nucleic acid Merck Index, 11th Edition, 9317 https://iupac...

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Erythrulose reductase

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In enzymology, an erythrulose reductase (EC 1.1.1.162) is an enzyme that catalyzes the chemical reaction erythritol + NADP+ ⇌ {\displaystyle \rightleftharpoons...

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Butanediol

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Butanetetrol (butanetetraol), including 4-carbon sugar alcohols Erythritol Threitol "Butanediol". PubChem. "Propanediol, methyl-". PubChem. This set index...

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Ethanol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Isopropyl alcohol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Transesterification

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Sorbitol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Ethchlorvynol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Xylitol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Glycerol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Amyl alcohol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Williamson ether synthesis

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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C4H10O4

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g/mol) may refer to: Erythritol, a sugar alcohol (or polyol) food additive Threitol, a four-carbon sugar alcohol; the diastereomer of erythritol This set index...

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Ethylene glycol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Isobutanol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Inositol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Butanol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Isomalt

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Maltitol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Primary alcohol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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Benzyl alcohol

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alcohols) Pentaerythritol Ethylene glycol (C2) Glycerol, Propylene glycol (C3) Erythritol, Threitol (C4) Xylitol (C5) Mannitol, Sorbitol (C6) Volemitol (C7)...

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