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Threitol

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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^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1719752
ChEBI	CHEBI:48300^Y
ChemSpider	147828^Y
DrugBank	DB03278
ECHA InfoCard	100.150.149
EC Number	621-282-7
Gmelin Reference	1782960
KEGG	C16884^Y
PubChem CID	169019
UNII	6DN82XBT5M^Y
CompTox Dashboard(EPA)	DTXSID801336604
InChI InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1^Y Key: UNXHWFMMPAWVPI-QWWZWVQMSA-N^Y 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
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 theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Threitol is thechiral four-carbonsugar alcohol with the molecular formula C₄H₁₀O₄. It is primarily used as an intermediate in the chemical synthesis of other compounds. It exists in theenantiomorphic forms D-threitol and L-threitol, the reduced forms of D- and L-threose. It is thediastereomer oferythritol, which is used as a sugar substitute.

In living organisms, threitol is found in theedible fungusArmillaria mellea.^[4]It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetleUpis ceramboides.^[5]

References

[edit]

^Threitol at Sigma-Alrich
^"2-Carb-19".
^"D-Threitol".pubchem.ncbi.nlm.nih.gov. Retrieved12 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

[edit]

Media related toThreitol at Wikimedia Commons

Alcohols

By consumption

Alcohols found in alcoholic drinks	1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert-Amyl alcohol tert-Butyl alcohol Tryptophol
Medical alcohol	Ethchlorvynol Methylpentynol Methanol poisoning Ethanol
Toxic alcohols	Isopropyl alcohol Methanol

Primary
alcohols (1°)

Methanol	4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol
Ethanol	1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol
Butanol	2-Methyl-1-butanol Isobutanol n-Butanol
Straight-chain saturated C₁ — C₉	Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic)
Straight-chain saturated C₁₀ — C₁₉	1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol
Straight-chain saturated C₂₀ — C₂₉	1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol
Straight-chain saturated C₃₀ — C₃₉	1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol
Straight-chain saturated C₄₀ — C₄₉	1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol

Secondary
alcohols (2°)

Propylene glycol methyl ether

Tertiary
alcohols (3°)

Hydric alcohols

Monohydric alcohols	Methanol (C₁) Ethanol (C₂) Isopropanol (C₃) 1-Butanol (C₄) 1-Pentanol (C₅) Cetyl alcohol (C₁₆)
Dihydric alcohols	Ethylene glycol Propylene glycol
Trihydric alcohols	Glycerol
Polyhydric alcohols (sugar alcohols)	Pentaerythritol Ethylene glycol (C₂) Glycerol,Propylene glycol (C₃) Erythritol,Threitol (C₄) Xylitol (C₅) Mannitol,Sorbitol (C₆) Volemitol (C₇)

Amyl alcohols

Aromatic alcohols

Saturated
fatty alcohols

Branched and
unsaturated
fatty alcohols

Sugar alcohols

C₁ — C₇	Methylene glycol (C₁) Ethylene glycol (C₂) Glycerol (C₃) Erythritol (C₄) Threitol (C₄) Arabitol (C₅) Ribitol (C₅) Xylitol (C₅) Mannitol (C₆) Sorbitol (C₆) Galactitol (C₆) Iditol (C₆) Volemitol (C₇)
Deoxy sugar alcohols	Fucitol
Cyclic sugar alcohols	Inositol
Glycylglycitols	Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol

Terpene alcohols

Monoterpene alcohols	Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol
Sesquiterpene alcohols	Bisabolol Farnesol Nerolidol Patchoulol
Diterpene alcohols	Phytol