Threitol

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470609419

| Reference =[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/377619 Threitol] at Sigma-Alrich

| ImageFile =threitol.png

| ImageSize =180px

| SystematicName = (2R,3R)-Butane-1,2,3,4-tetrol

| IUPACName=D-Threitol{{cite web | url=https://iupac.qmul.ac.uk/2carb/19.html | title=2-Carb-19 }}

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 2418-52-2

| Beilstein = 1719752

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 48300

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 147828

| DrugBank = DB03278

| EINECS = 621-282-7

| Gmelin = 1782960

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C16884

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = 6DN82XBT5M

| PubChem =169019

| InChI = 1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1

| InChIKey = UNXHWFMMPAWVPI-QWWZWVQMBP

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UNXHWFMMPAWVPI-QWWZWVQMSA-N

| SMILES = OC[C@@H](O)[C@H](O)CO

}}

|Section2={{Chembox Properties

| Formula =C₄H₁₀O₄

| MolarMass =122.12

| Appearance =Solid

| Density =

| MeltingPtC = 88 to 90

| MeltingPt_notes =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHS_ref={{cite web |title=D-Threitol |url=https://pubchem.ncbi.nlm.nih.gov/compound/169019#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=12 December 2021 |language=en}}

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|332+313|337+313|362|403+233|405|501}}

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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 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.{{cite book|last1=Elks|first1=J.|title=Dictionary of Drugs|last2=Ganellin|first2=C. R.|year=1990|doi=10.1007/978-1-4757-2085-3|isbn=978-1-4757-2087-7}}

It serves as a cryoprotectant (antifreeze agent) in the Alaskan beetle Upis ceramboides.{{cite journal| title=Cryoprotectant biosynthesis and the selective accumulation of threitol in the freeze-tolerant Alaskan beetle, Upis ceramboides |author1=Walters, K. R. Jr |author2=Pan, Q. |author3=Serianni, A. S. |author4=Duman, J. G. | journal=Journal of Biological Chemistry |year=2009 |volume= 284 |issue=25 | pages=16822–16831 | doi=10.1074/jbc.M109.013870|pmc=2719318 | pmid=19403530|doi-access=free }}