threonic acid

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 445763107

| Name = {{sm|l}}-threonic acid

| ImageFile = L-threonic acid.png

| ImageSize = 180px

| IUPACName = (2R,3S)-2,3,4-Trihydroxybutanoic acid

| Section1 = {{Chembox Identifiers

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

| CASNo = 3909-12-4

| CASNo_Comment = (D/L)

| CASNo2_Ref = {{cascite|changed|??}}

| CASNo2 = 20246-26-8

| CASNo2_Comment = (D)

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo3 = 7306-96-9

| CASNo3_Comment = (L)

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

| UNII1 = NTD0MI8XRT

| UNII1_Comment = (D/L)

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = 75B0PMW2JF

| UNII2_Comment = (L)

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 133224

| ChemSpiderID_Comment = (D)

| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID1 = 4573940

| ChemSpiderID1_Comment = (L)

| PubChem = 151152

| PubChem_Comment = (D)

| PubChem1 = 5460407

| PubChem1_Comment = (L)

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

| SMILES_Comment = (D)

| SMILES1 = C([C@@H]([C@H](C(=O)O)O)O)O

| SMILES1_Comment = (L)

| InChI = 1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1

| InChIKey = JPIJQSOTBSSVTP-GBXIJSLDSA-N

| InChI_Comment = (D)

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = JPIJQSOTBSSVTP-STHAYSLISA-N

| StdInChI_Comment = (L)}}

| Section2 = {{Chembox Properties

| C=4|H=8|O=5

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

| ConjugateBase = Threonate

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Threonic acid is a sugar acid derived from threose. The {{sm|l}}-isomer is a metabolite of ascorbic acid (vitamin C).{{cite journal | journal = Annual Review of Nutrition | volume = 6 | pages = 365–406 | year = 1986 | pmid = 3015170 | doi = 10.1146/annurev.nu.06.070186.002053 | title = The Biochemical Functions of Ascorbic Acid | author = S Englard and S Seifter}} One study suggested that because {{sm|l}}-threonate inhibits DKK1 expression in vitro, it may have potential in treatment of androgenic alopecia.{{Cite journal| last1 = Kwack | first1 = M. H.| last2 = Ahn | first2 = J. S.| last3 = Kim | first3 = M. K.| last4 = Kim | first4 = J. C.| last5 = Sun| first5 = Y. K.| title = Preventable effect of L-threonate, an ascorbate metabolite, on androgen-driven balding via repression of dihydrotestosteroneinduced dickkopf-1 expression in human hair dermal papilla cells| doi = 10.5483/BMBRep.2010.43.10.688| journal = BMB Reports| volume = 43| issue = 10| pages = 688–692| year = 2010| pmid = 21034532| doi-access = free}}