Threonic acid

Threonic acid is a sugar acid derived from threose. The l-isomer is a metabolite of ascorbic acid (vitamin C).[1] One study suggested that because l-threonate inhibits DKK1 expression in vitro, it may have potential in treatment of androgenic alopecia.[2]

l-Threonic acid
L-threonic acid.png
Names
IUPAC name
(2R,3S)-2,3,4-Trihydroxybutanoic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1 ☒N
    Key: JPIJQSOTBSSVTP-STHAYSLISA-N ☒N
  • (D): InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1
    Key: JPIJQSOTBSSVTP-GBXIJSLDSA-N
  • (D): C([C@H]([C@@H](C(=O)O)O)O)O
  • (L): C([C@@H]([C@H](C(=O)O)O)O)O
Properties
C4H8O5
Molar mass 136.103 g·mol−1
Conjugate base Threonate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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ReferencesEdit

  1. ^ S Englard and S Seifter (1986). "The Biochemical Functions of Ascorbic Acid". Annual Review of Nutrition. 6: 365–406. doi:10.1146/annurev.nu.06.070186.002053. PMID 3015170.
  2. ^ Kwack, M. H.; Ahn, J. S.; Kim, M. K.; Kim, J. C.; Sun, Y. K. (2010). "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". BMB Reports. 43 (10): 688–692. doi:10.5483/BMBRep.2010.43.10.688. PMID 21034532.