Threonic acid

l-threonic acid

Names
IUPAC name (2R,3S)-2,3,4-Trihydroxybutanoic acid
Identifiers
CAS Number	3909-12-4 (D/L) Y 20246-26-8 (D) N 7306-96-9 (L) Y
3D model (JSmol)	(D): Interactive image (L): Interactive image
ChemSpider	133224 (D) N 4573940 (L) N
PubChem CID	151152  (D) 5460407  (L)
UNII	NTD0MI8XRT  (D/L) Y 75B0PMW2JF  (L) Y
CompTox Dashboard (EPA)	DTXSID60223339
InChI 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
SMILES (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
Chemical formula	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). N  verify  (what is  YN ?) Infobox references

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]

References

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.