Threonic acid

l-Threonic acid
Names
	IUPAC name (2R,3S)-2,3,4-Trihydroxybutanoic acid
	Other names Threonate
Identifiers
CAS Number	3909-12-4 (D/L) ; 20246-26-8 (D) ; 7306-96-9 (L) ;
3D model (JSmol)	(D): Interactive image; (L): Interactive image;
ChemSpider	133224 (D) ; 4573940 (L) ;
PubChem CID	151152 (D); 5460407 (L);
UNII	NTD0MI8XRT (D/L) ; 75B0PMW2JF (L) ;
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 Key: JPIJQSOTBSSVTP-STHAYSLISA-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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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

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.
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.

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[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.