Threonic acid

Last updated
l-Threonic acid
L-threonic acid.png
IUPAC name
(2R,3S)-2,3,4-Trihydroxybutanoic acid
3D model (JSmol)
PubChem CID
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
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]

Related Research Articles

Antioxidants are compounds that inhibit oxidation. Oxidation is a chemical reaction that can produce free radicals, thereby leading to chain reactions that may damage the cells of organisms. Antioxidants such as thiols or ascorbic acid terminate these chain reactions. To balance the oxidative stress, plants and animals maintain complex systems of overlapping antioxidants, such as glutathione and enzymes, produced internally, or the dietary antioxidants vitamin C and vitamin E.

Vitamin C Nutrient in citrus fruits and other food

Vitamin C is a vitamin found in various foods and sold as a dietary supplement. It is used to prevent and treat scurvy. Vitamin C is an essential nutrient involved in the repair of tissue and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant.

Dehydroascorbic acid (DHA) is an oxidized form of ascorbic acid. It is actively imported into the endoplasmic reticulum of cells via glucose transporters. It is trapped therein by reduction back to ascorbate by glutathione and other thiols. The (free) chemical radical semidehydroascorbic acid (SDA) also belongs to the group of oxidized ascorbic acids.

L-gulonolactone oxidase is an enzyme that produces vitamin C, but is non-functional in Haplorrhini, in some bats, and in guinea pigs. It catalyzes the reaction of L-gulono-1,4-lactone with oxygen to L-xylo-hex-3-gulonolactone and hydrogen peroxide. It uses FAD as a cofactor. The L-xylo-hex-3-gulonolactone (2-keto-gulono-gamma-lactone) is able to convert to hexuronic acid spontaneously, without enzymatic action.


l-Kynurenine is a metabolite of the amino acid l-tryptophan used in the production of niacin.

Cholesterol 7 alpha-hydroxylase

Cholesterol 7 alpha-hydroxylase also known as cholesterol 7-alpha-monooxygenase or cytochrome P450 7A1 (CYP7A1) is an enzyme that in humans is encoded by the CYP7A1 gene which has an important role in cholesterol metabolism. It is a cytochrome P450 enzyme, which belongs to the oxidoreductase class, and converts cholesterol to 7-alpha-hydroxycholesterol, the first and rate limiting step in bile acid synthesis.

Peroxisome proliferator-activated receptor gamma Protein-coding gene in the species Homo sapiens

Peroxisome proliferator-activated receptor gamma, also known as the glitazone receptor, or NR1C3 is a type II nuclear receptor that in humans is encoded by the PPARG gene.


G-protein coupled receptor 31 also known as 12-(S)-HETE receptor is a protein that in humans is encoded by the GPR31 gene. The human gene is located on chromosome 6q27 and encodes a G-protein coupled receptor protein composed of 319 amino acids.

Leukotriene B<sub>4</sub> receptor 2

Leukotriene B4 receptor 2, also known as BLT2, BLT2 receptor, and BLTR2, is an Integral membrane protein that is encoded by the LTB4R2 gene in humans and the Ltbr2 gene in mice.


Dickkopf-related protein 1 is a protein that in humans is encoded by the DKK1 gene.


Cytochrome P450 2C18 is a protein that in humans is encoded by the CYP2C18 gene.


Solute carrier family 23 member 1 is a protein that in humans is encoded by the SLC23A1 gene.


Leukotriene-B(4) omega-hydroxylase 1 is an enzyme involved in the metabolism various endogenous substrates and xenobiotics. Most notable substrate of the enzyme is leukotriene B4, a potent mediator of inflammation. The enzyme is encoded by the CYP4F2 gene in humans.

12-Hydroxyeicosatetraenoic acid

12-Hydroxyeicosatetraenoic acid (12-HETE) is a derivative of the 20 carbon polyunsaturated fatty acid, arachidonic acid, containing a hydroxyl residue at carbon 12 and a 5Z,8Z,10E,14Z Cis–trans isomerism configuration in its four double bonds. It was first found as a product of arachidonic acid metabolism made by human and bovine platelets through their 12S-lipoxygenase enzyme(s). However, the term 12-HETE is ambiguous in that it has been used to indicate not only the initially detected "S" stereoisomer, 12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid, made by platelets, but also the later detected "R" stereoisomer, 12(R)-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acid made by other tissues through their 12R-lipoxygenase enzyme, ALOX12B. The two isomers, either directly or after being further metabolized, have been suggested to be involved in a variety of human physiological and pathological reactions. Unlike hormones which are secreted by cells, travel in the circulation to alter the behavior of distant cells, and thereby act as Endocrine signalling agents, these arachidonic acid metabolites act locally as Autocrine signalling and/or Paracrine signaling agents to regulate the behavior of their cells of origin or of nearby cells, respectively. In these roles, they may amplify or dampen, expand or contract cellular and tissue responses to disturbances.

L-galactonolactone dehydrogenase (EC, galactonolactone dehydrogenase, L-galactono-gamma-lactone dehydrogenase, L-galactono-gamma-lactone:ferricytochrome-c oxidoreductase, GLDHase, GLDase) is an enzyme with systematic name L-galactono-1,4-lactone:ferricytochrome-c oxidoreductase. This enzyme catalyses the following chemical reaction

Medicinal fungi are fungi which contain metabolites or can be induced to produce metabolites through biotechnology to develop prescription drugs. Compounds successfully developed into drugs or are under research include antibiotics, anti-cancer drugs, cholesterol and ergosterol synthesis inhibitors, psychotropic drugs, immunosuppressants and fungicides.

12-Hydroxyheptadecatrienoic acid Chemical compound

12-Hydroxyheptadecatrenoic acid is a 17 carbon metabolite of the 20 carbon polyunsaturated fatty acid, arachidonic acid. It was first detected and structurally defined by P. Wlodawer, Bengt I. Samuelsson, and M. Hamberg as a product of arachidonic acid metabolism made by microsomes isolated from sheep seminal vesicle glands and by intact human platelets. 12-HHT is less ambiguously termed 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid to indicate the S stereoisomerism of its 12-hydroxyl residue and the Z, E, and E cis-trans isomerism of its three double bonds. The metabolite was for many years thought to be merely a biologically inactive byproduct of prostaglandin synthesis. More recent studies, however, have attached potentially important activity to it.

13-Hydroxyoctadecadienoic acid

13-Hydroxyoctadecadienoic acid (13-HODE) is the commonly used term for 13(S)-hydroxy-9Z,11E-octadecadienoic acid. The production of 13(S)-HODE is often accompanied by the production of its stereoisomer, 13(R)-hydroxy-9Z,11E-octadecadienoic acid. The adjacent figure gives the structure for the (S) stereoisomer of 13-HODE. Two other naturally occurring 13-HODEs that may accompany the production of 13(S)-HODE are its cis-trans isomers viz., 13(S)-hydroxy-9E,11E-octadecadienoic acid and 13(R)-hydroxy-9E,11E-octadecadienoic acid. Studies credit 13(S)-HODE with a range of clinically relevant bioactivities; recent studies have assigned activities to 13(R)-HODE that differ from those of 13(S)-HODE; and other studies have proposed that one or more of these HODEs mediate physiological and pathological responses, are markers of various human diseases, and/or contribute to the progression of certain diseases in humans. Since, however, many studies on the identification, quantification, and actions of 13(S)-HODE in cells and tissues have employed methods that did not distinguish between these isomers, 13-HODE is used here when the actual isomer studied is unclear.

20-Hydroxyeicosatetraenoic acid

20-Hydroxyeicosatetraenoic acid, also known as 20-HETE or 20-hydroxy-5Z,8Z,11Z,14Z-eicosatetraenoic acid, is an eicosanoid metabolite of arachidonic acid that has a wide range of effects on the vascular system including the regulation of vascular tone, blood flow to specific organs, sodium and fluid transport in the kidney, and vascular pathway remodeling. These vascular and kidney effects of 20-HETE have been shown to be responsible for regulating blood pressure and blood flow to specific organs in rodents; genetic and preclinical studies suggest that 20-HETE may similarly regulate blood pressure and contribute to the development of stroke and heart attacks. Additionally the loss of its production appears to be one cause of the human neurological disease, Hereditary spastic paraplegia. Preclinical studies also suggest that the overproduction of 20-HETE may contribute to the progression of certain human cancers, particularly those of the breast.

Intravenous ascorbic acid

Intravenous Ascorbic Acid, is a type of therapy that delivers soluble ascorbic acid directly into the bloodstream, either administered via injection or infusion. Intravenous ascorbic acid is used as a dietary supplement for nutritional deficiencies and also, as complementary therapy to cancer treatments. The use of intravenous ascorbic acid as a cancer treatment or co-treatment has been a controversial topic since the emergence of misleading data in the 1970s. However, more recent research suggests an ability to decrease inflammation in the patient and to improve symptoms related to disease processes, and side effects of standard cancer treatments.


  1. S Englard and S Seifter (1986). "The Biochemical Functions of Ascorbic Acid". Annual Review of Nutrition. 6: 365–406. doi:10.1146/ 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.