tartronic acid

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470481857

| ImageFile = Tartronic_acid.svg

| ImageSize =

| PIN = Hydroxypropanedioic acid

| OtherNames = tartronic acid,
2-tartronic acid,
hydroxymalonic acid,
2-hydroxymalonic acid

|Section1={{Chembox Identifiers

| InChI1 = 1/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)

| InChIKey1 = ROBFUDYVXSDBQM-UHFFFAOYAD

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ROBFUDYVXSDBQM-UHFFFAOYSA-N

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

| CASNo = 80-69-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 34T0025E0L

| EINECS = 201-301-1

| PubChem = 45

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 44

| SMILES = O=C(O)C(O)C(=O)O

| InChI = 1/C3H4O5/c4-1(2(5)6)3 (7)8/h1,4H,(H,5,6)(H,7,8)

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 16513

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C02287

}}

|Section2={{Chembox Properties

| Formula = C₃H₄O₅

| MolarMass = 120.06 g/mol

| Appearance = white solid

| Density = 1.849 g/cm³

| MeltingPtC = 159

| MeltingPt_notes = (decomposes)

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| NFPA-H=2 | NFPA-F=0 | NFPA-R=0

}}

|Section4={{Chembox Related

| OtherFunction_label = carboxylic acids

| OtherFunction = Tartaric acid
Malic acid
Mesoxalic acid
Lactic acid
3-Hydroxypropionic acid
Malonic acid
Propionic acid
Oxalic acid

| OtherCompounds = Glyceric acid
Glyceraldehyde
Tartonaldehyde
Glycerol

}}

}}

Tartronic acid or 2-hydroxymalonic acid is an organic compound with the structural formula of HOHC(CO₂H)₂. This dicarboxylic acid is related to malonic acid. It is a white solid. It is produced by oxidation of glycerol:

:{{chem2|HOCH2CH(OH)CH2OH + 2 O2 -> HO2CCH(OH)CO2H + 2 H2O}}

Glyceric acid {{chem2|HOCH2CH(OH)CO2H}} is an intermediate.{{cite journal |doi=10.1007/s00253-009-2124-3|title=Biotechnological production of d-glyceric acid and its application |year=2009 |last1=Habe |first1=Hiroshi |last2=Fukuoka |first2=Tokuma |last3=Kitamoto |first3=Dai |last4=Sakaki |first4=Keiji |journal=Applied Microbiology and Biotechnology |volume=84 |issue=3 |pages=445–452 |pmid=19621222 |s2cid=9144557 }}{{cite journal |doi=10.1016/S1872-2067(19)63301-2|title=Selective oxidation of glycerol in a base-free aqueous solution: A short review |year=2019 |last1=Yang |first1=Lihua |last2=Li |first2=Xuewen |last3=Chen |first3=Ping |last4=Hou |first4=Zhaoyin |journal=Chinese Journal of Catalysis |volume=40 |issue=7 |pages=1020–1034 |s2cid=196894235 |doi-access=free }}

Its derivative, 2-methyltartronic acid, is isomalic acid.{{cite journal |doi=10.1107/S0567740878008596|title=Order–disorder phenomena in structures of carboxylic acids: The structures of fluoromalonic acid and hydroxymalonic acid at 20 and –150°C |year=1978 |last1=Roelofsen |first1=G. |last2=Kanters |first2=J. A. |last3=Kroon |first3=J. |last4=Doesburg |first4=H. M. |last5=Koops |first5=T. |journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry |volume=34 |issue=8 |pages=2565–2570 |doi-access=free |bibcode=1978AcCrB..34.2565R }}