3-Hydroxyvaleric acid

{{chembox

| Verifiedfields = changed

| verifiedrevid = 477218913

| ImageFile=3-hydroxypentanoic acid.png

| ImageSize=200px

| PIN=3-Hydroxypentanoic acid

| OtherNames=β-Hydroxyvaleric acid
β-Hydroxypentanoic acid

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 96952

| InChI = 1/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

| InChIKey = REKYPYSUBKSCAT-UHFFFAOYAT

| SMILES1 = O=C(O)CC(O)CC

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

| StdInChI = 1S/C5H10O3/c1-2-4(6)3-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

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

| StdInChIKey = REKYPYSUBKSCAT-UHFFFAOYSA-N

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

| CASNo=10237-77-1

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

| UNII = 9D6K40J6UZ

| PubChem=107802

| SMILES=CCC(CC(=O)O)O

}}

|Section2={{Chembox Properties

| C=5 | H=10 | O=3

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=784.8 g/L (estimated)

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

3-Hydroxyvaleric acid (3-hydroxypentanoic acid) is the organic compound with the formula {{chem2|CH3CH2CH(OH)CH2CO2H}}. It is one of the hydroxypentanoic acids.{{Ullmann |doi=10.1002/14356007.a13_507|title=Hydroxycarboxylic Acids, Aliphatic |year=2000 |last1=Miltenberger |first1=Karlheinz |isbn=3527306730}} It is made from odd carbon fatty acids in the liver and rapidly enters the brain. As opposed to 4-carbon ketone bodies, 3-hydroxyvaleric acid is anaplerotic, meaning it can refill the pool of TCA cycle intermediates. The triglyceride triheptanoin is used clinically to produce 3-hydroxyvalerate (the carboxylate form).{{cite journal| title=Parenteral and Enteral Metabolism of Anaplerotic Triheptanoin in Normal Rats| author=Renée P. Kinman| author2=Takhar Kasumov| author3=Kathryn A. Jobbins| author4=Katherine R. Thomas| author5=Jillian Adams| author6=Lisa N. Brunengraber| author7=Gerd Kutz| author8=Wolf-Ulrich Brewer| author9=Charles R. Roe| author10=Henri Brunengraber| name-list-style=amp| journal=Am J Physiol Endocrinol Metab| pages=E860–E866| volume=291| doi=10.1152/ajpendo.00366.2005| year=2006| pmid=16705058| issue=4 | url = http://ajpendo.physiology.org/cgi/reprint/00366.2005v1.pdf }}