Parasorbic acid

{{DISPLAYTITLE:Parasorbic acid}}

{{Chembox

| Name =Parasorbic acid

| ImageFile =Parasorbic acid2.svg

| ImageSize =150px

| ImageAlt = Skeletal formula of parasorbic acid

| ImageFile1 = Parasorbic-acid-3d-ball.png

| ImageSize1 = 175

| ImageAlt1 = Ball-and-stick model of the parasorbic acid molecule

| IUPACName = (6S)-5,6-dihydro-6-methyl-2H-pyran-2-one

| OtherNames = 2-methyl-2,3-dihydropyran-6-one, 2-Hexen-5-olide, 5-hydroxy-2-Hexenoic acid δ-lactone, parasorbic acid, sorbic oil, γ-Hexenolactone, (+)-(6S)-Parasorbic acid

|Section1={{Chembox Identifiers

| CASNo_Ref =

| CASNo = 10048-32-5

| ChemSpiderID_Ref =

| ChemSpiderID = 23250

| ChEBI_Ref =

| ChEBI = 7926

| ChEMBL_Ref =

| ChEMBL = 2252704

| DrugBank = DB14121

| KEGG = C08502

| PubChem = 441575

| UNII_Ref =

| UNII = DCN48OUK3T

| InChI = 1S/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3

| InChIKey = DYNKRGCMLGUEMN-UHFFFAOYSA-N

| SMILES = CC1OC(C=CC1)=O

}}

|Section2={{Chembox Properties

| Formula =C6H8O2

| MolarMass =112.128

| Appearance = colorless liquid

| Density = 1.0 g/mL (estimated)

| BoilingPtC = 227

| BoilingPt_notes = estimated

| Solubility = 50 g/L

| SolubleOther = estimated

}}

|Section3={{Chembox Thermochemistry

| DeltaHf = -360.03 kJ·mol−1

}}

|Section4={{Chembox Hazards

| Hazards_ref=

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|}}

| NFPA-H = 2

| NFPA-F = 2

| NFPA-R = 0

| MainHazards =

| FlashPtC =

| AutoignitionPtC =

}}

}}

Parasorbic acid is the cyclic lactone of sorbic acid. Thermal treatment or hydrolysis converts the lactone to sorbic acid.{{cite book|title=Natural food antimicrobial systems |year=2000|isbn=0-8493-2047-X|pages=637|url=https://books.google.com/books?id=_rmdPO9BNBcC&q=%22sorbic+acid%22&pg=PA637|editor= A. S. Naidu}}

Toxicity

Parasorbic acid is toxic and causes indigestion and nausea, however cooking and exposure to moisture convert it to the benign food preservative sorbic acid.{{cite journal |vauthors=Mason PL, Gaunt IF, Hardy J, Kiss IS, Butterworth KR, Gangolli SD |title=Long-term toxicity of parasorbic acid in rats |journal=Food Cosmet Toxicol |volume=14 |issue=5 |pages=387–394 |year=1976 |pmid=1010506 |doi=10.1016/S0015-6264(76)80174-5}}

See also

References

{{Reflist}}

{{DEFAULTSORT:Parasorbic acid}}

Category:Delta-lactones

Category:Preservatives

Category:Enones