Parasorbic acid

Parasorbic acid
Skeletal formula of parasorbic acid
Ball-and-stick model of the parasorbic acid molecule
Names
IUPAC name
(6S)-5,6-dihydro-6-methyl-2H-pyran-2-one
Other names
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
Identifiers
CAS Number
  • 10048-32-5
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:7926
ChEMBL
  • ChEMBL2252704
ChemSpider
  • 23250
DrugBank
  • DB14121
KEGG
  • C08502
PubChem CID
  • 441575
UNII
  • DCN48OUK3T
CompTox Dashboard (EPA)
  • DTXSID50871944 Edit this at Wikidata
InChI
  • InChI=1S/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3
    Key: DYNKRGCMLGUEMN-UHFFFAOYSA-N
  • CC1OC(C=CC1)=O
Properties
Chemical formula
 C6H8O2
Molar mass 112.128
Appearance colorless liquid
Density 1.0 g/mL (estimated)
Boiling point 227 °C (441 °F; 500 K) estimated
Solubility in water
 50 g/L
Solubility estimated
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)
 -360.03 kJ·mol−1
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Warning
H315, H319, H335
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

Parasorbic acid is the cyclic lactone of sorbic acid. Thermal treatment or hydrolysis converts the lactone to sorbic acid.[1]

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.[2]

See also

References

  1. ^ A. S. Naidu, ed. (2000). Natural food antimicrobial systems. p. 637. ISBN 0-8493-2047-X.
  2. ^ Mason PL, Gaunt IF, Hardy J, Kiss IS, Butterworth KR, Gangolli SD (1976). "Long-term toxicity of parasorbic acid in rats". Food Cosmet Toxicol. 14 (5): 387–394. doi:10.1016/S0015-6264(76)80174-5. PMID 1010506.