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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
KEGG
UNII
  • 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
C6H8O2
Molar mass 112.128
Appearance colorless liquid
Density 1.0 g/mL (estimated)
Boiling point 227 °C (441 °F; 500 K) estimated
50 g/L
Solubility estimated
Thermochemistry
-360.03 kJ·mol−1
Hazards
GHS labelling:
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).

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

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.

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.