Parasorbic acid

Last updated
Parasorbic acid
Parasorbic acid2.svg
Parasorbic-acid-3d-ball.png
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
PubChem CID
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
Appearancecolorless 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:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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. [1]

Contents

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.
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