Parasorbic acid

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Parasorbic acid
Skeletal formula of parasorbic acid
Ball-and-stick model of the parasorbic acid molecule
Names
IUPAC name
6-methyl-5,6-dihydro-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
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)
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]

Toxicity[edit]

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[edit]

References[edit]

  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.