Hexanal is a naturally occurring, volatile C-6 aldehyde formed via the lipoxygenase pathway in plants from linoleic acid ( Hildebrand, 1989 ). Volatiles formed by this pathway in wounded plants have antifungal properties, as shown by early
Peter L. Sholberg and Paul Randall
J. Song, R. Leepipattanawit, W. Deng, and R.M. Beaudry
Hexanal vapor inhibited hyphae growth of P. expansum Link. and B. cinerea Pers. on PDA media and on apple slices. After 48 hours exposure to 100 μl·liter–1 hexanal, the hyphae growth of both fungi was ≈ 50% that of nontreated controls. At a concentration of 250 μl·liter–1, neither fungi grew during the treatment period, however, some growth of both fungi occurred 120 hours after treatment. At concentrations of hexanal vapor of ≥450 μl·liter–1, the growth of both fungi ceased, and the organisms were apparently killed, neither showing regrowth when moved to air. When fungi were allowed to germinate and grow for 48 hours in hexanal-free air, a subsequent 48-hour exposure to 250 μl·liter–1 hexanal slowed colony growth relative to controls for several days and a 48-hour exposure to 450 μl·liter–1 stopped growth completely. Concentrations of hexanal that inhibited fungal growth on PDA also retarded decay lesion development on `Golden Delicious' and on `Jonagold' apple slices. Hexanal treatment stimulated aroma volatile production in `Jonagold' and `Golden Delicious' apple slices with hexanol and hexylacetate production strongly enhanced after 20 to 30 hours of treatment. A small amount of butylhexanoate and hexylhexanoate production also was noted. Since hexanal was converted to aroma-related volatiles by the fruit, the possibility of developing a system for nonresiduel antifungal agent is promising. This possibility was examined in modified-atmosphere packages.
Lihua Fan, Jun Song, and Randolph Beaudry
Hexanal vapor is a natural, metabolizable fungicide that inhibits fungal activity and enhances the aroma biosynthesis in sliced apple fruit. Whole apple fruit were inoculated at two points per fruit with Penicillium expansum at a concentration of 0.5 × 105 spore/ml and treated with hexanal vapors. Inoculated fruit were exposed to hexanal for 48 hr and kept for another 72 hr in hexanal-free air at 22°C. Treatments included 8.2–12.3 μmol·L–1 (200–300 ppm), 14.5-18.6 μmol·L–1 (350–450 ppm), and 24.8-28.9 μmol·L–1 (600–700 ppm), each with an air control. At a concentration of 200–300 ppm hexanal, there was no fungal growth during treatment, but lesion development was evident on 100% of the treated fruit following cessation of treatment. After 72 hr holding in air, lesion diameter was significantly smaller for treated fruit. When inoculated apple fruit were exposed to 350–450 ppm and 600–700 ppm hexanal vapors, the decay rate was 44.7% and 23.9%, respectively, while the decay rate of inoculated control apple fruit was 100% and 98%, respectively, after 72 hr holding in air. The development of aroma volatiles was investigated for both treated and untreated whole apple fruit. Hexanal was actively converted to aroma volatiles by `Golden Delicious' fruit and there was no detectable hexanal emanations. The amount of hexylacetate, hexylbutanoate, hexylhexanoate, hexylpropionate, butylhexanoate, and hexyl-2-methybutanoate were about 2- to 4-fold higher in treated apple fruit than in untreated apple fruit. `Mutsu' apple fruit were treated with 350–450 ppm hexanal for 48 hr and processed into apple sauce within 4 hr. An informal sensory evaluation for processed `Mutsu' apple revealed no apparent flavor difference between treated and control fruit sauce.
Jun Song, Rujida Leepipattanawit, Weimin Deng, and Randolph M. Beaudry
Hexanal vapor inhibited hyphae growth of Penicillium expansum and Botrytis cinerea on potato dextrose agar (PDA) and on apple (Malus domestica Borkh.) slices. After 48 hours exposure to 4.1 μmol·L-1 (100 ppm) hexanal, the hyphae growth of both fungi was about 50% that of untreated controls. At a concentration of 10.3 μmol·L-1 (250 ppm), neither fungus grew during the treatment period, however, some growth of both fungi occurred 120 hours after treatment. At concentrations of hexanal vapor of 18.6 μmol·L-1 (450 ppm) or more, the growth of both fungi ceased and the organisms were apparently killed, neither showing regrowth when moved to air. When fungi were allowed to germinate and grow for 48 hours in hexanal-free air, a subsequent 48-hour exposure to 10.3 μmol·L-1 hexanal slowed colony growth relative to controls for several days and a 48-hour exposure to 18.6 μmol·L-1 stopped growth completely. Concentrations of hexanal that inhibited fungal growth on PDA also retarded decay lesion development on `Golden Delicious' and on `Jonagold' apple slices. Hexanal was actively converted to aroma volatiles in `Jonagold' and `Golden Delicious' apple slices, with hexanol and hexylacetate production strongly enhanced after 20 to 30 hours treatment. A small amount of butylhexanoate and hexylhexanoate production was also noted. Within 16 hours after treatment, no hexanal could be detected emanating from treated fruit. Since hexanal was metabolized to aroma-related volatiles by the fruit slices, the possibility of hexanal being an essentially residue-less antifungal agent seems likely. The possibility of developing a system for treating apple slices with hexanal in modified-atmosphere packages was also examined. The permeability of low-density polyethylene (LDPE) film to hexanal and hexylacetate was, respectively, about 500- and 1000-fold higher than LDPE permeability to O2. The permeability of both compounds increased exponentially with temperature, with hexanal permeability increased 6-fold while hexylacetate increased only 2.5-fold between 0 and 30 °C.
R.J. Bender, J.K. Brecht, E.A. Baldwin, and T.M.M. Malundo
To determine the effects of fruit maturity, storage temperature, and controlled atmosphere (CA) on aroma volatiles, mature-green (MG) and tree-ripe (TR) `Tommy Atkins' mangoes (Mangifera indica L.) were stored for 21 days in air or in CA (5% O2 plus 10% or 25% CO2). The MG fruit were stored at 12 °C and the TR fruit at either 8 or 12 °C. Homogenized mesocarp tissue from fruit that had ripened for 2 days in air at 20 °C after the 21-day storage period was used for aroma volatile analysis. The TR mangoes produced much higher levels of all aroma volatiles except hexanal than did MG fruit. Both MG and TR mangoes stored in 25% CO2 tended to have lower terpene (especially p-cymene) and hexanal concentrations than did those stored in 10% CO2 and air-stored fruit. Acetaldehyde and ethanol levels tended to be higher in TR mangoes from 25% CO2 than in those from 10% CO2 or air storage, especially at 8 °C. Inhibition of volatile production by 25% CO2 was greater in MG than in TR mangoes, and at 8 °C compared to 12 °C for TR fruit. However, aroma volatile levels in TR mangoes from the 25% CO2 treatment were in all cases equal to or greater than those in MG fruit treatments. The results suggest that properly selected atmospheres, which prolong mango shelf life by slowing ripening processes, can allow TR mangoes to be stored or shipped without sacrificing their superior aroma quality.
Ravindranath V. Kanamangala, Niels O. Maness, Michael W. Smith, Gerald H. Brusewitz, Sue Knight, and Bhaggi Chinta
The unextracted and reduced lipid (supercritical carbon dioxide extraction of 22% and 27% (w/w) of total lipids) pecan [Carya illinoinensis (Wangenh.) K. Koch] kernels packaged in 21% O2, 79% N2 were analyzed for color, hexanal, sensory, fresh weight, and lipid class changes periodically during 37 weeks of storage at 25 °C and 55% relative humidity. Pecan nutmeats were lightened by partial lipid extraction. The pecan testa darkened (decreasing chromameter L*) with storage time. Most color changes occurred in the first 18 weeks. Hexanal concentration of reduced-lipid pecans was negligible throughout storage, while unextracted pecans reached excessive levels by week 22 of storage. Hexanal concentration, indicative of rancidity, was in agreement with sensory analysis results with the hexanal threshold level for objectionable rancidity ranging from 7 to 11 mg·kg-1 pecans. Weight change was negligible during storage, except in 27% reduced-lipid pecans. Free fatty acids increased with storage and were significantly higher in unextracted pecans than the reduced-lipid pecans at 0, 10, 18, 32, and 37 weeks of storage. Shelf life of pecans with partial lipid extraction was longer than unextracted pecans. In addition to decreasing the total amount of lipid available for oxidation, the free fatty acid lipid component that correlated with the development of rancidity was reduced by extraction.
Bo Zhang, Xue-Ren Yin, Ji-Yuan Shen, Kun-Song Chen, and Ian B. Ferguson
, 2002 ), and LOX-mediated peroxidation converts linoleic acid and linolenic acid to n -hexanal and ( E )-2-hexenal, respectively ( Hatanaka, 1993 ). The positive relationship between LOX activity and C6 aldehydes has been observed in olive ( Olea
John C. Beaulieu, Rebecca E. Stein-Chisholm, and Deborah L. Boykin
are 33 compounds recovered in substantial levels or believed to have aroma impact (J.C. Beaulieu, unpublished data). These are: ethyl acetate, ( E )-2-hexanal, ( Z )-3-hexenal, hexanal, heptanol ( E , Z )-2,6-nonadienal, ( E )-2-hexenol, ( Z )-2
James J. Polashock, Robert A. Saftner, and Matthew Kramer
are active against bacteria, fungi, and viruses ( Cowan, 1999 ; Dorman and Deans, 2000 ; Gardini et al., 2001 ; Utama et al., 2002 ). The incorporation of high concentrations of various antimicrobial volatiles, including hexanal and trans -2
Jessica L. Gilbert, Michael L. Schwieterman, Thomas A. Colquhoun, David G. Clark, and James W. Olmstead
, including trans-2-hexenol, trans-2-hexenal, linalool, α-terpineol, geraniol, limonene, cis-3-hexen-1-ol, nerol, 1-penten-3-ol, hexanal, and 1,8-cineole ( Baloga et al., 1995 ; Du et al., 2011 ; Hirvi and Honkanen, 1983 ; Horvat and Senter, 1985