Detail of "6728-31-0"

Reference

Identification of volatile aroma compounds from oxidized frozen whitefish (Coregonus clupeaformis)

Identification of volatile aroma compounds from oxidized frozen whitefish (Coregonus clupeaformis). Josephson, David B.; Lindsay, Robert C.; Stuiber, David A. (Dep. Food Sci., Univ. Wisconsin-Madison, Madison, WI 53706, USA). Can. Inst. Food Sci. Technol. J., 17(3), 178-82 (English) 1984. CODEN: CFSTB3. ISSN: 0315-5463. DOCUMENT TYPE: Journal CA Section: 17 (Food and Feed Chemistry) Volatile compds. collected on Tenax GC at 21° from oxidized whitefish (C. clupeaformis) were sepd. by fused silica capillary gas chromatog. and identified by mass spectrometry and retention indexes (IE). The major volatile compds. found in oxidized whitefish that were absent in freshly caught whitefish included (E,Z)- [4313-02-4] and (E,E)-2,4-heptadienal [4313-03-5], (E,Z)- [25152-83-4] and (E,E)-2,4-decadienal [25152-84-5], pentanal [110-62-3], (Z-E)- [78468-46-9] and (E,E)-3,5-octadien-2-one [30086-02-3], (Z,E)- [93128-37-1] and (E,E)-3,5-nonadien-2-one [80387-31-1], 3-octen-2-one [1669-44-9], 1-penten-3-one [1629-58-9], 2,3-pentanedione [600-14-6], and 1-pentadecene [13360-61-7]. Hexanal [66-25-1] (~40% total peak area) was the most abundant volatile compd. in oxidized whitefish, and much smaller amts. were found in fresh whitefish. (Z)-4-Heptenal [6728-31-0], a compd. reported to be responsible for the off-flavor that develops in frozen stored cod (Gadus morhua), was not found in oxidized whitefish.

Perfume compositions

Perfume compositions. (Naarden International N. V., Neth.). Neth. Appl. NL 7608333 31 Jan 1978, 11 pp. (Dutch). (Netherlands). CODEN: NAXXAN. CLASS: IC: A61K007-46. APPLICATION: NL 76-8333 27 Jul 1976. DOCUMENT TYPE: Patent CA Section: 62 (Essential Oils and Cosmetics) Section cross-reference(s): 23 4-Heptynal [21891-36-1], an intermediate in manuf. of the perfume and flavoring components cis-4-heptenal [6728-31-0], 2,6-nonadienal [26370-28-5], and 2,6-nonadienol [7786-44-9] and of the new perfume component 2,6-nonadienenitrile [67019-89-0], is readily prepd. from 1-butyne [107-00-6] and acrolein [107-02-8]. Thus, 240 g MeOH was cooled to 5°, 202 g HBr was passed in over 1.5 h, and 140 g acrolein was added over a further 1.5 h and stirred. The lower layer contained a-bromopropionaldehyde di-Me acetal (I) [36255-44-4]. To 0.75 L NH3 in a sep. vessel were added successively 0.1 g Fe(NO3)3, 3.5 g Li in small portions, 0.1 g Ph3CH, 34 g 1-butyne to form the Li butynylide, and 0.5 mol I with stirring. After evapn. of the NH3 and addn. of 105 g hexane, 25 g MeOH, and 105 mL water, the hexane layer was isolated, evapd., and distd. under vacuum to yield 4-heptynal di-Me acetal [66840-10-6], which was cleaved to 4-heptynal. 4-Heptynal was hydrogenated over Lindlar catalyst to cis-4-heptynal, and 15 g of this compd. was added to a refluxing mixt. of 12 g cyanoacetic acid [372-09-8] and a small amt. of b-alanine in 150 mL C6H6. The reaction mixt. was evapd. and the residue dissolved in 300 mL pyridine and refluxed for 1.5 h in the presence of Cu powder. The pyridine was distd. off, and the residue was distd. under vacuum to yield 7 g 2,6-nonadienenitrile. This compd. had a cucumber-like odor with reseda notes.