C-20 Hydrocarbons of butterfat

Abstract

Hydrocarbons were isolated from butterfat by cold-finger molecular distillation at 35°. The three major hydrocarbons were identified as the C-20 compounds, 3,7,11,15-tetramethylhexadec-1-ene (phyt-l-ene), 3,7,11,15-tetramethylhexadec-2-ene (phyt-2-ene), and 3-methylene-7,11,15-trimethylhexadec-l-ene (neophytadiene).The following hydrocarbons were also shown to be present: 2,6,10-trimethyltridecane, n-pentade-cane, n-hexadecane, 5-methylhexadecane, n-heptadecane, n-octadecane, and 2,6,10,14-tetramethylhexadecane (phytane). Of these saturated hydrocarbons, n-octadecane was the most abundant. The total concentration of the hydrocarbons reported here is of the order of 30 ppm of butterfat. Neophytadiene, but not phyt-l-ene or phyt-2-ene, was also isolated from pasture grass.Cold-finger molecular distillation of butterfat has been used in the investigation into the compounds responsible for the desirable flavor of butter (Forss et ai, 1966(Forss et ai, , 1967 Stark et ai, 1973). The three major classes of compounds thus isolated were acids, lactones, and hydrocarbons. The present paper describes the identification of the major components of the hydrocarbon fraction.EXPERIMENTAL SECTION

Significance of the Nonvolatile Minor Compounds of the Neutral Lipid Fraction as Markers of the Origin of Dairy Products

“…The relationship between the concentration of these compounds and the feeding system was demonstrated by literature data, in different matrixes. Urbach and Stark (18) observed that the level of 1-phytene and neophytadiene in butterfat decreased when the animal feeding changed from grass pasture to chopped lucerne hay and concluded that the precursor of 1-phytene and neophytadiene was the neophytadiene present in the pasture. Larick et al (35) observed similar results studying the hydrocarbon fraction of beef fat: feeding the animals with forage produced a beef fat richer in diterpenoids than that obtained from a grain diet.…”

Preliminary Lipid Analyses of Two Quaternary Sediments from the Middle America Trench, Southern Mexico Transect, Deep Sea Drilling Project Leg 66

“…The presence of the two other acyclic isoprenoid alkanes was suggested by the enhanced response of the m/z 183 MF (Albaiges, 1980) for the «-C 34 and «-C 35 peaks in GC-MS. From these mass spectral data the acyclic isoprenoid alkanes coeluting with these /z-alkanes are probably 2,6,10,14,17,21,25,29-octamethyl- hentriacontane (IV) and lycopane (2,6,10,14,19,23,27, 31-octamethyldotriacontane, V), since both possess prominent m/z 183 ions Kimble et al, 1974) and appropriate retention times. Trace concentrations (<0.7 ng/g) of two phytene isomers with mass spectra similar to that of phyt-2-ene (3, 7, 11, 15-tetramethylhexadec-2-ene, VI; Urbach and Stark, 1975) were found in Section 491-1-5.…”

Ninety-Day Feeding Study in Fischer-344 Rats of Highly Refined Petroleum-Derived Food-Grade White Oils and Waxes

“…In contrast to the F-344 rat response, human lipogranulomas have been described as benign, circumscribed lesions that contain mineral oil droplets in the center, but without evidence of inflammation, fibrosis, or clinically significant liver dysfunction (45). Furthermore, accumulation in humans is not unique to mineral oil and also has been described for plant long-chain alkanes (such as those that occur in leaves or fruit peel cuticles and in nut and seed oils and waxes) and those that are produced by animals (such as butter fat, fish oils, beeswax, and lanolin) (3,11,17,31,42 (7, 8, 15-17, 20, 38-41). Likewise, these publications indicate that metabolism of hydrocarbons shows species differences and that metabolism is probably mediated by cytochrome P-450 in the liver and in the intestine of some species (7,15,20,24,29).…”