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4 protocols using boron trifluoride diethyl etherate

1

Lipid Extraction and Fatty Acid Profiling

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Total lipids were extracted from diets and muscle of common carp with a mixture of chloroform/methanol (v/v, 2:1), followed by fatty acid methyl esters (FAME) using boron trifluoride diethyl etherate (ca. 48%, Acros Organics, Waltham, MA, USA). FAME were analysed and separated using a gas chromatograph (GC2010-plus, Shimadzu, Japan) as previously described [50 (link)]. Briefly, FAME samples were applied using on-column injection, and the oven temperature was programmed from 80 to 250 °C at a rate of 40 °C min−1 and held at 210 °C for 30 min. Individual FAME were identified through comparison with commercial standards (Sigma, St. Louis, MO,) and quantified with CLASS-GC2010-plus workstation (Shimadzu, Kyoto, Japan).
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2

Benzaldehyde Condensation Synthesis

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4-Hydroxybenzaldehyde
(from
Acros), acetone (from Acros), boron trifluoride diethyl etherate (from
Alfa), aniline (from Acros), paraformaldehyde (from PanReac), and
all solvents (high-performance liquid chromatography grade) were purchased
from various commercial sources and were used without further purification.
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3

Fatty Acid Composition Analysis

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The detection of dietary and muscle fatty acid compositions were performed according to the method described previously [17 (link)]. Briefly, total dietary and muscle lipids were extracted using a mixture of chloroform/methanol (v/v, 2:1) containing 0.01% butylated hydroxytoluene [43 (link)]. The fatty acid methyl esters (FAME) of total lipid were performed using boron trifluoride diethyl etherate (ca. 48%, Acros Organics, Waltham, MA, USA). The FAME were analyzed using gas chromatography (GC-2010 plus; Shimadzu, Kyoto, Japan), and individual FAME were identified through comparison with commercial standards (Sigma, St. Louis, MO, USA), and quantified by CLASS-GC2010-plus workstation (Shimadzu).
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4

Synthesis of Functionalized Adamantane Derivatives

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2,2′-(Adamantane-1,3-diyl)diacetic
acid (Sigma, 97%), boron trifluoride diethyl etherate (Acros, 48%
in Et2O), 4-chloro-1-butene (Acros, 98%), 9-chloro-1-nonene
(flourochem, >95%), 8-chloro-1-octene (flourochem, >95%), CDCl3 (Sigma, 99.8%), copper(II) chloride (CuCl2, Acros,
anhydrous 99%), Grubbs Catalyst 1st Generation (Sigma, 97%), HDPE
(Alfa Aesar, Mw = 125 kDa), hydrobromic
acid (Sigma, 47% in H2O), lithium aluminium hydride (Acros,
2.4 M in THF), magnesium purum, for Grignard reactions (Sigma, >99.5%),
1-phenyl-1-propyne (Acros, 99%), sulfuric acid (Fischer scientific,
>95%), THF anhydrous (Sigma, >99.9% inhibitor free), p-toluenesulfonyl hydrazide (Sigma, 97%), tripropylamine
(TCI, >98%), o-xylol anhydrous (Sigma, 97%) were
used and flash column
chromatography was performed on silica gel 60 (Macherey-Nagel GmbH,
40–63 μm, 230–400 mesh).
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