Synthesis and characterization of 1- and 2-monoglycerides of anteiso fatty acids

Serdarevich, B.; Carroll, K. K.

doi:10.1016/s0022-2275(20)39293-2

Cited by 48 publications

(15 citation statements)

References 24 publications

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“…The structure of compound 4 was essentially deduced from its NMR spectra [cf. Serdarevich & Carroll (1966), Hermetter & Paltauf (1982), and Kresge & Chen (1972)] (cf. Figures 2 and 3): NMR (DMF-¿7) 6.84 (1 H, d, / = 12 Hz, -OCH=), 6.10-6.35 (7 H, m, -CH=CH-), 5.65-5.75 (2 H, m, OCH=C/í-2 and =CH-CH2), 4.10 (2 H, dd, / = 6 and 12 Hz, -OCH2-), 3.80 (1 H, m, CHOU), 3.65 (2 H, dd, J = 4.5 and 12 Hz, -C/f2OH), 2.09 (2 H, m, =CHCf/2-), 1.23 [s, (CH2CH2)"], and 0.87 (3 H, t, J = 8 Hz, CH2Ctf3); NMR (C6D6) 6.35 (1 H, d, J = 12 Hz), 5.60-3.70 (2 H, m, -OCH=CHand =CH-CH2), 5.40-5.57 (7 H, m, -CH=CH-), 4.05 (2 H, dd, J = 2 In our previous paper (Bruce et al, 1982), to this proton was erroneously assigned a signal at & 5.14 (dd, 7=12 and 6 Hz).…”

Section: Resultsmentioning

confidence: 99%

Structures of fecapentaenes, the mutagens of bacterial origin isolated from human feces

Gupta¹,

Baptista²,

Bruce³

et al. 1983

Biochemistry

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Section: Resultsmentioning

confidence: 99%

Structures of fecapentaenes, the mutagens of bacterial origin isolated from human feces

Gupta¹,

Baptista²,

Bruce³

et al. 1983

Biochemistry

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“…The approximate positions of the acyl substitutions on the glycerol moieties of the glycerides are deduced from the 1H-and 13C NMR chemical shifts of the respective C(H)-1 to C(H)-2 signals. The length and unsaturation degree of the acyl group does not affect the chemical shifts of the carbon signals of glycerol, but they may change the chemical shifts of the respective protons slightly (22,23). In unsaturated fatty acyl glycerides, double bond-proton signals appear at the same range of chemical shifts (δ H ) that are observed for the H-2 glycerol of 2monoglycerides, 1,2-diglycerides, and triglycerides (23).…”

Section: Resultsmentioning

confidence: 94%

“…The length and unsaturation degree of the acyl group does not affect the chemical shifts of the carbon signals of glycerol, but they may change the chemical shifts of the respective protons slightly (22,23). In unsaturated fatty acyl glycerides, double bond-proton signals appear at the same range of chemical shifts (δ H ) that are observed for the H-2 glycerol of 2monoglycerides, 1,2-diglycerides, and triglycerides (23). On the other hand, the 13 showed the presence of another unsaturated and a saturated acyl chain in compound 3 (24).…”

Section: Resultsmentioning

confidence: 99%

Phytochemical Analysis and Biological Activity of Salvia compressa Vent.

et al. 2022

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Background: Salvia extracts have various biological activities and are rich sources of bioactive metabolites. Objectives: We identified five phytochemicals from S. compressa extract and assessed their biological properties. Methods: The plant's shoots were extracted using dichloromethane, and the constituents were isolated using column chromatography. High-resolution NMR spectroscopy characterized the chemical structures of the compounds (1 - 5). The cytotoxic effect of the extract was examined against MCF-7 cells by MTT reduction assay, while cisplatin was tested as a reference cytotoxic compound. The antibacterial activity was assessed using nutrient broth micro-dilution (NBMD), and chloramphenicol was used as the positive control Results: Citrostadienol (1), β-sitosterol (2), two glyceride esters of linolenic, linoleic, and palmitic acids (3, 4), and geraniol (5) were isolated from S. compressa for the first time. The extract showed activity against MCF-7 breast cancer cells and reduced cell viability to 68.2 ± 13.1% compared to the control drug at the concentration of 50 µg/mL, while it was not active against seven test bacteria. Conclusions: The anti-complementary activity of the isolated steroids suggests S. compressa for future anti-inflammatory research.

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“…Quantification of the degree of isomerization gave 6.0 and 6.7% 2-isomer in the synthesized 1-glycerol monocapronate and 1-glycerol monopalmitate, respectively. This may be due to acyl migration during acid hydrolysis of the acetoneketals (3) or during column chromatography on silica gel (Serdarevich and Carroll, 1966;Serdarevich, 1967).…”

Section: Resultsmentioning

confidence: 99%

Study of the Effect of DATEM. 1. Influence of Fatty Acid Chain Length on Rheology and Baking

Kohler

Grosch

1999

J. Agric. Food Chem.

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To answer the question of which fatty acid residue is the most effective, diacetyltartaric esters of monoglycerides (DATEMs) with fatty acids of chain lengths 6:0-20:0 were synthesized. The activity of synthesized DATEMs and commercial DATEM products was studied by means of rheological methods and a microscale baking test with 10 g of flour. Variation of the acyl residue from 6:0 to 22:0 showed that stearic acid (18:0) had the best effect on the baking activity of DATEM (loaf volume increased by 62%). DATEMs containing unsaturated fatty acids (18:1, 18:2) or DATEMs produced from diacylglycerols instead of monoacylglycerols showed a slight increase of the loaf volumes. A slight effect of DATEM on the rheology of dough was observed. However, much greater was the effect on the gluten isolated from doughs prepared with DATEM. The resistance of gluten to extension was increased after the addition of increasing amounts of DATEM (0.1-0.5%). Within the series of DATEMs derived from the homologous series of monoacylglycerols the product based on glycerol monostearate (18:0) showed a maximum increase of the gluten resistance.

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Synthesis and characterization of 1- and 2-monoglycerides of anteiso fatty acids

Cited by 48 publications

References 24 publications

Structures of fecapentaenes, the mutagens of bacterial origin isolated from human feces

Structures of fecapentaenes, the mutagens of bacterial origin isolated from human feces

Phytochemical Analysis and Biological Activity of Salvia compressa Vent.

Study of the Effect of DATEM. 1. Influence of Fatty Acid Chain Length on Rheology and Baking

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