Natural Abundance ²H Nuclear Magnetic Resonance Study of the Origin of (Z)-3-Hexenol

Abstract

The origin of 11 samples of (Z)-3-hexenol was studied by SNIF-NMR measurements. The results show a possible distinction between synthetic and extractive materials and those biogenerated from linolenic acid by enzymic fragmentation at position 13 of the carbon framework of the 13-hydroperoxide obtained by the action of oxygen in the presence of lipoxygenase, followed by baker's yeast-mediated reduction of the intermediate (Z)-3-hexenal. Particularly significant to this end result are the deuterium contents at relevant positions of (Z)-3-hexenol, such as 3+4 and 1. The results suggest that one sample might be a mixture of materials of extractive origin with those obtained by biodegradation from linolenic acid. Keywords: (Z)-3-Hexenol; naturality; SNIF-NMR; biogeneration

Quantifying tracer levels of2H2O enrichment from microliter amounts of plasma and urine by2H NMR

“…For all measurements, the intensity of the 2 H‐acetone signal was approximately 85–90% of the expected value based on a natural abundance 2 H‐enrichment of 150 ppm. There is considerable variation in background 2 H‐enrichment between different materials, with petroleum‐derived products being significantly depleted in 2 H (14). Because of these uncertainties, the 2 H natural abundance signal of acetone cannot be routinely used as an absolute reference for deuterium concentration and standard curves should be prepared for each consignment of acetone.…”

Natural Abundance 2H Nuclear Magnetic Resonance Study of the Origin of Raspberry Ketone

“…In light of the observations that site-specific deuterium distribution data of food components allowed in many instances (Fronza et al, 1995b(Fronza et al, , 1996bMartin and Martin, 1995;Barbeni et al, 1997) a clear definition of their origin, we carried out and present in this paper a 2 H NMR study on raspberry ketone samples obtained through a variety of procedures to verify the utility of Deuterium NMR data (61.4 MHz) were recorded at 306 K on a Bruker ARX 400 spectrometer equipped with a process controller, a 10-mm selective deuterium probehead, and a 19 F lock channel, under CPD (Waltz 16 sequence) proton decoupling conditions. Samples of 3 were prepared by weighing about 0.7 g of solid sample and solubilized into (a) 3 mL of benzene plus 0.6 mL of dioxane; or (b) 3.6 mL of dioxane.…”

Accurate Determination of Deuterium/Hydrogen Ratios in Natural Organic Compounds through a Nuclear Magnetic Resonance Time-Domain Reference Convolution Method: Application to Ethanol from Three Botanical Sources and Critical Analysis of Systematic Inaccuracies in Previous Methods

“…An appropriate benchmark for this type of problem is the so-called Martin method, a procedure for determining the site-specific ratios of deuterium to hydrogen, (D/H), at the different sites of an organic molecule by 2 H NMR (Martin et al, 1985;Martin and Brun, 1987). It has been shown in many cases that the (D/H) ratio can be related to the biological origin of the sample (Toulemonde et al, 1983;Schmidt, 1986;Martin and Martin, 1995a;Berbeni et al, 1997;Fronza et al, 1998). In the field of food and beverage control, this analysis has long proven a valuable help in detecting commercial frauds such as sugaring of musts (Martin and Martin, 1990), addition of exogenous sugar to fruit juices (Martin and Martin, 1995b), or flavor adulteration (Martin et al, 1993).…”