The Mass Spectra Analysis for α-Ionone and β-Ionone

Walwil, Abdalla Mustafa

doi:10.5539/ijc.v9n3p61

Cited by 5 publications

(7 citation statements)

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“…Helium gas was used as a carrier gas. β-Ionone retention times were confirmed using both standards and published mass spectrums [ 52 ]. Standard curves were built to quantify the extracted ionone concentration.…”

Section: Methodsmentioning

confidence: 99%

Engineering the oleaginous yeast Yarrowia lipolytica to produce the aroma compound β-ionone

et al. 2018

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Backgroundβ-Ionone is a fragrant terpenoid that generates a pleasant floral scent and is used in diverse applications as a cosmetic and flavoring ingredient. A growing consumer desire for natural products has increased the market demand for natural β-ionone. To date, chemical extraction from plants remains the main approach for commercial natural β-ionone production. Unfortunately, changing climate and geopolitical issues can cause instability in the β-ionone supply chain. Microbial fermentation using generally recognized as safe (GRAS) yeast offers an alternative method for producing natural β-ionone. Yarrowia lipolytica is an attractive host due to its oleaginous nature, established genetic tools, and large intercellular pool size of acetyl-CoA (the terpenoid backbone precursor).ResultsA push–pull strategy via genome engineering was applied to a Y. lipolytica PO1f derived strain. Heterologous and native genes in the mevalonate pathway were overexpressed to push production to the terpenoid backbone geranylgeranyl pyrophosphate, while the carB and biofunction carRP genes from Mucor circinelloides were introduced to pull flux towards β-carotene (i.e., ionone precursor). Medium tests combined with machine learning based data analysis and 13C metabolite labeling investigated influential nutrients for the β-carotene strain that achieved > 2.5 g/L β-carotene in a rich medium. Further introduction of the carotenoid cleavage dioxygenase 1 (CCD1) from Osmanthus fragrans resulted in the β-ionone production. Utilization of in situ dodecane trapping avoided ionone loss from vaporization (with recovery efficiencies of ~ 76%) during fermentation operations, which resulted in titers of 68 mg/L β-ionone in shaking flasks and 380 mg/L in a 2 L fermenter. Both β-carotene medium tests and β-ionone fermentation outcomes indicated the last enzymatic step CCD1 (rather than acetyl-CoA supply) as the key bottleneck.ConclusionsWe engineered a GRAS Y. lipolytica platform for sustainable and economical production of the natural aroma β-ionone. Although β-carotene could be produced at high titers by Y. lipolytica, the synthesis of β-ionone was relatively poor, possibly due to low CCD1 activity and non-specific CCD1 cleavage of β-carotene. In addition, both β-carotene and β-ionone strains showed decreased performances after successive sub-cultures. For industrial application, β-ionone fermentation efforts should focus on both CCD enzyme engineering and strain stability improvement.Electronic supplementary materialThe online version of this article (10.1186/s12934-018-0984-x) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Engineering the oleaginous yeast Yarrowia lipolytica to produce the aroma compound β-ionone

et al. 2018

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“…Usually the highest m/z ratio signal of the spectrum is the molecular ion, M + , if appears, not to confuse with the isotopic peaks, M + 1 and M + 2. Usually the isotopic peaks are in much smaller intensity relative to the M .+ peak (Walwil, 2017).…”

Section: Discussionmentioning

confidence: 99%

“…The MS spectra for α-Ionone and β-Ionone were analyzed earlier (Walwil, 2017). The intended analysis of MS spectra will cover, besides the current analysis, ester, and the earlier one, ketone, ionones, all other classes includes carboxylic acids, aldehydes, amides, amines, alcohols, ethers, etc.…”

Section: Introductionmentioning

confidence: 99%

Analysis of Butyl Butyrate Mass Spectrum

Walwil¹

2018

IJC

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The aim of this educational work is targeting chemistry students and interested instructors. The presented work will analyze the mass spectrum of butyl butyrate (butyl butanoate). The analysis will concentrate on the mechanisms showing how the characteristic fragments are formed. The mechanisms discussed in this paper include α-cleavage, β-cleavage, McLafferty Rearrangements, first and second proton transfer, a double proton transfer.

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“…The combined information from these two techniques are complementary to identify the functions and their positions. The aim is to obtain complementary information on the structure of the molecules; the fragments have provided additional data to verify identification of daughter products [34]. The syntheses of degradation products were also performed to confirm the identified products (see supplementary data).…”

Section: Identification Of Degradation Products By Nmr and Msmentioning

confidence: 99%

Identification of the Degradation Products from α‐Ionone Used as Stabiliser in “Green” Propellants through its Lifetime

Damseaux

Scholl

Damblon

et al. 2021

Propellants Explo Pyrotec

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A stabiliser is added to gun and rocket propellants to react with species responsible for degradation during decomposition. Propellant powder manufacturers and army personnel are confronted with toxicity during powder degradation and must replace current stabilisers with nontoxic molecules. According to the STANAG 4582 (North Atlantic Treaty Organization (NATO) Standardisation Agreement [1]), propellant powders must remain chemically stable for a minimum of ten years when stored at temperatures equivalent to an isothermal storage (25 °C). Single and double base smokeless powders with α-ionone as a "green" stabiliser are tested and the results show that the heat flow is stable over time and that the autocatalysis occurs 2 to 3 times later than in powders with conventional stabilisers. This stabiliser is efficient for all nitrate esterbased propellants. In the present paper, we identify and monitor the evolution of the main degradation products over time by nuclear magnetic resonance (NMR), mass spectrometry (MS) to unravel the stabilisation mechanism under accelerated aging conditions. A time-related fluctuation of their respective amounts (increasing then decreasing, then re-increasing, …) is observed, which indicates that the daughter products have also a stabilisation effect. The three major α-ionone daughter products are identified as: 3-oxo-α-ionone, 4-oxo-β-ionone and 4,5-epoxy-α-ionone.

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The Mass Spectra Analysis for α-Ionone and β-Ionone

Cited by 5 publications

References 1 publication

Engineering the oleaginous yeast Yarrowia lipolytica to produce the aroma compound β-ionone

Engineering the oleaginous yeast Yarrowia lipolytica to produce the aroma compound β-ionone

Analysis of Butyl Butyrate Mass Spectrum

Identification of the Degradation Products from α‐Ionone Used as Stabiliser in “Green” Propellants through its Lifetime

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