Results of experiment series I: C4-compounds

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1 Results of experiment series I: C4-compounds GC-MS-Results (total ion chromtogram and identification). PK: Number of peak identified RT: Retention time of the chromatogram Area Pct: % of the total measured area in the total ion chromatogram Ref: Reference Number CAS: CAS Number Qual: Quality of identification, above 80 % the compounds is regarded as identified. Table 1: Experiment with 1-Butanol, Headspace analysis (100 µl at 200 C), PK RT Area Pct Library/ID Ref CAS Qual Oxygen(DOT) Carbon dioxide Acetaldehyde Ethanol Acetone Propanoic acid, 2-hydroxy-2- methyl Butanal Pentanal Benzene Pentanone Penten-1-ol, (E) Toluene Ethylbenzene Benzene, 1,3-dimethyl Benzene, 1,3-dimethyl Benzene, propyl Benzene, 1-ethyl-4-methyl Benzene, 1-ethyl-2-methyl Benzene, 1,2,3-trimethyl Hexenal, 2-ethyl Benzene, 1-ethyl-3-methyl Indane Benzene, 1-propynyl Benzene, 1,2-diethyl Benzene, 2-ethyl-1,4-dimethyl Benzene, 1-ethyl-2,4-dimethyl Benzene, 2-ethenyl-1,4-dimethyl

2 Table 2: Experiment with 1-Butanol, SPE-analysis PK RT Area Pct Library/ID Ref CAS Qual Phenol Benzaldehyde, 2-hydroxy Phenol, 2-methyl Benzaldehyde, 2-methyl Phenol, 4-methyl Benzaldehyde, 2-methyl Benzenemethanol, 2- methyl Phenol, 2,3-dimethyl Phenol, 2-ethyl Phenol, 3,4-dimethyl Benzene, diethylmethyl Table 3: Experiment with 1-Butanal, Headspace analysis (100 µl at 200 C), PK RT Area Pct Library/ID Ref CAS Qual TRIDEUTEROACETONITRILE Acetaldehyde Propanone Propanal, 2-methyl Butanal Benzene Pentanone Heptene, (E) Butanal, 2-ethyl Toluene Hexanal Ethyl-trans-2-butenal Ethylbenzene Benzene, 1,3-dimethyl Heptanone Heptanone Benzene, 1,3-dimethyl Pentenal, 2-ethyl Hexanal, 2-ethyl Benzene, 1-ethyl-2-methyl Benzene, 1-ethyl-2-methyl Benzene, 1,2,3-trimethyl Hexenal, 2-ethyl Hexenal, 2-ethyl Indane Gibberellin A

3 Table 4: Experiment with 1-Butanal, SPE analysis PK RT Area Pct Library/ID Ref CAS Qual Butanol Pentanone Butanol Butanal, 2-ethyl ,3,5-Cycloheptatriene Hexanone Cyclopentanone Formamide Ethyl-trans-2-butenal Hexenal Ethylbenzene Heptanone Heptanone Heptanol Pentenal, 2-ethyl Cyclopenten-1-one, 3,4,5-trimethyl Pentenal, 2-ethyl Cyclohexane, 1,2-dimethyl-, cis Hexanal, 2-ethyl Benzaldehyde Benzene, 1-ethyl-2-methyl Bicyclo[2.2.1]heptan-2-ol, exo Phenol Benzene, 1,2,3-trimethyl Hexenal, 2-ethyl Hexenal, 2-ethyl Piperidinone Hexanol, 2-ethyl Benzenemethanol Benzene, 1,1'-(1-ethenyl-1, propanediyl)bis Phenol, 2-methyl Ethanone, 1-phenyl Phenol, 4-methyl Benzaldehyde, 4-methyl Butane, 1-[(2-methyl-2-propenyl)oxy] Heptane, 1-(2-butenyloxy)-, (E) Phenol, 2-ethyl Benzenemethanol, 2-methyl Phenol, 2,5-dimethyl Phenol, 3-ethyl Ethanone, 1-(3-methylphenyl) Naphthalene Phenol, 2,4-dimethyl Phenol, 2-(1-methylethyl) Ethanone, 1-(4-ethylphenyl) Benzene, 2,4-diethyl-1-methyl H-Inden-1-one, 2,3-dihydro Naphthalene, 1-methyl Ethanone, 1-(2,4-dimethylphenyl) Benzene, 1-ethenyl-3-ethyl-, mixt with 1-ethenyl-4-ethylbenzene Pyrimido[1,2-a]azepine, 2,3,4,6,7,8,9,10-octahydro

4 Table 5: Experiment with Butendiol, Headspace analysis (100 µl at 200 C) PK RT Area Pct Library/ID Ref CAS Qual Carbon dioxide Acetaldehyde Ethanol Furan ,3-Cyclopentadiene Propanal, 2-methyl Butanone Furan, 2-methyl Furan, tetrahydro Benzene Pentanone Cyclopentanol Toluene Ethylbenzene p-xylene Benzene, 1,3-dimethyl Benzene, 1-ethyl-4-methyl cis-bicyclo[4.3.0]nona-3,7-diene Benzene, 1-ethyl-2-methyl Benzene, 1,2,3-trimethyl Tetracyclo[ (2,8).0(4,6)]-non-2-ene Benzene, 1-propynyl Phenyl-1-butene Table 6: Experiment with Butendiol, SPE-analysis PK RT Area Pct Library/ID Ref CAS Qual Butanone Chloroform Furan, tetrahydro Buten-1-ol Butanol Pentanone Cyclopentanol Crotonaldehyde, 2-methyl Pentanone, 3-methyl H-Pyrrole Toluene Toluene Furanol, tetrahydro Cyclopentanone Undecanol Furanmethanol Cyclopentanone, 2-methyl Cyclopentanone, 3-methyl Ethylbenzene Benzene, 1,3-dimethyl Heptanone p-xylene Cyclopenten-1-one, 2-methyl Furanmethanol, tetrahydro Cyclopentanone, 2-ethyl Cyclohexene-1-carboxaldehyde

5 Hexanal, 2-ethyl Benzene, 1-ethyl-2-methyl Cyclohexene-1-carboxaldehyde, 1-methyl Phenol Benzene, 1,2,3-trimethyl Cyclopropane, tetramethylmethylene Octyne IMIDAZOLE-1,4,5-D Furanmethanol, tetrahydro Benzene, 1,2,3-trimethyl Benzene, 1-ethenyl-2-methyl Furan, 2-butyltetrahydro Benzene, 1-propynyl Phenol, 2-methyl Acetophenone Phenol, 4-methyl Indan, 1-methyl Phenol, 2,3-dimethyl Phenol, 2-ethyl H-Indene, 2,3-dihydro-5-methyl Phenol, 2,4-dimethyl Methylindene Benzene, (1-methyl-2-cyclopropen-1-yl) Phenol, 4-ethyl Phenol, 2,3-dimethyl Naphthalene Phenol, 2,3,5-trimethyl Phenol, 2,3,6-trimethyl Phenol, 2-ethyl-5-methyl Phenol, 3-ethyl-5-methyl Phenol, 2,3,5-trimethyl H-Inden-1-one, 2,3-dihydro Naphthalene, 2-methyl Naphthalene, 2-methyl Pentane, 1,1'-oxybis H-Inden-1-ol, 2,3-dihydro ETHYLADAMANTAN-1-OL Naphthalene, 2-ethyl Butanoic acid, 3-methylphenyl ester Acenaphthene Naphthalenol Naphthalenol Fluorene Phenanthrene

6 Results of experiment series II: Deuterated Glucose Fig. 1: Total ion chromatogram of the not-deuterated Glucose:

7 Table 7: As table the main peaks (not-deuterated glucose): PK RT Area Pct Library/ID Ref CAS Qual Amylene Hydrate Butanone, 3-methyl Toluene Cyclopentanone Tetrachloroethylene Propen-1-one, 2-methyl Cyclohexane, nitro CYCLOPENTEN-4-OL Acetic acid, propyl ester Pentane, 2,3,4-trimethyl Phenol Ethanol, 2-(2-ethoxyethoxy) Phenol, 2-methyl Acetophenone Phenol, 3-methyl Phenol, 2-ethyl The GC-MS of the experiment with normal glucose was used to get the product and the retension time of these products. In the product solution of the experiment with deuterated glucose e.g. deuterated phenol has the same retention time like phenol, but a different MSspektrum. Here the MS-spectrum of a compound is first compared with the literature data and than with the MS-spectrum of the deuterated compound. An increase of the molecular weight of a key fragment give the information, how many deuterium atoms are in this key fragment. Not for all compounds a clear quantification of the key compounds is possilbe, but for 3-methyl-2-butanon (1), hydroxyaceton (2), toluene (3), three different cyclopentanones (4-6) and three different phenols (7-9).

8 Fig. 2: Total ion chromatogram of the deuterated Glucose:

9 Fig. 3: Area % of identified products in the total ion chromatogram (Glucose conversion, most important deuterated compounds in black). Figure 3 shows the strong dominance of phenol in the total ion chromatogram. In addition, 3- methylbutanone, cyclopentanone and toluene show strong peaks. The methylcyclopentanones and hydroxyacetone are minor compounds. Trichloroethylene and the nitrocompound (Nr. 5 and 7 in Fig. 3) are artefacts from sample preparation.

10 Compound 1: 3-methyl-2-butanon Fig. 4: Non-deuterated product MS spectrum in comparison with literature: Fig. 5: Deuterated compound:

11 Compound 2: Hydroxyacetone Fig. 6: Non-deuterated product MS spectrum in comparison with literature: Fig. 7: Deuterated compound: In the deuterated sample the mass increase was m = 3 u. The main peaks are the same but a shift of the peaks m/z 32 and m/z 43 to m/z 44 and m/z 45 is obvious. The splitted CH2OH fragment is not able to have a OD- group therefore the increase of m/z31 to m/z 32 should be a consequence of the a CHD-OH-fragment formed.

12 This together with the mass increase of m/z 43 to m/z 44 and m/z 45 hints to a deuteration ration of 3 from 6 possible positions. Compound 3: Toluene Fig. 8: Non-deuterated product MS spectrum in comparison with literature: Fig. 9: Deuterated toluene: In the spectrum of the deuterated glucose experiment, there is a significant increase of mass of m = 5 u for m/z 93 to m/z 99 found. The five D-atoms are uniformly distributed at all C- atoms of the toluene. Four of them 4, but at lower intensity are found in the C5H5

13 -fragment at m/z 67, 68, 69 and 70 also. The last D-atom is separated by the formation of the C2H2-fragmente from the C7H7-Fragment. Compound 4: Cyclopentanone Fig. 10: Non-deuterated product MS spectrum in comparison with literature: Fig. 10: Deuterated product:

14 In the samples of deuterated glucose conversion, the molecular mass is increased by m = 4, corresponding to C5D4H3O. Now the fragments are investigated for an mass increase. At three C-atoms, not bonded to oxygen, the mass of the fragment is increased. There is one C-atom left, which has to be bonded to deuterium. The mass increase of m/z 55 and m/z 56 of m = 3 u to m/z 57, 58, 59, relative to the non-deuterated glucose experiments hints to 3 deuterium in the main fragment. This is formed by splitting of a C2H4D1 fragment. Only this way the strong peak at m/z 58 can be explained. The peak at m/z 30 prove the splitting off a C2D3 fragment with m/z 58, forming a carbonyl group. The three deuterium atoms can be found here again. Also the mass difference in respect of the molecule ion C5D4H3O, hints to this assumption

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