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6 protocols using methyl nonanoate

1

Fatty Acid Ester Synthesis Protocols

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The following chemicals were purchased with the highest purity available: hexanoic acid, octanoic acid, nonanoic acid, methyl nonanoate, ethyl nonanoate, ethyl hydrogen adipate, ethyl hydrogen pimelate, diethyl azelate and diethyl sebacate from Sigma; ethyl hydrogen suberate, ethyl hydrogen sebacate and diethyl suberate from Alfa Aesar; ethyl hydrogen azelate from TRC, diethyl adipate from Acros Organics; diethyl pimelate from Merck; dimethyl octadecanedioate from TCI; 0.2 M TMSH in MeOH from Macherey–Nagel; Coenzyme A from VWR and ATP from GE Healthcare.
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2

Metabolite Profiling of n-Paraffins

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Methanol of HPLC grade was purchased from Fisher Scientific (Fair lawn, NJ, USA). Standard of n-paraffins mixture (C7-C40) were purchased from ANPEL Laboratory Technologies (Shanghai) Inc. (Shanghai, China). Sodium chloride was obtained from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China). Methyl nonanoate, Ribitol, N-methyl-N-(trimethylsilyl) trifluoroacetamide (MSTFA) and methoxamine hydrochloride were purchased from Sigma Aldrich (Saint Louis, MO, USA). All the chemicals and reagents were of analytical grade.
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Comprehensive Flavor Compound Reference Protocol

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Reference standards (+) -β-Pinene (≥98.5%), 1-Octen-3-ol, borneol (≥95%), butyric acid (≥99.5%), citral (≥95%), cis-3-hexen-1-ol (≥98%), diacetyl, dimethyl sulphide, dimethyl trisulphide (≥98.5%), 3-methylbutanal (≥97%), 2-methylbutanal (≥95%), ethyl 2-methylbutanoate (99%), ethyl 2-methylpentanoate (internal standard, ≥99%), ethyl-3-methylbutanoate (≥98%), 3-methylbutyl-2-methylpropanoate (≥98%), 2-methylbutyl-2-methylpropanoate (≥95%), and ethyl cinnamate (99%), ethyl 2-methylpropanoate (≥99%), ethyl 3-methylbutanoate (≥98%), ethyl 4-methylpentanoate (≥97%), ethyl butanoate (≥99,5%), ethyl hexanoate (≥99.5%), eugenol (99.6%), furaneol (≥99%), geraniol (≥99%), hexanol (≥99%), 3-methylbutyl acetate (≥97%), linalool (97%), menthol (99%), methyl nonanoate (≥99.8%), myrcene (≥90%), geranyl acetate (≥97%), dimethyl disulphide (≥90%), limonene (97%), hexanal (≥98%), 3-hexenol (≥95%), 2-phenyl ethanol (≥99%), β-caryophyllene (≥80%), α-humulene (≥96%), humulene oxide, S-methyl 5-methylpentanthioate S-methyl hexanthioate, S-methyl 4-methylpentanoate and theaspirane (≥90%) were purchased from Sigma Aldrich (St. Louis, MO, USA).
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Volatile Metabolite Profiling Protocol

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The volatile standards were purchased from Sigma Aldrich (Saint Louis, MO, USA) and Shanghai Yuanye Ltd. (Shanghai, China). Detailed information of volatile standards was showed in Table S2. Methanol (HPLC-grade) from Fisher Scientific (Fair lawn, NJ, USA), ribitol (99%), N-methyl-N-(trimethylsilyl) trifluoroacetamide (98%) and methoxamine hydrochloride (98%) from Sigma Aldrich were applied for primary metabolites determination. A standard n-paraffin mixture (C7-C40) from ANPEL Laboratory Technologies Inc. (Shanghai, China), methyl nonanoate (98%) from Sigma Aldrich and aldrich sodium chloride (99%) from Sinopharm Chemical Reagent Co., Ltd. (Shanghai, China) were for volatile compounds profiling.
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5

Comprehensive Metabolite Profiling Protocol

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Fisher OptimaTM grade (Fisher Scientific, Hanover Park, IL, USA) solvents were used for sample preparation. Internal standards were obtained from Cambridge Isotope Laboratories, Inc. (Andover, MA, USA) (citric acid-d4, dl-glutamic acid-d5, d-sorbitol-13C1, and l-leucine-d3) or Sigma-Aldrich (St. Louis, MO, USA) (4-nitrobenzoic acid). Standards for obtaining retention indices (C4–C24 FAMEs, methyl nonanoate, and alkane standard mix (C10–C40)) and for urine pretreatment (urease from Canavalia ensiformis (Jack bean) type III) were obtained from Sigma-Aldrich. Derivatization chemicals were obtained from Thermo Scientific (Waltham, MA, USA) (Methoxamine (MOX) reagent and N-methyl-N-[trimethylsilyl]trifluoroacetamide (MSTFA) with 1% (v/v) trimethylchlorosilane (TMCS)).
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6

Analytical standards for n-paraffins

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The standard of the n-paraffins mixture (C7–C40) was purchased from ANPEL Laboratory Technologies Inc. (Shanghai, China). Methyl nonanoate was purchased from Sigma-Aldrich (Saint Louis, MO, USA). Methanol of HPLC grade and ethyl acetate were purchased from Fisher Scientific (Fair lawn, NJ, USA), and all other reagents were of analytical grade. DTC-15J Ultrasonic Cleaning Machine was obtained from DingtaiBiochemical Technology Equipment Manufacturing Co., Ltd. (Wuhan, China).
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