Tetradecanol

The chemical standards used, namely ocimene (94%); limonene (96%) and α-humulene (96%); myristicin and aromadendrene (97%); α-pinene and β-pinene (98%); linalool, 1,8-cineole, β-caryophyllene, eugenol, pentadecane, heptadecane and tetradecanol (99.0%) were all purchased from Sigma-Aldrich (Saint Louis, MO, USA).
Dillapiole, asaricin, and safrole, all with a purity higher than 99.7%, were obtained via fractional distillation, as described in Section 4.2.

Sodium borohydride (NaBH₄), hexadecyltrimethylammonium bromide (CTAB), Au chloride solution (HAuCl₄) 200 mg/dL in deionized water (ref # HT1004-100ML Sigma), ascorbic acid (AA), hexadecyltrimethylammonium chloride (CTAC) solution 25 wt. % in water (ref # 292737 Aldrich), polyvinylpyrrolidone Mw ~55,000 (PVP), methanol (MetOH), 1,3,3,1′,3′,3′,-hexamethyl-2,2′-indotricarbocyanine iodide (HITC), tetradecanol (TD), phosphate buffer saline (PBS), tris-EDTA buffer solution (TE), tween 20, sodium chloride (NaCl), hydrochloric acid (HCl) were purchased from Sigma-Aldrich. Sodium citrate dihydrate was purchased from BDH. Methoxy polyethylene glycol thiol Mw 5000 (mPEG-SH) was purchased from Nanocs. Magnetic beads were purchased from Life Technologies. All DNA sequences (Table S1) were synthesized by Integrated DNA Technologies (IDT, Coralville, IA). Millipore Synergy ultrapure water (DI) of resistivity = 18.2 MΩ cm was used in all nanoparticle synthesis solutions. Nuclease-free water was used in all experiments relating to RNA and DNA.

All dicarboxylic acids (oxalic, succinic, suberic, and sebacic), methanol, 1-decanol, and tetradecanol were acquired from Sigma Aldrich (St. Louis, MO, USA) with high purities (≥98%) as synthesis precursors. Dimethyl oxalate was purchased from Sigma Aldrich with purity ≥ 99% and was used for comparison with the self-synthesized one for validation of the synthesis procedure. 1-Pentanol was purchased by Roth GmbH (Karlsruhe, Germany) with purity ≥ 98%. The synthesis procedure was the same as reported by Ravotti et al. [18 (link)]; thus, concentrated sulfuric acid (H₂SO₄) was used as the acid catalyst (Sigma Aldrich, ≥99%), sodium sulfate anhydrous (Na₂SO₄) was used as a water-absorbing agent (Sigma Aldrich, ≥99%) for the elimination of water, and ethyl acetate (EtOAc) was used as the organic solvent for extraction (Sigma Aldrich, ≥99%). Cylohexane (Sigma Aldrich, GC quality, ≥99.9%) was used as the solvent for the Gas Chromatography coupled with Mass Spectrometry (GC-MS) analysis. All chemical materials listed above were used without any prior purification.