Cyclohexane

The working cis-1,3-docoseneamide (erucamide) was supplied by Cymit Quimica Croda Universal (4014 Walnut Pond Drive Houston, TX 77059 281-282-0022 Crompton (Witco) Corporation) (erucamide has a white coloration; its iodine value ranged from 75 to 82. The result of the acid number was 0.1 KOH mg/g, and the pour point ranged from 78 to 81 °C. The moisture content obtained was 0.4% max. The certified purity was 99% min). N-tetradecanamide (Alpha Aesar, Karlsruhe, Germany) was used as internal standard. Limonene (HPLC grade) was obtained from Scharlab (Barcelona, Spain). Hydrogen 99.9999% was from Linde (Cartagena, Colombia), nitrogen 99.9999% was from Linde (Cartagena, Colombia), cyclohexane 99.5% was from Panreac (Barcelona, Spain), and dichloromethane 99.99% was from Sigma Aldrich (Bangalore, India).

Samples. Saffron from the Protected Designation of Origin (PDO) “Azafrán de La Mancha” was directly purchased from the producer Agrícola Técnica de Manipulación y Comercialización (Minaya, Albacete, Spain). Category I saffron was ground and characterized according to ISO 3632:2011 [25 ] ( $A_{1\mathrm{cm}}^{1\%}$ 440 nm: 235 ± 2, $A_{1\mathrm{cm}}^{1\%}$ 257 nm: 97 ± 3, and $A_{1\mathrm{cm}}^{1\%}$ 330 nm: 22 ± 1). Cured ham was obtained from the company Benibaldo, S.A.U. (Albacete, Spain), and rice flour obtained from Panificadora Conquense Agrícola, S.A. (Cuenca, Spain), a usual product in the ham industry, was used in this study as a solid support to retain the patterns and for solid dilution of saffron.
Patterns. A total of four patterns of the major aromatic components of saffron were used. Safranal (purity: 90%), linalool (purity: 97%), isophorone (purity: 97%), and 2,6,6-trimethyl-2-cyclohexene-1,4-dione (purity: 98%) were obtained from Sigma-Aldrich (Madrid, Spain).
Solvent. Cyclohexane of analytical grade was obtained from Panreac (Barcelona, Spain).

The compounds bis(1,2,3,7,8-pentamethyl-2,2′-dipyrrolylmeten-9-yl)methane bis(difluoroborate) (1), (1,2,3,7,9-pentamethyl-2,2’-dipyrrolylmeten-8-yl)-(1,2,3,7,8-pentamethyl-2,2’-dipyrrolylmeten-9-yl)methane bis(difluoroborate) (2), and bis(1,2,3,7,9-pentamethyl-2,2′-dipyrrolylmeten-8-yl)methane bis(difluoroborate) (3) were synthesized according to proven technology [21 (link)]. The synthesis techniques and the results of the identification of 1–3 are presented in SI. Spectrophotometric-grade benzene, heptane, cyclohexane, toluene, ethanol, 1-propanol, DMF, DMSO, and acetone (for analysis, Panreac, Barcelona) were used without further purification. Solvent parameters (DN, SB, and ε) were taken from [32 (link)] and are listed in Table S2.