diphtheria, tetanus, acellular pertussis, inactivated poliomyelitis, hepatitis B (recombinant) and Haemophilus influenzae type b conjugate vaccine, adjuvanted

Alkylresorcinols (5‐alkyl‐1,3‐dihydroxybenzenes) are amphiphilic phenolic lipid compounds that are abundant in cereals with highest contents in rye. Alkylresorcinols are suspected to show a wide range of favourable biological activities. For such and further testing, highly pure alkylresorcinol standards are required. Especially, purities >> 98% were partly difficult to obtain in the past. Here, we aimed to isolate the most abundant (saturated) alkylresorcinols from rye using countercurrent chromatography. To achieve very high purity, alkylresorcinol‐containing extract (∼7.14 g) of rye grains (cold extracts with cyclohexane/ethyl acetate (46/54, w/w)) were preparatively transesterified followed by a preparative hydrogenation. Countercurrent chromatography separation of ∼1 g hydrogenated and transesterified rye grain extract using the solvent system n‐hexane–ethyl acetate–methanol–water (9:1:9:1, v/v/v/v) yielded 51.8 mg AR17:0, 77.4 mg AR19:0, 57.2 mg AR21:0, 28.8 mg AR23:0 and 11.5 mg AR25:0 with purities >99% in either case. The isolated alkylresorcinol homologues can be used for subsequent bioassays.