The ability to be used as an alternative solvent of a cis-rich pinane (cis/trans: 7/3), which was obtained for the first time at the multigram scale through an environmentally friendly catalytic hydrogenation of α/β-pinenes or turpentine oil under neat conditions over a Pd/C catalyst, was investigated and compared to n-hexane for the extraction of several bioactive compounds. Experimental evaluation as well as a simulation of the cis-rich pinane extraction capacity have been undertaken. The predictive approach was performed using the simulation software COSMO-RS (conductor like screening model for realistic solvents), which uses a statistical thermodynamics approach based on the result of quantum chemical calculation, for the understanding of dissolving mechanism. COSMO-RS simulation showed that the bio-based solvent is a good solvent to solubilize carotenoids, oil from rapeseed and aromas from caraway seeds. The experimental results indicated that the highest carotenoid yield was obtained with the cis-rich pinane with 95.4% of the maximum carotenoid content in carrots while n-hexane was only able to extract 78.1% of them. With respect to the extraction of oil from rapeseeds, both solvents showed similar extraction yields and no differences were observed in the fatty acid profiles. In relation to the aromas, the characterization of the essential oil extracted by the two solvents showed a similar composition, where carvone (64%) was the main component followed by limonene (34%). No selectivity of the solvents was observed for any of the two major compounds. The results indicate that the bio-based solvent could be a promising solvent for n-hexane substitution.

Starting materials for sustainable total synthesis often come from the chiral pool: carbohydrates, cyclitols, amino acids, and terpenes. In the terpene family, (−)‐sclareol has served as a sustainable, readily available, and versatile chiral building block for the synthesis of numerous natural products. (−)‐Sclareol possesses a unique structure that has consequently promoted its integration as a core framework within various structurally complex and biologically active substances, including sesquiterpenoids, diterpenoids, and sesterterpenoids. (−)‐Sclareol has facilitated access to diverse synthetic key intermediates, promoting the sustainable synthesis of several natural products. Herein, a review is presented covering the recent trends in sustainable total syntheses and the application of chiral pool approaches with emphasis on the preparation of natural products through diverse routes employing (−)‐sclareol as chiral educt. Innovative catalytic and synthetic protocols using (−)‐sclareol are also analyzed and discussed.

5‐lipoxygenase (5‐LO) catalyzes the biosynthesis of leukotrienes, potent lipid mediators involved in inflammatory diseases, and both 5‐LO and the leukotrienes are validated therapeutic targets. Caffeic acid phenethyl ester (CAPE) is an effective inhibitor of 5‐LO and leukotriene biosynthesis but is susceptible to hydrolysis by esterases. In this study a number of CAPE analogues were synthesized with modifications to the caffeoyl moiety and the replacement of the ester linkage with a ketone. Several new molecules showed better inhibition of leukotriene biosynthesis than CAPE in isolated human neutrophils and in whole blood with IC₅₀ values in the nanomolar (290‐520 nmol/L) and low micromolar (1.0‐2.3 µmol/L) ranges, respectively. Sinapic acid and 2,5‐dihydroxy derivatives were more stable than CAPE in whole blood, and ketone analogues were degraded more slowly in HepaRG hepatocyte cultures than esters. All compounds underwent modification consistent with glucuronidation in HepaRG cultures as determined using LC‐MS/MS analysis, though the modified sinapoyl ketone (10) retained 50% of its inhibitory activity after up to one hour of incubation. This study has identified at least one CAPE analogue, compound 10, that shows favorable properties that warrant further in vivo investigation as an antiinflammatory compound.