Enzyme-Catalysed Conversion of Atranol and Derivatives into Dimeric Hydrosoluble Materials: Application to the Preparation of a Low-Atranol Oakmoss Absolute

Abstract

Oakmoss absolute, a solvent extract from Evernia prunastri, is a valuable fragrance ingredient widely used in fine fragrance for almost two centuries. Some minor components of oakmoss absolute, such as atranol and chloroatranol, are attested contact allergens and their presence in fragrance and cosmetic products should be as low as possible. In this context, we have developed an enzyme-based protocol upon which these undesirable molecules are converted in a hydrosoluble dimeric material, and thus easily separated from the absolute by liquid–liquid extraction. Analytical and sensory analyses were performed to confirm the specificity of the process, the absence of alteration of the olfactory quality of the absolute, and the final titles of atranol and chloroatranol, which eventually were observed in the ppm range. This highly sustainable process is a viable alternative to conventional time-, energy-, and manpower-consuming techniques to produce very low-atranol oakmoss absolute.

Comprehensive Lichenometabolomic Exploration of Ramalina conduplicans Vain Using UPLC-Q-ToF-MS/MS: An Identification of Free Radical Scavenging and Anti-Hyperglycemic Constituents

“…The structures of the isolated compounds ( Figure 2 ) were determined by a combination of spectroscopic data (HRESIMS, 1 H and 13 C NMR) and in comparison with the reported literature data. They were identified as sekikaic acid ( 1 ) [ 21 ], 4′- O -methylnorhomosekikaic acid ( 2 ) [ 22 ], homosekikaic acid ( 3 ) [ 22 ], hyperhomosekikaic acid ( 4 ) [ 23 ], 2,4-dimethyldivaric acid ( 6 ) [ 24 ], divaricatic acid ( 7 ) [ 25 ], decarboxydivaricatic acid ( 8 ) [ 26 ], decarboxystenosporic acid ( 9 ) [ 26 ], methyldivaricatinate ( 10 ) [ 24 ], divaricatinic acid ( 11 ) [ 21 ], olivetolic acid ( 12 ) [ 27 ], divarinolmonomethylether ( 13 ) [ 21 ], and atranol ( 14 ) [ 28 ].…”

Salazinic Acid and Norlobaridone from the Lichen Hypotrachyna cirrhata: Antioxidant Activity, α-Glucosidase Inhibitory and Molecular Docking Studies

“…Comparing their physical and spectroscopic data with literature (Supplementary Materials), they were characterized as salazinic acid (11) [21], norlobaridone (12) [20], atranorin (13) [21], lecanoric acid (14) [21], lichesterinic acid (15) [22], protolichesterinic acid (16) [22], methyl hematommate (17) [23], iso-rhizonic acid (18) [24], atranol (19) [25], methyl atratate (20) [21] (Figure 3). Salazinic acid was obtained from a precipitate of the crude extract, while other compounds were purified from some chromatographic steps.…”

From biosynthesis in plants to post-biosynthetic enzymatic conversion. Generation of odor-impact rose oxides from citronellol-rich essential oils

“…Their use in industrial processes in purified form or in whole cell processes can lower production's cost and hazard. Various enzymes have already been used to modify natural complex substances such as essential oils (Antoniotti et al 2008;Bouhlel et al 2012;Notar Francesco et al 2017), absolutes, (Bouges et al 2018) essential oils distillation coproducts, or biobased raw materials (Schalk et al 2012;Diaz-Chavez et al 2013).…”