Biomimetic Transformation of p‑Menthene Glucosides into p‑Cymenes and Carvotanacetone

• Published in: Journal of natural products (Washington, D.C.) Vol. 82; no. 3; pp. 485 - 491
• Main Authors: Pardo-Novoa, Julio C, Arreaga-González, Héctor M, Galván-Gómez, Sinuhé, Rodríguez-García, Gabriela, del Río, Rosa E, Cerda-García-Rojas, Carlos M, Joseph-Nathan, Pedro, Gómez-Hurtado, Mario A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 22.03.2019; Amer Chemical Soc
• Subjects: Chemistry, Medicinal; Life Sciences & Biomedicine; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; ABSOLUTE-CONFIGURATION; ESSENTIAL OIL; IODINE; VOLATILE COMPOUNDS; DERIVATIVES; AROMATIZATION; CONSTITUENTS

A biomimetic transformation of p-menthene glucosides into aromatic monoterpenoids that alluded to mechanisms for essential oil metabolism, which lines up with the precepts of molecular economy, is described. Acid treatment of (−)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-d-glucopyranoside (1) and (−...