6379-73-3Relevant articles and documents
Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene
Schreiner, Linda,Bauer, Johannes,Ortner, Eva,Buettner, Andrea
supporting information, p. 834 - 842 (2020/03/30)
Thymoquinone was recently reported as having a unique pencil-like odor and being the impact compound for the cedar-like and cedar wood-based product smell such as pencils. The compounds thymol and carvacrol are structurally related odorants commonly found in plants and foods such as thyme and oregano, also having a significant contribution to their overall aroma. However, a systematic elucidation of the sensory properties in this class of oxygenated, aromatic monoterpenoids has not been carried out. To close this gap and gain new insights into structure-odor relationships leading to pencil-like and woody odors, 19 structurally related derivatives of p-cymene starting from thymol and carvacrol were synthesized and characterized. The compounds had odor thresholds ranging from 2.0 ng/L air to 388.8 ng/L air, being lowest for thymol and carvacrol and highest for thymohydroquinone. The compounds smelled mostly thyme-like, oregano-like, and pencil-like with phenolic, earthy, and medicinal variations in their odor character, which could be successfully linked to structural motifs.
Identification and structure-activity relationship study of carvacrol derivatives as Mycobacterium tuberculosis chorismate mutase inhibitors
Alokam, Reshma,Jeankumar, Variam Ullas,Sridevi, Jonnalagadda Padma,Matikonda, Siddharth Sai,Peddi, Santosh,Alvala, Mallika,Yogeeswari, Perumal,Sriram, Dharmarajan
, p. 547 - 554 (2014/08/05)
In the present study, we identified carvacrol, a major phenolic component of oregano oil as a novel small molecule inhibitor of Mycobacterium tuberculosis (MTB) chorismate mutase (CM) enzyme with IC50 of 1.06±0.4μM. Virtual screening of the BITS-Pilani in-house database using the crystal structure of the MTB CM bound transition state intermediate (PDB: 2FP2) as framework identified carvacrol as a potential lead. Further various carvacrol derivatives were evaluated in vitro for their ability to inhibit MTB CM enzyme, whole cell MTB and cytotoxicity as steps toward the derivation of structure-activity relationships (SAR) and lead optimization.
Solid-supported synthesis of bio-active carvacrol compounds using microwaves
Narkhede,More,Dalal,Mahulikar
, p. 2413 - 2418 (2008/09/21)
The most abundant and potent natural products having a broad spectrum of biological activity against various pests are terpenoids, especially monoterpenoids. The chemical modification of natural monoterpenoids has been reported to result in modified biological activity. The present work emphasizes the structural modification of carvacrol, a phenolic monoterpenoid, through the synthesis of different ether and ester derivatives that are useful for structure-activity relationship studies to exploit the potent molecules. The carvacrol was reacted with alkyl halides and acid chlorides under microwaves using solid supports such as silica gel, alumina, and fly ash to give ethers and esters, respectively. The synthesis of dimeric ether and ester compounds using dihalides and acid dichlorides was conducted with novel reactions. Additional features of the methodology include very fast reactions, higher yields and purities of the products, and an ecofriendly approach. Copyright Taylor & Francis Group, LLC.
