6379-73-3Relevant academic research and scientific papers
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.
Phenylimidazole derivative, synthesis method of phenylimidazole derivative and application of phenylimidazole derivative to pesticide
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Paragraph 0035, (2019/06/11)
The invention relates to a phenylimidazole derivative, a synthesis method of the phenylimidazole derivative and application of the phenylimidazole derivative to pesticide, particularly application tothe fungicide pesticide aspect, and belongs to the technical field of pesticide. In order to solve the technical problems, the invention provides a novel phenylimidazole derivative, a synthesis methodof the novel phenylimidazole derivative and application of the novel phenylimidazole derivative to the pesticide. The structure of the compound is shown as a formula I. The compound structure is simple and novel; the synthesis is easy; meanwhile, the fungicidal activity is realized; a better bacteriostasis or sterilization effect is achieved on important plant pathogenic fungi such as tomato early blight, tomato botrytis cinereal, cucumber fusarium oxysporum, magnaporthe grisea and rice rhizoctonia solani.
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.
Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks
Paptchikhine, Alexander,Itto, Kaori,Andersson, Pher G.
supporting information; experimental part, p. 3989 - 3991 (2011/06/09)
A range of 1,2,4-trisubstituted cyclohexadienes obtained from the Birch reaction were hydrogenated asymmetrically to produce synthetically valuable chiral compounds in high enantio- and diastereoselectivity. The Royal Society of Chemistry.
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.
Synthesis of biologically active carvacrol compounds using different solvents and supports
More,Narkhede,Dalal,Mahulikar
, p. 1957 - 1964 (2008/02/05)
Natural monoterpenoids have been documented for their acute toxicity and repellent, antifeedent, reproduction inhibitory, and insecticidal actions. The present work aims to derive a variety of ether and ester compounds using polymer-supported reactions from the polymer-supported carvacrol anion was reacted with alkyl halides and acid chlorides to afford carvacryl ethers and esters, respectively. Furthermore, a special study on the effect of different solvents and supports revealed that Amberlite IRA 400 (chloride form) was found to be the best polymer support and acetone among the solvents. Copyright Taylor & Francis Group, LLC.
GENERATION AND TRAPPING OF VINYLCARBENES AT AMBIENT TEMPARATURE: A ROUTE TO FUNCTIONALISED VINYL- AND ALLYLIDENE CYCLOPROPANES
Dulayymi, Juma'a R. Al.,Baird, Mark S.
, p. 7601 - 7614 (2007/10/02)
1,2-Dehalogenation of tetrachlorocyclopropanes (5, X = Cl, OMe, N-iPr2, SAllyl) by methyl lithium leads to dichlorocyclopropenes ( 6, X = Cl, OMe, i-NPr2, SAllyl); the first two of these react with electron rich and electron poor alkenes at 20 deg C to give cyclopropanes which are apparently derived by trapping of vinylcarbenes (8) rather than (20).Reaction of the derived vinylcyclopropanes with base leads either to ethyl cyclopropyl ketones or to allylidenecyclopropanes.
