87-44-5Relevant articles and documents
Method and Means for Releasing a Terpene Mixture to a Cannabis Flower During Storage
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, (2021/09/17)
A method and means for releasing a terpene mixture to a Cannabis flower during storage with may be from a cotton pulp card or a two-way humidity pack with an additional terpene blend for keeping a Cannabis flower fresh while naturally increasing the desired terpene levels. The product is a blend of humidity regulating agents infused with terpenes (plant derived) which allows for the product to be paired with herbal material to increase and maintain the relative humidity, while transferring the flavor/aroma/taste terpenes from the package into the herbal material. There are two embodiments, the first is a Terp Pack+Humidity (“Terp Pack+RH”) which contains a herban material to increase and maintain relative humidity, while releasing the infused terenes, and the second is more simply a Terp Pack (“Terp Pack”) which contains no humidity enhancing material and is only a carrier for releasing the terpene mixture.
COMPOSITIONS HAVING AN AGENT AND AN ENHANCER THEREOF, METHODS OF USE, AND DELIVERY SYSTEMS
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, (2020/03/23)
The present invention relates to compositions, and methods of use thereof, related to the endocannabinoid system and includes therapeutic compositions including an agent and an enhancer thereof, optionally, formulated for administration of the therapeutic compositions, preferably in a measured amount.
Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis
Bissegger, Fabian,Levi, Shani,Major, Dan T.,Némethová, Ivana,Prescimone, Alessandro,Schmid, Dario,Syntrivanis, Leonidas-Dimitrios,Tiefenbacher, Konrad
supporting information, p. 5894 - 5900 (2020/04/10)
Terpenes constitute one of the most structurally varied classes of natural products. A wide range of these structures are produced in nature by type I terpene cyclase enzymes from one single substrate. However, such reactivity has proven difficult to reproduce in solution with man-made systems. Herein we report the shortest synthesis of the tricyclic sesquiterpene presilphiperfolan-1β-ol to date, utilizing the supramolecular resorcinarene capsule as catalyst for the key step. This synthetic approach also allows access to unnatural derivatives of the natural product, which would not be accessible through the biosynthetic machinery. Additionally, this study provides useful insight into the biosynthesis of the presilphiperfolanol natural products, including the first experimental evidence consistent with the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.
An Unusual Skeletal Rearrangement in the Biosynthesis of the Sesquiterpene Trichobrasilenol from Trichoderma
Murai, Keiichi,Lauterbach, Lukas,Teramoto, Kazuya,Quan, Zhiyang,Barra, Lena,Yamamoto, Tsuyoshi,Nonaka, Kenichi,Shiomi, Kazuro,Nishiyama, Makoto,Kuzuyama, Tomohisa,Dickschat, Jeroen S.
supporting information, p. 15046 - 15050 (2019/09/12)
The skeletons of some classes of terpenoids are unusual in that they contain a larger number of Me groups (or their biosynthetic equivalents such as olefinic methylene groups, hydroxymethyl groups, aldehydes, or carboxylic acids and their derivatives) than provided by their oligoprenyl diphosphate precursor. This is sometimes the result of an oxidative ring-opening reaction at a terpene-cyclase-derived molecule containing the regular number of Me group equivalents, as observed for picrotoxan sesquiterpenes. In this study a sesquiterpene cyclase from Trichoderma spp. is described that can convert farnesyl diphosphate (FPP) directly via a remarkable skeletal rearrangement into trichobrasilenol, a new brasilane sesquiterpene with one additional Me group equivalent compared to FPP. A mechanistic hypothesis for the formation of the brasilane skeleton is supported by extensive isotopic labelling studies.
Convenient synthesis of deuterium labelled sesquiterpenes
Duhamel, Nina,Martin, Damian,Larcher, Roberto,Fedrizzi, Bruno,Barker, David
supporting information, p. 4496 - 4499 (2016/09/14)
Sesquiterpenes are an important class of molecules, with roles ranging from pollination and signalling to defense mechanisms. Despite their apparent importance, the limited number of commercial standards has hindered their study and precise quantification. Herein, we report the syntheses of fourteen labelled sesquiterpenes with a high level of deuterium incorporation (>95%) for applications in MS-based studies.
Doubly deuterium-labeled patchouli alcohol from cyclization of singly labeled [2-2H 1]farnesyl diphosphate catalyzed by recombinant patchoulol synthase
Faraldos, Juan A.,Wu, Shuiqin,Chappell, Joe,Coates, Robert M.
experimental part, p. 2998 - 3008 (2010/05/01)
Incubations of isotopically pure [2-2H1](E,E)- farnesyl diphosphate with recombinant patchoulol synthase (PTS) from Pogostemon cablin afforded a 65:35 mixture of monodeuterated and dideuterated patchoulols as well as numerous sesquiterpene hydrocarbons. Extensive NMR analyses ( 1H and 13C NMR, 1H homodecoupling NMR, HMQC, and 2H NMR) of the labeled patchoulol mixture and comparisons of the spectra with those of unlabeled alcohol led to the conclusion that the deuterium label was located at positions (patchoulol numbering system) C5 (both isotopomers, ca. 100%) and C12 (minor isotopomer, 30-35%), that is, an approximately 2:1 mixture of [5-2H1]- and [5,12- 2H2]-patchoulols. Low-resolution FIMS analyses and isotope ratio calculations further corroborated the composition of the mixture as mainly one singly deuterated and one doubly deuterated patchoulol. From a mechanistic point of view, the formation of [5,122H2] patchoulol is rationalized through the intermediacy of an unknown exocyclic [7,10:1,5]patchoul-4(12) ene (15-d1), which could incorporate a deuteron at the C-12 position on the pathway to doubly labeled patchoulol. The corresponding depletion of deuterium content observed in the hydrocarbon coproducts, β-patchoulene and α-guaiene (55% d0), identified the source of the excess label found in patchoulol-d2. Comparison of the PTS amino acid sequence with those of other sesquiterpene synthases, and examination of an active site model, suggested that re-orientation of leucine 410 side chain in PTS might facilitate the creation of a 2-pocket active site where the observed deuteron transfers could occur. The retention of deuterium at C5 in the labeled patchoulol and its absence at C4 rule out an alternative mechanism involving two consecutive 1,2-hydride shifts and appears to confirm the previously proposed occurrence of a 1,3hydride shift across the 5-membered ring. Anew, semisystematic nomenclature is presented for the purpose of distinguishing the three different skeletal structures of the patchoulane sesquiterpenes.
An unconventional approach to the enantioselective synthesis of caryophylloids
Larionov, Oleg V.,Corey
, p. 2954 - 2955 (2008/09/19)
The chiral enones 4 and ent-4 have been synthesized enantiomerically as configurationally stable compounds that can be used for the synthesis of caryophylloids. For instance, ent-4 has been converted to the marine natural product coraxeniolide A. Copyright
Solvent extraction process
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, (2008/06/13)
A process for extracting a compound or composition of matter from a raw material containing that compound or composition as a constituent part is described. The process comprises the steps of (1) contacting the raw material with an extraction solvent comprising a heptafluoropropane so as to extract the compound or composition from the raw material into the solvent, and (2) separating the solvent containing the extracted compound or composition from raw material. The process is particularly adapted for extracting flavours, fragrances and neutraceuticals from materials of plant origin.
A cDNA clone for β-caryophyllene synthase from Artemisia annua
Cai, Yu,Jia, Jun-Wei,Crock, John,Lin, Zhi-Xin,Chen, Xiao-Ya,Croteau, Rodney
, p. 523 - 529 (2007/10/03)
An homology-based cloning strategy yielded a full-length cDNA from Artemisia annua that encoded a protein of 60.3 kDa which resembled a sesquiterpene synthase in sequence. Heterologous expression of the gene in Escherichia coli provided a soluble recombinant enzyme capable of catalyzing the divalent metal ion-dependent conversion of farnesyl diphosphate to β-caryophyllene, a sesquiterpene olefin found in the essential oil of A. annua. In reaction parameters and kinetic properties, β-caryophyllene synthase resembles other sesquiterpene synthases of angiosperms. The β-caryophyllene synthase gene is expressed in most plant tissues during early development, and is induced in mature tissue in response to fungal elicitor thus suggesting a role for β-caryophyllene in plant defense.
Polystyrene-supported (catecholato)oxorhenium complexes: Catalysts for alcohol oxidation with DMSO and for deoxygenation of epoxides to alkenes with triphenylphosphine
Arterburn, Jeffrey B.,Liu, Minghua,Perry, Marc C.
, p. 3225 - 3236 (2007/10/03)
Polymer-supported catalysts offer practical advantages for organic synthesis, such as improved product isolation, ease of catalyst recycling, and compatibility with parallel solution-phase techniques. We have developed the (carboxypolystyrene-catecholato)rhenium catalyst 2 derived from tyramine (=4-(2-amino-ethyl)phenol), which is effective for alcohol oxidation with dimethylsulfoxide (DMSO) and for epoxide deoxygenation with triphenylphosphine. The supported [Re(catecholato)]catalyst 2 is air- and moisture-stable and can be recovered and used repeatedly without decreasing activity. The procedures work with non-halogenated solvents (toluene). DMSO for Re-catalyzed alcohol oxidation is inexpensive and safer for transport and storage than commonly used peroxide reagents. The oxidation procedure was best suited for aliphatic alcohols, and the mild conditions were compatible with unprotected functional groups, such as those of alkenes, phenols, nitro compounds, and ketones (see Tables 1 and 2). Selective oxidation of secondary alcohols in the presence of primary alcohols was possible, and with longer reaction time, primary alcohols were converted to aldehydes without overoxidation. Epoxides (oxirans) were catalytically deoxygenated to alkenes with this catalyst and Ph3P (see Table 3). Alkyloxiranes were converted to the alkenes with retention of configuration, while partial isomerization was observed in the deoxygenation of cis-stilbene oxide (cis-1.2-diphenyloxirane). These studies indicate that supported [Re(catecholato)] complexes are effective catalysts for O-atom-transfer reactions, and are well suited for applications in organic synthesis.
