📜(E)-8-(3,7-Dimethylocta-2,6-Dien-1-yl)-7-Hydroxy-2,2-Dimethyl-5-Pentyl-4H-Benzo[d][1,3]Dioxin-4-One置于水,Potassium Hydroxide体系中,用 1,4-二氧六环 用作溶剂,化学反应 18.0H,以64%的收率获得大麻萜酚 参考文献: Process For The Production Of Cannabinoids And Cannabinoid Acids[fr] Procédé De Production De Cannabinoïdes Et D'Acides Cannabinoïdes 标题: Process For The Production Of Cannabinoids And Cannabinoid Acids[fr] Procédé De Production De Cannabinoïdes Et D'Acides Cannabinoïdes 摘要:本发明涉及一种制备多种已知和新型大麻素的过程,包括大麻酚醇(cbg,1),大麻酚醇酸(cbga,2),大麻酚酮(cbgv,3),大麻酚酮酸(cbgva,4)等以及其他天然存在的单环大麻素和其他类似物,利用一系列烯丙基重排和芳构化的级联序列从简单廉价的起始原料中制备.系列5的新型大麻素也作为本发明的一部分声明.与从大麻唾液中分离或通过与单萜烃的缩合反应等反应合成的微量大麻素不同,这些合成的大麻素更容易以高纯度水平获得.特别是这些大麻素,包括但不限于大麻酚醇(cbg,1),大麻酚醇酸(cbga,2),大麻酚酮(cbgv,3)和大麻酚酮酸(cbgva,4),可以在不受杂质污染的情况下获得,Ra和rb的变化(例如cbg与cbgv的污染).
专利号:US-11046978-B2 优先权日:2016-03-16 标 题:Synthesis of isoprenoids and derivatives 发明人:GONZALEZ RAMON; CLOMBURG JAMES M; CHEONG SEOKJUNG 权利人:UNIV RICE WILLIAM M 摘要:This disclosure generally relates to the use of enzyme combinations or recombinant microbes comprising same to make isoprenoid precursors, isoprenoids and derivatives thereof including prenylated aromatic compounds. Novel metabolic pathways exploiting Claisen, aldol, and acyioin condensations are used instead of the natural mevalonate (MVA) pathway or 1-deoxy-d-xylulose 5-phosphate (DXP) pathways for generating isoprenoid precursors such as isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), and geranyl pyrophosphate (GPP). These pathways have the potential for better carbon and or energy efficiency than native pathways. Both decarboxylative and non-carboxylative condensations are utilized, enabling product synthesis from a number of different starting compounds. These condensation reactions serve as a platform for the synthesis of isoprenoid precursors when utilized in combination with a variety of metabolic pathways and enzymes for carbon rearrangement and the addition/removal of functional groups. Isoprenoid alcohols are key intermediary products for the production of isoprenoid precursors in these novel synthetic metabolic pathways.
专利号:US-2020079715-A1 优先权日:2018-09-06 标题 :2-position modification for synthesis of resorcinol scaffolding 发明人:DAVIS ROBERT; BLACK JACOB; SMELTZER THOMAS; COLVIN SEAN 权利人:CANOPY HOLDINGS LLC 摘要:A resorcinol with modifications at the 2-position is provided. The reactant resorcinol may have a variety of functional groups at each of the 1, 3, and 5 position such as a hydroxide, a lower alkyl group, a phenyl, a substituted phenyl, a lower alkenyl, or a lower alkynyl sp 2 carbon group (e.g., substituted phenyl, vinyl), sp (e.g., alkyne), hydrogen. The resorcinol is modified at the 2-position with a nucleophile or an electrophile. The resulting resorcinol may serve as a stable intermediate for the synthesis of cannabinoid or cannabinoid derivatives.
专利号:US-11466283-B2 优先权日:2016-08-18 标 题:Plants and methods for increasing and decreasing synthesis of cannabinoids 发明人:ROSCOW ROBERT F 权利人:CANOPY GROWTH CORP 摘要:This disclosure relates to new plants and methods for increasing and decreasing synthesis of cannabinoids. The plants disclosed herein comprise unnatural ratios and concentrations of cannabinoids in plants of genus Cannabis . The methods disclosed herein comprise manipulating the biosynthetic pathway of cannabinoids to produce plants of genus Cannabis with unnatural ratios and concentrations of cannabinoids.
专利号:US-12264143-B2 优先权日:2020-12-17 标 题:Synthesis of cannabinoids and cannabinoid precursors, and related compounds, formulations, and methods of use 发明人:SAMMIS GLENN M; ROGGEN MARKUS 权利人:NALU BIO INC 摘要:Methods are provided for the synthesis of cannabinoids, including cannabidiol (CBD), cannabinol (CBN), cannabichromene (CBC), cannabidiolic acid (CBDA), cannabigerol (CBG), cannabigerolic acid (CBGA), cannabidivarin (CBDV), cannabidibutol (CBD-C4), dihydrocannabidiol (DCBD), tetrahydrocannabivarin (THCV), analogs thereof, and precursors to the foregoing. One method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((−)-trans-Δ9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.
专利号:US-10981850-B2 优先权日:2019-04-15 标 题 :One-step flow-mediated synthesis of cannabidiol (CBD) and derivatives 发明人:PORCO JOHN A; BEELER AARON B; BROWN LAUREN E; TRILLES RICHARD V 权利人:UNIV BOSTON 摘要:Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.
专利号:US-10538790-B2 优先权日:2016-04-04 标题 :Bioenzymatic synthesis of THC-v, CBV and CBN and their use as therapeutic agents 发明人:KAVARANA MALCOLM J; PEET RICHARD C 权利人:TEEWINOT TECH LIMITED 摘要:The present invention provides methods for producing cannabinoids. More specifically, the invention is directed to the bio-enzymatic synthesis of THC-v, CBV and CBN by contacting a compound according to Formula I with a cannabinoid synthase enzyme. Also described is a system for producing these pharmaceutically important cannabinoids and the use of such cannabinoids as therapeutic agents.
参考文献:10.1089/jop.2011.0041 摘要:Szczesniak A, Maor Y, Robertson H, Hung O, Kelly MEM. Nonpsychotropic Cannabinoids, Abnormal Cannabidiol and Canabigerol-Dimethyl Heptyl, Act at Novel Cannabinoid Receptors to Reduce Intraocular Pressure. Journal of Ocular Pharmacology and Therapeutics. 2011 Oct;27(5):427–35. doi: 10.1089/jop.2011.0041.