20053-40-1

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of ?9-Tetrahydro Cannabinol.

Upstream product

• 4497-92-1 2-carene 
• 20053-58-1 (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide 
• 936-91-4 3-carene epoxide 
• 54145-81-2 1,2-epoxy-8-hydroxy-p-menthane 
• 98-55-5 terpineol 
• 76338-34-6 1α-hydroxy-2β-phenylseleno-trans-p-menthan-8-ol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 

Downstream Products

• 107602-68-6 (4aR,8aR)-4a,7,8,8a,-tetrahydro-1,1,6-trimethyl-1H-2-benzopyran-3(4H)-one 
• 87791-00-2 6-(1-hydroxy-1-methylethyl)-3-methyl-2-cyclohexen-1-one 
• 76338-37-9 1,8-diacetoxy-trans-p-menth-2-ene 
• 31262-37-0 tetrahydrocannabivarin 
• 1972-08-3 dronabinol 
• 80-53-5 trans-terpin 

Relevant academic research and scientific papers

Dye-sensitized intrazeolite photooxygenation of 4-substituted cyclohexenes. Remote substituent effects in regioselectivity and diastereoselectivity

The product distribution in the dye-sensitized photooxygenation of α-terpinyl acetate and terpinen-4-ol is quite similar in solution, however, by zeolite Y confinement, is substantially influenced by the position of the remote polar substituents relative

Heterologous expression of geraniol dehydrogenase for identifying the metabolic pathways involved in the biotransformation of citral by Acinetobacter sp. Tol 5

The biotransformation of citral, an industrially important monoterpenoid, has been extensively studied using many microbial biocatalysts. However, the metabolic pathways involved in its biotransformation are still unclear, because citral is a mixture of the trans-isomer geranial and the cis-isomer neral. Here, we applied the heterologous expression of geoA, a gene encoding geraniol dehydrogenase that specifically converts geraniol to geranial and nerol to neral, to identify the metabolic pathways involved in the biotransformation of citral. Acinetobacter sp. Tol 5 was employed in order to demonstrate the utility of this methodology. Tol 5 transformed citral to (1R,3R,4R)-1-methyl-4-(1-methylethenyl)-1,3-cyclohexanediol and geranic acid. Biotransformation of citral precursors (geraniol and nerol) by Tol 5 transformant cells expressing geoA revealed that these compounds were transformed specifically from geranial. Our methodology is expected to facilitate a better understanding of the metabolic pathways involved in the biotransformation of substrates that are unstable and include geometric isomers.

METHODS AND INTERMEDIATES FOR THE SYNTHESIS OF DELTA-9 TETRAHYDROCANNABINOL

Processes are disclosed for the synthesis of Delta-9 tetrahydrocannabinol which result in an improved Y-THC/Y-THC ratio, and intermediates are disclosed that may be used in the synthesis of Delta-9 tetrahydrocannabinol such that improved Y-THCIY-THC ratios are achieved. The intermediates may be cyclic compounds prepared from 2-Carene. There is also provided a scaleable process for the preparation of (+)-p-menth-2-ene-1, 8-diol,, another intermediate used in the synthesis of delta-9-tetrahydrocannibinol.

Stereoselective Cyclization assisted by the Selenyl Group. Biogenetic-type Synthesis in the p-Menthane Series

Acid-catalysed cyclization of the β-hydroxyselenide (3), derived from linalyl acetate (1), afforded the trans-p-menthanes (4) and (5), the structures of which were confirmed by their transformation into (6), (11), (8), and (13), and alternative syntheses of these compounds.The structure determination of some products obtained by the reaction of limonene and α-terpineol epoxides with phenylselenium anion was also carried out.

Studies on the stereochemical course of selenium-assisted cyclisation: Biogenetic-type synthesis in the p-menthan series

Acid-catalysed cyclisation of the β-hydroxy selenide (3) denved from linalyl acetate (1) afforded the trans-p-methans (4) and (5), the structures of which were confirmed by their transformation into (6), (8), (9), and (11) and by alternative synthesis of these compounds.