Next Article in Journal
Analysis of the Influence of Lactiplantibacillus plantarum and Lacticaseibacillus rhamnosus Strains on Changes in the Hexachlorobenzene Content in Fermented Mare Milk during Refrigerated Storage
Previous Article in Journal
Chemical Data and Relationships for a Scoring Algorithm of Extra Virgin Olive Oil’s Nutritional Value
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molecules
Volume 29
Issue 2
10.3390/molecules29020526
molecules-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Article

Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210

by
Wenbin Shao
1,2,
Pingyong Liao
1,2,
Xiaoyan Zhang
3,
Binbin Fan
3,
Ruijia Chen
1,2,
Xilong Chen
1,2,
Xuejun Zhao
1,2,* and
Wenbin Liu
1,2,*
1
Shanghai Key Laboratory of Crime Scene Evidence, Shanghai Research Institute of Criminal Science and Technology, Shanghai 200072, China
2
Shanghai Yuansi Standard Science and Technology Co., Ltd., Shanghai 200072, China
3
State Key Laboratory of Bio-Fibers and Eco-Textiles, Institute of Marine Biobased Materials, Collage of Materials Science and Engineering, Qingdao University, Qingdao 266071, China
*
Authors to whom correspondence should be addressed.
Molecules 2024, 29(2), 526; https://doi.org/10.3390/molecules29020526
Submission received: 19 December 2023 / Revised: 16 January 2024 / Accepted: 18 January 2024 / Published: 21 January 2024
(This article belongs to the Section Organic Chemistry)
Browse Figures
Versions Notes

Abstract

Cannabinoid metabolites have been reported to be more potent than their parent compounds. Among them, ajulemic acid (AJA) is a side-chain analog of Δ9-THC-11-oic acid, which would be a good template structure for the discovery of more potent analogues. Herein, we optimized the key allylic oxidation step to introduce the C-11 hydroxy group with a high yield. A series of compounds was prepared with this condition applied including HU-210, 11-nor-Δ8-tetrahydrocannabinol (THC)-carboxylic acid and Δ9-THC-carboxylic acid.
Keywords: phytocannabinoids; metabolites; ajulemic acid; Riley oxidation phytocannabinoids; metabolites; ajulemic acid; Riley oxidation
Graphical Abstract

Share and Cite

MDPI and ACS Style

Shao, W.; Liao, P.; Zhang, X.; Fan, B.; Chen, R.; Chen, X.; Zhao, X.; Liu, W. Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210. Molecules 2024, 29, 526. https://doi.org/10.3390/molecules29020526

AMA Style

Shao W, Liao P, Zhang X, Fan B, Chen R, Chen X, Zhao X, Liu W. Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210. Molecules. 2024; 29(2):526. https://doi.org/10.3390/molecules29020526

Chicago/Turabian Style

Shao, Wenbin, Pingyong Liao, Xiaoyan Zhang, Binbin Fan, Ruijia Chen, Xilong Chen, Xuejun Zhao, and Wenbin Liu. 2024. "Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210" Molecules 29, no. 2: 526. https://doi.org/10.3390/molecules29020526

APA Style

Shao, W., Liao, P., Zhang, X., Fan, B., Chen, R., Chen, X., Zhao, X., & Liu, W. (2024). Syntheses of Cannabinoid Metabolites: Ajulemic Acid and HU-210. Molecules, 29(2), 526. https://doi.org/10.3390/molecules29020526

Article Metrics

Back to TopTop