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Usage

Uses

Used in Pharmaceutical Industry:
6-Epiharpagide is used as a potential treatment for pain and inflammatory conditions due to its anti-inflammatory and analgesic properties. It may inhibit the production of pro-inflammatory molecules and reduce pain, making it a promising candidate for the development of new pharmaceutical drugs.
Used in Traditional Medicine:
6-Epiharpagide has been studied for its potential use in traditional medicine for managing conditions such as arthritis and rheumatism. Its natural remedy properties for pain and inflammation make it a valuable component in various traditional medicine practices.

Upstream product

• 20770-66-5 Pentaacetylprocumbid 
• 20770-66-5 penta-O-acetylprocumbide 

Relevant academic research and scientific papers

Chemistry and Stereochemistry of Iridoids, V. - Crystal and Molecular Structure of Hexaacetylleonuride - Stereochemical Correlations of Some Iridoid Glucosides

Leonuride (ajugol, 1a) and myoporoside (2) are C-6 epimers, the configurations of which are specified differently in the literature.By X-ray structure analysis of hexaacetylleonuride (1d) the absolute configuration of leonuride (1a) is fixed, to which the configurations of catalpol (3a), antirrhinoside (6a), and harpagide (7a) as well as procumbide (14a) and 6-epi-harpagide (15a) are linked by chemical correlation.

Effect of an 8-Hydroxymethyl Substituent on the Base-Catalyced Ring Opening of 7,8-Epoxyiridoid Glucosides

Base-catalyzed ring opening of 7,8-epoxyiridoids has been found to be dependent on the substitution pattern at C-8.Epoxyiridoids 5, 6, and 10 (CH3-8) react in barium or sodium hydroxide solutions through a normal SN2 process, yielding the expected 7α,8β-diols while for iridoids 3 and 4 (CH2OH-8) the stereochemistry of the final diol function is reversed (7β,8α).This abnormal SN2 process is explained by a preliminary "epoxide migration" from carbons 7,8 to 8,10 followed by normal oxirane cleavage.Participation of the CH2OH-8 substituent in the cleavage reaction is proved by the behavior of the hexa-O-methyl derivative 3 which gives the normal 7α,8β-diol.Four new nonnatural iridoid glucosides (9, 11, 14, 16) are also described and spectroscopically (1H and 13C NMR) characterized.