63573-61-5

Upstream product

• 69252-85-3 Acetic acid (1S,7R)-7-methyl-1-((3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-ylmethyl ester 
• 69252-94-4 Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((1S,4aS,7S,7aR)-4,7-dimethyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-1-yloxy)-tetrahydro-pyran-3-yl ester 
• 61081-60-5 tarennoside pentaacetate 

Downstream Products

• 27934-98-1 ipolamiide 
• 27856-54-8 lamiide 
• 550-45-8 iridodial 

Relevant academic research and scientific papers

BIOSYNTHESIS OF ANTIRRHINOSIDE IN ANTIRRHINUM MAJUS

Feeding experiments with deuterium labelled 8-epi-iridodial glucoside, 8-epi-iridotrial glucoside and the corresponding aglucones gave incorporation of all compounds into antirrhinoside in Antirrhinum majus.A higher incorporation of 8-epi-iridotrial than of 8-epi-iridotrial glucoside indicates that the former is an intermediate in the biosynthesis of antirrhinoside although a definite proof could not be obtained. Key Word Index - Antirrhinum majus; Scophulariaceae; antirrhinoside; 8-epi-deoxyloganic acid; 8-epi-iridodial; 8-epi-iridodial glucoside; 8-epi-iridotrial; 8-epi-iridotrial glucoside; iridoid glucosides; biosynthesis; 2H-labelling.

Studies on Monoterpene Glucosides and Related Natural Products. LV. Iridane Skeleton Formation from Acyclic Monoterpenes in the Biosynthesis of Iridoid Glucosides in Gardenia jasminoides f. grandiflora Cell Suspension Cultures

Administration of (3)H- or (13)C-labeled acyclic monoterpenes to Gardenia jasminoides f. grandiflora cell suspension cultures showed that tarennoside (20) and gardenoside (21) were biosynthesized in the cell cultures via the cyclization of 10-oxogeranial (5a)/10-oxoneral (5b) to iridodial cation (14), followed by extensive randomization of the carbon atoms 3 and 11.Furthermore, the intermediacy of (R)-(+)- and (S)-(-)-10-hydroxycitronellol (24a, 24b) and (R)-(+)- and (S)-(-)-9,10-dihydroxycitronellol (28a, 28b) was disproved.Keywords - iridoid glucoside; biosynthesis; iridane skeleton formation; 10-oxocitral; iridodial cation; tarennoside; Gardenia jasminoides; cell culture