26660-57-1

Basic information

• Product Name: Deoxyloganin
• Synonyms: Deoxyloganin;(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,6,7,7aα-hexahydro-7α-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester;(1S)-1α-(β-D-Glucopyranosyloxy)-7α-methyl-1,4aα,5,6,7,7aα-hexahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester;7-Deoxyloganin
• CAS NO: 26660-57-1
• Molecular Formula: C₁₇H₂₆O₉
• Molecular Weight: 374.38294
• Mol File: 26660-57-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 563.5°Cat760mmHg
• Flash Point: 201.2°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 4.82E-15mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: Deoxyloganin(CAS DataBase Reference)
• NIST Chemistry Reference: Deoxyloganin(26660-57-1)
• EPA Substance Registry System: Deoxyloganin(26660-57-1)

Safety Data

• Hazardous Substances Data: 26660-57-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C17H26O9/c1-7-3-4-8-9(15(22)23-2)6-24-16(11(7)8)26-17-14(21)13(20)12(19)10(5-18)25-17/h6-8,10-14,16-21H,3-5H2,1-2H3/t7-,8+,10+,11+,12+,13-,14+,16-,17-/m0/s1

Upstream product

• 141913-22-6 6,6-bis(ethylthio)-7-deoxyloganin tetraacetate 
• 24512-66-1 (1S,4aS,7aR)-7-Methyl-1-((2S,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-carboxylic acid methyl ester 
• 24512-66-1 7-deoxyloganin tetracetate 
• 49776-64-9 geniposide penta-acetate 
• 20586-16-7 tetraacetyl-6,10-bis(deoxy)aucubin-4-carboxylic acid methyl ester 
• 54621-23-7 10-dehydrogeniposide tetraacetate 
• 54621-24-8 (1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 73528-65-1 ixoside monomethyl ester tetraacetate 
• 51491-54-4 cornin tetraacetate 
• 1252030-52-6 (S,E)-3-methoxy-3-oxoprop-1-en-1-yl 5-methylcyclopent-1-enecarboxylate 
• 1252030-48-0 (S)-5-methylcyclopent-1-enecarboxylic acid 
• 1252030-45-7 (S)-ethyl 5-((tert-butyldimethylsilyl)oxy)cyclopent-1-enecarboxylate 
• 1252030-47-9 (S)-ethyl 5-methylcyclopent-1-enecarboxylate 
• 1252030-49-1 (S)-5-methylcyclopent-1-enecarbonyl chloride 

Downstream Products

• 485-43-8 iridomyrmecin 
• 21651-62-7 nepetalactone 
• 60419-55-8 (+)-teucriumlactone 
• 21699-53-6 isodihydronepetalactol 
• 72963-55-4 8-epi-iridotrial glucoside 
• 72963-55-4 iridotrialglucoside 
• 18524-94-2 loganin 
• 27856-54-8 lamiide 

Relevant articles and documents

Concise formal synthesis of (-)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters

NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β- unsaturated acids provides the cyclopentapyranone core of (-)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps startin

SYNTHESIS OF IRIDOLACTONES ISOLATED FROM SILVER VINE

The naturally occurring iridolactones, nepetalactone, isodihydronepetalactone, and iridomyrmecin are synthesized in optically active forms starting from natural glycoside geniposide.The stereogenic centers were introduced with highly stereoselective hydrogenations.

BIOSYNTHESIS OF THE IRIDOID GLUCOSIDE CORNIN IN VERBENA OFFICINALIS

The biosynthesis of cornin (verbenalin) and dihydrocornin in Verbena officinalis has been investigated.The incorporation of deoxyloganin was found to be largely independent of the incubation time between one day and a week.An improved method for the preparation of deoxygeniposide from gardenoside is reported and -iridodial glucoside and iridotrial glucoside were prepared from the former.Feeding experiments with young plants using these glucosides, as well as the aglucones, showed much better incorporations for the latter compounds as measured by 2H NMR spectroscopy. 13C-labelled 10-hydroxygeraniol, 10-hydroxycitronellol, iridodial, iridotrial, iridodial glucoside, iridotrial glucoside, deoxyloganic acid aglucone were prepared. -Mevalonic acid and the above compounds were fed to plants of medium age, and all gave incorporations measurable by 13C NMR spectroscopy into dihydrocornin.The postulated existence of two different metabolic pathways in the biosynthesis of cornin in young and old plants, respectively, could not be established as complete scrambling between the C-3 and C-11 in the iridoid skeleton apparently takes place with all the early precursors.The complete pathway from iridoidal forwards to hastatoside has been elucidated.Key Word Index- Verbena officinalis; Verbenaceae; cornin; dihydrocornin; iridoid glucosides; biosynthesis; 13C-labelling; 2H-labelling.