Loganetin

Base Information

• Chemical Name: Loganetin
• CAS No.: 29748-10-5
• Molecular Formula: C11H16 O5
• Molecular Weight: 228.245
• Mol file: 29748-10-5.mol

Synonyms:Cyclopenta[c]pyran-4-carboxylicacid, 1,4a,5,6,7,7a-hexahydro-1,6-dihydroxy-7-methyl-, methyl ester, [1R-(1a,4aa,6a,7a,7aa)]-; Cyclopenta[c]pyran-4-carboxylic acid, 1,4aa,5,6,7,7aa-hexahydro-1,6a-dihydroxy-7a-methyl-, methyl ester (8CI);Loganetin; Loganigenin; Loganigenine; Loganin aglycon; Loganin aglycone;Loganol; Loganoside aglycon

Chemical Property of Loganetin

Chemical Property:

• Boiling Point: 375.7±42.0 °C(Predicted)
• PKA: 12.12±0.70(Predicted)
• PSA: 75.99000
• Density: 1.307±0.06 g/cm3(Predicted)
• LogP: 0.02500

Purity/Quality:

98%min ^*data from raw suppliers

Loganetin >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: loganetin works in synergy with 5-fluorouracil to inhibit carcinogenesis of human gastric cancer cells via down-regulation of Wnt/β-catenin pathway

Technology Process of Loganetin

There total 5 articles about Loganetin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

williamsoside B → β-D-glucose (492-61-5) + methyl-(1R,6S,7R)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate (29748-10-5) + 3-(C-hydroxymethyl)-α-D-erythrofuranose (30738-01-3)

Guidance literature:

With sulfuric acid; In methanol; for 8h; Reflux;

DOI:10.3390/molecules16053869

Reference yield:

loganigenin-1β-O-β-D-glucopyranosyl-6'-O-β-D-glucopyranoside (389806-47-7) → methyl-(1R,6S,7R)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate (29748-10-5) + D-glucose (50-99-7) + loganin (18524-94-2)

Guidance literature:

With water; at 25 ℃; for 2h;

DOI:10.1007/s10600-009-9257-6

Reference yield:

2',3',4',6'-tetra-O-acetylloganin (76703-84-9) → methyl-(1R,6S,7R)-1,6-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate (29748-10-5) + 2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3)

Guidance literature:

With water; Acidic conditions;

DOI:10.1007/s10600-009-9257-6

upstream raw materials:

loganigenin-1β-O-β-D-glucopyranosyl-6'-O-β-D-glucopyranoside

2',3',4',6'-tetra-O-acetylloganin

loganin

Downstream raw materials:

dinklageine

Acetic acid (4aR,6S,7R,7aS)-7-methyl-3-oxo-octahydro-cyclopenta[c]pyran-6-yl ester

cantleyine

tetrahydrocantleyine

Refernces

• 1、 Makarevich,Kovalenko,Gusarova,Gubin. "Iridoids from Symphoricarpos albus". experimental part. p. 40 - 44. Retrieved 2009/06/20.