methyl 7-methyl-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Base Information

• Chemical Name: methyl 7-methyl-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
• CAS No.: 548-37-8
• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.372
• NSC Number: 118055
• Wikidata: Q105030386
• Mol file: 548-37-8.mol

Synonyms:MLS002706776;methyl 1-(hexopyranosyloxy)-7-methyl-5-oxo-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylate;methyl 7-methyl-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate;NSC118055;NSC-118055;Verbenalol, .beta.-D-glucopyranoside;SMR001574175;Cyclopenta[c]pyran-4-carboxylic acid,4a,5,6,7,7a-hexahydro-7-methyl-5-oxo-, methyl ester, [1S-(1.alpha.,4a.alpha.,7.alpha.,7a.alpha.)]-

Chemical Property of methyl 7-methyl-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 1.95E-17mmHg at 25°C
• Melting Point: 180-182°C
• Refractive Index: 1.59
• Boiling Point: 610.1 °C at 760 mmHg
• PKA: 12.79±0.70(Predicted)
• Flash Point: 219.4 °C
• PSA: 151.98000
• Density: 1.5 g/cm³
• LogP: -1.94260
• Storage Temp.: 2-8°C
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 388.13694696
• Heavy Atom Count: 27
• Complexity: 619

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Verbenalin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1CC(=O)C2C1C(OC=C2C(=O)OC)OC3C(C(C(C(O3)CO)O)O)O
• Uses: cell growth inhibitor, coagulant Verbenalin is an iridoid glucoside isolated found in Verbena officinalis and other herb plants.

Technology Process of methyl 7-methyl-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate

There total 4 articles about methyl 7-methyl-5-oxo-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate 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: 55.8%

C18H24O11 → verbenalin (548-37-8,16606-70-5)

Guidance literature:

With Wilkinson's catalyst; In methanol; at 5 - 20 ℃; for 4.33333h; Temperature; Inert atmosphere;

Reference yield:

→ verbenalin (548-37-8)

Guidance literature:

DOI:10.1016/S0040-4020(01)99268-3

Reference yield:

→ verbenalin (548-37-8,16606-70-5)

Guidance literature:

Biosynthese;

Downstream raw materials:

dihydrocornin

Refernces