(1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Base Information

• Chemical Name: (1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• CAS No.: 5945-50-6
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.344
• Hs Code.: 29389090
• NSC Number: 88926,291303
• DSSTox Substance ID: DTXSID40974857
• Mol file: 5945-50-6.mol

Synonyms:Monotropeine;(1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid;Cyclopenta[c]pyran-4-carboxylic acid,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-, [1S-(1.alpha.,4a.alpha.,7.beta.,7a.alpha.)]-;DTXSID40974857;NSC88926;NSC291303;1-(Hexopyranosyloxy)-7-hydroxy-7-(hydroxymethyl)-1,4a,7,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Chemical Property of (1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.68E-24mmHg at 25°C
• Melting Point: 170-173 °C
• Refractive Index: 1.685
• Boiling Point: 717.6 °C at 760 mmHg
• PKA: 4.31±0.60(Predicted)
• Flash Point: 262 °C
• PSA: 186.37000
• Density: 1.73 g/cm³
• LogP: -3.34670
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 390.11621151
• Heavy Atom Count: 27
• Complexity: 634

Purity/Quality:

98% ^*data from raw suppliers

Monotropein ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)(CO)O
• Isomeric SMILES: C1=C[C@@]([C@@H]2[C@H]1C(=CO[C@H]2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)(CO)O
• Description: Monotropein is an iridoid glycoside originally isolated from M. officinalis roots and has diverse biological activities. It increases cell viability and migration of bone marrow-derived endothelial progenitor cells (BM-EPCs) when used at concentrations ranging from 0.1 to 1,000 μM. Monotropein inhibits apoptosis and reduces levels of matrix metalloproteinase-3 (MMP-3) and MMP-13 in chondrocytes. It inhibits LPS-induced nuclear translocation of NF-κB and reduces COX-2, inducible nitric oxide synthase (iNOS), TNF-α, and IL-1β mRNA expression in RAW 264.7 cells. Monotropein (100 and 200 mg/kg) reduces colonic myeloperoxidase (MPO) activity, COX-2 and iNOS mRNA expression, and disease severity in a mouse model of ulcerative colitis induced by dextran sulfate sodium (DSS; ). It increases bone mineral content, bone mineral density, and improves bone microstructure in ovariectomized mice when administered at doses of 40 or 80 mg/kg. Monotropein (20 and 30 mg/kg) reduces acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats. It also decreases macrophage infiltration and wound healing time and increases blood vessel formation in a rat model of wound healing.

Technology Process of (1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid

There total 1 articles about (1S,4aS,7R,7aS)-7-hydroxy-7-(hydroxymethyl)-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylic acid 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:

Andromedoside (36138-58-6,75044-72-3) → monotropein (5945-50-6,94482-97-0)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 24h;

DOI:10.1002/ardp.19803130809

upstream raw materials:

Andromedoside