6-Epiharpagide

Base Information

• Chemical Name: 6-Epiharpagide
• CAS No.: 6926-08-5
• Molecular Formula: C15H24O10
• Molecular Weight: 364.35
• Hs Code.: 29389090
• European Community (EC) Number: 230-050-0
• Wikidata: Q105342673
• Mol file: 6926-08-5.mol

Synonyms:ajugol;harpagide;leonuride;myoporoside

Chemical Property of 6-Epiharpagide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.663
• Boiling Point: 637.1 °C at 760 mmHg
• PKA: 12.10±0.70(Predicted)
• Flash Point: 339.1 °C
• PSA: 169.30000
• Density: 1.66 g/cm³
• LogP: -3.11500
• Storage Temp.: 2-8°C
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 364.13694696
• Heavy Atom Count: 25
• Complexity: 528

Purity/Quality:

99% ^*data from raw suppliers

Harpagide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Useful:

• Canonical SMILES: CC1(CC(C2(C1C(OC=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• Uses: Harpagide is an iridoid glycoside along with Harpagoside (H105275) with the potential to be strong anti-inflammatory agents providing the bulk of the observed effects from their plant origins.

Technology Process of 6-Epiharpagide

There total 10 articles about 6-Epiharpagide 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: 83.0%

8-acetylharpagide → (1S,4aS,5R,7S,7aR)-7-Methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4a,5,7-triol (6926-08-5)

Guidance literature:

With sodium hydride; In methanol; at 20 ℃; for 0.333333h;

DOI:10.1021/np030238b

Reference yield: 70.0%

Pentaacetylantirrhinosid (20770-66-5,35993-19-2) → (1S,4aS,5R,7S,7aR)-7-Methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4a,5,7-triol (6926-08-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 4h; Heating;

Reference yield:

8-O-4-hydroxycinnamoylharpagide (87686-74-6) → (1S,4aS,5R,7S,7aR)-7-Methyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4a,5,7-triol (6926-08-5)

Guidance literature:

With sodium hydroxide; Multistep reaction; 1.) MeOH, reflux, 1 h;

upstream raw materials:

8-O-4-hydroxycinnamoylharpagide

Pentaacetylantirrhinosid

penta-O-acetylantirrhinoside

8-O-cis-cinnamoyl-6-O-β-D-glucosylharpagide

Refernces

• 1、 Kitagawa,Nishimura,Takei,Yosioka. "On the iridoid constituent isolated from the roots of Scrophularia buergeriana Miq.". . p. 1254 - 1256. Retrieved 1967.
• 2、 -. "Use of harpagid-related compounds for prevention and treatment of osteoporosis, arthritis and ruptured disc and pharmaceutical composition containing the same". . . Retrieved 2008/06/13.
• 3、 Weinges, Klaus,Zourari, Maria,Smuda, Hubert,Rodewald, Hans,Nixdorf, Matthias,Irngartinger, Hermann. "Chemistry and Stereochemistry of Iridoids, V. - Crystal and Molecular Structure of Hexaacetylleonuride - Stereochemical Correlations of Some Iridoid Glucosides". . p. 1063 - 1081. Retrieved 2007/10/02.