Hyperforin

Base Information

• Chemical Name: Hyperforin
• CAS No.: 11079-53-1
• Molecular Formula: C35H52O4
• Molecular Weight: 536.795
• Hs Code.: 29144000
• European Community (EC) Number: 601-000-9
• UNII: RM741E34FP
• DSSTox Substance ID: DTXSID90891409
• Nikkaji Number: J15.315J,J3.035.504K
• Wikipedia: Hyperforin
• Wikidata: Q412742,Q105121483
• Pharos Ligand ID: 4TJXJ5WKSP7U
• Metabolomics Workbench ID: 53223
• ChEMBL ID: CHEMBL501711,CHEMBL1237210
• Mol file: 11079-53-1.mol

Synonyms:hyperforin;IDN5607;IDN5706;octahydrohyperforin;tetrahydrohyperforin

Chemical Property of Hyperforin

Chemical Property:

• Appearance/Colour: White to off-white powder.
• Vapor Pressure: 8.53E-18mmHg at 25°C
• Melting Point: 79-80℃
• Refractive Index: 1.518
• Boiling Point: 616.825 °C at 760 mmHg
• PKA: 4.8 (50% aq ethanol)
• Flash Point: 340.861 °C
• PSA: 71.44000
• Density: 1.011 g/cm³
• LogP: 8.98970
• Storage Temp.: -20°C
• XLogP3: 9.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 536.38656014
• Heavy Atom Count: 39
• Complexity: 1140

Purity/Quality:

99% ^*data from raw suppliers

Hyperforin ≥85%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(=O)C12C(=O)C(=C(C(C1=O)(CC(C2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
• Isomeric SMILES: CC(C)C(=O)[C@]12C(=O)C(=C([C@](C1=O)(C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)O)CC=C(C)C
• Uses: St. John’s wort is a widely consumed herbal preparation which has been claimed to have a number of medicinal properties. It contains a number of known lipid signalling mediators, including chlorogenic acid, hypericin, hyperforin, and I3,II8-biapigenin. Hyperforin exhibits two activities which may alter the action of other concurrent medications. It inhibits the activity of several CYP450 enzymes, with CYP2D6 being the most sensitive with an IC50 of about 10 μg/ml. Hyperforin is also a ligand for the steroid X receptor (SXR). Since one activity of this receptor is the induction of CYP450 expression, the exact nature of hyperforin’s drug-drug interactions must be evaluated on a case-by-case basis. However, these interactions certainly complicate its use as a human therapeutic.[Cayman Chemical] Hyperforin may be used:as a reference standard for calibration curve generation in high-perfornamce liquid chromatography (HPLC) analysisto test its cytotoxic effect and apoptosis induction in mouse embryonic cellsas a pregnane X receptor (PXR) in porcine brain capillary endothelial cells for transport assay

Technology Process of Hyperforin

There total 1 articles about Hyperforin 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:

→ Hyperferin (11079-53-1)

Guidance literature:

Hyperferin-3,5-dinitrobenzoat (II), 1) Ethanol, 1N KOH, 2) neutr., H2SO4;

Reference yield: 81.0%

2,4,6-trimethoxybenzoyl chloride (42833-84-1) + hyperforin (11079-53-1) → 2,4,6-Trimethoxy-benzoic acid (1R,5R,6R,7S)-5-isobutyryl-6-methyl-1,3,7-tris-(3-methyl-but-2-enyl)-6-(4-methyl-pent-3-enyl)-4,9-dioxo-bicyclo[3.3.1]non-2-en-2-yl ester

Guidance literature:

With pyridine; at 20 ℃; for 0.5h;

DOI:10.1021/np0105681

Reference yield: 45.0%

2,4-dinitrobenzoyl chloride (20195-22-6) + hyperforin (11079-53-1) → hyperforin 3,5-dinitrobenzoate

Guidance literature:

With pyridine; at 20 ℃; for 0.5h;

DOI:10.1021/np0105681

Downstream raw materials:

hyperforin (dicyclohexylammonium) salt