11079-53-1

Basic information

• Product Name: HYPERFORIN
• Synonyms: 4-HYDROXY-6R-METHYL-1R,3,7S-TRIS(3-METHYL-2-BUTENYL)-5S-(2-METHYL-1-OXOPROPYL)-6R-(4-METHYL-3-PENTENYL)-BICYCLO[3.3.1]NON-3-ENE-2,9-DIONE;HYPERFORIN;Bicyclo[3.3.1]non-3-ene-2,9-dione, 4-hydroxy-6-;methyl-1,3,7-tris(3-methyl-2-buten-1-yl)-5-(2-methyl-1-oxopropyl)-6-(4-methyl-3-penten-1-yl)-,(1R,5S,6R,7S)-;(1R,5S)-4-Hydroxy-6-methyl-1,3,7β-tris(3-methyl-2-butenyl)-5-(2-methyl-1-oxopropyl)-6α-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione;HYPERFORIN MIX(P);Hyperforin (solution in Ethanol)
• CAS NO: 11079-53-1
• Molecular Formula: C₃₅H₅₂O₄
• Molecular Weight: 536.78
• EINECS: 200-659-6
• Product Categories: Miscellaneous Natural Products;AntidepressantsNutrition Research;Anti-Proliferative AgentsNeurobiology;Antitumor Agents;Biochemicals Found in Plants;Cancer Research;Isoprenoid/terpenoid;Pharmacologicals
• Mol File: 11079-53-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 79-80℃
• Boiling Point: 616.825 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: /solution
• Density: 1.010±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 8.53E-18mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: -20°C
• PKA: 4.8 (50% aq ethanol)
• CAS DataBase Reference: HYPERFORIN(CAS DataBase Reference)
• NIST Chemistry Reference: HYPERFORIN(11079-53-1)
• EPA Substance Registry System: HYPERFORIN(11079-53-1)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol
• WGK Germany: 3
• Hazardous Substances Data: 11079-53-1(Hazardous Substances Data)

Usage

Description

Hyperforin is a prenylated carbobicyclic acylphloroglucinol derivative produced by St. John's Wort, Hypericum perforatum. It is a phloroglucinol component and a pregnane X receptor ligand. Hyperforin exhibits two main activities: it inhibits the activity of several CYP450 enzymes, with CYP2D6 being the most sensitive, and it acts as a ligand for the steroid X receptor (SXR), which is involved in the induction of CYP450 expression.

Uses

Used in Pharmaceutical Industry:
Hyperforin is used as a reference standard for calibration curve generation in high-performance liquid chromatography (HPLC) analysis. This allows for the accurate measurement and quantification of various compounds in pharmaceutical research and development.
Used in Biomedical Research:
Hyperforin is used to test its cytotoxic effect and apoptosis induction in mouse embryonic cells. This helps researchers understand the compound's potential impact on cell growth and death, which can be valuable in the development of new therapeutic agents.
Used in Drug Transport Studies:
Hyperforin is used as a pregnane X receptor (PXR) ligand in porcine brain capillary endothelial cells for transport assays. This helps researchers investigate the role of PXR in drug transport across the blood-brain barrier, which is crucial for the development of drugs targeting the central nervous system.

Biochem/physiol Actions

Hyperforin is an active antidepressant and an inhibitor of cytochrome P450 3A4 (CYP3A). It elicits antioxidant and antibacterial activity. Hyperforin is also embryotoxic and inhibits tumor proliferation. It effectively inhibits dopamine, serotonin and norepinephrine.

InChI:InChI=1/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,37H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1

Downstream Products

• 238074-03-8 hyperforin (dicyclohexylammonium) salt 

Related news

Antidepressant-like activity of HYPERFORIN (cas 11079-53-1) and changes in BDNF and zinc levels in mice exposed to chronic unpredictable mild stress07/16/2019

Chronic unpredictable mild stress (CUMS) - a rodent model of depression mimics a variety of neurochemical and behavioral alterations similar to those seen in human depression. This study evaluated the antidepressant activity of hyperforin in the CUMS model using fluoxetine (FLX) as a reference d...detailed