56690

Hypericin from Hypericum perforatum

~95% (HPLC)

• Synonym(s): 4,5,7,4′,5′,7′-Hexahydroxy-2,2′-dimethylnaphthodianthrone, Cyclo werrol, Hypericum red
• Empirical Formula (Hill Notation): C₃₀H₁₆O₈
• CAS Number: 548-04-9
• Molecular Weight: 504.44
• Beilstein/REAXYS Number: 1917913
• EC Number: 208-941-0
• MDL number: MFCD00016683
• UNSPSC Code: 12352202
• PubChem Substance ID: 57651594
• NACRES: NA.77

Properties

• assay: ~95% (HPLC)
• Quality Level: 100
• solubility: 1 M NaOH: 10 mg/mL, turbid, dark green
• SMILES string: Cc1cc(O)c2C(=O)c3c(O)cc(O)c4c5c(O)cc(O)c6C(=O)c7c(O)cc(C)c8c1c2c(c34)c(c78)c56
• InChI: 1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3
• InChI key: BTXNYTINYBABQR-UHFFFAOYSA-N

Description

General description

Hypericin hydrophobic is a red color pigment occurring naturally in Hypericum perforatum. Its fluorescence is measured at 600 nm. It is localized in the intracellular membranes including nuclear membrane, mitochondrial membrane, Golgi apparatus, lysosomes and endoplasmic reticulum.

Application

Hypericin from Hypericum perforatum has been used:

• in the broth macrodilution test and antibacterial assay against bacterial strains
• as a medium supplement for human malignant melanoma cells for irradiation and localization studies
• as a ligand for pregnane X receptor (PXR) and as defatting medium supplement for primary human hepatocytes culture

Biochem/physiol Actions

Hypericin is a potent inhibitor of protein kinase C (PKC), telomerase, cytochrome P450 and reverse transcriptase. It is exploited for its photosensitizing functionality in photodynamic therapy (PDT) and photodynamic diagnosis (PDD) in cancer cells.

Anthraquinone-derivative within St. John′s wort. Antibacterial effective against Gram-positive and Gram-negative bacteria.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves