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56690

Sigma-Aldrich

Hypericin aus Hypericum perforatum

~95% (HPLC)

Synonym(e):

4,5,7,4′,5′,7′-Hexahydroxy-2,2′-dimethylnaphthodianthron

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About This Item

Empirische Formel (Hill-System):
C30H16O8
CAS-Nummer:
548-04-9
Molekulargewicht:
504.44
Beilstein:
1917913
EG-Nummer:
208-941-0
MDL-Nummer:
MFCD00016683
UNSPSC-Code:
12352202
PubChem Substanz-ID:
57651594
NACRES:
NA.77

Assay

~95% (HPLC)

Qualitätsniveau

100

Löslichkeit

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

InChIKey

BTXNYTINYBABQR-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

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.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

H-Sätze

H302

Gefahreneinstufungen

Acute Tox. 4 Oral

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Antibacterial effect of hypericin
Feyziouglu B, et al.
African Journal of Microbiology Research, 7(11), 979-982 (2013)
I Lopez-Bazzocchi et al.
Photochemistry and photobiology, 54(1), 95-98 (1991-07-01)
The polycyclic compound hypericin, a known photodynamic agent, was investigated for antiviral activity in the presence and absence of light. The three viruses tested: murine cytomegalovirus; Sindbis virus; and human immunodeficiency virus type 1, were all susceptible to hypericin; but
Hypericin in the light and in the dark: two sides of the same coin
Jendvzelovska Z, et al.
Frontiers in Plant Science, 7, 560-560 (2016)
Susceptibility of In Vitro Melanoma Skin Cancer to Photoactivated Hypericin versus Aluminium (III) Phthalocyanine Chloride Tetrasulphonate
Ndhundhuma IM and Abrahamse H
BioMed Research International, 2017 (2017)
Noemí Rubio et al.
Autophagy, 8(9), 1312-1324 (2012-08-15)
Although reactive oxygen species (ROS) have been reported to evoke different autophagic pathways, how ROS or their secondary products modulate the selective clearance of oxidatively damaged organelles is less explored. To investigate the signaling role of ROS and the impact
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