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56690

Sigma-Aldrich

Hypericin from Hypericum perforatum

~95% (HPLC)

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Synonym(s):
4,5,7,4′,5′,7′-Hexahydroxy-2,2′-dimethylnaphthodianthrone, Cyclo werrol, Hypericum red
Empirical Formula (Hill Notation):
C30H16O8
CAS Number:
Molecular Weight:
504.44
Beilstein/REAXYS Number:
1917913
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

~95% (HPLC)

Quality Level

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

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This Item
E8886PHL89226400076-M
Hypericin from Hypericum perforatum ~95% (HPLC)

56690

Hypericin from Hypericum perforatum

Erythrosin extra bluish certified by the Biological Stain Commission

E8886

Erythrosin extra bluish

Hypericin phyproof® Reference Substance

PHL89226

Hypericin

Hypericin Polycyclic dione that has anti-retroviral activity.

400076-M

Hypericin

solubility

1 M NaOH: 10 mg/mL, turbid, dark green

solubility

water: 1 mg/mL, clear

solubility

-

solubility

ethanol: 1 mg/mL, methanol: 1 mg/mL, DMSO: 10 mg/mL

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.

pictograms

Exclamation mark

signalword

Warning

hcodes

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


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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)
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)
Antibacterial effect of hypericin
Feyziouglu B, et al.
African Journal of Microbiology Research, 7(11), 979-982 (2013)
Fleury Augustin Nsole Biteghe et al.
Journal of photochemistry and photobiology. B, Biology, 211, 111982-111982 (2020-09-01)
Aberrant anti-cancer drug efflux mediated by membrane protein ABC transporters (ABCB5 and ABCG2) is thought to characterize melanoma heterogeneous chemoresistant populations, presumed to have unlimited proliferative and self-renewal abilities. Therefore, this study primarily aimed to investigate whether continuous exposure of

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