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56690

Sigma-Aldrich

Hypericin from Hypericum perforatum

~95% (HPLC)

Synonym(s):

4,5,7,4′,5′,7′-Hexahydroxy-2,2′-dimethylnaphthodianthrone, Cyclo werrol, Hypericum red

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About This Item

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

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

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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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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