Skip to Content
Merck

56690

Hypericin from Hypericum perforatum

~95% (HPLC)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C30H16O8
CAS Number:
548-04-9
Molecular Weight:
504.44
NACRES:
NA.77
PubChem Substance ID:
57651594
EC Number:
208-941-0
Beilstein/REAXYS Number:
1917913
MDL number:
MFCD00016683
UNSPSC Code:
51101500

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI key

BTXNYTINYBABQR-UHFFFAOYSA-N

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

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

assay

~95% (HPLC)

solubility

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

Quality Level

100

Related Categories

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

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

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCH3742
BCBX5645
BCBR2643V
BCBP4996V
BCBM7861V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service