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Merck

H9252

Sigma-Aldrich

Hypericin from Hypericum perforatum

≥85% (HPLC), powder

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:
Molecular Weight:
504.44
Beilstein:
1917913
EC Number:
MDL number:
UNSPSC Code:
12352202

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Assay

≥85% (HPLC)

form

powder

color

black

solubility

1 M NaOH: 10 mg/mL
ethanol: 5 mg/mL (with sonication)
DMSO: soluble

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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Biochem/physiol Actions

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

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Martin-Pierre Sauviat et al.
Journal of natural products, 70(4), 510-514 (2007-02-13)
The effects and the mode of action of hypericin (1) were studied, in the dark, on the action potential (AP) and the L-type Ca2+ channel of frog atrial heart muscle, using intracellular microelectrode and patch-clamp techniques, respectively. In the presence
Souvik Kusari et al.
Journal of natural products, 72(10), 1825-1835 (2009-09-15)
The possible microbial mechanism of hypericin (1) and emodin (2) biosynthesis was studied in axenic submerged culture conditions in the endophytic fungus Thielavia subthermophila, isolated from Hypericum perforatum. The growth and secondary metabolite production of the endophyte remained independent of
Souvik Kusari et al.
Journal of natural products, 71(2), 159-162 (2008-01-29)
For the first time, an endophytic fungus has been isolated from the stems of the medicinal herb Hypericum perforatum (St. John's Wort). The fungus produced the napthodianthrone derivative hypericin ( 1) in rich mycological medium (potato dextrose broth) under shake
Appolinary Kamuhabwa et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 3(8), 772-780 (2004-08-06)
Photodynamic therapy (PDT) involves the local or systemic administration of a photosensitizing drug that, upon light irradiation and presence of oxygen, results in tissue damage such as tumor destruction. Hypericin, a hydroxylated phenanthroperylenequinone, is obtained from Hypericum perforatum plants. Hypericin
Binghu Jiang et al.
Theranostics, 3(9), 667-676 (2013-09-21)
Hypericin has been widely studied as a potent photosensitizer for photodynamic therapy in both preclinical and clinical settings. Recently, hypericin has also been discovered to have a specific avidity for necrotic tissue. This affinity is also observed in a series

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