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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:
548-04-9
Molecular Weight:
504.44
Beilstein:
1917913
EC Number:
208-941-0
MDL number:
MFCD00016683
UNSPSC Code:
12352202

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, 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
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
Constance Lay Lay Saw et al.
Cancer letters, 241(1), 23-30 (2005-11-24)
Early cancer detection is critical in improving disease management outcomes. Cancer diagnosis presents unique difficulties mainly due to its pathological presentation and poor accessibility that could limit the usefulness of conventional white light endoscopy in early cancer detection. Fluorescence endoscopy
Apoptotic and anti-apoptotic signaling pathways induced by photodynamic therapy with hypericin.
P Agostinis et al.
Advances in enzyme regulation, 40, 157-182 (2000-06-01)
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