Hypericin Chemical Properties

Melting point:

299-301°C

Boiling point:

1020.3±65.0 °C(Predicted)

Density 

1.915±0.06 g/cm3(Predicted)

RTECS 

SF8472000

storage temp. 

-20°C

solubility 

1 M NaOH: 10 mg/mL

form 

powder

pka

6.91±0.20(Predicted)

color 

black

Water Solubility 

Soluble in ethanol, dimethyl sulfoxide, methanol, acetone, ethylmethylketone, pyridine and sodium hydroxide. Insoluble in water.

Sensitive 

Light Sensitive

Merck 

14,4863

BRN 

1917913

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

InChIKey

BTXNYTINYBABQR-UHFFFAOYSA-N

LogP

10.827 (est)

CAS DataBase Reference

548-04-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-40-43

Safety Statements 

22-36-36/37

RIDADR 

2811

WGK Germany 

3

F 

8

HS Code 

29145090

MSDS

• Language:English Provider:SigmaAldrich

Hypericin Usage And Synthesis

Hypericum perforatum extracts

Hypericin is an extract of Hypericum perforatum L.In 1957. It is first isolated from the Garcinia species Hypericum perforatum by human beings. Hypericin belongs to the bianthrone compounds, and it is the most biologically active substances. Hypericin is a yellowish brown to brown mobile powder, with slightly bitter taste. It is soluble in water, and can emit a special fragrance. It can inhibit the central nervous and has a sedative effect. Adding it to health care products can enhance immunity. It is also used as antidepressant drugs in Europe (especially in Germany). Hypericin also has a strong anti-viral effect, which can directly act on swine fever, foot and mouth disease and other viruses. In addition, it also has a good effect on killing highly pathogenic avian influenza virus.
Hypericum perforatum is one of the world's best-selling herbs in recent years, mainly containing hyperoside, quercetin, chlorogenic acid, caffeic acid, imanin, hypericin and other ingredients.
Hypericin is a few thousandths of the whole Hypericum perforatum. There are certain requirements for its extraction and testing. Methanol extraction method is common used in the past. Due to the toxicity of methanol, now the method is   converted to use ethanol to obtain the active ingredient.

Indications

Hypericin is an anti-virus and pure Chinese medicine preparations. It is the first choice for the prevention and treatment of avian influenza drugs.
1, avian influenza, atypical Newcastle disease, infectious bronchitis, avian infectious laryngotracheitis , bursa of Fabricius, duck plague, duck viral hepatitis, egg drop syndrome and other viral diseases.
2, poultry fever caused by high fever, dyspnea, cough, head and face swelling, crown hair purple, lack of energy, decreased feed intake, egg drop, producing more abnormal eggs.
3, for classical swine fever, blue ear disease, parvovirus, viral enteritis, infectious gastroenteritis and immune dysfunction.
4, Hypericin has a strong anti-viral effect both in vivo and in vitro. It has a strong inhibitory effect on the early replication of HIV. Hypericin can lead to cancer cell programmed death, with anti-cancer effect. It has a enhanced immune function  for activating mononuclear phagocytic cells. In addition, it has a strong role in killing the highly pathogenic H5N1 and H9N2 subtype of avian influenza virus.

Uses

(1) Antidepressant, increase immunity.
(2) For the treatment of antidepressants, increase immunity.

Description

An anthroquinone derivative that is naturally found in the flower of H. perforatum (St. John’s wort) and has antidepressant, antiviral, and anticancer activities. Hypericin inhibits neuronal uptake of serotonin, norepinephrine, dopamine, GABA and L-glutamate, contributing to its antidepressant effects. It exerts broad spectrum phototoxic affects (IC₅₀ = 140 - 1,570 nM) through induction of apoptotic signaling and formation of reactive oxygen species (ROS) in cancer cells. Hypericin also has in vitro activity, which can be enhanced with photo-activation, against a variety of viruses including HIV, influenza virus, hepatitis C, murine cytolomegalovirus, and herpes viruses.

Chemical Properties

Powder

Uses

It was used as reference standard in determining hypericins in St. John′s Wort using HPLC method.

Definition

ChEBI: Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene.

General Description

Produced by HWI Analytik
Exact content can be found on the certificate

Biological Activity

Photosensitive antiviral, anticancer and antidepressant agent derived from Hypericum perforatum (St John's wort). Inactivates enveloped viruses (including HIV), inhibits tyrosine kinases (IC 50 = 7.5 μ M) and is preferentially cytotoxic to tumor cells upon stimulation by visible light.

Biochem/physiol Actions

Primary TargetPKC

storage

+4°C

Purification Methods

Crystallise hypericin from pyridine by addition of methanolic HCl. [Beilstein 8 IV 3761.]

References

1) Kubin et al., (2005) Hypericin – the facts about a controversial agent; Current Pharm. Des., 11 233 2) Theodossiou et al., (2009) The multifaceted photocytotoxic profile of hypericin; Mol. Pharmacol., 6 1775

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