EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

hypericin
cyclosan

Supplier Sponsors

CAS Number: 548-04-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:208-941-0
FDA UNII: 7V2F1075HD
Nikkaji Web:J6.443B
Beilstein Number:1917913
MDL:MFCD00016683
XlogP3-AA:6.90 (est)
Molecular Weight:504.45112000
Formula:C30 H16 O8
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
US Patents:Search
EU Patents:Search
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point:1020.33 °C. @ 760.00 mm Hg (est)
Flash Point:1084.00 °F. TCC ( 584.60 °C. ) (est)
logP (o/w): 10.827 (est)
Soluble in:
 water, 6.262e-006 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Hypericin 98%
BOC Sciences
For experimental / research use only.
Hypericin >98%
Odor: characteristic
Use: Antidepressive. It was initially believed that the anti-depressant pharmacological activity of hypericin was due to inhibition of monoamine oxidase enzyme. Antineoplastic and antitumor
Changsha Organic Herb
St. John’s Wort Extract Hypericum perforatum
Coompo
For experimental / research use only.
Hypericin from Plants ≥98%
Odor: characteristic
Use: Hypericin is a naphthodianthrone, a red-colored anthraquinone-derivative. Hypericin is believed to act as an antibiotic, antiviral and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine β-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine. In the last three decades, hypericin has also become the subject of intensive biochemical research and is proving to be a multifunctional agent in drug and medicinal applications. Recent studies report antidepressive, antineoplastic, antitumor and antiviral activities of hypericin; intriguing information even if confirmation of data is incomplete and mechanisms of these activities still remain largely unexplained. In other contemporary studies, screening hypericin for inhibitory effects on various pharmaceutically important enzymes such as MAO (monoaminoxidase), PKC (protein kinase C), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450), has yielded results supporting therapeutic potential. Research of hypericin and its effect on GABA-activated (gamma amino butyric acid) currents and NMDA (N-methyl-D-aspartat) receptors also indicate the therapeutic potential of this substance whereby new insights in stroke research (apoplexy) are expected. Also in the relatively newly established fields of medical photochemistry and photobiology, intensive research reveals hypericin to be a promising novel therapeutic and diagnostic agent in treatment and detection of cancer (photodynamic activation of free radical production). Hypericin is not new to the research community, but it is achieving a new and promising status as an effective agent in medical diagnostic and therapeutic applications. New, although controversial data, over the recent years dictate further research, re-evaluation and discussion of this substance. It was initially believed that the anti-depressant pharmacological activity of hypericin was due to inhibition of monoamine oxidase enzyme. The crude extract of Hypericum is a weak inhibitor of MAO-A and MAO-B. Isolated hypericin does not display this activity, but does have some affinity for NMDA receptors. This points in the direction that other constituents are responsible for the MAOI effect. The current belief is that the mechanism of antidepressant activity is due to the inhibition of reuptake of certain neurotransmitters. Hypericin, a powerful naturally occurring photosensitizer, is found in Hypericum perforatum plants, commonly known as St. John's wort. In recent years increased interest in hypericin as a potential clinical anticancer agent has arisen since several studies established its powerful in vivo and in vitro antineoplastic activity upon irradiation. Investigations of the molecular mechanisms underlying hypericin photocytotoxicity in cancer cells have revealed that this photosensitizer can induce both apoptosis and necrosis in a concentration and light dose-dependent fashion. Moreover, Photodynamic therapy (PDT) with hypericin results in the activation of multiple pathways that can either promote or counteract the cell death program.
ExtraSynthese
For experimental / research use only.
Hypericin (HPLC) ≥95%
Glentham Life Sciences
Hypericin
Santa Cruz Biotechnology
For experimental / research use only.
Hypericin
Sigma-Aldrich
For experimental / research use only.
Hypericin
primary pharmaceutical reference standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for hypericin usage levels up to:
 not for fragrance use.
 
Recommendation for hypericin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281051
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0000548049
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281051
Pubchem (sid):134977630
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C07606
HMDB (The Human Metabolome Database):HMDB34271
FooDB:FDB012603
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 st. john's wort
Search Trop Picture
 
Synonyms:
 cyclo werrol
 cyclo-werol
 cyclosan
1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-phenanthro[1,10,9,8-opqra]perylene-7,14-dione
1,3,4,6,8,13-hexahydroxy-10,11-dimethylphenanthro(1,10,9,8-opqra)perylene-7,14-dione
1,3,4,6,8,13-hexahydroxy-10,11-diméthylphénanthro[1,10,9,8-opqra]pérylène-7,14-dione
4,5,7,4',5',7'-hexahydroxy-2,2'-dimethyl-mesonapthtodianthron
4,4',5,5',7,7'-hexahydroxy-2,2'-dimethylnaphthodianthrone
4,5,7,4',5',7'-hexahydroxy-2,2'-dimethylnaphthodianthrone
 hypericine
 hypericum red
 phenanthro[1,10,9,8-opqra]perylene-7,14-dione, 1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-
 vimrxyn
 

Articles:

PubMed:St. John's wort reversal of meningeal nociception: A natural therapeutic perspective for migraine pain.
PubMed:Do Other Hypericum Species Have Medical Potential As St. John's Wort (Hypericum perforatum)?
PubMed:[Chemical constituents from Hypericum perforatum].
PubMed:Pilot-scale culture of hypericum perforatum L. Adventitious roots in airlift bioreactors for the production of bioactive compounds.
PubMed:Molecularly imprinted polymer for specific extraction of hypericin from Hypericum perforatum L. herbal extract.
PubMed:Improvement of hairy root cultures and plants by changing biosynthetic pathways leading to pharmaceutical metabolites: Strategies and applications.
PubMed:Assessment of antimicrobial and antiprotozoal activity of the olive oil macerate samples of Hypericum perforatum and their LC-DAD-MS analyses.
PubMed:Between species diversity of Hypericum perforatum and H. maculatum by the content of bioactive compounds.
PubMed:Effective inactivation of food pathogens Listeria monocytogenes and Salmonella enterica by combined treatment of hypericin-based photosensitization and high power pulsed light.
PubMed:Plant-derived bioactive compounds produced by endophytic fungi.
PubMed:Effect of St. John's Wort standardized extract and hypericin on in vitro placental calcium transport.
PubMed:Determination of enantiomerization barriers of hypericin and pseudohypericin by dynamic high-performance liquid chromatography on immobilized polysaccharide-type chiral stationary phases and off-column racemization experiments.
PubMed:Identification of human intracellular targets of the medicinal Herb St. John's Wort by chemical-genetic profiling in yeast.
PubMed:Bioactive constituent production in St. John's Wort in vitro hairy roots. Regenerated plant lines.
PubMed:Hypericin and hyperforin production in St. John's wort in vitro culture: influence of saccharose, polyethylene glycol, methyl jasmonate, and Agrobacterium tumefaciens.
PubMed:Evaluation of the light-sensitive cytotoxicity of Hypericum perforatum extracts, fractions, and pure compounds.
PubMed:Comparison of methods for the exhaustive extraction of hypericins, flavonoids, and hyperforin from Hypericum perforatum L.
PubMed:Approach to novel functional foods for stress control 4. Regulation of serotonin transporter by food factors.
PubMed:Herbal drug quality and phytochemical composition of Hypericum perforatum L. affected by ash yellows phytoplasma infection.
PubMed:The significance of "nonsignificance" in randomized controlled studies: a discussion inspired by a double-blinded study on St. John's wort (Hypericum perforatum L.) for premenstrual symptoms.
PubMed:Liquid chromatographic determination of St. John's wort components in functional foods.
PubMed:Instability of St. John's wort (Hypericum perforatum L.) and degradation of hyperforin in aqueous solutions and functional beverage.
PubMed:Clinic at the health food store? Employee recommendations and product analysis.
PubMed:Determination of St. John's wort components in dietary supplements and functional foods by liquid chromatography.
PubMed:Impact of hypericum (St.-John's-wort) given prenatally on cognition of mice offspring.
PubMed:Inhibition of c-erbB-2 expression an activity in human ovarian carcinoma cells by hypericin.
PubMed:Effects of a methanolic extract and a hyperforin-enriched CO2 extract of Hypericum perforatum on alcohol intake in rats.
PubMed:Optimization of extraction conditions for active components in Hypericum perforatum using response surface methodology.
PubMed:Effects of Hypericum perforatum extraction on alcohol intake in Marchigian Sardinian alcohol-preferring rats.
PubMed:Toxins in chrysomelid beetles Possible evolutionary sequence from de novo synthesis to derivation from food-plant chemicals.
 
Notes:
Widespread in Hypericum spp. esp. Hypericum perforatum (St John's Wort) Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint John's wort). Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine ?-hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine.
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