Hypericin

• CAS: 548-04-9
• Catalog Number: ACM548049
• Category: Inhibitors
• Molecular Weight: 504.44
• Molecular Formula: C30H16O8
• Description: Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis.
• Synonyms: Anthroquinone
• Canonical SMILES: CC1=CC(=C2C3=C1C4=C5C(=C(C=C4C)O)C(=O)C6=C(C=C(C7=C6C5=C3C8=C7C(=CC(=C8C2=O)O)O)O)O)O
• Boiling Point: 930.1 °C at 760 mmHg (Predicted)
• Melting Point: 299-301°C
• Appearance: Powder
• Storage: Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
• Hazard Statements: Xn
• Refractive Index: 2.13
• Safety Description: 22-36-36/37
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsGuttiferaeHyperlcurn perforatum L.
• Supplemental Hazard Statements: H302-H317
• Symbol: GHS07

Custom Q&A

What is the molecular formula of hypericin?

The molecular formula of hypericin is C30H16O8.

What is the molecular weight of hypericin?

The molecular weight of hypericin is 504.4 g/mol.

Where is hypericin naturally found?

Hypericin is naturally found in the yellow flowers of Hypericum perforatum (St. John's wort).

What is the role of hypericin?

Hypericin has a role as an antidepressant.

What are some synonyms for hypericin?

Some synonyms for hypericin include Hipericin, Hipericina, and Hypericum red.

How does hypericin exert its antidepressant effect?

Hypericin appears to inhibit the neuronal uptake of serotonin, norepinephrine, dopamine, GABA, and L-glutamate, contributing to its antidepressant effect.

What is the InChI of hypericin?

The InChI of hypericin is 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/h3-6,33-38H,1-2H3.

What chemical properties of hypericin contribute to its potential antiviral and antineoplastic activities?

Hypericin appears to prevent the replication of encapsulated viruses and exerts potent phototoxic effects by triggering apoptotic signaling.

What is the IUPAC Name of hypericin?

The IUPAC Name of hypericin is 9,11,13,16,18,20-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.1 2,10 .0 3,8 .0 4,25 .0 19,27 .0 21,26 .0 14,28 ]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione.

What are some identifiers for hypericin?

Some identifiers for hypericin include CAS number 548-04-9, ChemIDplus, and ChEMBL ID CHEMBL286494.

Synthetic Use

Upstream Synthesis Route 1

• 120667-79-0

• 548-04-9

Reference: [1]Brockmann et al.
[Chemische Berichte, 1957, vol. 90, p. 2302,2314]

Upstream Synthesis Route 2

• 117041-40-4

• 548-04-9

Reference: [1]Current Patent Assignee: SCHENLEY IND - US2707704, 1952, A

Upstream Synthesis Route 3

• 548-03-8

• 548-04-9

Reference: [1]Gonçalves, Renato S.; Rabello, Bruno R.; César, Gabriel B.; Pereira, Paulo C. S.; Ribeiro, Marcos A. S.; Meurer, Eduardo C.; Hioka, Noboru; Nakamura, Celso V.; Bruschi, Marcos L.; Caetano, Wilker
[Organic Process Research and Development, 2017, vol. 21, # 12, p. 2025 - 2031]