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Hypericin

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Identification
Molecular formula
C30H16O8
CAS number
548-04-9
IUPAC name
9,11,13,16,18,20-hexahydroxy-5,24-dimethyl-octacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione
State
State

At room temperature, Hypericin is a solid. It is notable for its brilliant red appearance.

Melting point (Celsius)
320.00
Melting point (Kelvin)
593.00
Boiling point (Celsius)
785.00
Boiling point (Kelvin)
1 058.00
General information
Molecular weight
504.44g/mol
Molar mass
504.4390g/mol
Density
1.6500g/cm3
Appearence

Hypericin is a red-colored compound, appearing as a crystalline solid. It can exhibit a range of darker shades, often displaying a deep red to almost brown hue, depending on its form and purity.

Comment on solubility

Solubility of 9,11,13,16,18,20-hexahydroxy-5,24-dimethyl-octacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione

The solubility of the compound with the chemical formula C30H16O8 is an intriguing subject of study due to its complex structure and multiple hydroxyl (–OH) groups. The solubility of such compounds often depends on a variety of factors including:

  • Polarity: With six hydroxyl groups, this compound is likely to exhibit significant polarity, enhancing its interaction with polar solvents like water.
  • Hydrogen bonding: The presence of multiple –OH groups allows for strong hydrogen bonding, which can increase solubility in polar solvents.
  • Molecular weight: Compared to simpler compounds, the molecular weight of this compound (approximately 480 g/mol) may influence its solubility dynamics as larger molecules often have lower solubility in certain solvents.
  • Structural rigidity: The complex octacyclic structure may also influence how well it interacts with solvents, potentially hindering solubility in various organic solvents or water.

In summary, while we can predict that the hydroxyl groups will improve solubility in polar environments, the compound's extensive structure may present challenges. This highlights the need for empirical studies to fully understand its solubility characteristics.

Interesting facts

Exploring 9,11,13,16,18,20-Hexahydroxy-5,24-Dimethyl-Octacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]Octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-Tridecaene-7,22-Dione

This complex compound, often referred to as a polycyclic compound due to its extensive ring structures, is a fascinating example of molecular architecture in organic chemistry. Here are some interesting facts:

  • Natural Origins: Many polycyclic compounds like this are derived or inspired by natural products, potentially playing roles in biological processes.
  • Structural Complexity: The numerous rings and functional groups present in this molecule suggest a high level of structural complexity which can influence its chemical behavior significantly.
  • Potential Applications: Compounds with such intricate structures often attract attention for their potential applications in pharmaceuticals and materials science, showcasing diverse biological activities.
  • Research Opportunities: The study of this compound opens doors to exploring challenges in synthesis, reactivity, and properties that could lead to novel discoveries in organic chemistry.
  • Historical Significance: Polycyclic compounds have a rich history in chemical research, often leading to the introduction of new methodologies and techniques in synthetic chemistry.

As noted by a prominent chemist, "The beauty of organic compounds lies in their complexity; they are like puzzles waiting to be solved." This statement rings especially true for 9,11,13,16,18,20-hexahydroxy-5,24-dimethyl-octacyclo compound, challenging scientists to unlock its secrets and potential.

From its elaborate structure to its potential roles in various fields, this compound is a quintessential example of how intricate organic molecules can influence a wide range of scientific disciplines.

Synonyms
hypericin
548-04-9
Hypericum red
hypericine
hipericin
hipericina
Cyclosan
Hyperizin
Cyclo-Werol
Mycoporphyrin
SGX301
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione
C30H16O8
Cyclo werrol
SGX-301
VIMRxyn
EINECS 208-941-0
NSC407313
Hypericin [USAN]
NSC 407313
NSC 622946
NSC-407313
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethylnaphthodianthrone
CCRIS 8166
CHEBI:5835
7V2F1075HD
Hypericin (SGX301)
MFCD00016683
NSC622946
(component of) Hypericum spp (st. John's wort)
Hypericin & Visible light
HYPERICIN [WHO-DD]
CHEMBL286494
4,5,7,4',5',7'-Hexahydroxy-2,2'-dimethyl-mesonapthtodianthron
DTXSID40203270
Hypericin (USAN)
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro(1,10,9,8-opqra)perylene-7,14-dione
Phenanthro[1,10,9,8-opqra]perylene-7,14-dione, 1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-
1372719-41-9
9,11,13,16,18,20-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione
1:6:8:10:11:13-hexahydroxy-3:4-dimethyl-meso-naphthodianthrene-7:14-dione
Phenanthro(1,10,9,8-opqra)perylene-7,14-dione, 1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-
hexahydroxy(dimethyl)[?]dione
5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
Hypericina
UNII-7V2F1075HD
Cyclo werro
hypericin [INN]
9,11,13,16,18,20-hexahydroxy-5,24-dimethyloctacyclo(13.11.1.12,10.03,8.04,25.019,27.021,26.014,28)octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione
HYPERICIN [MI]
BiomolKI_000032
BiomolKI2_000040
SCHEMBL3182
BIDD:PXR0084
BMK1-D8
CHEMBL5082596
SCHEMBL10262695
DTXCID40125761
YDOIFHVUBCIUHF-UHFFFAOYSA-N
Hypericin - CAS 548-04-9
Hypericin from Hypericum perforatum
HY-N0453
BDBM50060874
CCG-36081
HB3934
HSCI1_000202
LMPK13040001
WHO 11835
AKOS015895658
AC-6048
CS-5687
FH01456
NSC-622946
NCGC00162454-01
NCGC00163378-01
NCGC00163378-02
AS-74733
NCI60_003879
NCI60_006799
NS00001496
C07606
D12433
M01850
SR-05000002344
HYPERICIN (CONSTITUENT OF ST. JOHN'S WORT)
Hypericin from Hypericum perforatum, ~95% (HPLC)
Hypericin, primary pharmaceutical reference standard
SR-05000002344-2
BRD-K29673530-001-03-9
BRD-K29673530-001-05-4
Z1736866019
HYPERICIN (CONSTITUENT OF ST. JOHN'S WORT) [DSC]
Hypericin is known as an anthroquinone derivative found in St. John's Wort.
1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylene-7,14-dione, 9CI
1,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro [1,10,9,8-opqra]perylene-7,14-dione P-conformer
208-941-0
5,7,11,18,22,24-HEXAHYDROXY-13,16-DIMETHYLOCTACYCLO[13.11.1.1(2),(1)?.0(3),?.0?,(2)?.0(1)?,(2)?.0(2)(1),(2)?.0(1)?,(2)?]OCTACOSA-1,3,5,7,10,12,14(28),15(27),16,18,21,23,25-TRIDECAENE-9,20-DIONE
5,7,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1(2),(1)?.0(3),?.0?,(2)?.0(1)?,(2)?.0(2)(1),(2)?.0(1)?,(2)?]octacosa-1,3,5,7,10,12,14(28),15,17,19(27),21(26),22,24-tridecaene-9,20-dione
5,9,11,18,22,24-hexahydroxy-13,16-dimethyloctacyclo[13.11.1.1(2),(1)?.0(3),?.0?,(2)?.0(1)?,(2)?.0(2)(1),(2)?.0(1)?,(2)?]octacosa-1(27),2(28),3,5,8,10,12,14,16,18,21(26),22,24-tridecaene-7,20-dione
9,11,13,16,18,22-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.1(2),(1)?.0(3),?.0?,(2)?.0(1)?,(2)?.0(2)(1),(2)?.0(1)?,(2)?]octacosa-1(26),2,4(25),5,8,10(28),11,13,15,17,19(27),21,23-tridecaene-7,20-dione
9,11,13,16,18,22-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.1(2),(1)?.0(3),?.0?,(2)?.0(1)?,(2)?.0(2)(1),(2)?.0(1)?,(2)?]octacosa-1,3,5,8,10(28),11,13,15(27),16,18,21,23,25-tridecaene-7,20-dione
Phenanthro[1,9,8-opqra]perylene-7,14-dione,1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-, stereoisomer
rac-(3aM,10aM)-1,3,4,6,8,13-hexahydroxy-10,11- dimethylphenanthro[1,10,9,8-opqra]perylene-7,14- dione