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Artemisinin

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Identification
Molecular formula
C15H22O5
CAS number
63968-64-9
IUPAC name
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
State
State

At room temperature, artemisinin is in a solid state, typically in the form of crystalline powder.

Melting point (Celsius)
152.00
Melting point (Kelvin)
425.00
Boiling point (Celsius)
239.00
Boiling point (Kelvin)
512.00
General information
Molecular weight
282.33g/mol
Molar mass
282.3320g/mol
Density
1.3300g/cm3
Appearence

Artemisinin appears as a white or pale yellow crystalline powder. It is notable for its lack of odor and slightly bitter taste.

Comment on solubility

Solubility of (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione

The solubility of this compound in various solvents can be quite intriguing due to its complex structure. Understanding its solubility helps in numerous applications ranging from synthesis to medicinal chemistry. Here are some key points to consider:

  • Solvent Polarity: This compound is expected to exhibit differing solubility in polar and non-polar solvents. Polar solvents might induce better solubility due to interactions with functional groups.
  • Hydrogen Bonding: The presence of a hydroxyl group may enhance solubility in water and alcohols, as it can participate in hydrogen bonding, which often increases solubility.
  • Molecular Weight: With a relatively high molecular weight, solubility could be limited in highly polar solvents.
  • Temperature Influence: Solubility may increase with temperature, which is a common characteristic of organic compounds.
  • pH Dependency: Changes in pH can also affect solubility, especially if the compound can ionize or if it has acidic or basic functional groups.

It is often stated that, "solubility is a key property that influences the bioavailability and distribution of chemicals in biological systems." Thus, careful evaluation of solubility is essential for practical applications of this intriguing compound.

Interesting facts

Interesting Facts about 9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione

This fascinating compound is a member of the azulene family, renowned for its rich blue color. Azulenes have a unique structure that stands out in the world of organic chemistry, offering exciting opportunities for scientific exploration. Here are some interesting aspects of this compound:

  • Biological Significance: Compounds in the azulene family, including this one, are noted for their potential therapeutic properties. They may exhibit anti-inflammatory and antioxidant activities, making them targets for pharmaceutical research.
  • Synthetic Challenges: The synthesis of such complex structures often requires intricate multi-step processes, highlighting the challenges and creativity involved in modern organic chemistry. Scientists develop various reactions and methodologies to construct these compounds efficiently.
  • Applications in Dyes: Due to their vivid colors, azulenes are sometimes employed in dye applications. This compound's potential as a dye provides a fascinating intersection between chemistry and art, showcasing the practical applications of organic structures.
  • Unique Structural Features: The presence of both hydroxy and methyl groups alongside a methylene bridge lends this compound distinctive properties, impacting its reactivity and interactions with other molecules. The specific stereochemistry, denoted by the detailed nomenclature, plays a crucial role in determining how this compound behaves in various chemical environments.
  • Research Potential: Scientists continue to investigate derivatives of azulenes for their unique photophysical properties, opening doors to advancements in materials science and nanotechnology.

In summary, the compound exemplifies the intricate beauty and complexity of organic molecules, serving as a reminder of the endless potential within the realm of chemistry. As we continue to study compounds like this, we unravel the secrets of nature and potentially pave the way for innovative applications that can benefit various fields.

Synonyms
HELENALIN
6754-13-8
Helenalin A
PF 56
HSDB 3490
NSC 85236
UNII-4GUY9L896T
BRN 0028081
4GUY9L896T
CHEBI:5635
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
HELENALIN [MI]
HELENALIN [HSDB]
NSC-85236
(-)-HELENALIN
6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
DTXSID50217868
4-18-00-01434 (Beilstein Handbook Reference)
Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
(3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
6.ALPHA.,8.BETA.-DIHYDROXY-4-OXOAMBROSA-2,11(13)-DIEN-12-OIC ACID 12,8-LACTONE
(3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
(3AS-(3A.ALPHA.,4.ALPHA.,4A.BETA.,7A.ALPHA.,8.ALPHA.,9A.ALPHA.))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione
(3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno(6,5-b)furan-2,5-dione
DTXCID00140359
6alpha,8betaDihydroxy4oxoambrosa2,11(13)dien12oic acid 12,8lactone
Ambrosa2,11(13)dien12oic acid, 6alpha,8betadihydroxy4oxo, 12,8lactone
Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone (8CI)
(3aS)3,3aalpha,4alpha,4a,7aalpha,8,9,9aalphaOctahydro4hydroxy4abeta,8 alphadimethyl3methyleneazuleno(6,5b)furan2,5dione
(3AS-(3AALPHA,4ALPHA,4ABETA,7AALPHA,8ALPHA,9AALPHA))-3,3A,4,4A,7A,8,9,9A-OCTAHYDRO-4-HYDROXY-4A,8-DIMETHYL-3-METHYLENEAZULENO(6,5-B)FURAN-2,5-DIONE
Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-(9CI)
Azuleno(6,5b)furan2,5dione, 3,3a,4,4a,7a,8,9,9aoctahydro4hydroxy4a,8dimethyl3methylene, (3aS(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))
NSC85236
MLS000728512
SMR000445626
(3aR,5R,5aR,8aR,9S,9aS)-9-Hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione
MLS002701927
NF-kappaB inhibitor
BSPBio_001312
cid_23205
SCHEMBL161593
CHEMBL338474
BDBM43484
HMS1791B14
HMS1989B14
HMS2236C04
EX-A10269
HB3927
AKOS040741831
Ambrosa-2,11(13)-dien-12-oic acid, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone
NCGC00163416-01
NCGC00163416-02
Azuleno[6,5-b]furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-
MS-23694
NCI60_041870
HY-119970
CS-0078850
NS00094722
C09473
G13013
Q387505
WLN: T C575 DYVO MV KUTJ A1 BQ DU1 I1
BRD-K26302255-001-02-3
Ambrosa-2, 6.alpha.,8.beta.-dihydroxy-4-oxo-, 12,8-lactone
(3aR,5R,5aR,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-9-oxidanyl-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone
4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
Azuleno[6,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3a.alpha.,4.alpha.,4a.beta.,7a.alpha.,8.alpha.,9a.alpha.)]-