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Forskolin

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Identification
Molecular formula
C22H34O7
CAS number
66575-29-9
IUPAC name
[13-acetoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate
State
State

At room temperature, Forskolin is typically found in a solid state as a crystalline powder.

Melting point (Celsius)
233.00
Melting point (Kelvin)
506.15
Boiling point (Celsius)
412.00
Boiling point (Kelvin)
685.15
General information
Molecular weight
410.49g/mol
Molar mass
410.4910g/mol
Density
1.3400g/cm3
Appearence

Forskolin is a labdane diterpene produced by the Indian Coleus plant (Coleus forskohlii). As an isolated compound, it appears as a white to off-white crystalline powder.

Comment on solubility

Solubility of C22H34O7

The solubility of the compound [13-acetoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate in various solvents is influenced by its complex structure and functional groups. Understanding the solubility of this compound can be articulated as follows:

  • Polar Solvents: Due to the presence of multiple hydroxyl (-OH) groups and an ester moiety, this compound exhibits reasonable solubility in polar solvents like water and methanol, although this may be limited in comparison to smaller molecules.
  • Non-Polar Solvents: The saturated hydrocarbon segments of the tetradecanoate component indicate that the compound is likely to have enhanced solubility in non-polar organic solvents such as hexane and chloroform.
  • Temperature Dependence: Like many organic compounds, solubility can increase with temperature. Therefore, exploring the solubility at various temperatures may yield interesting insights.
  • Concentration Effects: As the concentration of this compound in solution increases, its solubility behavior should also be considered, particularly in terms of potential precipitation or phase separation at higher concentrations.

In conclusion, the solubility of C22H34O7 is multifaceted and is significantly affected by the solvent type, temperature, and concentration. Further experimental investigation is recommended to characterize its solubility profile more completely.

Interesting facts

Interesting Facts about 13-acetoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl tetradecanoate

This compound is quite intriguing due to its complex structure and functional groups that offer potential for various applications in both research and industry. Here are some noteworthy points:

  • Natural Origin: This compound can often be derived from natural sources, as many similar structures are found in plant metabolites. These natural derivatives frequently demonstrate a range of biological activities.
  • Structural Complexity: The tetracyclic structure indicates a sophisticated arrangement of carbon rings, which is often a characteristic of sterols and terpenoids, compounds known for their diverse roles in biology.
  • Biological Relevance: Compounds similar to this one have been studied for their potential medicinal properties, including anti-inflammatory and antioxidant activities. The presence of hydroxyl (-OH) groups may also contribute to these effects by enhancing solubility and reactivity.
  • Synthetic Challenges: The synthesis of such a complex compound can pose significant challenges in organic chemistry. Techniques may include cyclic mechanisms or multi-step reactions to achieve the desired stereochemistry and functionalization.
  • Potential Applications: Beyond their biological implications, compounds like this may have roles in developing new materials or could serve as intermediates in the synthesis of pharmaceuticals.

In conclusion, the study of 13-acetoxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl tetradecanoate not only showcases the beauty of molecular architecture but also highlights the importance of complex organic compounds in modern science.

Synonyms
Phorbol myristate acetate
Phorbol acetate, myristate
[13-acetyloxy-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxo-14-tetracyclo[8.5.0.02,6.011,13]pentadeca-3,8-dienyl] tetradecanoate
PMA
12-o-Tetradekanoylphorbol-13-acetat
NSC626496
Pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
1H-Cyclopropa[3,4]benz[1,2-e]azulene, tetradecanoic acid deriv.
[acetoxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] tetradecanoate
CHEBI:93813
DTXSID20860183
PHEDXBVPIONUQT-UHFFFAOYSA-N
Phorbol 12-myristate-13-acetate
LSM-4341
9a-(Acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate
LS-15381
4.beta.-Phorbol-12-myristate-13-acetate
BRD-A15079084-001-01-1
Q27165536
9a-(Acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl tetradecanoate
9a-(Acetyloxy)-4a.alpha.,7b.beta.-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a.beta.,1b.alpha.,4,4a,5,7a.beta.,7b,8,9,9a-decahydro-1H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate, (9.alpha.,9a.beta.)- #
Myristic acid, 9-ester with 1,1a-.alpha.,1b-.beta.,4,4a,7a-.alpha.,7b,8,9,9a-decahydro-4a-.beta.,7b-.alpha.,9-.beta.,9a-.alpha.-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-.alpha.-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one, 9a-acetate
Myristic acid, 9-ester with 1,1a.alpha.,1b.beta.,4,4a,7a.alpha.,7b,8,9,9a-decahydro-4a.beta.,7b.alpha.,9.beta.,9a.alpha.-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8.alpha.-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5-one 9a-acetate, (+)-
Tetradecanoic acid, 9a-(acetyloxy)-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1H-cyclopropa[3,4]benz[1,2-e]azulen-9-yl ester, [1aR-(1a.alpha.,1b.beta.,4a.beta.,7a.alpha.,7b.alpha.,8.alpha.,9.beta.,9a.alpha.)]-