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Forskolin

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Identification
Molecular formula
C22H34O7
CAS number
66575-29-9
IUPAC name
[(1S,2S,6R,10S,11R,13S,14R,15R)-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
Forskolin is generally in the solid state at room temperature.

As a diterpene compound, it is stable in solid form. When used in various formulations, it may be dissolved in alcohols or other solvents.

Melting point (Celsius)
228.00
Melting point (Kelvin)
501.15
Boiling point (Celsius)
650.00
Boiling point (Kelvin)
923.15
General information
Molecular weight
410.50g/mol
Molar mass
410.4880g/mol
Density
1.2209g/cm3
Appearence

Forskolin is typically available as a white to off-white crystalline powder. Due to its chemical nature, it usually appears clear and colorless in its pure form. In commercial preparations, it may sometimes appear as a brownish powder depending on the extent of purity and presence of any other compounds as additives or stabilizers.

Comment on solubility

Solubility of [(1S,2S,6R,10S,11R,13S,14R,15R)-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

Understanding the solubility of complex chemical compounds like [(1S,2S,6R,10S,11R,13S,14R,15R)-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 can be quite intricate due to its specific structural features. Here are some key points to consider:

  • Polarity: The presence of multiple hydroxy groups contributes to the compound's polarity, which influences its solubility in polar solvents such as water.
  • Hydrophobic Regions: The long hydrocarbon chain (tetradecanoate) provides significant hydrophobic properties that might limit solubility in aqueous environments.
  • Solvent Interactions: Solubility can vary widely depending on the solvent used. For instance, its solubility may increase in organic solvents like ethanol or chloroform due to the hydrophobic nature of the molecule.
  • Thermodynamic Factors: Temperature and pressure can also affect the solubility of this compound. Generally, increased temperature may lead to enhanced solubility for organic compounds.

In general, it is crucial to conduct experimental assessments using different solvents to accurately ascertain the solubility characteristics of this complex compound, as theoretical predictions may not always align with empirical results. Understanding these solubility parameters is fundamental in applications ranging from pharmaceuticals to industrial chemical formulations.

Interesting facts

Interesting Facts about the Compound

This fascinating compound, known for its complex structure and unique properties, belongs to a class of chemical entities that exhibit various biological activities. Below are some interesting insights that highlight its significance in the world of chemistry:

  • Natural Origin: This compound is often derived from plants, showcasing nature's incredible ability to synthesize intricate organic molecules.
  • Biodiversity: The compound has structural characteristics that reflect the diversity of natural products, particularly in its tetracyclic framework, making it an interesting subject for studies on natural product chemistry.
  • Biological Relevance: Many compounds with similar structures are known to possess medicinal properties, such as anti-inflammatory or antimicrobial effects. This leads to questions about whether this specific compound could have potential pharmacological applications.
  • Complexity: The stereochemistry of this compound, with multiple chiral centers, displays the complexity of organic molecules and challenges in their synthesis, characterization, and study.
  • Functional Groups: The presence of hydroxyl (–OH) and acetoxy (–OCOCH₃) groups suggests potential reactivities, demonstrating how functional group manipulation can lead to diverse chemical behaviors.
  • Applications in Synthesis: The intricate structure of this compound can serve as a valuable template for organic synthesis, aiding chemists in developing methodologies for crafting new compounds with desired functionalities.

In conclusion, the examination of this compound not only broadens our understanding of complex organic chemistry but also opens doors to exploring its potential applications in medicine and materials science. As chemists continue to delve into the world of such molecules, the intersections of nature and synthetic chemistry will undoubtedly yield exciting developments.

Synonyms
Phorbol 12-myristate 13-acetate
16561-29-8
phorbol-12-myristate-13-acetate
12-O-Tetradecanoylphorbol-13-acetate
Tetradecanoylphorbol acetate
12-O-Tetradecanoylphorbol 13-acetate
Factor A1
Phorbol myristate acetate
phorbol 13-acetate 12-myristate
PMA (tumor promoter)
Phorbol 12-tetradecanoate 13-acetate
TPA (phorbol derivative)
Pma (phorbol ester)
Tpa (phorbol ester)
Phorbol monoacetate monomyristate
Phorbol-myristate acetate
Phorbol 12-myristate 13-acetate diester
13-O-Acetylphorbol 12-myristate
Phorbol acetate, myristate
12-O-Tetradecanoyl phorbol acetate
beta-Phorbol 12-myristate 13-acetate
NSC 262244
12-Tetradecanoylphorbol 13-monoacetate
4beta-Phorbol 12-myristate 13-acetate
13-Tetradecanoylphorbol acetate
NI40JAQ945
CHEBI:37537
Phorbol-12-myristate 13-acetate
12-Tetradecanoylphorbol-13-acetate
12-o-Tetradekanoylphorbol-13-acetat
NSC-262244
4beta-Phorbol-12-myristate-13-acetate
DTXSID5023798
NSC262244
Pentahydroxy-tigliadienone-monoacetate(c)monomyristate(b)
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-(1aalpha,1bbeta,4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha))-
5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-beta-tetramethyl-, 9a-acetate 9-myristate
Myristic acid, 9-ester with 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-5H-cyclopropa(3,4)benz(1,2-e)azulen-5-one 9a-acetate, (+)-
[(1S,2S,6R,10S,11R,13S,14R,15R)-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
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
Acetate, Phorbol Myristate
Myristate Acetate, Phorbol
Acetate, Tetradecanoylphorbol
12 Myristoyl 13 acetylphorbol
12-Myristoyl-13-acetylphorbol
((1S,2S,6R,10S,11R,13S,14R,15R)-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
(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo(8.5.0.0^(2,6).0^(11,13))pentadeca-3,8-dien-14-yl tetradecanoate
(1S,2S,6R,10S,11R,13S,14R,15R)-13-(acetyloxy)-1,6-dihydroxy-8-(hydroxymethyl)-4,12,12,15-tetramethyl-5-oxotetracyclo[8.5.0.0^{2,6}.0^{11,13}]pentadeca-3,8-dien-14-yl tetradecanoate
12 O Tetradecanoyl Phorbol 13 Acetate
12-O-Tetradecanoyl Phorbol 13-Acetate
13-Acetate, 12-O-Tetradecanoyl Phorbol
Phorbol 13-Acetate, 12-O-Tetradecanoyl
DTXCID30819884
Tetradecanoylphorbol Acetate, 4a alpha
Phorbol ester
12-Tetradecanoylphorbol 13-acetate
TPA
PMA
MFCD00036736
CCRIS 716
HSDB 3542
CHEMBL279115
(1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-acetoxy-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
Phorbol 12-myristate 13-acetate (PMA)
C36H56O8
yristate
UNII-NI40JAQ945
NSC626496
-yl ester
tetradecanoyl-beta-phorbol acetate
12-o-tetradecanoyl-phorbol-13-acetate
BRN 2407201
SpecPlus_000801
Spectrum2_001911
Spectrum4_000889
Spectrum5_001855
MolMap_000041
UPCMLD-DP069
12-O-Tetradekanoylphorbol-13-acetat [German]
BIDD:PXR0145
CBiol_002014
BSPBio_001024
KBioGR_000364
KBioGR_001298
KBioSS_000364
SPECTRUM330004
DivK1c_006897
SPBio_001902
1H-Cyclopropa[3,4]benz[1,2-e]azulene, tetradecanoic acid deriv.
GTPL2341
orb1296136
[acetoxy-dihydroxy-(hydroxymethyl)-tetramethyl-oxo-[?]yl] tetradecanoate
SCHEMBL29353795
UPCMLD-DP069:001
UPCMLD-DP069:002
BCBcMAP01_000182
KBio1_001841
KBio2_000364
KBio2_002932
KBio2_005500
KBio3_000707
KBio3_000708
Bio1_000300
Bio1_000789
Bio1_001278
Bio2_000352
Bio2_000832
HMS1362D05
HMS1792D05
HMS1990D05
HMS3403D05
Phorbol 13 Acetate 12 Myristate
BNB65429
EX-A6920
-one 9a-acetate, (+)- (8CI)
BDBM50099066
CCG-39863
HB0502
NSC262644
AKOS024418767
CS-6053
FP15184
FS-4842
LMPR0104330002
NSC-262644
NSC-626496
IDI1_002107
NCGC00161633-01
NCGC00161633-04
NCGC00161633-05
4-.beta.-Phorbol 12-myristate 13-OAc
AC-33957
DA-49086
HY-18739
Tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-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
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-(1aa,1bb,4ab,7aa,7ba, 8a,9b,9aa))-
Phorbol 12-myristate 13-acetate (PMA)?
12-o-tetradecanoylphorbol-13-acetate (tpa)
NS00025422
P1585
PHORBOL-12-TETRADECANOYL-13-ACETATE
C05151
4abeta,7aalpha,7balpha,8alpha,9beta,9aalpha)]-
Q416716
12-O-TETRADECANOYLPHORBOL-13-ACETATE [HSDB]
BRD-K68552125-001-03-8
BRD-K68552125-001-04-6
BRD-K68552125-001-05-3
PHORBOL 12-MYRISTATE 13-ACETATE DIESTER [MI]
Phorbol-12-myristate-13-acetate - CAS 16561-29-8
Phorbol 12-myristate 13-acetate, synthetic, >=98.0% (TLC)
PMA, for use in molecular biology applications, >=99% (TLC)
Phorbol 12-myristate 13-acetate, >=99% (TLC), film or powder
12-O-tetradecanoyl phorbol-13-acetate;Cocarcinogen A1; Cocarcinogen C3
[(1S,2S,6R,10S,11R,13S,14R,15R)-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
11016-13-0
4beta,9alpha,12beta,13alpha,20-Pentahydroxytiglia-1,6-dien-3-one 12-tetradecanoate 13-acetate
5H-Cyclopropa(3,4)benz(1,2-e)azulen-5-one, 1,1a-beta,1b-alpha,4,4a,7a-beta,7b,8,9,9a-decahydro-4a-alpha,7b-beta,9-alpha,9a-beta-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8-beta-tetramethyl-, 9a-acetate 9-m
Myristic acid, 9-ester with 1,1aalpha,1bbeta,4,4a,7aalpha,7b,8,9,9a-decahydro-4abeta,7balpha,9beta,9aalpha-tetrahydroxy-3-(hydroxymethyl)-1,1,6,8alpha-tetramethyl-5H-cyclopropa[3,4]benz[1,2-e]azulen-5
tetradecanoic acid, (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-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
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-(1aalpha,1bbeta,