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Ajmalicine

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Identification
Molecular formula
C27H34N2O8
CAS number
483-04-5
IUPAC name
methyl (1R,15S,17R,18R,19S,20S)-17-(4-ethoxycarbonyloxy-3,5-dimethoxy-benzoyl)oxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
State
State
Ajmalicine is typically in a solid state at room temperature, appearing as a white crystalline powder that is stable under standard conditions.
Melting point (Celsius)
196.00
Melting point (Kelvin)
469.15
Boiling point (Celsius)
312.00
Boiling point (Kelvin)
585.15
General information
Molecular weight
534.56g/mol
Molar mass
534.5610g/mol
Density
1.3200g/cm3
Appearence

Ajmalicine is a white crystalline solid. It typically appears as a fine powder and is odorless.

Comment on solubility

Solubility of Methyl (1R,15S,17R,18R,19S,20S)-17-(4-ethoxycarbonyloxy-3,5-dimethoxy-benzoyl)oxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

The solubility of the compound methyl (1R,15S,17R,18R,19S,20S)-17-(4-ethoxycarbonyloxy-3,5-dimethoxy-benzoyl)oxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate can be influenced by several factors:

  • Polarity: Due to the presence of multiple functional groups such as esters and methoxy groups, the overall polarity of the molecule may vary, affecting its ability to dissolve in different solvents.
  • Solvent Interaction: It is likely to have better solubility in organic solvents like ethanol or dimethyl sulfoxide (DMSO) compared to polar solvents such as water.
  • Temperature: An increase in temperature can enhance solubility, making the compound more soluble in hot solvent conditions.

As a general rule, "like dissolves like," meaning that polar solvents are suitable for polar compounds, and non-polar solvents work best for non-polar compounds. The diverse functionalization of this compound suggests that careful consideration of solvent choice is crucial for achieving optimal solubility. Always consult experimental data for precise solubility values, as theoretical predictions may not account for specific interactions that can occur in practical applications.

Interesting facts

Interesting Facts about Methyl (1R,15S,17R,18R,19S,20S)-17-(4-Ethoxycarbonyloxy-3,5-dimethoxy-benzoyl)oxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-Dodecahydroyohimban-19-Carboxylate

This compound is a fascinating member of the yohimbine family, known for its complex structure that offers various avenues of research and application. The intricate arrangement of its stereocenters contributes to its unique biological activity, which has made it a subject of interest in both pharmacological studies and synthetic organic chemistry.

Key Highlights:

  • Biological Significance: Yohimbine, from which this compound is derived, has historically been used for its aphrodisiac properties and may also hold potential in treating certain medical conditions, such as erectile dysfunction.
  • Synthetic Chemistry: The synthesis of this compound involves multiple steps and strategic functional group modifications, showcasing the elegance and complexity of organic synthesis.
  • Potential Applications: Researchers are exploring this compound's potential in drug development, particularly in areas related to neuropharmacology, due to its interaction with adrenergic receptors.
  • Structural Complexity: This compound features a multitude of functional groups, including ester linkages and methoxy groups, which can lead to diverse chemical reactivity and biological interactions.
  • Research Challenges: The stability and reactivity of the compound under different conditions present interesting challenges for chemists, requiring optimization techniques in synthetic procedures.

This compound serves as an excellent example of the synergy between organic synthesis and pharmacology, illustrating the vital role that complex natural products play in the development of therapeutic agents. As ongoing studies explore its full range of effects, it is likely to remain a prominent compound in chemical research.

Synonyms
syrosingopine
84-36-6
Syringopine
Isotense
Londomin
Neoreserpan
Siringina
Menatensina
Syrosingopin
Singoserp
Ipores
Elufinesin
Etropres
Novoserpina
Seringina
Serpagon
Siringal
Siringone
Siriserpin
Siroshuten
Vegaserpina
Nichiserpine-S
Revelox-wirkstoff
SU 3118
Sirosingopina
Methyl carbethoxysyringoyl reserpate
Carbethoxysyringoyl methylreserpate
HF-41T
NSC-77030
PPG46JF0EG
SU-3118
Syrosingopine (Su-3118)
Methyl reserpate ester of syringic acid ethyl carbonate
Syringic acid ethyl carbonate ester with methyl reserpate
DTXSID9023629
NSC77030
Zentos
Syrosingopine (>90%)
NSC 77030
methyl (1R,15S,17R,18R,19S,20S)-17-(4-ethoxycarbonyloxy-3,5-dimethoxybenzoyl)oxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Syrosingopinum
Syrosingopinum [INN-Latin]
Sirosingopina [INN-Spanish]
3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 4-hydroxy-3,5-dimethoxybenzoate (ester) ethyl carbonate (ester) (8CI)
Benzoic acid, 4-hydroxy-3,5-dimethoxy-, ethyl carbonate, ester with methyl reserpate
Reserpic acid, methyl ester, ester with 4-hydroxy-3,5-dimethoxybenzoic acid ethyl carbonate
EINECS 201-527-0
UNII-PPG46JF0EG
CAS-84-36-6
Siringina (TN)
Syrosingopine [INN:BAN:JAN:NF]
NCGC00016336-01
Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate 4-hydroxy
Prestwick_457
MFCD00017411
Methyl 18-O-(4-ethoxycarbonyloxy-3,5-dimethoxybenzyoyl)reserpat
Prestwick3_000564
18-O-(3,5-Dimethoxy-4-ethoxycarbonyloxybenzoyl)eserpsaeuremethylester
Syrosingopine (JAN/INN)
SYROSINGOPINE [MI]
SYROSINGOPINE [INN]
SYROSINGOPINE [JAN]
BSPBio_000348
Methyl 18beta-(4-(ethoxycarbonyloxy)-3,5-dimethoxybenzoyloxy)-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylat
MLS002153876
Yohimban-16-carboxylic acid, 18-((4-((ethoxycabonyl)oxy)-3,5-dimethoxybenzoyl)oxy)-11,17-dimethoxy-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
SCHEMBL219705
SYROSINGOPINE [MART.]
SYROSINGOPINE [WHO-DD]
BPBio1_000384
DTXCID703629
CHEMBL1399124
CHEBI:32175
Syrosingopine - Bio-X trade mark
ZCDNRPPFBQDQHR-SSYATKPKSA-N
HMS2096B10
HMS2234L13
HY-N4115
Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate 4-hydroxy
YOHIMBAN-16-CARBOXYLIC ACID, 18-((4-((ETHOXYCARBONYL)OXY)-3,5-DIMETHOXYBENZOYL)OXY)-11,17-DIMETHOXY-, METHYL ESTER, (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-
Tox21_110379
BDBM50606665
s9907
AKOS037643554
CCG-208497
FS65931
NCGC00179590-02
NCGC00179590-04
3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 4-hydroxy-3,5-dimethoxybenzoate (ester) ethyl carbonate (ester)
AS-16863
BS300129
SMR001233230
CS-0032125
NS00038492
Methyl reserpate,5-dimethoxybenzoic acid ester
D01659
G12066
SR-01000838851
SR-01000838851-3
BRD-K14200658-001-02-6
Q27164011
Benzoic acid,5-dimethoxy-, ethyl carbonate, ester with methyl reserpate
WLN: T F6 D5 C666 EM ON&&TTTJ HO1 SOVR CO1 EO1 DOVO2& TO1 UVO1
Reserpic acid, ester with 4-hydroxy-3,5-dimethoxybenzoic acid ethyl carbonate
3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester, 4-hydroxy-3,5-dimethoxybenzoate (ester) ethyl carbonate (ester)
3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester, ester with 4-hydroxy-3,5-dimethoxybenzoic acid ethyl carbonate
methyl (3beta,16beta,17alpha,18beta,20alpha)-18-({[4-{[(ethyloxy)carbonyl]oxy}-3,5-bis(methyloxy)phenyl]carbonyl}oxy)-11,17-bis(methyloxy)yohimban-16-carboxylate
Yohimban-16-carboxylic acid,5-dimethoxybenzoyl]oxy]-11,17-dimethoxy-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-