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Monensin

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Identification
Molecular formula
C36H62O11
CAS number
17090-79-8
IUPAC name
(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
State
State

At room temperature, Monensin is typically a solid. It is often available in the form of a crystalline powder, suitable for various applications in veterinary medicine and agriculture.

Melting point (Celsius)
82.00
Melting point (Kelvin)
355.15
Boiling point (Celsius)
255.80
Boiling point (Kelvin)
528.95
General information
Molecular weight
670.87g/mol
Molar mass
670.8680g/mol
Density
1.2700g/cm3
Appearence

Monensin appears as a white to off-white crystalline powder. It may also form colorless to white crystals under certain conditions. The compound is typically odorless or may have a very faint characteristic odor.

Comment on solubility

Solubility Characteristics

The solubility of the compound (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione can be quite complex, given its intricate structure and multiple functional groups. Here are some key points to consider:

  • Hydrophilicity vs. Hydrophobicity: The presence of hydroxyl groups (-OH) generally increases solubility in polar solvents like water. However, the hydrophobic character from the bulky alkyl groups may counterbalance this effect, limiting its solubility.
  • Solvent Dependency: Solubility is likely to be solvent-dependent. It may exhibit higher solubility in organic solvents such as ethanol or methanol compared to water due to the combination of polar and non-polar structure segments.
  • Temperature Influence: Like many organic compounds, solubility may also vary appreciably with temperature—increasing temperature often enhances solubility.
  • pH Effects: The ionization state of the hydroxyl groups can also affect solubility; thus, adjusting the pH of the solution could lead to enhanced solubility under certain conditions.

In conclusion, although the presence of functional groups suggests potential for solubility, the compound's overall structure likely results in limited solubility in aqueous environments. Research into specific solubility metrics would be essential for a comprehensive understanding.

Interesting facts

Interesting Facts about (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione

This intriguing compound, often referenced in the realm of organic and medicinal chemistry, possesses a complex molecular structure that highlights the beauty of chemical diversity and synthesis. Here are some fascinating insights about this compound:

  • Unusual Structure: The compound has a unique bicyclic framework, indicating a specific arrangement of atoms that can lead to various reactivity patterns. Its tricyclic nature suggests it may exhibit interesting stereochemistry.
  • Functional Groups: The presence of multiple hydroxyl groups (–OH) implies that the compound can engage in hydrogen bonding, potentially influencing its reactivity and solubility in different environments.
  • Applications in Medicine: Compounds of similar structures are often explored for their biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The unique arrangement of functional groups may enhance its pharmacological properties.
  • Synthesis Challenges: The synthetic pathways leading to such complex molecules typically involve multi-step reactions, using various strategies such as cyclization and functional group transformations.
  • Research Potential: As scientists continue to unravel the potential applications of this compound, research is ongoing to explore its utility in drug design and material science.

In summary, (1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione represents an exciting intersection of structural complexity and potential utility, making it a valued topic of study in contemporary chemistry. As the old adage goes, "Chemistry is the central science," and compounds like this one illustrate just how true that is!

Synonyms
monocrotaline
Crotaline
315-22-0
Monocrotalin
(-)-Monocrotaline
NCI-C56462
CCRIS 416
CHEBI:6980
HSDB 3513
A 6080
Retronecine cyclic 2,3-dihydroxy-2,3,4-trimethylglutarate
UNII-73077K8HYV
BRN 0048732
MLS002153902
DTXSID9020902
73077K8HYV
(13-alpha,14-alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
MONOCROTALINE [MI]
14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
MONOCROTALINE [HSDB]
MONOCROTALINE [IARC]
NSC 28693
DTXCID50902
20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13alpha,14alpha)-
(3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
4-27-00-06660 (Beilstein Handbook Reference)
12-beta,13-beta-Dihydroxy-12-alpha,13-alpha,14-alpha-trimethylcrotal-1-enine
NSC-28693
14,19-Dihydro-12,13-dihydroxy(13-alpha,14-alpha)-20-norcrotalanan-11,15-dione
(2,3,4-gh)pyrrolizine-2,6(3H)-dione, (4,5,8,10,12,13,13a,13b)-octahydro-4,5-dihydroxy-3,4,5-trimethyl-2H-(1,6)dioxacycloundecino-
NCGC00164256-01
20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-
MONOCROTALINE (IARC)
(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-octahydro-4,5-dihydroxy-3,4,5-trimethyl-, (3R,4R,5R,13aR,13bR)-
2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-, (3R-(3R*,4R*,5R*,13AR*,13BR*))-
20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13.alpha.,14.alpha.)-
SR-01000838886
(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo(8.5.1.013,16)hexadec-10-ene-3,7-dione
(3R,4R,5R,13aR,13bR)-4,5-dihydroxy-3,4,5-trimethyl-4,5,8,10,12,13,13a,13b-octahydro-2H-(1,6)dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione
2H-(1,6)DIOXACYCLOUNDECINO(2,3,4-gh)PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13a,13b-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-,(3R,4R,5R,13aR,13bR)-
2H-[1,6]DIOXACYCLOUNDECINO[2,3,4-gh]PYRROLIZINE-2,6(3H)-DIONE, 4,5,8,10,12,13,13a,13b-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-,(3R,4R,5R,13aR,13bR)-
CAS-315-22-0
Prestwick_338
MFCD00084656
Spectrum_001224
Prestwick0_000603
Prestwick1_000603
Prestwick2_000603
Prestwick3_000603
Spectrum2_000906
Spectrum3_000947
Spectrum4_001057
Spectrum5_001233
BSPBio_000506
KBioGR_001354
KBioSS_001704
DivK1c_000959
SCHEMBL164486
SPECTRUM1502252
SPBio_000752
SPBio_002725
BPBio1_000558
CHEMBL521035
MEGxp0_001899
ACon0_000305
ACon1_000179
HMS502P21
KBio1_000959
KBio2_001704
KBio2_004272
KBio2_006840
KBio3_002014
(13-.alpha.,14-.alpha.)-14,19-Dihydro-12,13-dihydroxy-20-norcrotalanan-11,15-dione
12.beta.,13.beta.-Dihydroxy-12.alpha.,13.alpha.,14.alpha.-trimethylcrotal-1-enine
14,19-Dihydro-12,13-dihydroxy(13.alpha.,14.alpha.)-20-norcrotalanan-11,15-dione
2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine, 20-norcrotalanan-11,15-dione deriv.
2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine, 20-norcrotalanan-11,15-dione deriv.
Monocrotaline, analytical standard
NINDS_000959
HMS1569J08
HMS1921P04
HMS2096J08
HMS2235J12
HY-N0750
MSK14173
Tox21_112094
Tox21_201509
Tox21_302874
BDBM50480309
CCG-39621
s3812
AKOS015969712
AKOS032962048
Tox21_112094_1
CS-6164
FM64904
FS-5652
SDCCGMLS-0066675.P001
IDI1_000959
NCGC00179538-01
NCGC00179538-02
NCGC00179538-03
NCGC00256518-01
NCGC00259060-01
NCGC00262539-03
1ST14173
AC-34918
SMR001233251
JACS 72: 158 (1950)
SR-01000838886-3
SR-01000838886-4
BRD-K65508953-001-05-5
BRD-K65508953-001-08-9
Q27107379
Retronecine cyclic 2,3dihydroxy2,3,4trimethylglutarate
12beta,13betaDihydroxy12alpha,13alpha,14alphatrimethylcrotal1enine
(13alpha,14alpha)14,19Dihydro12,13dihydroxy20norcrotalanan11,15dione
12beta,13beta-Dihydroxy-12alpha,13alpha,14alpha-trimethylcrotal-1-enine
14,19Dihydro12,13dihydroxy(13alpha,14alpha)20norcrotalanan11,15dione
(13alpha, 14alpha)-14,19-Dihydro-12,13-dihydroxy-20-norcrotolanan-11,15-dione
14,19-Dihydro-12,13-dihydroxy(13alpha,14alpha)-20-norcrotalanan-11,15-dione
20Norcrotalanan11,15dione, 14,19dihydro12,13dihydroxy, (13alpha,14alpha)
(1R,4R,5R,6R,16R)-5,6-dihydroxy-4,5,6-trimethyl-2,8-dioxa-13-azatricyclo[8.5.1.0??,??]hexadec-10-ene-3,7-dione
(2,3,4-GH)PYRROLIZINE-2,6(3H)-DIONE, (4,5,8,10,12,13,13A,13B-OCTAHYDRO-4,5-DIHYDROXY-3,4,5-TRIMETHYL-2H-(1,6)DIOXACYCLOUNDECINO-
(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
(3R,4R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
109525-74-8
20-Norcrotalanan-11,15-dione, 14,19-dihydro-12,13-dihydroxy-, (13-alpha,14-alpha)-(9CI)
628-506-2
rel-(3R,4R,5R,8a1R,13aR)-4,5-Dihydroxy-3,4,5-trimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione