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Spiramycin

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Identification
Molecular formula
C43H74N2O14
CAS number
8025-81-8
IUPAC name
(2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
State
State

Spiramycin is a solid at room temperature, commonly supplied as a powder. It is not soluble in water, which affects its formulation for pharmaceutical purposes. It is often provided in forms that allow for better absorption.

Melting point (Celsius)
145.00
Melting point (Kelvin)
418.15
Boiling point (Celsius)
310.00
Boiling point (Kelvin)
583.15
General information
Molecular weight
843.05g/mol
Molar mass
843.0460g/mol
Density
1.3300g/cm3
Appearence

Spiramycin typically appears as a white or slightly yellowish crystalline powder. It is often administered in the form of tablets or as a component in topical formulations. The powder is hygroscopic and may have a slightly bitter taste.

Comment on solubility

Solubility Characteristics

The solubility of the compound (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol can be quite intricate, as it presents multiple functional groups that influence its behavior in various solvents.

Factors Influencing Solubility:

  • Hydrophilic Groups: The presence of hydroxyl (-OH) groups significantly enhances solubility in polar solvents like water.
  • Hydrophobic Regions: However, the compound contains bulky hydrophobic components, which may limit its solubility in purely aqueous environments.
  • Structural Complexity: Its intricate structure, featuring multiple interconnected rings and functional groups, contributes to unique solubility properties.

In practical terms, one could expect the solubility to vary widely depending on the solvent employed. It tends to be more soluble in polar solvents compared to non-polar ones. As a general rule, “like dissolves like”—meaning the solubility will be maximized when the solvent is similar in polarity to the compound. Consequently, achieving good dissolving conditions might involve:

  1. Utilizing co-solvents to accommodate both hydrophilic and hydrophobic components.
  2. Adjusting temperature and pH to enhance interaction with the solvent.

Thus, understanding the solubility behavior of this compound is essential for applications in pharmaceuticals and material sciences, ensuring optimal conditions for its use.

Interesting facts

Interesting Facts about the Compound

The compound represented by the name (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-yl]oxy-tetrahydropyran-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol is a remarkably complex organic molecule, showcasing the intricate nature of modern chemistry.

Key Highlights:

  • Stereochemistry: This compound exhibits multiple stereocenters, indicated by the extensive use of S and R notations, which contributes to its potential for unique biological activities.
  • Biological Importance: Many compounds of similar structural complexity are known for their therapeutic properties, such as acting as natural products or pharmaceuticals with anti-inflammatory or anti-cancer effects.
  • Structural Diversity: The presence of various functional groups, including hydroxyl and ether moieties, allows this compound to participate in numerous chemical reactions, underscoring its versatility in organic synthesis.
  • Potential Applications: Due to its intricate structure, this compound could be explored in drug development, particularly in designing drugs that target specific biological pathways or mechanisms.

As a student of chemistry, encountering such a multifaceted molecule encourages a deeper appreciation for the art of molecular design and the endless possibilities it holds. As one researcher eloquently stated, "The complexity of molecular architecture reflects the richness of life itself." This compound not only serves as a testament to synthetic capabilities but also offers a glimpse into the potential future discoveries within the realm of organic chemistry.

Synonyms
Tomatine
Lycopersicin
alpha-Tomatine
17406-45-0
A''-Tomatidine
Tomatin
Tomatidine, glycoside
CHEBI:9630
DTXSID5040413
31U6547O08
DTXCID3020413
NSC-9223
NSC-234440
beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl-(1-3))-O-beta-D-glucopyranosyl-(1-4)-
(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-[beta-D-xylopyranosyl-(1-3)]-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside
(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1-2)-(beta-D-xylopyranosyl-(1-3))-beta-D-glucopyranosyl-(1-4)-beta-D-galactopyranoside
2-(2-(4,5-dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
241-429-5
(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-((1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icosane-6,2'-piperidine)-16-yl)oxyoxan-3-yl)oxy-5-hydroxy-6-(hydroxymethyl)-4-((2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl)oxyoxan-3-yl)oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Tomatine from Tomato
(3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
.alpha.-Tomatine
HSDB 3558
beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-
NSC 9223
EINECS 241-429-5
NSC 234440
BRN 0078250
AI3-17141
UNII-31U6547O08
(3beta,5alpha,25S)-spirosolan-3-yl beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
Tomatine; Lycopersicin
TOMATINE [HSDB]
TOMATINE [MI]
(3beta,5alpha,22beta,25S)-Spirosolan-3-yl O-beta-D-glucopyranosyl-(1-2)-O-(beta-D-xylopyranosyl)-(1-3))-O-(beta-D-glucopyranosyl-(1-4)-beta-D-Galactopyranoside
4-27-00-01954 (Beilstein Handbook Reference)
SCHEMBL239168
CHEMBL525778
orb1303749
MSK3007
HY-N2166
Tox21_111530
BDBM50480249
LMST01150015
s9444
AKOS040756083
CCG-270615
OT07656
beta-D-Galactopyranoside, (3beta,5alpha,22beta,25S)-spirosolan-3-yl O-beta-D-glucopyranosyl-(1->2)-O-(beta-D-xylopyranosyl)-(1->3)-O-beta-D-glucopyranosyl-(1->4)-
MS-31885
CAS-17406-45-0
CS-0019466
NS00025717
T3636
Q288051
(22S,25S)-5alpha-spirosolan-3beta-yl beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranosyl-(1->4)-beta-D-galactopyranoside
Lycopersicin;(3?,5?,22?,25S)-Spirosolan-3-yl O-?-D-glucopyranosyl-(1-2)- O-[?-D-xylopyranosyl-(1-3)]-O-?-D-glucopyranosyl-(1-4)-?-D-g alactopyranoside