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Lobeline

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Identification
Molecular formula
C15H21NO2
CAS number
3781-49-9
IUPAC name
[(2S,3R,4R)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate
State
State

Lobeline is typically found in a solid state at room temperature.

Melting point (Celsius)
124.00
Melting point (Kelvin)
397.20
Boiling point (Celsius)
489.20
Boiling point (Kelvin)
762.30
General information
Molecular weight
275.34g/mol
Molar mass
275.3360g/mol
Density
1.2200g/cm3
Appearence

Lobeline appears as a white crystalline powder that is often used in its sulfate form for medical applications. The compound is odorless in its pure form and has a slightly bitter taste.

Comment on solubility

Solubility Characteristics

The compound [(2S,3R,4R)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate exhibits interesting solubility traits due to its structural features. The presence of both polar and non-polar groups significantly influences its interaction with solvents.

Factors Affecting Solubility:

  • Functional Groups: The hydroxyl group and acetate group enhance solubility in polar solvents such as water and alcohols, promoting hydrogen bonding.
  • Aromatic Ring: The methoxyphenyl moiety extends its hydrophobic character, leading to decreased solubility in purely polar solvents.
  • Sterics: The steric hindrance provided by the pyrrolidine ring affects molecular packing and can influence solubility behavior.

As a result, this compound may demonstrate:

  • Good solubility in polar solvents (e.g., methanol, ethanol).
  • Limited solubility in non-polar solvents (e.g., hexane, toluene).

In summary, the solubility of [(2S,3R,4R)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate is a balance of its polar and non-polar characteristics, making it versatile for various applications in different solvent systems.

Interesting facts

Interesting Facts about (2S,3R,4R)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate

This compound, often noted for its complex structure and unique properties, is a member of the pyrrolidine family, which has gained attention in various fields of study. Here are some intriguing aspects of this compound:

  • Synthetic Utility: The presence of the hydroxyl and acetate functional groups in its structure enhances its reactivity, making it an excellent candidate for synthetic organic chemistry.
  • Pharmacological Interest: Compounds derived from pyrrolidine structures have been widely researched for their potential use in pharmaceuticals, including their roles in drug design and development.
  • Chirality: This specific compound boasts a chiral center, which results in different stereoisomers that may exhibit varied biological activities. The importance of chirality in drug efficacy cannot be overstated, as different enantiomers can have drastically different effects on living organisms.
  • Biological Applications: Recent studies have indicated that pyrrolidine derivatives may possess significant antiviral, antibacterial, and anticancer properties, making them valuable in the search for new therapeutic agents.

As a scientist or chemistry student, delving into the properties and applications of (2S,3R,4R)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl acetate offers a captivating glimpse into modern chemical research. The compound serves as a bridge connecting fundamental chemistry to practical applications in medicine and industry. As the well-known chemist, Dr. Jane Goodall, once said, "In science, we must be interested in new ideas, but we must also be interested in old ideas." This compound exemplifies the refreshing blend of traditional and innovative chemistry.

Synonyms
(+)-Anisomycin
(+)-Flagecidin
Anisomycin, (+)-
3,4-Pyrrolidinediol, 2-(p-methoxybenzyl)-, 3-acetate, (2S,3R,4R)-
27958-09-4
074BVA859D
(2S,3R,4R)-(+)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
(2S,3R,4R)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine
3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2S,3R,4R)-
3,4-Pyrrolidinediol, 2-((4-methoxyphenyl)methyl)-, 3-acetate, (2S-(2alpha,3alpha,4beta))-
RefChem:199599
GlyTouCan:G63894BZ
G63894BZ
[(2S,3R,4R)-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate
UNII-074BVA859D
GNF-Pf-4549
Prestwick_720
Prestwick0_000412
Prestwick1_000412
Prestwick2_000412
NCIMech_000436
SCHEMBL59587
SPBio_002303
CHEMBL583157
CHEBI:94762
DTXSID301328373
HMS1569C06
HMS3402H18
(2S,3R,4R)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3-yl acetate
CCG-35934
CCG-36487
s7409
AKOS030213121
SMP1_000023
NCI60_001006
NS00011714
BRD-K82261406-001-01-2
3,4-PYRROLIDINEDIOL, 2-((4-METHOXYPHENYL)METHYL)-, 3-ACETATE, (2S-(2.ALPHA.,3.ALPHA.,4.BETA.))-