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Amygdalin

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Identification
Molecular formula
C20H27NO11
CAS number
29883-15-6
IUPAC name
2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile
State
State
Solid at room temperature.
Melting point (Celsius)
200.00
Melting point (Kelvin)
473.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
457.43g/mol
Molar mass
457.4290g/mol
Density
1.4000g/cm3
Appearence
Amygdalin appears as white crystalline needles with a characteristic bitter taste. It is typically found in certain fruit seeds, notably apricots and almonds.
Comment on solubility

Solubility of 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile (C20H27NO11)

The solubility of 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile is quite complex due to its intricate structure, which features several hydroxyl groups and multiple sugar moieties. The presence of these functional groups generally enhances solubility in polar solvents.

Factors Influencing Solubility:

  • Hydroxyl Groups: With multiple –OH groups, this compound is likely to interact favorably with water, increasing its solubility.
  • Molecular Weight: The relatively high molecular weight may result in reduced solubility compared to smaller compounds.
  • Polarity: The overall polarity derived from both hydroxyl groups and the aromatic phenyl ring influences solubility significantly.

In general, such a compound may demonstrate good solubility in polar solvents like water and alcohols, while exhibiting limited solubility in nonpolar solvents. As expressed in the words of solubility theory, "like dissolves like," meaning that polar compounds tend to dissolve well in polar solvents.

In practical applications, understanding the solubility characteristics of this compound is crucial, particularly in fields such as pharmaceuticals, where solubility can directly affect the bioavailability and efficacy of a drug.

Interesting facts

Interesting Facts about 2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile

This complex compound, often referred to as a glycoside or a polyol derivative, showcases a fascinating structure that reflects the intricate nature of organic chemistry. Here are some intriguing aspects of this compound:

  • Glycosidic Bonds: The presence of multiple hydroxyl groups and tetrahydropyran rings in its structure indicates that this compound likely participates in glycosidic bonding, which is crucial in the formation of various biomolecules like sugars.
  • Biological Significance: Compounds that contain multiple hydroxyl groups, as seen in this molecule, often play vital roles in biological processes, including acting as reducing agents or participating in metabolic pathways.
  • Potential Applications: This compound may be explored for applications in pharmaceuticals due to its possible bioactivity. Compounds with similar structures have been studied for their antioxidant properties, which could be leveraged in health-related applications.
  • Chirality: The multiple stereocenters in this compound grant it chirality, which can lead to different enantiomers. Chirality is a key feature in drug design, as different enantiomers can exhibit vastly different effects in biological systems.
  • Complexity in Synthesis: The synthesis of such a large and structurally complex molecule poses significant challenges. Chemists often require advanced techniques and the use of protective groups to selectively form bonds while minimizing side reactions.

As noted by many chemists, “The beauty of chemistry lies in the complexity of its compounds and their myriad of applications.” This compound exemplifies that beauty through its rich structure and the potential avenues it opens in scientific research.

The study of compounds like this one not only enhances our understanding of organic chemistry but also paves the way for future advancements in various fields, from pharmaceuticals to materials science.

Synonyms
amygdalin
D-Amygdalin
Isoamygdalin
Amygdaloside
Glucoprunasin
29883-15-6
51371-34-7
2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
DL-Amygdalin
Mandelonitrile-beta-gentiobioside
NSC251222
Mandelonitrile-.beta.-gentiobioside
D(-)-Mandelonitrile-.beta.-D-gentiobioside
D-(-)-Amygdalin
Benzeneacetonitrile, .
AMYGDALIN(D)
AMYGDALIN,(DL)
Mandelonitrile gentiobioside
CHEMBL1967951
SCHEMBL13387202
GTPL12451
DTXSID20872004
XUCIJNAGGSZNQT-UHFFFAOYSA-N
HMS3341N01
HMS3655P16
AKOS024282419
NSC-251222
OM05087
Benzeneacetonitrile, .alpha.-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-
NCGC00380662-01
2-phenyl-2-(3,4,5-trihydroxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6 -tetrahydropyran-2-yloxy)]methyl}(2H-3,4,5,6-tetrahydropyran-2-yloxy))ethaneni trile
Benzeneacetonitrile, .alpha.-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-glucopyranosyl)oxy]-, (R)-
LS-14805
NCI60_002005
NS00097233
[(6-O-Hexopyranosylhexopyranosyl)oxy](phenyl)acetonitrile #
alpha-[(6-O-Hexopyranosylhexopyranosyl)oxy]benzeneacetonitrile
Benzeneacetonitrile,a-[(6-O-b-D-glucopyranosyl-b-D-glucopyranosyl)oxy]-
Benzeneacetonitrile, .alpha.-[(6-O-.beta.-D-glucopyranosyl-.beta.-D-gluco-pyranosyl)oxy]-
D-Mandelonitrile-b-D-glucoside-6-O-b-D-glucoside;D-Mandelonitrile-b-gentiobioside
1173199-73-9
2-phenyl-2-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-acetonitrile