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Heparin

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Identification
Molecular formula
C19H29NO20S
CAS number
9005-49-6
IUPAC name
(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylate
State
State

At room temperature, heparin is typically found as a solid powder. In physiological and pharmaceutical formulations, it is used in aqueous solutions.

Melting point (Celsius)
275.00
Melting point (Kelvin)
548.15
Boiling point (Celsius)
207.00
Boiling point (Kelvin)
480.15
General information
Molecular weight
13000.00g/mol
Molar mass
13 000.0000g/mol
Density
2.1830g/cm3
Appearence

Heparin is typically found as a white or off-white, granular or powdery substance. It is highly hygroscopic and usually available in its sodium salt form, which is soluble in water.

Comment on solubility

Solubility of (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylate

The compound (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylate exhibits notable solubility characteristics due to its intricate structure, featuring multiple hydroxyl and sulfonate groups. These functional groups significantly impact its interactions with solvents. Here are some key points regarding its solubility:

  • Hydrophilicity: The presence of multiple hydroxyl (-OH) and sulfonate (-SO₃⁻) groups enhances its affinity for polar solvents, particularly water.
  • Solvent Compatibility: This compound is likely to dissolve effectively in aqueous solutions, given its ionic and polar features.
  • pH Dependence: Solubility may vary with changes in pH, as the ionization of the sulfonate group could alter the compound's interaction with water.
  • Concentration Effects: At higher concentrations, solubility might be limited due to intermolecular interactions, which can lead to precipitation.

In conclusion, the solubility of this compound is primarily influenced by its numerous functional groups, which favor interactions with polar solvents. Its hydrophilic nature makes it particularly suitable for applications in aqueous environments, though conditions such as pH and concentration must be considered for optimal solubility behavior.

Interesting facts

Interesting Facts About (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxy-tetrahydropyran-4-yl]oxy-3,4,5-trihydroxy-tetrahydropyran-2-carboxylate

This complex compound, often referred to in biochemical research, holds significant interest due to its unique structural properties and potential applications. Here are some intriguing aspects:

  • Stereochemistry: The compound features multiple stereochemical centers, making it a chiral molecule. Its specific stereoconfiguration contributes to its biological activity, reflecting the importance of chirality in drug design and development.
  • Biological Relevance: The presence of functional groups such as acetamido and sulfonato suggests potential roles in biochemical pathways, possibly as intermediates or inhibitors in enzymatic reactions.
  • Glycosylation: This compound could likely participate in glycosylation processes, highlighting its relevance in carbohydrate chemistry and its potential impact on cellular interactions.
  • Research Applications: Compounds of this nature are often investigated for their roles in medicinal chemistry, particularly in designing targeted therapies for diseases where carbohydrate moieties play critical roles, such as diabetes.
  • Molecular Complexity: The intricate structure, featuring multiple hydroxyl groups and carboxylate functionalities, showcases the vast diversity within organic compounds. This complexity can lead to varied reactivity and interactions with biological systems.

As researchers delve deeper into the chemistry of such compounds, we often find that they challenge our understanding and inspire new developments. “Every molecule tells a story,” and compounds like this one are pivotal characters in the narrative of scientific discovery.


In summary, this compound not only offers a glimpse into the fascinating world of synthetic and naturally occurring medicines but also serves as a reminder of the intricate dance of functionality and structure in biochemistry.

Synonyms
DERMATAN SULFATE
Chondroitin sulfate B
beta-Heparin
Dermatan sulphate
Dermatan hydrogen sulfate
24967-94-0
Chondroitinsulfuric acid type B
Dermatan, 4-(hydrogen sulfate)
Dermatan sulfate, low molecular weight
beta Heparin
Sulfate, Dermatan
Sulfate B, Chondroitin
DTXSID40179683
RefChem:388920
J3OC7JVS54
CHEBI:18376
246-552-8
Dermatan L-iduronate
(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfonatooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
Dermatan 4-sulfate
Desmin 370
Chondroitinsulfuric acid
Chondroitinsulfuric acid B
Chondroitin sulfate type B
Chondroitinsulfuric acid, type B
MF701
Dermatan Sulfate Sodium Salt
Dermatan, hydrogen sulfate (ester)
EINECS 246-552-8
DS 435
MF 701
dermatan 4'-sulfate
CHEBI:58465
YD58324
NS00120253
6-[3-acetamido-2-hydroxy-6-(hydroxymethyl)-5-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid