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Methyl-α-D-glucosamine

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Identification
Molecular formula
C7H15NO5
CAS number
583-55-1
IUPAC name
(2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol
State
State

At room temperature, methyl-α-D-glucosamine is a solid.

Melting point (Celsius)
187.00
Melting point (Kelvin)
460.15
Boiling point (Celsius)
280.00
Boiling point (Kelvin)
553.15
General information
Molecular weight
195.22g/mol
Molar mass
195.2150g/mol
Density
1.5723g/cm3
Appearence

Methyl-α-D-glucosamine typically appears as a white crystalline powder. It is highly soluble in water, lending to its use in various biochemical applications.

Comment on solubility

Solubility of (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol

The solubility of (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol is influenced by several factors, predominantly its functional groups and structural characteristics. This compound is a type of sugar alcohol or polyol, which often exhibits the following solubility traits:

  • High Solubility in Water: Due to the presence of multiple hydroxyl (-OH) groups, this compound is likely to be highly soluble in water. The hydrogen bonding interactions between the hydroxyl groups and water molecules enhance its solubility.
  • Limited Solubility in Organic Solvents: Due to its polar nature from the numerous hydroxyl groups, it tends to have limited solubility in non-polar organic solvents. This is commonly observed with polar compounds.
  • Effect of Temperature: Like many compounds, its solubility may increase with temperature. Warmer solvents often have greater capacity to dissolve solid solutes.

In summary, the solubility profile of (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol indicates strong compatibility with aqueous environments while demonstrating challenges when interacting with non-polar solvents. As stated, “the more hydroxyl groups present, the more soluble the compound typically becomes!”

Interesting facts

Interesting Facts about (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol

The compound known as (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol is a fascinating molecule with several noteworthy characteristics that intrigue both chemists and researchers alike:

  • Stereochemistry: This compound exhibits specific stereochemistry with multiple stereocenters, contributing to distinct spatial arrangements that can affect its biological activity and interactions.
  • Biological Relevance: Due to its structure, this compound may function as a pivotal intermediate in various biochemical pathways, particularly those involving amino sugars or polyols.
  • Pharmaceutical Potential: The presence of a methylamino group suggests potential uses in medicinal chemistry, where such molecules can exhibit intriguing pharmacological properties.
  • Chirality: The chirality of this compound can lead to different biological efficacy and safety profiles. It demonstrates the critical importance of considering enantiomers in drug design.
  • Applications in Synthesis: This type of pentol may also serve as a precursor for synthesizing other complex molecules, highlighting its importance in organic synthesis.

As highlighted by the great chemist Linus Pauling, "The structure of a substance is a critical determinant of its function." This notion emphasizes the significance of comprehending the structure of (2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol in various scientific fields, from pharmaceuticals to biochemistry.


Overall, the study of this compound not only broadens our understanding of organic chemistry and stereochemistry but also underscores the intricate connections between molecular structure and biological activity.

Synonyms
meglumine
N-Methyl-D-glucamine
6284-40-8
N-Methylglucamine
Meglumin
1-Deoxy-1-(methylamino)-D-glucitol
D-Glucitol, 1-deoxy-1-(methylamino)-
Meglumina
Methylglucamine
N-Methylsorbitylamine
Megluminum
1-Deoxy-1-methylaminosorbitol
(2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol
Megluminum [INN-Latin]
Meglumina [INN-Spanish]
(2R,3R,4R,5S)-6-(Methylamino)hexane-1,2,3,4,5-pentaol
Sorbitol, 1-deoxy-1-methylamino-
d(-)-n-methylglucamine
6HG8UB2MUY
EINECS 228-506-9
N-Methyl-D(-)-glucamine
Meglumine [USP:INN:BAN:JAN]
MEGLUMINE [INN]
MEGLUMINE [JAN]
MEGLUMINE [II]
NSC-7391
MEGLUMINE [VANDF]
NSC-52907
MEGLUMINE [MART.]
MEGLUMINE [USP-RS]
MEGLUMINE [WHO-DD]
MEGLUMINE [WHO-IP]
N-METHYLGLUCAMINE [MI]
MEGLUMINE [ORANGE BOOK]
DTXSID0023244
MEGLUMINE [EP MONOGRAPH]
CHEBI:59732
MEGLUMINE [USP MONOGRAPH]
EC 228-506-9
NSC52907
MEGLUMINE (II)
NSC 7391
Megluminum (INN-Latin)
Meglumina (INN-Spanish)
NSC 52907
MEGLUMINE (MART.)
MEGLUMINE (USP-RS)
Glucitol, 1-deoxy-1-(methylamino)-, D-
DTXCID503244
MEGLUMINE (EP MONOGRAPH)
MEGLUMINE (USP MONOGRAPH)
Meglumine (USP:INN:BAN:JAN)
C7H17NO5
UNII-6HG8UB2MUY
MFCD00004707
NSC7391
1-deoxy-1-methylamino-d-glucitol
N-methyl-glucamine
N-Methyl glucamine
NCGC00166125-01
CAS-6284-40-8
Meglumine (Standard)
Meglumine (Excipient)
antimoniate de mAglumine
SCHEMBL2193
BIDD:GT0676
METHYLGLUCAMINE [INCI]
Meglumine (JP17/USP/INN)
CHEMBL1200570
HY-B0342A
HY-B0342R
P01CB01
MEGLUMINUM [WHO-IP LATIN]
1-deoxy-1-(methylamino)-glucitol
1-Methylamino-1-deoxy-D-glucitol
HMS2089B05
HMS3714B10
Pharmakon1600-01300029
HY-B0342
Tox21_112330
Tox21_302037
NSC759607
s1974
AKOS005167162
AKOS015850890
N-methyl-1-amino-1-deoxy-D-glucitol
Tox21_112330_1
AC-4692
CCG-220884
MM07027
NSC-759607
RP10191
Meglumine 100 microg/mL in Acetonitrile
NCGC00166125-02
NCGC00255365-01
AC-17087
AS-12002
SBI-0206683.P002
1-Deoxy-1-methylamino-D-glucitol;Meglumine
Meglumine, meets USP testing specifications
M0227
SW199350-2
D01796
AB00430469-03
AB00430469_05
EN300-2394659
Q288875
SR-05000001446
N-Methyl-D-glucamine, 99.0-100.5% (titration)
SR-05000001446-1
BRD-K28595280-001-01-1
BRD-K28595280-001-03-7
BRD-K28595280-001-04-5
BRD-K28595280-001-05-2
N-Methyl-D-glucamine, Vetec(TM) reagent grade, 99%
N-Methyl-D-glucamine, ReagentPlus(R), >=99.0% (T)
Z1255485274
(2R,3R,4R,5S)-6-methylamino-hexane-1,2,3,4,5-pentaol
Meglumine, United States Pharmacopeia (USP) Reference Standard
N-methyl-(2 (S),3 (R),4 (R),5 (R),6-pentahydroxy-hexyl)-amine
Meglumine, Pharmaceutical Secondary Standard; Certified Reference Material
N-Methyl-D-glucamine, European Pharmacopoeia (EP) Reference Standard
228-506-9