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Alpha-lipoic acid

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Identification
Molecular formula
C8H14O2S2
CAS number
1077-28-7
IUPAC name
5-[(3R)-dithiolan-3-yl]pentanoic acid
State
State

Alpha-lipoic acid is typically a solid at room temperature. It is stable under normal conditions and can dissolve in some organic solvents.

Melting point (Celsius)
60.00
Melting point (Kelvin)
333.00
Boiling point (Celsius)
160.00
Boiling point (Kelvin)
433.00
General information
Molecular weight
206.33g/mol
Molar mass
206.3280g/mol
Density
1.1900g/cm3
Appearence

Alpha-lipoic acid is a yellow to pale yellow crystalline compound. It typically appears as a powder or crystals and can have a faint characteristic odor.

Comment on solubility

Solubility of 5-[(3R)-dithiolan-3-yl]pentanoic acid

The compound 5-[(3R)-dithiolan-3-yl]pentanoic acid (C8H14O2S2) exhibits interesting solubility characteristics due to its unique molecular structure. Here are some key points regarding its solubility:

  • Polar Functional Groups: The presence of both carboxylic acid (–COOH) and dithiolane (–S2) groups contributes to the compound’s solubility in polar solvents.
  • Solvent Compatibility: This compound is likely more soluble in polar solvents such as water or methanol, but may have limited solubility in non-polar organic solvents.
  • Hydrogen Bonding: The ability of the carboxylic acid group to form hydrogen bonds enhances its solubility in aqueous solutions.
  • Temperature Dependence: As with many organic compounds, solubility can vary with temperature, often increasing at elevated temperatures.

In summary, the solubility of 5-[(3R)-dithiolan-3-yl]pentanoic acid is influenced by its molecular structure, particularly due to the combination of polar functional groups and hydrophilic interactions. Understanding the solubility behavior is crucial for its potential applications in various chemical processes and formulations.

Interesting facts

Interesting Facts about 5-[(3R)-dithiolan-3-yl]pentanoic acid

5-[(3R)-dithiolan-3-yl]pentanoic acid is a fascinating compound that showcases the complexity of organic chemistry. Here are some intriguing aspects of this molecule:

  • Sulfur Chemistry: The presence of the dithiolane group introduces interesting reactivity patterns, making this compound a subject of study for chemists interested in sulfur-containing compounds.
  • Biological Relevance: Compounds containing similar thiol groups may play significant roles in biological systems, potentially impacting metabolism and antioxidant activity.
  • Applications in Material Science: The unique structural features of this acid suggest potential applications in creating novel materials with enhanced properties, such as improved flexibility and resilience.
  • Synthesis Interest: The synthetic pathways to develop such compounds can be quite challenging, often requiring the application of cross-coupling reactions or functional group modifications to achieve the desired structure.

Overall, 5-[(3R)-dithiolan-3-yl]pentanoic acid exemplifies the intricate relationship between structure and function in organic molecules. Its unique characteristics hold promise for future research, particularly in the fields of medicinal chemistry and materials science.

Synonyms
lipoic acid
1200-22-2
(R)-lipoic acid
(R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
(R)-(+)-1,2-Dithiolane-3-pentanoic acid
(R)-alpha-Lipoic acid
(+)-alpha-Lipoic acid
1,2-Dithiolane-3-pentanoic acid, (3R)-
R-alpha-Lipoic acid
Thioctic acid d-form
D-Thioctic acid
R-(+)-Thioctic acid
Berlition
Thiogamma
Lipoec
Tiobec
(R)-1,2-Dithiolane-3-pentanoic acid
5-[(3R)-dithiolan-3-yl]pentanoic acid
R-Lipoic acid
(R)-(+)-lipoic acid
(R)-6,8-thioctic acid
(R)-1,2-Dithiolane-3-valeric Acid
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
(R)-(+)-Lipoate
alpha-(+)-Lipoic acid
1,2-Dithiolane-3R-pentanoic acid
(R)-(+)-a-Lipoic acid
MFCD01631142
(r)-(+)-alpha-lipoic acid
R-(+)-Lipoic acid
Lipoic acid (Standard)
R-LA
VLL71EBS9Z
(3R)-1,2-Dithiolane-3-pentanoic Acid
R-(+)-alpha-Lipoic acid
CHEMBL134342
Heparlipon
CHEBI:30314
C8H14O2S2
Thioderm
Tiobec Retard
R-Lipoate
Byodinoral 300
UNII-VLL71EBS9Z
Thioctanoic acid
(+)-thioctic acid
(R)-Thioctic Acid
R-alpha Lipoic acid
ARLIPOIC ACID
Thioctic acid, d form
(y)-alpha-Lipoic Acid
1,2-Dithiolane-3-pentanoic acid, (R)-
(+)-|A-Lipoic acid
(?)-alpha-Lipoic Acid
(R)-5-(1,2-Dithiolan-3-yl)pentanoicacid
SCHEMBL7924
(+)- alpha -Lipoic acid
ARLIPOIC ACID [INN]
Lopac0_001129
(R)-(+)-?-Lipoic Acid
(R)-(+)-|A-Lipoic Acid
GTPL4822
DTXSID20152651
D-THIOCTIC ACID [WHO-DD]
.ALPHA.-LIPOIC ACID, D-
GLXC-03742
HMS3263B19
THIOCTIC ACID D-FORM [MI]
Tox21_501129
BDBM50106731
HY-18733R
LMFA01130001
s3998
(+)-1,2-Dithiolane-3-valeric Acid
(R)-6,8-DITHIOOCTANOIC ACID
AKOS015892879
AC-8133
CCG-205204
CS-5076
DB00166
FL24904
LP01129
SDCCGSBI-0051097.P002
NCGC00094396-01
NCGC00094396-02
NCGC00094396-03
NCGC00094396-04
NCGC00094396-05
NCGC00094396-06
NCGC00261814-01
AC-11124
AS-11009
HY-18733
( inverted question mark)-alpha-Lipoic Acid
CS-0694941
EU-0101129
L0207
NS00068623
(R)-(+)--Lipoic acid;R-(+)-Thioctic acid
T 5625
(R)-(+)-alpha-Lipoic acid, analytical standard
EN300-7352963
SR-01000076163
(R)-(+)-1,2-Dithiolane-3-pentanoic acid, 97%
(R)-(+)-alpha-Lipoic acid, >=98.0% (HPLC)
SR-01000076163-1
Q27887203
Z1269228108
( inverted question mark)-1,2-Dithiolane-3-pentanoic acid
R-(+)-alpha-Lipoic acid; (R)-5-(1,2-Dithiolan-3-yl)pentanoic acid
(3R)-1,2-Dithiolane-3-pentanoic acid;(R)-(+)-1,2-Dithiolane-3-pentanoic acid;(+)-1,2-Dithiolane-3-valeric acid