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Mevalonic acid

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Identification
Molecular formula
C6H12O4
CAS number
1115-20-4
IUPAC name
3-hydroxy-3-methyl-pentanedioic acid
State
State

At room temperature, Mevalonic acid is typically found as a solid in its pure form. Due to its crystallization, it may appear powdery or as fine crystalline granules.

Melting point (Celsius)
58.00
Melting point (Kelvin)
331.15
Boiling point (Celsius)
200.00
Boiling point (Kelvin)
473.15
General information
Molecular weight
148.16g/mol
Molar mass
148.1570g/mol
Density
1.2500g/cm3
Appearence

Mevalonic acid is a white or slightly off-white crystalline solid. It may appear as powdery granules or crystalline powder depending on its form of purification. It is hygroscopic and can absorb moisture from the air.

Comment on solubility

Solubility of 3-Hydroxy-3-Methyl-Pentanedioic Acid

3-Hydroxy-3-methyl-pentanedioic acid, with the chemical formula C6H12O4, demonstrates notable solubility characteristics in various solvents, primarily due to its functional groups. This compound contains hydroxyl (-OH) and carboxylic acid (-COOH) groups, which play a crucial role in its solubility.

Solubility in Water

In aqueous solutions, 3-hydroxy-3-methyl-pentanedioic acid exhibits moderate to high solubility. The presence of polar hydroxyl and carboxyl groups enhances interactions with water molecules, allowing for effective dissolution. Key points include:

  • Hydrogen Bonding: The hydroxyl and carboxylic acid groups can form hydrogen bonds with water, facilitating solubility.
  • pH Influence: At different pH levels, the ionization of the carboxylic group can further increase solubility, especially in alkaline conditions.

Solubility in Organic Solvents

Regarding organic solvents, 3-hydroxy-3-methyl-pentanedioic acid shows limited solubility in non-polar solvents like hexane or toluene due to its polar nature. However, it may dissolve more readily in polar organic solvents such as:

  • Methanol
  • Ethanol
  • Dimethyl sulfoxide (DMSO)

Overall, the solubility of 3-hydroxy-3-methyl-pentanedioic acid is heavily influenced by its chemical structure, creating distinct profiles in both polar and non-polar environments. Understanding these properties is crucial for applications in chemistry and biochemistry.

Interesting facts

Interesting Facts about 3-Hydroxy-3-methyl-pentanedioic Acid

3-Hydroxy-3-methyl-pentanedioic acid, commonly known as mesaconic acid, is a fascinating compound with several noteworthy characteristics:

  • Metabolic Significance: This compound plays a crucial role in various biochemical pathways, particularly in the metabolism of amino acids and fatty acids.
  • Natural Occurrence: It is found in some natural sources, which hints at its importance in biological processes. For instance, mesaconic acid can be found in certain fungi and plants.
  • Synthesis Potential: The compound can be synthesized through various chemical reactions, making it an interesting subject for synthetic organic chemistry. The possibility of creating derivatives opens doors for diverse applications.
  • Applications in Medicine: Mesaconic acid and its derivatives are being explored for their medicinal properties, including anti-inflammatory and antibacterial activities.
  • Research Opportunities: Due to its structural features, 3-hydroxy-3-methyl-pentanedioic acid presents numerous opportunities for research in fields such as medicinal chemistry and biochemistry.

In summary, 3-hydroxy-3-methyl-pentanedioic acid is not just a simple compound; its roles in metabolism, potential applications in medicine, and opportunities for synthetic exploration make it a subject of great interest within the scientific community. As one research article stated, "the intricate nature of mesaconic acid reveals the complexity of biochemical interactions." This compound indeed exemplifies how chemistry bridges the gap between simple molecules and their vast implications in life sciences.

Synonyms
MEGLUTOL
503-49-1
3-Hydroxy-3-methylglutaric acid
3-Hydroxy-3-methylpentanedioic acid
Dicrotalic acid
Lipoglutaren
Pentanedioic acid, 3-hydroxy-3-methyl-
Medroglutaric acid
beta-Hydroxy-beta-methylglutaric acid
Meglutolum
3-hydroxy-3-methyl-glutaric acid
HMGA
CB 337
Meglutol [USAN:INN]
Meglutolum [INN-Latin]
CB-337
3-Hydroxy-3-methylglutarate
Glutaric acid, 3-hydroxy-3-methyl-
EINECS 207-971-1
CLA99KCD53
(S)-Meglutol
NSC 361411
NSC-361411
BRN 1769194
3-Hydorxy-3-methylglutaric acid
CHEBI:16831
beta-Hydroxy-beta-Methylglutarate
3-Hydroxymethylglutarate
MEGLUTOL [USAN]
MEGLUTOL [INN]
MEGLUTOL [MI]
MEGLUTOL [MART.]
CHEMBL50444
3-Hydroxy-3-methylpentane-1,5-dioic Acid
HMG
DTXSID90198304
4-03-00-01166 (Beilstein Handbook Reference)
(S)-3-Hydroxy-3-methylglutaric acid
Meglutolum (INN-Latin)
MEGLUTOL (MART.)
Dicrotalic acid;3-Hydroxy-3-methylglutaric acid
(S)-3-Hydroxy-3-methylglutarate
MFCD00002712
UNII-CLA99KCD53
meglutolo
Dicrotalate
Menotrophin?
Meglutol (USAN/INN)
bmse000335
b-Hydroxy-b-methylglutarate
3-Methyl-3-hydroxyglutarate
SCHEMBL28443
MLS001066390
b-Hydroxy-b-methylglutaric acid
GTPL2960
MEGxp0_001907
3 Hydroxy 3 methylglutaric Acid
3-Methyl-3-hydroxyglutaric acid
ACon1_000502
beta Hydroxy beta Methylglutarate
C10AX05
DTXCID80120795
Acid, 3-Hydroxy-3-methylglutaric
HMS3264B09
Pharmakon1600-01506183
HY-B1189
3 Hydroxy 3 methylpentanedioic Acid
3-HYDROXY-3-METHYLPENTANE-1
BDBM50160720
NSC361411
NSC760412
Acid, 3-Hydroxy-3-methylpentanedioic
AKOS000280741
CCG-213633
CS-4798
DB04377
FH57974
NSC-760412
NCGC00169018-01
AS-63885
GLUTARIC ACID, BETA-HYDROXY METHYL
SMR000471861
3-Hydroxy-3-methylglutaric acid, >=95%
DB-071173
H0436
NS00014740
(3R)-3,5,5-trihydroxy-3-methylpentanoic acid
C03761
D04897
F17049
AB00698060_04
Dicrotalic acid; 3-Hydroxy-3-methylglutaric acid
Q524670
SR-01000763754
3-Hydroxy-3-methylpentane-1 pound not5-dioic Acid
SR-01000763754-2
A90FC159-16ED-49CA-9A7F-D90B0A5B3EBC
BRD-K00495673-001-05-2
3-Hydroxy-3-methylglutaric acid, purum, >=95.0% (GC)
3-Hydroxy-3-methyl-pentanedioic acid;3-Hydroxy-3-methyl-glutaric acid
207-971-1
XII