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Levulinic acid

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Identification
Molecular formula
C5H8O3
CAS number
123-76-2
IUPAC name
4-oxopentanoic acid
State
State
Levulinic acid at room temperature is solid in its pure form but can also appear as a viscous liquid if there are impurities or at slightly elevated temperatures.
Melting point (Celsius)
33.00
Melting point (Kelvin)
306.15
Boiling point (Celsius)
245.00
Boiling point (Kelvin)
518.15
General information
Molecular weight
116.12g/mol
Molar mass
116.1150g/mol
Density
1.1659g/cm3
Appearence

Levulinic acid is a white crystalline powder that can also appear as a colorless to pale yellow liquid under certain conditions. It is slightly soluble in water and has a distinctive light odor.

Comment on solubility

Solubility of 4-Oxopentanoic Acid

4-Oxopentanoic acid, with the chemical formula C5H8O3, displays intriguing solubility characteristics that are worth noting:

  • Water Solubility: 4-Oxopentanoic acid is moderately soluble in water. This is due to the presence of both a carboxylic acid group and a carbonyl group, enabling hydrogen bonding with water molecules.
  • Organic Solvents: It is also soluble in a variety of organic solvents, such as alcohols and ethers, showing a greater affinity for organic rather than aqueous environments.
  • pH Effects: The solubility can vary with pH; in more basic conditions, the carboxylic acid group may deprotonate, increasing its solubility in water.

It's often noted that "the solubility of a compound can significantly affect its reactivity and applications in chemical processes." Thus, understanding solubility not only facilitates its use in synthetic pathways but also enhances its functionality in various chemical applications.

Overall, the solubility behavior of 4-oxopentanoic acid underscores its versatile role in both aqueous and organic environments, pivotal for a range of biochemical processes and reactions.

Interesting facts

Interesting Facts About 4-Oxopentanoic Acid

4-Oxopentanoic acid, also known as 2-oxo-4-pentenoic acid, is a fascinating compound that plays a significant role in various fields of chemistry and biochemistry. Here are some intriguing facts about this compound:

  • Key Metabolic Intermediate: 4-Oxopentanoic acid acts as an important intermediate in metabolic pathways, particularly in the synthesis of amino acids and other organic compounds.
  • Applications in Synthesis: This compound is utilized in the synthesis of various pharmaceuticals and agrochemicals, making it a valuable building block in organic chemistry.
  • Versatile Reactivity: The presence of a carbonyl group allows for a range of chemical reactions, including Michael addition and aldol condensation, which are fundamental in organic synthesis.
  • Biological Relevance: Compounds that are structurally related to 4-oxopentanoic acid have been studied for their potential roles in metabolic disorders, hinting at a connection to human health and disease.
  • Potential in Research: Its unique structure makes it an intriguing subject for research, especially in exploring new methodologies for chemical synthesis and drug design.

As with many organic acids, the study of 4-oxopentanoic acid sheds light on the complexity of chemical reactions and the intricate nature of biological systems. Its dual nature of being both a synthetic building block and a metabolic intermediate highlights the interconnectedness of chemistry and life.

With ongoing research, new applications and insights into compounds like 4-oxopentanoic acid continue to emerge, emphasizing the ever-evolving nature of the field of chemistry.

Synonyms
LEVULINIC ACID
4-Oxopentanoic acid
Laevulinic acid
Pentanoic acid, 4-oxo-
4-Oxovaleric acid
3-Acetylpropionic acid
4-Ketovaleric acid
gamma-Ketovaleric acid
Acetopropionic acid
Laevulic acid
Valeric acid, 4-oxo-
beta-Acetylpropionic acid
USAF CZ-1
Propionic acid, 3-acetyl-
4-Oxopentansaeure
Acidum laevulinicum
FEMA No. 2627
3-Acetylpropionsaeure
3-Ketobutane-1-carboxylic acid
.beta.-Acetylpropionic acid
NSC 3716
Pentanoic acid, 4-oxo
g-Ketovalerate
.gamma.-Ketovaleric acid
UNII-RYX5QG61EI
b-Acetylpropionate
NSC-3716
EINECS 204-649-2
g-Ketovaleric acid
Acetylpropionic acid
BRN 0506796
b-Acetylpropionic acid
DTXSID8021648
CHEBI:45630
AI3-03377
Valeric acid, 4-oxo-(levulinic acid)
LEVULINIC ACID [MI]
LEVULINIC ACID [FCC]
LEVULINIC ACID [FHFI]
DTXCID701648
4-03-00-01560 (Beilstein Handbook Reference)
CALCIUM LEVULATE
Levulinic acid, calcium salt
Diasporal
4Oxopentansaeure
4Oxovaleric acid
4Ketovaleric acid
4oxopentanoic acid
3Acetylpropionsaeure
gammaOxovaleric acid
magnesium laevulinate
gammaKetovaleric acid
4-ketopentanoic acid
Valeric acid, 4oxo
3Acetylpropionic acid
gammaOxopentanoic acid
Pentanoic acid, 4oxo
betaAcetylpropionic acid
Propionic acid, 3acetyl
3Ketobutane1carboxylic acid
3-Ketobutane-1-carboxylate
LEVULINIC ACID [INCI]
4-Oxopentanoic acid, 4-ketovaleric acid
PENTANOIC ACID,4-OXO MFC5 H8 O3
inchi=1/c5h8o3/c1-4(6)2-3-5(7)8/h2-3h2,1h3,(h,7,8
jooxcmjarbkpkm-uhfffaoysa-n
123-76-2
Levulic acid
LEVA
Levulinsaeure
4-oxo-pentanoic acid
RYX5QG61EI
NSC3716
laevulinate
levulate
levulinate
4-ketovalerate
4-oxovalerate
gamma-ketovalerate
3-acetylpropionate
beta-acetylpropionate
CAS-123-76-2
MFCD00002796
Laevulinsaeure
levulenic acid
4-Oxopentanoicacid
Levulinic acid, 98%
Levulinic acid (Standard)
WLN: QV2V1
SCHEMBL20868
Levulinic acid, >=97%, FG
CHEMBL1235931
BDBM82191
HY-Y0839R
Levulinic acid, analytical standard
GYB18552
HY-Y0839
Levulinic acid, natural, 99%, FG
Tox21_201483
Tox21_302729
BBL027404
GEO-04255
LMFA01060006
s6207
STK802043
AKOS000119608
DB02239
FL37560
PB48051
NCGC00249052-01
NCGC00256314-01
NCGC00259034-01
4-Oxovaleric acid;3-Acetylpropionic acid
VS-08535
DB-003710
PENTANOIC ACID,4-OXO MFC5 H8 O3
CS-0015813
L0042
NS00012787
EN300-20219
D70802
SBI-0633496.0002
Q903322
SR-01000944838
SR-01000944838-1
F2191-0253
Z104477318
Laevulinic acid; 4-Oxopentanoic acid; 4-Oxovaleric acid; gamma-Ketovaleric acid; Levulic acid; 4-Oxo-pentanoic acid