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Hexadecanedioic acid

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Identification
Molecular formula
C16H30O4
CAS number
505-54-4
IUPAC name
hexadecanedioic acid
State
State

At room temperature, hexadecanedioic acid is a solid.

Melting point (Celsius)
128.10
Melting point (Kelvin)
401.30
Boiling point (Celsius)
408.40
Boiling point (Kelvin)
681.60
General information
Molecular weight
286.41g/mol
Molar mass
284.4440g/mol
Density
1.0580g/cm3
Appearence

Hexadecanedioic acid, commonly known as thapsic acid, typically appears as a white crystalline solid. It is a saturated aliphatic dicarboxylic acid and is insoluble in water but soluble in many organic solvents.

Comment on solubility

Solubility of Hexadecanedioic Acid

Hexadecanedioic acid, known chemically as 1,16-hexadecanedioic acid or C16H30O4, exemplifies interesting solubility characteristics due to its unique molecular structure.

This diacid exhibits different solubility behaviors in various solvents:

  • Water: Hexadecanedioic acid is generally considered insoluble in water. This low solubility is primarily attributed to its long hydrocarbon chain, which repels polar water molecules.
  • Organic Solvents: In contrast, this compound shows better solubility in non-polar organic solvents, such as hexane and ether. The non-polar nature of these solvents aligns well with the hydrophobic characteristics of the hydrocarbon chain.
  • Temperature Influence: Solubility can also increase with temperature; thus, at elevated temperatures, hexadecanedioic acid may dissolve better in various organic solvents due to increased molecular motion.

As with many carboxylic acids, structural characteristics significantly impact solubility:

  • The length of the hydrocarbon chain
  • The presence of functional groups

To summarize, while hexadecanedioic acid is largely insoluble in water due to its long carbon chain, it is more soluble in non-polar organic environments, highlighting the classic principle of "like dissolves like". This characteristic enhances its applicability in various chemical processes.

Interesting facts

Interesting Facts about Hexadecanedioic Acid

Hexadecanedioic acid, also known as palmitic acid, is a fascinating dicarboxylic acid that belongs to the class of fatty acids. It plays a significant role not only in biochemistry but also has practical applications in various industries. Here are some intriguing aspects of this compound:

  • Biological Importance: This compound is a key intermediate in lipid metabolism in human cells and is involved in the synthesis of long-chain fatty acids.
  • Source: Naturally occurring in several natural oils, including palm oil, hexadecanedioic acid is derived from the processing of fats and oils.
  • Industrial Uses: Hexadecanedioic acid is utilized in the production of polyamides and polyurethanes, making it valuable in manufacturing fibers and coatings.
  • Health Implications: While it has biological significance, excessive consumption of fatty acids like hexadecanedioic acid is linked to health issues, including obesity and cardiovascular diseases.
  • Research Applications: Scientists study hexadecanedioic acid to understand its role in metabolic disorders and as a potential biomarker for certain diseases.

In the words of chemist and biochemist John W. Wiley, “The understanding of fatty acids like hexadecanedioic acid is essential for comprehending the larger picture of human health and disease.” This underscores the important balance required in consumption and study, highlighting its significance in both medicine and industry.

In summary, hexadecanedioic acid combines biological necessity with a variety of practical applications, making it a noteworthy compound in the realm of chemistry.

Synonyms
HEXADECANEDIOIC ACID
Thapsic acid
1,16-Hexadecanedioic acid
1,14-Tetradecanedicarboxylic acid
Thaspic acid
Hexadecane-1,16-dioic acid
Thapsate
SVZ90045Y2
EINECS 208-013-5
NSC 15164
NSC-15164
n-Tetradecane-.omega.,.omega.'-dicarboxylic acid
1,14-Tetradecanedicarboxylate
UNII-SVZ90045Y2
n-Tetradecane-omega,omega'-dicarboxylic acid
DTXSID2060129
CHEBI:73722
DTXCID9040847
alpha,Omega-tetradecanedicarboxylic acid
208-013-5
qqhjdpromqrdla-uhfffaoysa-n
505-54-4
MFCD00002746
NSC15164
1,16-hexadecanedioate
HEXADECANEDIOICACID
Hexadecandioic acid
1,14-tetradecane dicarboxylic acid
a,w-Tetradecanedicarboxylate
Hexadecanedioic acid, 96%
SCHEMBL36069
MEGxp0_000578
a,w-Tetradecanedicarboxylic acid
CHEMBL4519590
n-Tetradecane-w,w'-dicarboxylate
BCP25937
LMFA01170022
n-Tetradecane-w,w'-dicarboxylic acid
s6147
AKOS015839798
CS-W018947
HY-W018161
AC-32524
AS-11659
FH140370
SY047592
Thapsic acid;Hexadecanedioate;Palmitic acid
DB-051793
H0293
NS00015590
Hexadecanedioic acid, purum, >=98.0% (GC)
C19615
Q27144068
RF8