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2-(2-Hydroxyphenyl)acetic acid

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Identification
Molecular formula
C8H8O3
CAS number
614-75-5
IUPAC name
2-(2-hydroxyphenyl)acetic acid
State
State

At room temperature, 2-(2-Hydroxyphenyl)acetic acid is a solid.

Melting point (Celsius)
154.00
Melting point (Kelvin)
427.20
Boiling point (Celsius)
350.60
Boiling point (Kelvin)
623.80
General information
Molecular weight
152.15g/mol
Molar mass
152.1470g/mol
Density
1.3010g/cm3
Appearence

2-(2-Hydroxyphenyl)acetic acid is a white to off-white crystalline solid.

Comment on solubility

Solubility of 2-(2-hydroxyphenyl)acetic acid

2-(2-hydroxyphenyl)acetic acid, often referred to as a metabolic derivative of salicylic acid, exhibits some interesting solubility characteristics:

  • Water Solubility: This compound generally has moderate water solubility. Its ability to dissolve in water can be attributed to the presence of the hydroxyl group, which enhances intermolecular hydrogen bonding.
  • Solvent Preferences: 2-(2-hydroxyphenyl)acetic acid is more soluble in organic solvents compared to water. Common organic solvents in which it can dissolve include:
    • Ethyl acetate
    • Ethanol
    • Dichloromethane
  • pH Influence: The solubility may be influenced by the pH of the solution. In more acidic or alkaline conditions, the ionization of the carboxylic acid group can enhance solubility in aqueous environments.

As a general principle, it can be stated that the solubility of organic compounds is heavily influenced by their functional groups, and the presence of hydroxyl and carboxylic acid functional groups in 2-(2-hydroxyphenyl)acetic acid aids its solubility profile. Thus, understanding these factors is crucial when considering the application of this compound in various chemical and pharmaceutical contexts.

Interesting facts

Interesting Facts about 2-(2-Hydroxyphenyl)acetic Acid

2-(2-Hydroxyphenyl)acetic acid, often referred to in scientific literature as salicylic acid derivate, is an intriguing organic compound with various applications and properties that attract the attention of chemists and biologists alike. Here are some insightful aspects of this compound:

  • Biological Importance: This compound holds significant relevance in the pharmaceutical industry due to its role as a precursor to various medications, particularly anti-inflammatory drugs.
  • Mechanism of Action: Its structural similarity to salicylic acid allows it to function as a non-steroidal anti-inflammatory drug (NSAID), acting by inhibiting cyclooxygenase (COX) enzymes, effectively reducing pain and inflammation.
  • Versatile Applications: Beyond its medicinal properties, 2-(2-hydroxyphenyl)acetic acid is studied for its potential use in:
    • Cosmetics as an active ingredient for skin care products.
    • Agriculture as a plant growth regulator, enhancing resistance to various stresses.
    • In various synthetic pathways in organic chemistry.
  • Historical Context: The discovery of derivatives of this compound can be traced back to early herbal medicine practices, showcasing how traditional remedies have influenced the development of modern pharmaceuticals.
  • Synthesis Routes: Chemists are continually exploring innovative methods to synthesize this compound with improved efficiency, including approaches like green chemistry principles, aiming to reduce environmental impact.

In summary, 2-(2-hydroxyphenyl)acetic acid exemplifies the intersection of chemistry and biology, reflecting how small molecular changes can lead to significant shifts in biological activity and potential applications. It serves as a reminder of the importance of understanding the intricate relationships between molecular structure and function in the advancement of science and medicine.

Synonyms
2-Hydroxyphenylacetic acid
614-75-5
2-(2-hydroxyphenyl)acetic acid
(2-Hydroxyphenyl)acetic acid
2-Hydroxybenzeneacetic acid
Benzeneacetic acid, 2-hydroxy-
O-HYDROXYPHENYLACETIC ACID
Acetic acid, (o-hydroxyphenyl)-
(o-Hydroxyphenyl)acetic acid
ortho-Hydroxyphenylacetic acid
MFCD00004323
Hydroxyphenylacetic acid
o-Hydroxy phenylacetic acid
2-HPAA
UK3R9Q59AV
CHEMBL240714
CHEBI:28478
NSC-62000
(2-HYDROXYPHENYL)-ACETIC ACID
2-Hydroxyphenylaceticacid
UNII-UK3R9Q59AV
2-hydroxy phenylacetic acid
Hydroxyphenylacetate
OHP
EINECS 210-393-2
NSC 62000
2-Hydroxybenzeneacetate
(o-hydroxyphenyl)-Acetate
bmse000715
2'-hydroxyphenylacetic acid
2-hydroxy-phenylacetic acid
2-hydroxy-benzeneacetic acid
SCHEMBL72309
2-(Hydroxyphenyl)acetic acid
(o-hydroxyphenyl)-Acetic acid
Acetic acid, 2-hydroxyphenyl-
(2-hydroxy-phenyl)-acetic acid
DTXSID1060633
BDBM16426
NSC62000
HYDROXYPHENYLACETIC ACID, O-
s6154
STL301502
AKOS004909470
AC-2695
CS-W016306
FH24476
FS-2587
HY-W015590
BP-13099
PD099467
DB-013545
H0340
NS00014664
EN300-50865
C05852
2-Hydroxyphenylacetic acid, ReagentPlus(R), 99%
Q27103728
7C10F5F6-7BF6-48EE-85EE-22D3FA4D62B1
Z608061328
2-Hydroxyphenylacetic acid, Vetec(TM) reagent grade, 98%
(o-Hydroxyphenyl)acetic acid;2-HPAA;2-Hydroxybenzeneacetic acid
InChI=1/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11