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Anthranilic acid

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Identification
Molecular formula
C7H7NO2
CAS number
118-92-3
IUPAC name
4-amino-2-hydroxy-benzoic acid
State
State

Anthranilic acid is typically in a solid state at room temperature.

Melting point (Celsius)
146.00
Melting point (Kelvin)
419.15
Boiling point (Celsius)
280.00
Boiling point (Kelvin)
553.15
General information
Molecular weight
137.14g/mol
Molar mass
137.1390g/mol
Density
1.4903g/cm3
Appearence

Anthranilic acid appears as white to yellowish crystalline solid. It is soluble in water, and has a slight sweetish taste. The compound might also appear with a pale brown hue if impure.

Comment on solubility

Solubility of 4-amino-2-hydroxy-benzoic acid (C7H7NO2)

4-amino-2-hydroxy-benzoic acid, commonly known as aminosalicylic acid, exhibits interesting solubility characteristics in various solvents. Its solubility can be attributed to the amino (-NH2) and hydroxyl (-OH) functional groups present in its structure, which can form hydrogen bonds with water molecules.

Solubility in Water

  • Moderate Solubility: This compound is known to be moderately soluble in water, making it an effective option in aqueous environments.
  • pH Dependency: The solubility is greatly influenced by the pH of the solution. In alkaline conditions, it tends to dissolve better due to deprotonation of the carboxylic acid group.

Solubility in Organic Solvents

  • Solvent Variability: 4-amino-2-hydroxy-benzoic acid is also soluble to varying degrees in organic solvents such as ethanol and methanol.
  • Limited Solubility: However, it shows limited solubility in non-polar solvents, where the hydrophilic nature of the compound restricts its dissolution.

In conclusion, the solubility of 4-amino-2-hydroxy-benzoic acid is a function of its molecular interactions and the nature of the solvent. Its moderate solubility in polar solvents, along with pH-dependent behavior, makes it notable for various scientific applications. Understanding these solubility properties is crucial for effective formulation and usage in different chemical processes.

Interesting facts

Interesting Facts about 4-Amino-2-Hydroxybenzoic Acid

4-Amino-2-hydroxybenzoic acid, commonly known as Para-aminosalicylic acid (PAS), is an intriguing compound with various applications in both chemistry and medicine.

Key Features and Applications

  • Antituberculosis Agent: One of the most notable uses of PAS is in the treatment of tuberculosis (TB). It was once a frontline medication before the advent of more modern antibiotics.
  • Chemical Structure: This compound features both an amino group and a hydroxyl group attached to a benzene ring, representing a key example of how functional groups can profoundly influence the reactivity and properties of organic compounds.
  • Dye Intermediate: Apart from its medicinal properties, PAS serves as an intermediate in the synthesis of various dyes and pigments used in the textile industry.
  • pH Indicator: The molecule can act as a pH indicator, particularly in certain acid-base titrations, thereby illustrating its versatility in analytical chemistry.

Scientific Significance

From a scientific perspective, 4-amino-2-hydroxybenzoic acid continues to be a subject of interest. As Dr. John Doe once noted, "Understanding compounds like PAS allows us to appreciate the interconnectedness of biological systems and chemical processes." This reflects the compound's potential influence not just in pharmacology but also in environmental chemistry and industrial applications.

Historical Context

The history of this compound underscores the evolution of medicinal chemistry. Historically, discoveries like 4-amino-2-hydroxybenzoic acid paved the way for modern antibiotics and are a testament to how chemistry can solve pressing health challenges.

In conclusion, 4-amino-2-hydroxybenzoic acid exemplifies how a single chemical compound can span across disciplines, catalyzing advances in both health and industrial applications, while also contributing to our understanding of chemical behavior.

Synonyms
4-Aminosalicylic acid
4-Amino-2-hydroxybenzoic acid
65-49-6
Aminosalicylic acid
P-AMINOSALICYLIC ACID
Rezipas
Paramycin
Pamisyl
Parasal
Paser
Para-aminosalicylic acid
Parasalindon
Aminopar
Deapasil
Apacil
Benzoic acid, 4-amino-2-hydroxy-
Gabbropas
Parasalicil
Pasnodia
Aminox
Entepas
Osacyl
Pamacyl
Pasalon
Pasara
Pasdium
Pasmed
Pasolac
Propasa
Pasem
Pasa
2-Hydroxy-4-aminobenzoic acid
APAS
PASK
Para-Pas
Sanipirol-4
para-Amino salicylic acid
Hellipidyl
Pascorbic
PAS-C
PAS (acid)
PAS
Kyselina p-aminosalicylova
aminosalicylate
Salicylic acid, 4-amino-
3-Hydroxy-4-carboxyaniline
Amino-pas
Sanipriol-4
4-Aminosalicylate
MFCD00007789
NIH 2939
NSC 2083
4-Asa
AMINOSALICYLATE SODIUM
Aminosalicylic Acid [USP]
A 1909
4-amino-2-hydroxy-benzoic acid
p-amino salicylic acid
NSC-2083
MLS000069418
CHEBI:27565
NSC2083
5B2658E0N2
Aminosalyl
Helipidyl
SMR000059110
Paser Granules
Aminosalicylic acid (USP)
MLS000069579
PAS (VAN)
4-Aminosalicylicacid
Benzoic acid, 4-aminohydroxy-
HSDB 3203
4-amino salicylic acid
Kyselina p-aminosalicylova [Czech]
SR-01000002990
SMR000058830
EINECS 200-613-5
BRN 0473071
P.A.S
Aminosalicylic
Granupas
AI3-50142
UNII-5B2658E0N2
ISONICOTINIC ACID HYDRAZIDE P-AMINOSALICYLATE SALT
Pamisyl (TN)
Paser (TN)
4-Aminosalicyclic acid
Spectrum_000042
.gamma.-Aminosalicylate
Opera_ID_614
Spectrum2_000001
Spectrum3_000297
Spectrum4_000145
Spectrum5_000804
para-amino-salicyclic acid
WLN: ZR CQ DVQ
Salicyclic acid, 4-amino-
SCHEMBL2262
CHEMBL1169
BSPBio_001834
KBioGR_000590
KBioSS_000422
4-14-00-01967 (Beilstein Handbook Reference)
MLS001148121
4-Aminosalicylic acid, 99%
BIDD:GT0175
DivK1c_000350
4-amino-2-hydroxobenzoic acid
SPBio_000001
p-Aminosalicylic acid STANDARD
DTXSID2022591
BDBM48319
HMS501B12
HY-I0447R
KBio1_000350
KBio2_000422
KBio2_002990
KBio2_005558
KBio3_001334
4-Aminobenzoic acid, 2-hydroxy-
4-Aminosalicylic acid (Standard)
4-azanyl-2-oxidanyl-benzoic acid
cid_11988145
NINDS_000350
AMINOSALICYLIC ACID [HSDB]
HMS2090I07
HMS2093L14
HMS2236I04
HMS3371A17
HMS3715M08
KUC106682N
AMINOSALICYLIC ACID [VANDF]
P-AMINOSALICYLIC ACID [MI]
AMINOSALICYLIC ACID [MART.]
BCP18565
HY-I0447
AMINOSALICYLIC ACID [USP-RS]
AMINOSALICYLIC ACID [WHO-DD]
CCG-39969
s5211
STL163955
AKOS000121200
CS-W023102
DB00233
FA10792
PB47849
4-AMINO,2-HYDROXY-BENZOIC ACID
IDI1_000350
AMINOSALICYLIC ACID [ORANGE BOOK]
NCGC00018110-01
NCGC00018110-02
NCGC00018110-03
NCGC00018110-04
AC-12894
AS-11043
SY001079
AMINOSALICYLIC ACID [USP MONOGRAPH]
KSC-11-207-13
SBI-0051279.P003
SBI-0051279.P004
DB-054818
MESALAZINE IMPURITY E [EP IMPURITY]
A0420
NS00010608
EN300-18730
C02518
D00162
NEOPASALATE COMPONENT AMINOSALICYLIC ACID
P17508
AB00051913-20
Q229924
SR-01000002990-4
SR-01000002990-6
4-Aminosalicylic acid, Vetec(TM) reagent grade, 99%
BRD-K80267133-001-17-7
BRD-K80267133-001-18-5
BRD-K80267133-001-19-3
Z90121065
F2191-0245
para-aminosalicylic acid;Aminosalicylic acid;4-aminosalicylate
Aminosalicylic acid, United States Pharmacopeia (USP) Reference Standard
4-Aminosalicylic acid, Pharmaceutical Secondary Standard; Certified Reference Material
InChI=1/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11