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5-Aminosalicylic acid

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Name

5-Aminosalicylic acid

EINECS 201-919-1
CAS No. 89-57-6 Density 1.491 g/cm3
PSA 83.55000 LogP 1.25380
Solubility <0.1 g/100 mL at 21 °C in water Melting Point 275-280 °C (dec.)(lit.)
Formula C7H7NO3 Boiling Point 403.9 °C at 760 mmHg
Molecular Weight 153.137 Flash Point 198.1 °C
Transport Information N/A Appearance Off-white crystals
Safety 26-36-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 89-57-6 (5-Aminosalicylic acid) Hazard Symbols IrritantXi
Synonyms

Benzoic acid, 5-amino-2-hydroxy-;Asacol (TN);Benzoic acid, 5-amino-2-hydroxy-, hydrochloride;Pentasa (TN);Rowasa;Canasa;5-amino-2-hydroxy-benzoate;Mesalazine (JAN);5-amino-2-hydroxy-benzoic acid hydrochloride;Salofalk;Asacol;Mesalamine [USAN];Mesalazine;p-Aminosalicylsaeure [German];sodium 5-amino-2-hydroxy-benzoate;5-Amino Salicylic Acid;Mesalamine;Claversal;4-14-00-02058 (Beilstein Handbook Reference);5-amino-2-hydroxy-benzoic acid;Pentasa;Mesalazina [Spanish];Mesalamine (USP);Benzoic acid,5-amino-2-hydroxy-;Mesalazinum [Latin];Rowasa (TN);m-Aminosalicylic acid;Sodium 5-aminosalicylate;5-Aminosalicyclic Acid;Mesalazine5-Aminosalicylic acid;5-Aminosalicylic acid (Mesalazine);Malasazine;2-Hydroxy-5-aminobenzoic acid;Masalazine;

Article Data 80

5-Aminosalicylic acid Synthetic route

96-97-9

5-nitrosalicylic acid

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
Stage #1: 5-nitrosalicylic acid at 95 - 98℃; pH=2;
Stage #2: With sodium hydroxide at 85 - 95℃; for 2.5h; pH=11.5 - 12; Product distribution / selectivity;
91.6%
With G-CAT; R-CAT In water at 95 - 98℃; Product distribution / selectivity;91.6%
With hydrogenchloride; zinc In water for 4h; Reflux;88%
124-38-9

carbon dioxide

123-30-8

4-amino-phenol

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
Stage #1: 4-amino-phenol With sodium hydroxide at 130 - 150℃; Kolbe-Schmitt reaction;
Stage #2: carbon dioxide under 67506.8 Torr; Kolbe-Schmitt reaction; Autoclave; Heating;
Stage #3: With sulfuric acid pH=2 - 3; Kolbe-Schmitt reaction;
90.5%
Stage #1: carbon dioxide; 4-amino-phenol With sodium carbonate; sodium chloride at 200℃; under 7500.75 Torr; for 6h; Kolbe-Schmidt Synthesis; Autoclave;
Stage #2: With hydrogenchloride In water pH=1 - 6; Reagent/catalyst; Temperature; Pressure;
90%
In tetrahydrofuran for 8h; Quantum yield; UV-irradiation; Schlenk technique;34 %Spectr.
124-38-9

carbon dioxide

103-90-2

4-acetaminophenol

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 4-acetaminophenol With potassium hydroxide at 220℃; under 37503.8 Torr; for 1h;
Stage #2: With hydrogenchloride; water at 80℃; pH=4; Reagent/catalyst; Temperature; Pressure; Time;
90%

5-(4'-sulphophenylazo)salicylic acid sodium salt

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite In water for 0.00555556h; microwave irradiation;71%
21460-89-9

2-hydroxy-5-phenylazobenzoic acid methyl ester

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
With hydrogenchloride; tin
With phenylhydrazine at 100 - 120℃;
96-97-9

5-nitrosalicylic acid

A

89-57-6

5-Aminosalicylic Acid

B

51-59-2

N-Acetyl-5-aminosalicylic acid

Conditions
ConditionsYield
With tin; acetic acid dann verduennt man mit Wasser und faellt mit Schwefelwasserstoff;
With tin; acetic acid
51-78-5

p-aminophenol hydrochloride

15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
With potassium carbonate at 200℃; under 36775.4 Torr;
21460-89-9

2-hydroxy-5-phenylazobenzoic acid methyl ester

100-63-0

phenylhydrazine

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
at 100 - 120℃;
21460-90-2

2-hydroxy-5-phenylazo-benzoic acid ethyl ester

100-63-0

phenylhydrazine

89-57-6

5-Aminosalicylic Acid

Conditions
ConditionsYield
at 100 - 120℃;
100-63-0

phenylhydrazine

3147-53-3

2-hydroxy-5-phenylazo-benzoic acid

A

89-57-6

5-Aminosalicylic Acid

B

62-53-3

aniline

5-Aminosalicylic acid Consensus Reports

Reported in EPA TSCA Inventory.

5-Aminosalicylic acid Specification

1. Introduction of 5-Aminosalicylic acid
5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammatory bowel disease, such as ulcerative colitis and mild-to-moderate Crohn's disease. The IUPAC Name is 5-Amino-2-hydroxybenzoic acid. And the classification code is Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-Inflammatory Agents, Non-Steroidal; Anti-inflammatory; Antirheumatic Agents; Drug/Therapeutic Agent; Human Data; Peripheral Nervous System Agents; Sensory System Agents.

2. Properties of 5-Aminosalicylic acid
Melting Point: 275-280 °C  
Polar Surface Area: 38.77 ?2
Index of Refraction: 1.691
Molar Refractivity: 39.3 cm3
Molar Volume: 102.6 cm3
Surface Tension: 83.3 dyne/cm
Density: 1.491 g/cm3
Flash Point: 198.1 °C
Enthalpy of Vaporization: 69.09 kJ/mol
Boiling Point: 403.9 °C at 760 mmHg
Vapour Pressure: 3.01E-07 mmHg at 25°C

3. Toxicity of 5-Aminosalicylic acid

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 51mg/kg/5D-I (51mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Lancet. Vol. 1, Pg. 917, 1984.
man TDLo oral 321mg/kg/15D- (321mg/kg) SKIN AND APPENDAGES (SKIN): PHOTOSENSITIVITY: AFTER SYSTEMIC EXPOSURE American Journal of Gastroenterology. Vol. 94, Pg. 3386, 1999.
man TDLo oral 2057mg/kg/17W (2057mg/kg) BLOOD: AGRANULOCYTOSIS Lancet. Vol. 341, Pg. 1476, 1993.
man TDLo oral 6857mg/kg/17W (6857mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LIVER: "JAUNDICE, CHOLESTATIC"
Journal of Hepathology. Vol. 26, Pg. 425, 1997.
monkey LDLo oral 3gm/kg (3000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

KIDNEY, URETER, AND BLADDER: HEMATURIA
Oyo Yakuri. Pharmacometrics. Vol. 47, Pg. 509, 1994.
mouse LD50 intraperitoneal 469mg/kg (469mg/kg)   Archiv der Pharmazie Vol. 332, Pg. 321, 1999.
mouse LD50 oral 3370mg/kg (3370mg/kg)   Archiv der Pharmazie Vol. 332, Pg. 321, 1999.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   National Technical Information Service. Vol. OTS0570511,
rat LD50 intraperitoneal 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Oyo Yakuri. Pharmacometrics. Vol. 47, Pg. 505, 1994.
rat LD50 oral 2800mg/kg (2800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: OTHER CHANGES
National Technical Information Service. Vol. OTS0570511,
women TDLo oral 8mg/kg (8mg/kg) BEHAVIORAL: HEADACHE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Lancet. Vol. 1, Pg. 917, 1984.
women TDLo oral 80mg/kg/1D-I (80mg/kg) CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
American Journal of Gastroenterology. Vol. 93, Pg. 470, 1998.
women TDLo oral 5400mg/kg/90D (5400mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS American Journal of Gastroenterology. Vol. 92, Pg. 2302, 1997.
women TDLo oral 8760mg/kg/1Y- (8760mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Clinical Nephrology. Vol. 49, Pg. 265, 1998.
women TDLo oral 21800mg/kg/39 (21800mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BLOOD: EOSINOPHILIA
American Journal of Gastroenterology. Vol. 91, Pg. 1039, 1996.


4. Safety Information of 5-Aminosalicylic acid
Poison by intraperitoneal route. Moderately toxic by ingestion. Human systemic effects by ingestion: hypermotility, diarrhea, dermatitis, increased body temperature. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing. 
S24/25: Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: VO1400000
F: 8-10-23
Hazard Note: Irritant
HS Code: 29225000

5. Use of 5-Aminosalicylic acid
5-Aminosalicylic acid can be used in the active metabolite of Sulfasalazine. It is administered orally or as a suppository. When administered orally, it is usually in a time-released or extended released form so it will work for an extended period of time.

6. Side Effects of 5-Aminosalicylic Acid
When taken as a suppository, possible side effects are usually limited to GI system, including but not limited to: Diarrhea; Cramping; Increased Flatulence.

7. Other details of 5-Aminosalicylic acid
Chemical Stability: Air sensitive. Light sensitive.
Conditions to Avoid: Incompatible materials, light, dust generation, exposure to air, temperatures above 30°C.
Incompatibilities with Other Materials Strong oxidizing agents, acids, acid chlorides, iron, acid anhydrides, chloroformates.
Hazardous Decomposition Products Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization Will not occur.
First Aid Measures:
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Ingestion: Get medical aid. Wash mouth out with water.
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician: Treat symptomatically and supportively.
Handling and Storage:
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Do not store in direct sunlight. Store in a tightly closed container. Store at around 20°C. Store under an inert atmosphere.

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