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| CAS No.: | 89-57-6 |
|---|---|
| Name: | 5-Aminosalicylic acid |
| Article Data: | 80 |
| Molecular Structure: | |
|
|
|
| Formula: | C7H7NO3 |
| Molecular Weight: | 153.137 |
| 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; |
| EINECS: | 201-919-1 |
| Density: | 1.491 g/cm3 |
| Melting Point: | 275-280 °C (dec.)(lit.) |
| Boiling Point: | 403.9 °C at 760 mmHg |
| Flash Point: | 198.1 °C |
| Solubility: | <0.1 g/100 mL at 21 °C in water |
| Appearance: | Off-white crystals |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36-24/25 |
| PSA: | 83.55000 |
| LogP: | 1.25380 |
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| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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. |
| Conditions | Yield |
|---|---|
| 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% |
- 89-57-6
5-Aminosalicylic Acid
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride; tin | |
| With phenylhydrazine at 100 - 120℃; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| at 100 - 120℃; |
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Consensus Reports
Reported in EPA TSCA Inventory.
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: 
Xi
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.