HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Hydroxyanthranilic Acid
2-AMINO-3-HYDROXYBENZOIC ACID · 3-HYDROXY-ANTHRANILATE · 3-HYDROXYANTHRANILLIC ACID · 3-Ohaa · NSC 522891 · JACS-548-93-6 · 3-oxyanthranilicacid · 3-Oxyanthranilic acid
Identifiers & Physical Properties
| CAS No. | 548-93-6 |
|---|---|
| Molecular formula | C7H7NO3 |
| Average molar mass | 153.14 g/mol |
| Monoisotopic mass | 153.04259308 g/mol |
| SMILES | Nc1c(O)cccc1C(=O)O |
| InChIKey | WJXSWCUQABXPFS-UHFFFAOYSA-N |
| PubChem CID | 86 |
| ChEMBL | CHEMBL445304 |
| ChEBI | CHEBI:15793 |
| EC No. | 208-962-5 |
| DTXSID | DTXSID40203290 |
Chemical & Physical Properties
| XLogP | 0.9 |
|---|---|
| Topological polar surface area | 83.6 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 1 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 160 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Color/Form | LEAFLETS IN WATER |
| Solubility | SLIGHTLY SOL IN WATER, SOL IN HOT WATER, ALCOHOL, ETHERSOL IN CHLOROFORMDMSO (Slightly), Methanol (Slightly, Heated) |
| Melting point | 164 °C240 °C (dec.)(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 131.2 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]131.3 Ų [M+H]+ |
| Boiling point | 276.03°C (rough estimate) |
| Density | 1.3585 (rough estimate) |
| Refractive index | 1.5500 (estimate) |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Physical state | Liquid or Low Melting Solid |
| pKa (acidity coefficient) | pK1: 2.5(+1)pK2: 5.192(0)pK3: 10.118(OH) (25°C) |
| Color | Clear colorless to white to yellow to orange |
| Major applications | peptide synthesis |
| InChI | InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) |
| InChIKey | WJXSWCUQABXPFS-UHFFFAOYSA-N |
| SMILES | C(O)(=O)C1=CC=CC(O)=C1N |
| CAS DataBase Reference | 548-93-6(CAS DataBase Reference) |
| FDA UNII | 1UQB1BT4OT |
| UNSPSC Code | 12352106 |
| NACRES | NA.22 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Warning |
| GHS hazard statements | H302+H312+H332-H315-H319-H335-H351 |
| GHS precautionary statements | P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xn |
| Risk statements (R) | 20/21/22-36/37/38-40 |
| Safety statements (S) | 22-26-36 |
| Water hazard class (WGK) | 3 |
| RTECS number | DG2625000 |
| Customs code | 29225000 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Hazardous substances data | 548-93-6(Hazardous Substances Data) |
Safety & Regulations
| GHS classification | WarningH302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (97.6%) |
| Interactions | TRYPTOPHAN ADMIN RAISED OUTPUT OF FREE FORM /OF 3-HYDROXYANTHRANILIC ACID/ PRINCIPALLY IN HUMAN URINE...EFFECT OF CIGARETTE SMOKING ON (CARCINOGEN) 3-HYDROXY ANTHRANILIC ACID EXCRETION WAS STUDIED ON 20 NORMAL INDIVIDUALS IN FASTING STATE. SMOKING INCR EXCRETION OF THIS METABOLITE IN URINE SIGNIFICANTLY. |
| Human Toxicity Excerpts | SINCE FREE FORM WITH CARCINOGENIC POTENTIAL WAS EXCRETED...& INCR ONLY IN SUBJECTS TREATED WITH TRYPTOPHAN, RELATIONSHIP /WITH/...CARCINOGENESIS... RELEVANT TO MAN. ... INTAKE OF TRYPTOPHAN &/OR RATE OF TRYPTOPHAN METAB... IMPORTANT, SINCE RATES OF HYDROLYSIS OF 3-HYDROXYANTHRANILIC ACID CONJUGATES ARE TOO SLOW...PATTERNS OF URINARY EXCRETION OF FREE & CONJUGATED FORMS OF 3-HYDROXYANTHRANILIC ACID CHANGE STRIKINGLY IN DIFFERENT SPECIES OF MAMMALS, & THIS MAY BE IMPORTANT SINCE 3-HYDROXYANTHRANILIC ACID, A TRYPTOPHAN METABOLITE, IS SUSPECTED OF CAUSING BLADDER CANCER.THE POSSIBLE ROLE OF ENDOGENOUS TRYPTOPHAN METABOLITES & OF 1 TYROSINE METABOLITE IN INDUCING BLADDER CANCER IN HUMANS IS DISCUSSED. |
| Non-Human Toxicity Excerpts | ...REPORTED TO INDUCE CHROMATID BREAKS IN CULTURED HUMAN EMBRYO CELLS @ CONCN OF 30 MG/L. ONE CHROMOSOME TRANSLOCATION WAS OBSERVED IN 338 METAPHASE CELLS EXAMINEDNONE WERE SEEN IN 300 CONTROL METAPHASE CELLS.CARCINOGENIC EFFECT WAS SHOWN BY 3-HYDROXYANTHRANILIC ACID IMPLANTED INTO THE BLADDER WALL IN MICE.RESULTS DID NOT SUPPORT HYPOTHESIS THAT TRYPTOPHAN METABOLITES PRODUCED BY INTESTINAL MICROFLORA ARE MAJOR ETIOLOGIC FACTORS IN CANCER OF COLON, THEY WERE NEG IN AMES TEST.3-HYDROXYANTHRANILIC ACID ADMIN SC TO MICE @ 2.5 MG TWICE WEEKLY FOR 10 WK INDUCED TUMORS IN THE URINARY BLADDER.PRESENCE OF 20% 3-HYDROXYANTHRANILIC ACID IN THE PELLETS MADE NO CHANGE IN THE INCIDENCE OF TUMORS. |
| Probable Routes of Human Exposure | HYDROXYANTHRANILIC ACID WAS FOUND IN BOTH SERUM & BLOOD CLOTS OF WORKERS CONTACTING ANILINE DYES. |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| RTECS number | DG2625000 |
| Customs code | 29225000 |
| Risk statements (R) | 20/21/22-36/37/38-40 |
| Signal word | Warning |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xn |
| Safety statements (S) | 22-26-36 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H302+H312+H332-H315-H319-H335-H351 |
| Hazard class | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313 |
| Hazardous substances data | 548-93-6(Hazardous Substances Data) |
Applications & Uses
Uses
3-Hydroxyanthranilic Acid is one of the tryptophan’s metabolites along the kynurenine pathway. 3-Hydroxyanthranilic Acid has been shown to induce apoptosis in T cells.