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3-Hydroxyanthranilic acid

3-Hydroxyanthranilic acid structure

3-Hydroxyanthranilic acid 

structure
  • CAS No:

    548-93-6

  • Formula:

    C7H7NO3

  • Chemical Name:

    3-Hydroxyanthranilic acid

  • Synonyms:

    Benzoic acid,2-amino-3-hydroxy-;Anthranilic acid,3-hydroxy-;2-Amino-3-hydroxybenzoic acid;3-Hydroxyanthranilic acid;NSC 522891

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

3-Hydroxyanthranilic acid is a tryptophan metabolite in the kynurenine pathway.


Solid


3-hydroxyanthranilic acid is an aminobenzoic acid that is benzoic acid substituted at C-2 by an amine group and at C-3 by a hydroxy group. It is an intermediate in the metabolism of the amino acid tryptophan. It has a role as a human metabolite and a mouse metabolite. It is an aminobenzoic acid and a monohydroxybenzoic acid. It derives from an anthranilic acid. It is a conjugate acid of a 3-hydroxyanthranilate. It is a tautomer of a 2,3-dihydro-3-oxoanthranilic acid.|An oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.

3-Hydroxyanthranilic acid Basic Attributes

153.14

153.14

208-962-5

1UQB1BT4OT

522891

DTXSID40203290

LEAFLETS IN WATER

2922509090

Characteristics

83.6

0.9

Solid

1.5±0.1 g/cm3

164 °C

356.8°C at 760 mmHg

169.6±26.5 °C

1.691

SLIGHTLY SOL IN WATER, SOL IN HOT WATER, ALCOHOL, ETHER; SOL IN CHLOROFORM

-20ºC

131.2 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|127.8 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|128.4 Ų [M-H]-

Safety Information

NONH for all modes of transport

3

20/21/22-36/37/38-40

S22-S26-S36

DG2625000

Xn

P261-P280-P305 + P351 + P338

H302 + H312 + H332-H315-H319-H335-H351

|Warning|H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

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.

HYDROXYANTHRANILIC ACID WAS FOUND IN BOTH SERUM & BLOOD CLOTS OF WORKERS CONTACTING ANILINE DYES.

Drug Information

Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)

SIGNIFICANT PERCENTAGE OF PT WITH NON-OCCUPATIONAL 'SPONTANEOUS' BLADDER CANCER EXCRETE HIGHER AMT OF...3-HYDROXYANTHRANILIC ACID THAN NORMAL CONTROL INDIVIDUALS...|...EXCRETED MAINLY IN FREE FORM IN HUMAN SUBJECTS, AS SULFATE ESTERS IN RATS, & AS GLUCURONIDES IN GUINEA-PIGS.|FOLLOWING IP INJECTION OF 0.2 MUMOLE (14)C-3-HYDROXYANTHRANILIC ACID TO MICE, 54 & 64% OF (14)C RECOVERED WAS FOUND IN CO2, AFTER 1 & 24 HR, RESPECTIVELY. AT 24 HR CARCASS & FECES CONTAINED 19% OF (14)C, & ONLY 17% WAS FOUND IN URINE.|AFTER SC INJECTION OF (3)H-LABELED 3-HYDROXYANTHRANILIC ACID INTO MICE, (3)H WAS DISTRIBUTED MAINLY IN LIVER & KIDNEYS, & AFTER 6 HR, (3)H REMAINED IN LYMPHOID ORGANS.|For more Absorption, Distribution and Excretion (Complete) data for 2-AMINO-3-HYDROXY-BENZOIC ACID (6 total), please visit the HSDB record page.

YIELDS 2-AMINO-3-CARBOXYPHENYL SULFATE IN GUINEA PIGS, MICE & RATS; WATANABE M & MINEGISHI K, BIOCHEM PHARMAC, 21, 1347 (1972). YIELDS CINNABARINIC ACID IN RATS; SUBBA RAO PV & VAIDYANATHAN CS, BIOCHEM J, 99, 317 (1966). IN MICE, MORGAN LR, SINGH R, SYLVES T V & WEIMORTS D, CANCER RES, 27, 2395 (1967). /FROM TABLE/|YIELDS ALPHA-AMINO-BETA-CARBOXYMUCONIC SEMIALDEHYDE IN PIG. WISS O & BETTENDORF G, HOPPE-SEYLER'S Z PHYSIOL CHEM, 306, 10 (1957). YIELDS 2-AMINO-3-CARBOXYPHENYL-BETA-D-GLUCURONIDE IN GUINEA PIGS, MICE, RATS; WATANABE M, CHKUBO K & TAMURA Z, BIOCHEM PHARMAC, 21, 1337 (1972). /FROM TABLE/|INCUBATION OF 3-HYDROXYANTHRANILIC ACID WITH 100,000 G SUPERNATANT OF MALE RAT LIVER, PRODUCED TRACES OF 3-METHOXYANTHRANILIC ACID.|NO SIGNIFICANT DIFFERENCES IN LEVEL OF ACTIVITY WERE FOUND AMONG STRAINS FOR HYDROXYANTHRANILATE OXYGENASE.

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.

3 Hydroxyanthranilic Acid

3-Hydroxyanthranilic acid Use and Manufacturing

Uses

NONE|BIOLOGICAL INTERMEDIATE IN THE CONVERSION OF TRYPTOPHAN TO ACETYL-COENZYME A; BIOLOGICAL INTERMEDIATE IN THE BIOSYNTHESIS OF NIACIN FROM TRYPTOPHAN IN NIACIN-DEFICIENT ANIMALS

Production

(1975) NOT PRODUCED COMMERCIALLY IN US|(1977) NOT PRODUCED COMMERCIALLY IN US

SPECTROPHOTOMETRY IN URINE.

Computed Properties

Molecular Weight:153.14
XLogP3:0.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:83.6
Heavy Atom Count:11
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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