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Anthranilic Acid

HCID 227
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Basic information

CAS
118-92-3
Standard SMILES
Nc1ccccc1C(=O)O
InChIKey
RWZYAGGXGHYGMB-UHFFFAOYSA-N
Molecular formula
C7H7NO2
Average molar mass
137.14 g/mol
Monoisotopic mass
137.04767846

Overview

Anthranilic acid appears as odorless white to pale-yellow or tan crystalline powder with a sweetish taste. (NTP, 1992)

Names & identifiers

Preferred name
Anthranilic Acid
IUPAC
2-aminobenzoic acid
English name
Anthranilic acid
Molecular formula
C7H7NO2
Molecular weight
137.14

Names & synonyms

anthranilic acid2-aminobenzoic acid118-92-3o-aminobenzoic acidvitamin L1o-Carboxyaniline2-Carboxyanilineo-Anthranilic acidBenzoic acid, 2-amino-1-Amino-2-carboxybenzeneortho-Aminobenzoic acidBenzoic acid, o-amino-
Show more names
2-aaAnthranilic acid (VitaMin L1)2-AbzAntranilic acidanthranilicAnthranilic Acid 99 %
2-azaniumylbenzoateCarboxyanilineKyselina anthranilovaNCI-C01730Vitamin LKyselina o-aminobenzoova2-amino-Benzoic acidDTXSID8020094

Database identifiers

CAS
118-92-3、1321-11-5、98072-80-1
PubChem CID
227
DTXSID
DTXSID8020094
ChEMBL
CHEMBL14173
ChEBI
CHEBI:30754
UNII
0YS975XI6W
EC Number
204-287-5、308-537-5
Nikkaji
J2.912B

Properties

Computed structural propertiesFilling in

XLogP
1.2
Topological polar surface area
63.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
10
Formal charge
0
Complexity
136

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Aminobenzoic Acids

Dye

Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP · 3 items

log Kow = 1.21

1.21

0.99-1.3

TasteSweetish taste
Density · 5 items

1.412 (NTP, 1992) - Denser than water; will sink

1.412 at 20 °C

1.4 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

1.412 @ 20°C

Color/Form · 3 items

White to pale yellow, crystalline powder

Leaves from alcohol

NEEDLE-LIKE CRYSTALS

Solubility · 6 items

less than 0.1 mg/mL at 68 °F (NTP, 1992)

Freely soluble in alcohol, ether

Soluble in ethanol, ethyl ether, slightly soluble in trifluoroacetic acid, benzene, very soluble in chloroform, pyridine

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 0.3% (1 of 321) of reports.

Danger

H318 (49.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, P305+P354+P338, P317, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 321 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 4 items

Chemical: Benzoic acid, 2-amino-

List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)

Status: Active Update: 27-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10130

Anthranilic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Anthranilic acid and its calcium salt: Human health tier II assessment
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Fire PotentialCombustible. /from table/
Health Hazards · 1 item

SYMPTOMS: Symptoms of exposure to this compound may include nausea, vomiting, acidosis, rash, fever, methemoglobinemia and possibly hepatitis. Other symptoms of exposure include allergic reaction and cyanosis (bluing of skin). Skin contact may cause irritation, itching and dermatitis. It may also cause pruritus. Eye contact may cause irritation. Exposure may cause respiratory irritation, mucous membrane irritation, conjunctivitis and liver inflammation.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 6 items

...Occurs as a metabolite of tryptophan, it is intermediate in biosynthesis of this amino acid in some microorganisms.

Formed from n-acetylanthranilic acid, anthranilamide, o-chloracetamidobenzoic acid, chorismic acid, n-formylanthranilic acid, n-hydroxyanthranilic acid, indole-3-acetic acid, isatic acid, isatin, methyl red, o-nitrobenzoic acid.

Yields anthranilic acid-n-beta-d-glucuronide in rat and rabbit; anthraniloyl-beta-d-glucuronic acid in rat and rabbit: Boyland E & Fahmy AR, Biochem J 91: 73 (1964). Arborine in Glycosmis; arborinine in Glycosmis: Groeger D & Johne S, Z Naturf, B 23: 1072 (1968) /from table/

Yields 1-(O-carboxyphenylamino)-1-deoxyribulose-5-phosphate in Neurospora; Wegman J & Demoss JA, J Biol Chem 240: 3781 (1965); in Aerobacter; Egan AF & Gibson F, Biochim Biophys Acta 130: 276 (1966); in Salmonella; Smith D & Bauerle RH, Biochemistry 8: 1451 (1969) /from table/

For more Metabolism/Metabolites (Complete) data for ANTHRANILIC ACID (9 total), please visit the HSDB record page.

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

MeSH Pharmacological ClassificationDrugs used to prevent SEIZURES or reduce their severity.
Absorption, Distribution and Excretion · 2 items

Less than 10% of dose (18 or 101 mg/kg bw)...given by ip injection was excreted in bile of rats...

... Anthranilic acids brain tissue concentrations in rat brain were significantly lower at birth as compared with those found prenatally; then ... increased in the first postnatal week and decreased thereafter.

Tissue LocationsEpidermis
Cellular LocationsCytoplasm
Metabolite PathwaysTryptophan metabolism

Uses & manufacturing

Related reactions

383 records
New reaction record
HRID 10152 reaction equation
HRID 10152As reactantuspto-grants-2006_08
HRID 11099 reaction equation
HRID 11099As reactantuspto-grants-2006_08
HRID 16188 reaction equation
HRID 16188As reactantuspto-grants-2010_06
HRID 23769 reaction equation
HRID 23769As reactantuspto-grants-2005_02
HRID 36312 reaction equation
HRID 36312As reactantuspto-grants-1995_05
HRID 36313 reaction equation
HRID 36313As reactantuspto-grants-1995_05
HRID 42036 reaction equation
HRID 42036As reactantuspto-grants-2013_09
HRID 62486 reaction equation
HRID 62486As reactantuspto-grants-2016_09
Page 1 of 48

Compound notes

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In water, 3.5X10+3 mg/L at 25 °C

3.5 mg/mL

Solubility in water, g/100ml at 20 °C: 0.35 (poor)

Flash Point · 4 items

340 °F (NTP, 1992)

150 °C

150 °C /from table/

150 °C

Boiling Point · 2 items

Sublimes (NTP, 1992)

Sublimes

Decomposition200 °C
Melting Point · 4 items

291 to 295 °F (NTP, 1992)

144-146 °C

146.5 °C

146-148 °C

Vapor Density · 2 items

4.7 (calculated) (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Relative vapor density (air = 1): 4.7

Physicochemical properties

Melting point
144 · 144-148 °C(lit.)
Boiling point
251.96 °C · 251.96°C (rough estimate)
bulk density
500 kg/m3 · 500kg/m3
Density
1.412 · 1.412
vapor density
4.7 · 4.7 (vs air)
vapor pressure
0.1 Pa · 0.1Pa at 52.6℃
refractive index
1.5323 · 1.5323 (estimate)
Flash point
150 °C · 150°C
storage temp.
0 °C · Store at 0°C
solubility
ethanol: may be clear to slightly hazy
pka
2.108 · 2.108(at 25℃)
form
powder
color
White to pale yellow crystalline
PH Range
Non-B uorescence (1.5) light blue B uorescence (3.0)
Water Solubility
5.7 g/L · 5.7 g/L (25 ºC)
Merck
14 · 14,422
BRN
471803 · 471803
Henry's Law Constant
2.6 · 2.6×105 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Stable. Incompatible with strong oxidizing agents.
Major Application
bottom antireflective coatings, semiconductor devices, inks, hair dyes, cosmetics, treatment of chronic inflammatory diseases, depression
Cosmetics Ingredients Functions
SKIN CONDITIONING - MISCELLANEOUS
InChI
1S/C7H7NO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,8H2,(H,9,10)
InChIKey
RWZYAGGXGHYGMB-UHFFFAOYSA-N
SMILES
Nc1c(cccc1)C(=O)O
LogP
0.99 at · 0.99 at 23℃ and pH3.7
Toxicology and Carcinogenesis
Bioassay of Anthranilic Acid for Possible Carcinogenicity (CASRN 118-92-3)
CAS DataBase Reference
118 · 118-92-3(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
0 YS975XI6W · 0YS975XI6W
IARC
3 · 3 (Vol. 16, Sup 7) 1987
NIST Chemistry Reference
Anthranilic acid(118-92-3)
EPA Substance Registry System
Anthranilic acid (118-92-3)
UNSPSC Code
12352106 · 12352106
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05
Signal word
Danger
Hazard statements
318 · H318
Precautionary statements
280 · P280-P305+P351+P338
Hazard Codes
Xi
Risk Statements
36 · 36-37-36/37/38
Safety Statements
26 · 26-36-39
WGK Germany
2 · 2
RTECS
2450000 · CB2450000
Autoignition Temperature
530 °C · >530°C
TSCA
TSCA listed
HS Code
29224300 · 29224300
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 · Eye Dam. 1
Hazardous Substances Data
118 · 118-92-3(Hazardous Substances Data)
REACH Registrations
Active
Hazards SummaryEmergency treatment: methemoglobinemia; [HSDB] Causes somnolence and ataxia in lethal-dose feeding studies of rats; [RTECS] An eye irritant; [ICSC] May cause irritation, methemoglobinemia, and liver injury; [CAMEO] An irritant; [MSDSonline]
FDA Requirements · 1 item

The following chemical has been specifically designated by the Administrator of the Drug Enforcement Administration as subject to the provisions of this part and parts 1309 and 1313 of this chapter. Anthranilic acid, its esters and its salts are List 1 chemicals; DEA Code: 8530.

Reactive GroupAcids, Carboxylic
Special ReportsDHEW/NCI; Bioassay of o-Anthranilic Acid for Possible Carcinogenicity (1978) Technical Rpt Series No. 36 DHEW Pub No. (NIH) 78-836
Reactivity ProfileANTHRANILIC ACID is incompatible with strong oxidizers. (NTP, 1992)
Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Anthranilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Chemical DangersOn combustion, forms nitrogen oxides. The solution in water is a weak acid. Reacts with oxidants. This generates fire hazard.

Safety & protection

Fire Fighting · 2 items

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use powder, water spray, foam, carbon dioxide.

First Aid Measures · 4 items

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Seek medical attention if you feel unwell.

First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from oxidants.
Fire Fighting ProceduresPowder, water spray, foam, carbon dioxide. /from table/
Storage ConditionsSeparated from strong oxidants. /from table/
Cleanup MethodsRemove all ignition sources. Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting, then remove to safe place. Do NOT let this chemical enter the environment.
Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.

Preventive Measures · 2 items

Local exhaust or breathing protection. Protective gloves. Safety goggles, or eye protection in combination with breathing protection if powder. Do not eat, drink, or smoke during work. /from table/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Eye PreventionWear safety spectacles.

Toxicology

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Ecotoxicity Values · 2 items

LC50 Leuciscus idus (freshwater fish; Ide) 215-1000 mg/L for 1 hr /conditions of bioassay not specified/

LC50 Leuciscus idus (Freshwater fish, Ide) 100-215 mg/L for 96 hr /conditions of bioassay not specified/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a log Kow of 1.21(2) and a regression-derived equation(3), indicates that anthranilic acid is expected to have high mobility in soil(SRC). The pKa of anthranilic acid is 2.14(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of anthranilic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Anthranilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.8X10-4 mm Hg(SRC), determined from a fragment constant method(7). Anthranilic acid (10 ppm) degraded 100% in 2 days using a 1% suspension of Niagara silt loam at 25 °C(8).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 110(SRC), determined from a log Kow of 1.21(2) and a regression-derived equation(3), indicates that anthranilic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.8X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Anthranilic acid was shown to degrade rapidly in a variety of aqueous aerobic and anaerobic screening test(7-16). Anthranilic acid photodegrades rapidly in natural seawater(17). Anthranilic acid is shown to have a maximum absorption at 337 nm(18) and therefore may be susceptible to direct photolysis by sunlight(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), anthranilic acid, which has an estimated vapor pressure of 2.8X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase anthranilic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 10 hours(SRC), calculated from its rate constant of 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 items

The substance can be absorbed into the body by ingestion.

Endogenous, Ingestion, Dermal (contact)

Toxicity Summary · 1 item

Uremic toxins such as anthranilic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

Signs and Symptoms · 2 items

Redness. Pain.

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=118-92-3]

Effluent ConcentrationsAnthranilic acid was detected in ammunition plant wastewater in Stadtallendorf, Germany(1).
ICSC Environmental DataThe substance is harmful to aquatic organisms. This substance may be hazardous to the environment. Special attention should be given to birds.
Soil Adsorption/Mobility · 1 item

The Koc of anthranilic acid is estimated as 110(SRC), using a log Kow of 1.21(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that anthranilic acid is expected to have high mobility in soil. The pKa of anthranilic acid is 2.14(4), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

Regulatory information

FDA Requirements · 1 item

The following chemical has been specifically designated by the Administrator of the Drug Enforcement Administration as subject to the provisions of this part and parts 1309 and 1313 of this chapter. Anthranilic acid, its esters and its salts are List 1 chemicals; DEA Code: 8530.

Atmospheric Standards · 1 item

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Anthranilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Safety data

wgk
2
tsca
TSCA listed
rtecs
CB2450000
hs_code
29224300
risk_code
36-37-36/37/38
Signal word
Danger
Symbol(GHS)
GHS05
hazard_code
Xi
safety_code
26-36-39
Storage Class
11 - Combustible Solids
Hazard statements
H318
REACH Registrations
Active
Hazard Classifications
Eye Dam. 1
Autoignition Temperature
>530°C
Precautionary statements
P280-P305+P351+P338
Hazardous Substances Data
118-92-3(Hazardous Substances Data)
Uses · 6 items

Used as an intermediate for dyes, drugs, pesticides, perfumes, flavors, and bird and insect repellents; Also used as a mold inhibitor in soya sauce and to enhance the milk production in cows; [HSDB]

Farming (Feed Additives) [Category: Industry]

Dyes, drugs, perfumes, and pharmaceuticals.

CHEM INT FOR CI ACID YELLOW 121, VAT VIOLET 13, VAT BLUE 1, CI DIRECT BROWN 112, MORDANT YELLOW, MORDANT RED 9, MORDANT BROWN 40, & PIGMENT RED 60, & FOR ITS ESTERS USED IN PERFUMES & FUNGICIDES, & IN SACCHARIN; CADMIUM SALT- AN ASCARICIDE IN SWINE; MOLD INHIBITOR IN SOYA SAUCE

As mold inhibitor in soya sauce; its esters have found applications in perfumes, synthetic flavors, bird and insect repellents, as fungicides for syrups

THERAP CAT (VET): The cadmium salt has been used as an acaricide in swine

U.S. Exports · 2 items

(1972) No Data

(1975) No Data

U.S. Imports · 2 items

(1972) 1.02X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 5.00X10+6 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3 items

(1972) PROBABLY GREATER THAN 9.08X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3092]

Methods of Manufacturing · 4 items

...PREPARED BY FISCHER IN 1896 BY HEATING 2-NITROSOBENZOIC ACID WITH AQ AMMONIUM SULFIDE @ 100 °C...PRODUCED COMMERCIALLY BY HOFMANN REACTION, IN WHICH PHTHALIMIDE IS REACTED WITH SODIUM HYPOCHLORITE & CAUSTIC SODA...

PREPD BY REDUCTION OF O-NITROBENZOIC ACID

TREATMENT OF PHTHALIMIDE WITH AN ALKALINE HYPOBROMITE SOLN.

2-Aminobenzoic acid is usually made from phthalic anhydride via sodium phthalamate. Oxidative decarboxylation (the Hofmann reaction) is carried out by the addition of sodium hypochlorite solution at 60 - 100 °C followed by acidification. The product is purified with activated carbon and bisulfite.

Formulations/PreparationsGRADES: TECHNICAL (95-98%); 99% OR BETTER.
DEA Listed Chemicals · 2 items

Anthranilic acid, its esters, and its salts

A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)

General Manufacturing Information · 2 items

Benzoic acid, 2-amino-: ACTIVE

VITAMIN L & VITAMIN L1 FORMERLY USED TO DESCRIBE ANTHRANILIC ACID.

Applications · 3 items

UsesAnthranilic acid can be used in organic synthesis to generate the benzyne intermediate. It is used as an intermediate for production of dyes, pigments, and saccharin. It and its esters are used in preparing perfumes to imitate jasmine and orange, pharmaceuticals and UV-absorber as well as corrosion inhibitors for metals and mold inhibitors in soya sauce.

UsesDyes, drugs, perfumes, and pharmaceuticals.

General DescriptionOdorless white to pale-yellow or tan crystalline powder with a sweetish taste.

Upstream & downstream products

Upstream raw materials

Sodium benzoateSodium hypochloriteAmmonium hydroxideChlorineWaterPhthalic anhydrideHydrochloric acidSodium hydroxideActivated carbonSulfuric acid

Downstream products

Tranilast2-Chloro-9-(3-(dimethylamino)propyl)-th&2-Hydrazinobenzoic acid hydrochlorideBenzoic acid, 2-[[1-amino-7-[[4-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sulfo-2-naphthalenyl]azo]-2-methoxyphenyl]azo]-8-hydroxy-3,6-disulfo-2-naphthalenyl]azo]-5-[[6-amino-5-[(3-carboxy-4-hydroxyphenyl)azo]-1-hydroxy-3-sul6,10,12-trichloronaphth[2,3-c]acridine-5,8,14(13H)-trioneMethyl Red2-Iodobenzoic acidLobenzaritEthyl anthranilatePhenazine-1-carboxylic acid2,2'-Dithiosalicylic acidtrisodium [mu-[2-[[1-hydroxy-6-[[[[5-hydroxy-6-[(2-hydroxy-5-sulphophenyl)azo]-7-sulpho-2-naphthyl]amino]carbonyl]amino]-3-sulpho-2-naphthyl]azo]benzoato(7-)]]dicuprate(3-)2-Amino-5-iodobenzoic acid3-IndazolinoneVat Red 414-hydroxy-1-methyl-3-[(3-nitrophenyl)azo]-2-quinoloneFluorescent Brightener PfN-Benzylanthranilic acid2-Chlorothioxanthone2-Fluorobenzoic acid2-Dimethylaminobenzoic acidN-Phenylanthranilic acidN-Acetylanthranilic acid4-Hydroxyquinazolinebarium(2+) hydrogen 2-[(2-hydroxy-3,6-disulphonato-1-naphthyl)azo]benzoatePhenylethyl Anthranilate3,5-Dibromobenzoic acid2-Amino-5-bromobenzoic acidN-(2-Carboxyphenyl)glycine9-AminoacridineClozapineReactive Blue X-R2,5-Dibromobenzoic acid1-Benzyl-3-hydroxy-1H-indazole2-(4-chlorophenylthio)benzoic acidCopper, 2,2'-[carbonylbis[imino(1-hydroxy-3-sulfo-6,2-naphthalenediyl)azo]]bis[benzoic acid] complex1,3-Benzodithiolylium tetrafluoroborate6-Iodoquinazolin-4-oneIsatoic Anhydride4-Chloroquinazoline

Additional notes

DefinitionChEBI: An aminobenzoic acid that is benzoic acid having a single amino substituent located at position 2. It is a metabolite produced in L-tryptophan-kynurenine pathway in the central nervous system.