Ethyl 2-aminobenzoate

log Kow = 2.57

2.57

Fruity odor

FAINT ORANGE-FLOWERS ODOR

1.117 at 68 °F (NTP, 1992) - Denser than water; will sink

1.1174 at 20 °C/4 °C

1.115-1.120

Insoluble (NTP, 1992)

Very soluble in ether, alcohol

Soluble in propylene glycol

SOLUBILITY IN 60% ALCOHOL: 1:7; 70% ALC: 1:2

Slightly soluble in water; Soluble in propylene glycol and fixed oils

Soluble (in ethanol)

514 °F at 760 mmHg (NTP, 1992)

268 °C at 760 mm Hg

129.00 to 130.00 °C. @ 9.00 mm Hg

267 °C

This chemical does not meet GHS hazard criteria for 84.7% (261 of 308) of all reports.

Warning

H315 (15.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 308 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Benzoic acid, 2-amino-, ethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: No longer Valid Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23487

Benzoic acid, 2-amino-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Ethyl anthranilate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

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.

Use water spray, carbon dioxide, dry chemical, or "alcohol" foam. Use water to keep fire-exposed containers cool. If leak or spill has not ignited, use water spray to disperse vapors and to protect men attempting to stop leak.

Water spray may be used to flush spills away from exposures and to dilute spills to nonflammable mixtures.

Personnel protection: Wear self-contained breathing apparatus.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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.

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.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 600(SRC), determined from a log Kow of 2.57(2) and a regression-derived equation(3), indicates that ethyl anthranilate is expected to have low mobility in soil(SRC). Volatilization of ethyl anthranilate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Ethyl anthranilate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-3 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2007).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 600(SRC), determined from a log Kow of 2.57(2) and a regression-derived equation(3), indicates that ethyl anthranilate is 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 1.6X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Hydrolysis is expected to be a slow environmental fate process; estimated second order hydrolysis half-lives are 5.8 years and 210 days at pH values of 7 and 8, respectively(5). According to a classification scheme(6), an estimated BCF of 19(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl anthranilate, which has an estimated vapor pressure of 2.3X10-3mm 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 ethyl anthranilate 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 11 hours(SRC), calculated from its rate constant of 3.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethyl anthranilate does absorb light at UV max of 330 nm(4) and therefore may be susceptible to direct photolysis by sunlight.

The Koc of ethyl anthranilate is estimated as 600(SRC), using a log Kow of 2.57(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethyl anthranilate is expected to have low mobility in soil.

An estimated BCF of 19 was calculated in fish for ethyl anthranilate(SRC), using a log Kow of 2.57(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Henry's Law constant for ethyl anthranilate is estimated as 1.6X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethyl anthranilate is expected to be essentially nonvolatile from water surfaces(2). Ethyl anthranilate's Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Ethyl anthranilate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-3 mm Hg(SRC), determined from a fragment constant method(3).

/GENOTOXICITY/ Ethyl anthranilate was tested for mutagenicity in the Salmonella/ microsome preincubation assay using the standard protocol approved by the National Toxicology Program. Ethyl anthranilate was tested at doses of 0.01, 0.033, 0.10, 0.33, 0.50, and 0.80 mg/plate in as many as 5 Salmonella typhimurium strains (TA 1535, TA 1537, TA 97, TA 98, and TA 100) in the presence and absence of rat or hamster liver S-9. Ethyl anthranilate was negative in these tests and the highest ineffective dose tested without significant toxicity in any S. typhimurium strain was 0.33 mg/plate. Total clearing of the background bacterial lawn occurred in nearly all cultures tested at doses above this level.

/OTHER TOXICITY INFORMATION/ Listed in FDA's Food Additive Database as a chemical for which fully up-to-date toxicology information has been sought.

The rate constant for the vapor-phase reaction of ethyl anthranilate with photochemically-produced hydroxyl radicals has been estimated as 3.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 3.8X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 5.8 years and 210 days at pH values of 7 and 8, respectively(2). Ethyl anthranilate does absorb light at UV max of 330 nm(3) and therefore may be susceptible to direct photolysis by sunlight.

Occupational exposure to ethyl anthranilate may occur through dermal contact with this compound at workplaces where ethyl anthranilate is produced or used. Use data suggest the general population may be exposed to ethyl anthranilate via ingestion of food, and dermal contact with this compound and other products containing ethyl anthranilate. (SRC)

Ethyl anthranilate's production and use as a perfume and flavor additive may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 2.3X10-3 mm Hg at 25 °C indicates ethyl anthranilate will exist solely as a vapor in the atmosphere. Vapor-phase ethyl anthranilate will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 11 hours. Ethyl anthranilate does absorb light at UV max of 330 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, ethyl anthranilate is expected to have low mobility based upon an estimated Koc of 600. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.6X10-8 atm-cu m/mole. Biodegradation data were not available. If released into water, ethyl anthranilate is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 19 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is expected to be a slow environmental fate process; estimated second order hydrolysis half-lives are 5.8 years and 210 days at pH values of 7 and 8, respectively. Occupational exposure to ethyl anthranilate may occur through dermal contact with this compound at workplaces where ethyl anthranilate is produced or used. Use data suggest the general population may be exposed to ethyl anthranilate via ingestion of food, and dermal contact with this compound and other products containing ethyl anthranilate. (SRC)

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

Ethyl anthranilate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Found in grapes; Used in perfumery, flavoring, and as an inert ingredient in pesticides; [HSDB]

Farming (Pesticides) [Category: Industry]

FLAVOR ADDITIVE IN BAKERY PRODUCTS, GELATIN & PUDDINGS, FROZEN MILK DESSERTS, FLAVORED BEVERAGES, CANDY TOPPINGS, CHEWING GUM

Perfumery and flavors, similar to methyl anthranilate.

Reported uses (ppm): (FEMA, 1994)

Anthranilic acid, ethyl ester is a List 3: Inerts of unknown toxicity (other) Pesticide Ingredient.

(1972) No Data

(1975) No Data

(1972) No Data

(1975) No Data

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

REACTION OF ANTHRANILIC ACID & ETHANOL IN THE PRESENCE OF ACID CATALYSTS

BY ESTERIFICATION OF ANTHRANILIC ACID WITH ETHANOL IN PRESENCE OF ACID CATALYSTS; BY REACTING SODIUM HYPOCHLORITE WITH AN ALKALINE ALCOHOLIC SOLN OF PHTHALIMIDE.

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Benzoic acid, 2-amino-, ethyl ester: ACTIVE

REPORTED USES: 5.9 PPM IN NON-ALCOHOLIC BEVERAGES; 7.6 PPM IN ICE CREAM, ICES; 19 PPM IN CANDY; 23 PPM IN BAKED GOODS; 14 PPM IN GELATINS & PUDDINGS; 79 PPM IN CHEWING GUM.

USEFUL IN CONCORD GRAPE WINE FLAVORS, MANDARIN.

FEMA NUMBER 2421