METHYL ANTHRANILATE

1. PRODUCT IDENTIFICATION

Parameter	Information
Product Name	Methyl Anthranilate
Synonyms	Methyl 2-aminobenzoate, 2-Aminobenzoic acid methyl ester, 2-Carbomethoxyaniline, Methyl o-aminobenzoate, Anthranilic acid methyl ester, Neroli oil artificial, Bird Shield, ReJex-iT, Nevoli oil
CAS Number	134-20-3
EC Number (EINECS)	205-132-4
FEMA Number	2682
Molecular Formula	C₈H₉NO₂
Molecular Weight	151.16 g/mol
Chemical Class	Ester (Anthranilic acid derivative)
Appearance	Clear to pale yellow liquid; exhibits light blue fluorescence
Odor	Fruity, Concord grape-like, sweet, with a musty and berry nuance
Purity	≥ 99% (typical)

2. CHEMICAL STRUCTURE

2.1. Molecular Structure

Methyl anthranilate is an ester derived from anthranilic acid (2-aminobenzoic acid) and methanol. It consists of a benzene ring substituted with an amino group (-NH₂) at the ortho position and a methyl ester group (-COOCH₃) at position 1. The compound exhibits a characteristic ortho-substitution pattern that contributes to its unique chemical and sensory properties.

Structural Formula:

              O
              ||
    NH₂       C - O - CH₃
     |        |
     \        /
      \______/
       Benzene Ring

SMILES: COC(=O)c1ccccc1N

InChI Key: VAMXMNNIEUEQDV-UHFFFAOYSA-N

2.2. Functional Groups

Functional Group	Location	Properties
Amino Group (-NH₂)	Ortho position on benzene ring	Basic; can form salts with acids; contributes to aroma
Ester Group (-COOCH₃)	Position 1 on benzene ring	Hydrolyzes to anthranilic acid and methanol; responsible for fruity odor
Aromatic Ring (Benzene)	Core structure	Provides stability; participates in π-π interactions

3. PHYSICAL AND CHEMICAL PROPERTIES

Property	Value	Notes
Appearance	Clear to pale yellow liquid	Exhibits light blue fluorescence
Odor	Fruity, Concord grape-like	Sweet, musty, berry nuance at dilution
Melting Point	24.0 – 24.5 °C	Solidifies at room temperature if cooled
Boiling Point	256 °C at 760 mmHg	-
Flash Point	~108 – 123 °C (closed cup)	Combustible liquid
Density	1.168 g/cm³ at 25 °C	Heavier than water
Refractive Index	1.582 – 1.606 at 20 °C	-
Vapor Pressure	0.027 – 1 mmHg at 20 °C	-
Vapor Density	5.2 (air = 1)	Heavier than air
Water Solubility	2.85 g/L (slightly soluble)	Slightly soluble in water
Solubility in Organics	Freely soluble	Soluble in ethanol, fixed oils, propylene glycol
Insolubility	Insoluble in glycerol, paraffin oil	-
log P (octanol/water)	1.88 – 2.04	Indicates moderate lipophilicity
pKa	2.23 (for the +1 form at 25°C)	Weak base
pH (aqueous solution)	7.5 – 8.0 at 20 °C	Slightly basic
Surface Tension	43.71 mN/m at 25 °C	-
Explosive Limits	1.4 – 7.8% (V)	-
Henry's Law Constant	5.2×10⁰ mol/(m³·Pa) at 25 °C	-
Autoignition Temperature	986 °F (530 °C)	-

4. STABILITY AND REACTIVITY

Parameter	Information
Chemical Stability	Stable under normal temperatures and pressures
Sensitivity	Sensitive to air and light
Conditions to Avoid	Light, heat, air exposure; strong oxidizing agents
Incompatible Materials	Strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, strong bases, peroxides, phenols
Hazardous Decomposition Products	Carbon monoxide (CO), carbon dioxide (CO₂), nitrogen oxides (NOx)
Hazardous Polymerization	Will not occur

5. OCCURRENCE AND SOURCES

Methyl anthranilate naturally occurs in various essential oils and fruits:

Source Type	Examples
Essential Oils	Neroli, bergamot, ylang-ylang, orange blossom, jasmine, tuberose, gardenia, lemon, mandarin, champaca
Fruits	Concord grapes, grapefruit, strawberry, lime, tangerine
Other	Cocoa, coffee, rue oil

6. APPLICATIONS (EXTENDED)

Methyl anthranilate is a versatile compound with applications spanning multiple industries. Its unique fruity-grape aroma profile and relatively safe toxicological profile make it valuable across numerous sectors.

6.1. Flavors & Fragrances Industry

Methyl anthranilate is one of the most widely used aroma chemicals in the flavor and fragrance industry. Its sweet, fruity, grape-like character makes it indispensable for many applications.

6.1.1. Fragrance Applications

Application Area	Function	Details
Fine Perfumery	Fruity-floral note	Provides grape, orange blossom, and neroli accords; blends well with floral, citrus, and woody notes
Soap and Detergents	Odor masking and fragrance	Used to impart pleasant fruity notes to soaps, laundry detergents, and fabric softeners; stable in alkaline conditions
Cleaning Products	Fresh scent	Added to household cleaners, surface sprays, and dishwashing liquids for a pleasant, lingering grape aroma
Aromatherapy Products	Calming fragrance	Used in essential oil blends, diffusers, and candles for its relaxing and sweet olfactory profile
Cosmetics and Personal Care	Fragrance component	Incorporated into lotions, creams, shampoos, conditioners, and body washes for fruity-floral character
Air Fresheners	Ambient fragrance	Used in room sprays, plug-in diffusers, and car air fresheners for a sweet, appealing scent
Candles and Wax Melts	Scented products	Provides a strong, pleasant hot-throw fragrance in candle formulations

6.1.2. Flavor Applications

Application Area	Function	Details
Beverage Industry	Grape flavor	Used in grape-flavored sodas, juices, fruit punches, and sports drinks; often the key component of artificial grape flavor
Confectionery	Candy and gum flavor	Provides grape flavor to hard candies, gummies, chewing gums, and lozenges
Baked Goods	Flavor enhancement	Used in cookies, cakes, pastries, and frostings for fruity notes
Dairy Products	Fruit flavoring	Added to yogurts, ice creams, and puddings for grape and berry profiles
Pharmaceuticals	Flavor masking	Used in syrups, chewable tablets, and liquid medications to mask bitter or unpleasant active ingredients
Electronic Cigarettes	E-liquid flavoring	Used as a flavoring agent in vape liquids (subject to regional regulations)
Alcoholic Beverages	Flavor component	Used in wine flavoring, liqueurs, and flavored spirits for grape and floral notes
Fruit Preparations	Natural flavor enhancement	Blended with natural fruit extracts to enhance berry and stone fruit profiles

6.1.3. Fragrance and Flavor Formulation Guidelines

Formulation Type	Typical Usage Level	Compatibility
Fine Fragrances	0.1 – 2.0%	Blends with citrus, floral, woody, and gourmand notes
Soap and Detergents	0.5 – 3.0%	Stable in alkaline conditions
Candles and Waxes	1.0 – 5.0%	Good hot-throw performance
Food and Beverages	5 – 50 ppm	GRAS for food use
Cosmetic Lotions	0.5 – 2.0%	Compatible with most cosmetic bases

6.2. Agriculture and Pest Management

Methyl anthranilate has gained significant importance in agriculture as a safe, non-toxic bird repellent and pest management agent.

6.2.1. Bird Repellent Applications

Application Area	Function	Details
Crop Protection	Non-lethal bird deterrent	Used to protect corn, sunflowers, rice, and fruit crops from bird damage; EPA registered in the US
Golf Courses	Turf protection	Applied to golf greens to prevent bird damage to turf; safe for use in recreational areas
Airports	Aviation safety	Used to reduce bird strike risks by deterring birds from airfields and runways
Orchards and Vineyards	Fruit protection	Protects grapes, berries, and tree fruits from bird feeding damage
Seed Treatment	Repellent coating	Applied to agricultural seeds to prevent bird predation during germination
Avian Pest Control	Humane alternative	Non-toxic, non-lethal alternative to lethal bird control methods
Wildlife Management	Deterrent	Used in parks, gardens, and urban areas to manage bird populations humanely

6.2.2. Insect Pest Management

Application Area	Function	Details
Western Corn Rootworm	Repellent	Repels larvae of western corn rootworm, a major pest of corn crops
Thrips Control	Repellent	Effective against various thrips species
Natural Pest Management	Biological control	Considered as a natural and environmentally friendly alternative in integrated pest management (IPM) programs

6.2.3. Agricultural Formulation Types

Formulation Type	Application Method	Best For
Liquid Spray	Aerial or ground application	Large-scale crop protection
Granular Formulation	Soil or surface application	Seed treatment and targeted repellency
Encapsulated Formulation	Slow-release application	Extended protection, reduced reapplication

6.3. Pharmaceuticals & Healthcare

Methyl anthranilate serves multiple functions in the pharmaceutical and healthcare sectors.

6.3.1. Pharmaceutical Applications

Application Area	Function	Details
Drug Formulation	Excipient	Used as a flavoring agent and excipient in oral pharmaceutical formulations
Flavor Masking	Taste and odor correction	Masks unpleasant tastes of active pharmaceutical ingredients in syrups, suspensions, and chewable tablets
Vitamin and Syrup Production	Flavor enhancement	Improves palatability of vitamins, cough syrups, and liquid medications
API Synthesis	Starting material	Used as a starting material in the synthesis of biologically active derivatives and pharmaceutical intermediates
Topical Formulations	Fragrance component	Added to creams, ointments, and gels for pleasant odor
Oral Care Products	Flavoring agent	Used in mouthwashes, toothpastes, and breath fresheners

6.3.2. Pharmacological Research

Research Area	Application	Findings
Analgesic Research	Antinociceptive properties	Demonstrated antinociceptive properties in preclinical studies; potential for pain relief applications
Anti-inflammatory Studies	Anti-inflammatory activity	Some studies indicate potential anti-inflammatory effects
Antimicrobial Studies	Biofilm inhibition	Exhibits quorum sensing inhibition; effective against A. sobria biofilm formation
CNS Research	Neuropharmacological effects	Studied for potential effects on the central nervous system

6.4. Industrial Applications

Methyl anthranilate serves various functions across industrial sectors.

6.4.1. Chemical Synthesis and Manufacturing

Application Area	Function	Details
Organic Synthesis	Intermediate	Used as an intermediate in the synthesis of dyes, pigments, and specialty chemicals
Dye and Pigment Industry	Intermediate	Precursor for anthranilic acid-derived dyes; used in azo dye production
Polymer and Plastic Additives	Additive synthesis	Plays a role in the production of specialty polymer additives
Coatings	Chemical intermediate	Used in the synthesis of coating additives and specialty resins
Electroplating	Additive	Used as an additive to improve plating characteristics
Metalworking Fluids	Odor masking	Added to metalworking fluids and cutting oils to mask unpleasant odors
Agrochemicals	Intermediate	Used as a building block for synthesis of various agrochemical active ingredients
Specialty Chemicals	Building block	Versatile intermediate for synthesis of various specialty chemicals

6.5. Other Applications

Application Area	Function	Details
Pet Products	Humane repellent	Used in pet-safe bird repellent sprays; considered safe for mammals when used as directed
Biotechnology Research	Natural compound testing	Tested as a natural compound in various experimental biotechnology studies
Quorum Sensing Inhibition	Antibiofilm agent	Inhibits A. sobria biofilm formation; potential for biofilm control applications
Ecotoxicity Studies	Environmental research	Used as a model compound for studying environmental fate and effects
E-Liquids	Flavoring agent	Reported use in electronic cigarette liquids (subject to regional regulations; not recommended in regulated markets)
Surface Coatings	Specialty coatings	Used in the formulation of specialty coatings for fragrance release
Paper and Packaging	Fragrance incorporation	Used for incorporating grape/berry scents into paper products and packaging materials
Textile Finishing	Aroma encapsulation	Used in scented textile finishing applications
Polymer Industry	Monomer/monomer precursor	Some research into its use as a bio-derived monomer precursor

7. APPLICATION USE LEVELS BY SECTOR

Industry	Application	Typical Use Level	Notes
Beverages	Flavoring	5 – 50 ppm	FEMA GRAS
Confectionery	Flavoring	10 – 100 ppm	Candy, gum
Baked Goods	Flavoring	5 – 30 ppm	Cookies, cakes
Dairy	Flavoring	10 – 50 ppm	Ice cream, yogurt
Fine Fragrance	Aroma chemical	0.1 – 2.0%	Perfume concentrates
Soap and Detergents	Fragrance	0.5 – 3.0%	Alkaline stable
Cosmetics	Fragrance	0.5 – 2.0%	Lotions, creams
Candles	Scent	1.0 – 5.0%	Hot-throw performance
Agriculture	Bird repellent	5 – 20% (active)	Spray formulations
Pharmaceuticals	Flavor masking	10 – 500 ppm	Syrups, tablets
Animal Feed	Repellent additive	1 – 5%	Non-mammal toxicity

8. TOXICOLOGICAL PROFILE (DETAILED)

Parameter	Value
Acute Oral Toxicity (LD50, Rat)	2,910 mg/kg
Acute Dermal Toxicity (LD50, Rabbit)	> 5,000 mg/kg
Skin Irritation	Moderate; may cause irritation on contact
Eye Irritation	Causes serious eye irritation (Category 2A, H319)
Inhalation	Causes respiratory tract irritation
Ingestion	May cause GI irritation; high doses cause somnolence and coma
Dermal Sensitization	Negative in patch tests; some reports in fragrance allergies
Mutagenicity	Mutagen in some studies; requires further evaluation
Reproductive Effects	Reproductive effector in studies
Carcinogenicity	Not classified by IARC, NTP, or OSHA
ADI (Acceptable Daily Intake)	0 – 1.5 mg/kg (JECFA)
FDA Status	GRAS for food applications
EPA Status	Registered as a bird repellent
IFRA Compliance	Restricted in fragrance formulations (current IFRA standards)

9. IFRA REGULATORY RESTRICTIONS

Restriction	Details
IFRA Standard	Restricted; maximum allowable use level in finished products varies by category
Primary Concern	Potential sensitization risk
Category 1 (Lip Products)	0.001%
Category 4 (Creams/Lotions)	0.001%
Category 6 (Mouthwash)	0.0002%
Category 11 (Facial Cleansers)	0.0002%

Note: IFRA standards are regularly updated. Always consult the most current IFRA guidelines.

10. GHS CLASSIFICATION

Hazard Class	Category	H-Statement
Eye Irritation	Category 2A	H319: Causes serious eye irritation
Aquatic Toxicity	Category 3	H401: Toxic to aquatic life

Signal Word: WARNING

Hazard Pictograms: GHS07 (Exclamation Mark)

Hazard Statements (H-Codes):

Code	Statement
H319	Causes serious eye irritation
H401	Toxic to aquatic life

11. PRECAUTIONARY STATEMENTS (P-CODES)

Code	Statement
P264	Wash hands thoroughly after handling
P273	Avoid release to the environment
P280	Wear protective gloves/eye protection/face protection
P305+P351+P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing
P337+P313	If eye irritation persists: Get medical advice/attention

12. FIRST AID MEASURES

Route of Exposure	Action to Be Taken
Inhalation	Move to fresh air immediately. If symptoms (wheezing, coughing, shortness of breath) develop, call a physician
Skin Contact	Wash with plenty of soap and water. Remove contaminated clothing. If irritation develops, seek medical attention
Eye Contact	Rinse immediately with plenty of water for at least 15 minutes. Remove contact lenses if present. If irritation persists, seek medical attention
Ingestion	DO NOT INDUCE VOMITING. If conscious, give 1-2 glasses of water to dilute. Call a poison center or physician immediately
Note	Show this safety data sheet to the attending physician

13. FIRE-FIGHTING MEASURES

Parameter	Information
Fire Hazard	Combustible liquid; must be preheated before ignition can occur
Flash Point	~108-123 °C (closed cup)
Suitable Extinguishing Media	Water spray, alcohol-resistant foam, dry chemical, carbon dioxide (CO₂)
Special Hazards	May emit toxic fumes (carbon oxides, nitrogen oxides) under fire conditions
Protective Equipment	Firefighters should wear self-contained breathing apparatus (SCBA) and full protective clothing

14. ACCIDENTAL RELEASE MEASURES

Parameter	Information
Personal Protection	Use personal protective equipment. Avoid breathing vapors, mist, or gas
Ventilation	Ensure adequate ventilation
Containment	Absorb spill with inert material (e.g., vermiculite, sand, earth)
Cleaning Methods	Collect in suitable, closed containers for disposal. Solvent wash contaminated surfaces with alcohol followed by soap and water
Environmental Precautions	Do not let product enter drains or water bodies

15. HANDLING AND STORAGE

Parameter	Information
Handling Precautions	Use in well-ventilated areas. Avoid contact with skin, eyes, and clothing. Avoid inhalation of vapor or mist
Storage Conditions	Keep tightly closed in a cool, dry, well-ventilated place. Protect from light and heat. Store under inert atmosphere
Storage Temperature	Room temperature recommended; refrigerated conditions may be beneficial
Storage Class (TRGS 510)	10: Combustible liquids
Incompatibilities	Strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, strong bases, peroxides, phenols
Shelf Life	Typically 24 months under recommended storage conditions

16. EXPOSURE CONTROL AND PERSONAL PROTECTION

Parameter	Information
Engineering Controls	Use explosion-proof ventilation equipment to maintain below exposure limits
Eye Protection	Safety glasses with side-shields or chemical safety goggles (EN166)
Skin Protection	Impervious gloves (nitrile rubber recommended; break-through time ≥ 480 min). Appropriate protective clothing
Respiratory Protection	Full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) cartridge
Hygiene Measures	Wash hands thoroughly before breaks and at end of workday. Remove contaminated clothing and wash before reuse

17. REGULATORY INFORMATION

Region / Authority	Status
USA (FDA)	GRAS for food applications
USA (EPA)	Registered for use as bird repellent
EU (FLAVIS)	Listed as flavoring substance
JECFA	Evaluated; ADI = 0-1.5 mg/kg
FDA 21 CFR 117	Compliant
EU Regulation 1334/2008 & 178/2002	Compliant
IFRA	Restricted; consult current IFRA standards
Kosher/Halal	Available (grade dependent)
California Prop 65	Not listed
IARC	Not classified as carcinogen
NTP	Not listed
OSHA	Not otherwise classified as hazardous

18. ENVIRONMENTAL INFORMATION

Parameter	Information
Aquatic Toxicity	Toxic to aquatic life (H401)
Biodegradability	Fully biodegradable
Environmental Precautions	Do not allow to enter drains, sewers, or water bodies
Ecotoxicity Classification	WGK (Germany): Not specifically classified
Bioaccumulation	Not expected to bioaccumulate significantly
Persistence	Readily degradable under environmental conditions

19. SYNONYMS AND OTHER NAMES

Methyl 2-aminobenzoate
2-Aminobenzoic acid methyl ester
2-Carbomethoxyaniline
Methyl o-aminobenzoate
Anthranilic acid methyl ester
Neroli oil, artificial
Bird Shield
ReJex-iT
Nevoli oil
o-Aminobenzoic acid methyl ester
FEMA 2682
Methyl anthranilate (INCI)

20. QUICK REFERENCE TABLE

Property	Value
CAS Number	134-20-3
EC Number	205-132-4
FEMA Number	2682
Molecular Formula	C₈H₉NO₂
Molecular Weight	151.16 g/mol
Appearance	Clear to pale yellow liquid
Odor	Fruity, Concord grape-like
Melting Point	24-24.5 °C
Boiling Point	256 °C
Flash Point	108-123 °C
Density	1.168 g/cm³ at 25 °C
Water Solubility	2.85 g/L (slightly soluble)
log P	1.88-2.04
GHS Signal Word	WARNING
Hazard Statements	H319, H401
Shelf Life	24 months
FDA Status	GRAS
UN Number	Not applicable

21. CRITICAL NOTICES AND BEST PRACTICES

CRITICAL NOTICES:

Light and Air Sensitivity: Methyl anthranilate is sensitive to light and air. Store in tightly closed containers under inert atmosphere in amber glass or opaque packaging. Protect from light.
Eye Irritation: Causes serious eye irritation (H319). Always wear safety goggles when handling. In case of eye contact, rinse thoroughly for at least 15 minutes and seek medical attention if irritation persists.
Combustible Nature: Combustible liquid with flash point > 100°C. Avoid ignition sources. Use appropriate fire-fighting measures.
Incompatibility: Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, strong bases, peroxides, and phenols.
Environmental Hazard: Toxic to aquatic life (H401). Prevent release into drains, sewers, or water bodies.
IFRA Compliance: Restricted in fragrance formulations. Always consult current IFRA standards for maximum allowable use levels.

BEST PRACTICE RECOMMENDATIONS:

Handling: Use in well-ventilated areas; avoid eye/skin contact; wear appropriate PPE.

Storage: Keep tightly closed in a cool, dry place; protect from light and heat; store under inert atmosphere.

Transport: Not classified as dangerous goods; protect from moisture and heat.

Disposal: Dispose in accordance with local regulations; do not release into environment.

Documentation: Always consult the current Safety Data Sheet (SDS) for the specific product before use.

LEGAL DISCLAIMER

This Technical Data Sheet (TDS) is for informational purposes only and is prepared based on available technical data. The user is solely responsible for determining the suitability of the product for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, handling, transport, waste, and regulatory compliance information, the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier must be consulted. This document does not substitute professional advice. IFRA standards and FDA regulations are subject to change; consult current regulations for compliance.

Methyl Anthranilate, Methyl 2-aminobenzoate, 134-20-3