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Menthyl anthranilate is an oil-soluble ester derived from menthol and anthranilic acid that functions as a chemical sunscreen agent, primarily absorbing ultraviolet A (UV-A) radiation.
Because it does not provide significant UV-B protection, Menthyl anthranilate is rarely used alone but is combined with other UV filters such as avobenzone or oxybenzone to achieve broad-spectrum sun protection.
Although its usage has declined with the advent of newer, more efficient filters, Menthyl anthranilate remains FDA-approved at concentrations up to 5% and continues to be used in niche sunscreens, lip balms, and dermatological products.
CAS Number: 865-47-4
EC Number: 212-718-0
Molecular Formula: C18H25NO2
Molecular Weight: 287.40 g/mol
Synonyms: MENTHYL ANTHRANILATE, Meradimate, 134-09-8, Meradimate [INN], Menthyl-O-aminobenzoate, (5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoate, Anthranilic acid, p-menth-3-yl ester, Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 2-aminobenzoate, 2-isopropyl-5-methylcyclohexyl 2-aminobenzoate, J9QGD60OUZ, DTXSID3047895, Cyclohexanol,5-methyl-2-(1-methylethyl)-, 1-(2-aminobenzoate), 5-methyl-2-(propan-2-yl)cyclohexyl 2-aminobenzoate, NCGC00159361-02, DTXCID3027871, CAS-134-09-8, CCRIS 2468, Menthyl o-aminobenzoate, EINECS 205-129-8, UNII-J9QGD60OUZ, Meradimato, Meradimate [USAN:USP:INN], Neo heliopan MA, Meradimate (USP/INN), MERADIMATE [USAN], Menthyl anthranilate, 98%, MERADIMATE [MART.], MERADIMATE [USP-RS], MERADIMATE [WHO-DD], SCHEMBL18884, 5-Methyl-2-(1-methylethyl)cyclohexanol-2-aminobenzoate, CHEMBL1597075, MENTHYL ANTHRANILATE [MI], CHEBI:135974, MERADIMATE [USP MONOGRAPH], Tox21_111602, Tox21_200561, BBL028008, STK083062, AKOS001387784, AKOS017278349, DB11096, Menthyl anthranilate, analytical standard, NCGC00159361-06, NCGC00258115-01, VS-08642, DB-042217, NS00008634, D04927, 2-aminobenzoic acid (2-isopropyl-5-methyl-cyclohexyl) ester, Meradimate, United States Pharmacopeia (USP) Reference Standard, Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-(2-aminobenzoate), Menthyl anthranilate, Pharmaceutical Secondary Standard, Certified Reference Material,2-Aminobenzoic acid 5-methyl-2-isopropylcyclohexyl ester, Menthyl Anthranilate (500 mg/ampule) (Meradimate), 2-isopropyl-5-Methylcyclohexyl 2-aMinobenzoate, Menthyl o-aminobenzoate, Meradimate (500 mg/ampule) (Menthyl Anthranilate), MERADIMATE, MERADIMATE,USP, 5-Methyl-2-(1-methylethyl)-cyclohexanol 2-aminobenzoate
Menthyl anthranilate is an organic compound that functions primarily as a chemical sunscreen agent, belonging to the anthranilate class of UV filters.
Menthyl anthranilate is an oil-soluble ester derived from menthol and anthranilic acid, giving it both UV-absorbing capability and a mild mint-like odor.
Menthyl anthranilate is especially effective at absorbing UVA radiation (320–360 nm), though it does not cover the entire UVA spectrum, which is why it is commonly combined with other UV filters such as oxybenzone or avobenzone to achieve broad-spectrum protection.
In sunscreen formulations, Menthyl anthranilate helps protect the skin from photoaging, pigmentation, and long-term DNA damage caused by UVA exposure, while reducing the risk of skin cancer associated with chronic sun damage.
Beyond sunscreens, Menthyl anthranilate is also used in certain cosmetics and personal care products like lip balms, lotions, and daily moisturizers with SPF, owing to its stability and compatibility with other ingredients.
Although less widely used today compared to newer filters, Menthyl anthranilate remains an FDA-approved sunscreen active in the United States at concentrations up to 5%, reflecting its long history of safety and regulatory acceptance.
Menthyl anthranilate is currently required to be named as Menthyl anthranilate in all FDA approved OTC products.
Menthyl anthranilate is approved by the FDA and Health Canada to be used as an ingredient in sunblocking products.
Menthyl anthranilate is an organic compound that is primarily used as a sunscreen agent due to its ability to absorb ultraviolet (UV) radiation.
Menthyl anthranilate is a sunscreening agent.
Menthyl anthranilate is one of the 17 ingredients approved by the Food and Drug Administration for use in over-the-counter sunscreen products.
Menthyl anthranilate is used in a maximal concentration of 5% in different products as a UV filter.
Menthyl anthranilate is an ester derived from anthranilic acid and menthol, which gives it mild aromatic properties and makes it suitable for various cosmetic and personal care applications.
Menthyl anthranilate is particularly effective at absorbing UV-A rays, which are responsible for skin aging, DNA damage, and an increased risk of skin cancer caused by prolonged sun exposure.
Unlike some other sunscreen ingredients that provide broad-spectrum protection, Menthyl anthranilate is mainly effective against UV-A radiation and is often combined with other UV filters in sunscreen formulations to enhance overall sun protection.
Menthyl anthranilate is considered to be relatively gentle on the skin and is less likely to cause irritation compared to some chemical sunscreens, making it a preferred ingredient in products designed for individuals with sensitive skin.
In addition to its role in sun protection, Menthyl anthranilate is sometimes used in cosmetics and skincare products for its mild antioxidant properties, which help reduce oxidative stress and protect the skin from environmental damage.
Menthyl anthranilate is also found in certain pharmaceutical and dermatological formulations where UV protection is necessary to prevent photosensitivity reactions.
Although Menthyl anthranilate was once commonly used in commercial sunscreen formulations, its usage has declined in some regions due to the increasing demand for broader-spectrum UV filters and concerns about its overall effectiveness compared to newer alternatives.
However, Menthyl anthranilate is still recognized by regulatory agencies such as the United States Food and Drug Administration (FDA) as a safe and approved sunscreen ingredient.
Menthyl anthranilate is used as an active ingredient in sunscreens or as a sunblock factor in different products.
Menthyl anthranilate fits under the category of broad-spectrum absorbent agent.
These characteristics are important to consider due to the fact that this kind of ingredients can either absorb or reflect UV radiation.
Menthyl anthranilate is also important to know the type of rays that cover.
UVA rays are the responsible of causing sun damage and reaching deeper layers of the skin while UVB can only cause sunburn in the outer layer of the skin.
When an agent is of broad spectrum, this means that this agent is capable of acting in both UVA and UVB rays.
Menthyl anthranilate remains a valuable compound in the field of dermatology and cosmetic science due to its ability to provide targeted UV-A protection while being gentle on the skin.
Menthyl anthranilate continues to be an ingredient in select sunscreens, skincare products, and pharmaceutical formulations aimed at shielding the skin from harmful radiation and oxidative stress.
Menthyl anthranilate acts by absorbing both the UVA and UVB radiation, this provides this ingredient with a broad spectrum and it explains why it is highly used in different products such as lip balms, lipsticks, and moisturizers.
Menthyl anthranilates protective effective action does not cover completely the UVA rays as it only reaches 336 nm.
This has been proven even thought Menthyl anthranilate has a theoretical protective coverage range between 200-380 nm.
Its function is related to the intrinsic structure of Menthyl anthranilate which is an ortho-disubstituted aminobenzoate.
This structure allows easy electron delocalization and shifts in the maximum absorption.
Menthyl anthranilate is an organic chemical compound that has been widely used as a UV-A sunscreen filter due to its ability to absorb long-wave ultraviolet radiation.
Structurally, Menthyl anthranilate is an ester derived from menthol and anthranilic acid, which gives it a mild aromatic scent and makes it oil-soluble, allowing for easy formulation in various cosmetic and pharmaceutical products.
Unlike physical sunscreens like zinc oxide or titanium dioxide, which act as UV reflectors, Menthyl anthranilate functions as a chemical absorber, converting UV radiation into heat and preventing it from penetrating deeper into the skin.
One of the key benefits of Menthyl anthranilate is its selective absorption of UV-A rays, which are known to penetrate the skin more deeply than UV-B rays and contribute to long-term damage such as photoaging, collagen breakdown, and an increased risk of skin cancer.
However, since Menthyl anthranilate does not offer significant protection against UV-B rays, which are responsible for sunburns, Menthyl anthranilate is rarely used alone in sunscreens and is instead combined with other active ingredients that provide a more comprehensive broad-spectrum defense against sun damage.
Menthyl anthranilate is particularly useful in formulations designed to reduce the risk of premature aging, hyperpigmentation, and other UV-induced skin concerns.
Menthyl anthranilate is provided as delivered and specified by the issuing Pharmacopoeia.
All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.
Sunscreen products are intended to be applied to the body every day, over the course of a lifetime.
The companies that make and sell sunscreen ingredients and products should test them thoroughly for potential short-term and long-term health effects.
This includes toxicity testing for irritation and skin allergies, as well as testing for skin absorption and the potential to cause cancer, disrupt the hormone system and impact reproduction and development.
Menthyl anthranilate is a chemical UVA absorber found in personal care products including sunscreens, insect repellants, hair care, and cosmetic products.
Chemical sunscreen agents diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range.
In cosmetics and personal care products, Menthyl anthranilate is used in the formulation of sun protection products, eyebrow pencils, foundations, and lipsticks.
When used in sun protection products in the United States, Menthyl Anthranilate must be called Menthyl anthranilate.
Menthyl anthranilate, when applied to the skin, absorbs UV rays.
In addition to causing sunburn, UV radiation is a significant cause of premature aging of the skin and contributes to the development of melanoma and other forms of skin cancer.
Menthyl anthranilate is an organic sunscreen agent primarily used to absorb ultraviolet A (UV-A) radiation, which is known to cause long-term skin damage such as premature aging, DNA mutations, and an increased risk of skin cancer.
Menthyl anthranilate belongs to the class of chemical sunscreens that function by absorbing UV radiation and dissipating it as heat, thereby preventing the harmful rays from penetrating deeper into the skin.
Menthyl anthranilate is derived from menthol and anthranilic acid, giving it mild aromatic properties and a relatively stable molecular structure that allows it to function effectively in various sunscreen formulations.
Unlike broad-spectrum UV filters that protect against both UV-A and UV-B rays, Menthyl anthranilate is specifically designed to absorb UV-A rays, which penetrate the skin more deeply than UV-B rays and contribute to the degradation of collagen and elastin, leading to wrinkles, sagging, and other signs of aging.
Because of its limited UV-B protection, Menthyl anthranilate is rarely used as a standalone sunscreen agent but is instead combined with other active ingredients that provide complementary UV-B protection, such as zinc oxide, titanium dioxide, avobenzone, and octinoxate, to ensure comprehensive sun defense.
In addition to its role in sun protection, Menthyl anthranilate has been explored for its antioxidant properties, which may help mitigate oxidative stress caused by environmental pollutants and UV exposure.
This characteristic makes Menthyl anthranilate a potential ingredient in skincare products designed to combat free radical damage and reduce inflammation.
Furthermore, due to its relatively low potential for skin irritation and sensitization, Menthyl anthranilate is considered suitable for use in sunscreens formulated for individuals with sensitive or reactive skin.
Menthyl anthranilate is also used in after-sun lotions, lip balms, anti-aging creams, and other skincare products where UV protection is beneficial.
Regulatory bodies such as the U.S. Food and Drug Administration (FDA) have approved Menthyl anthranilate for use in sunscreen formulations at concentrations of up to 5%, although its popularity has declined in recent years due to the emergence of newer, more efficient broad-spectrum UV filters.
Despite this, Menthyl anthranilate remains an accepted and legal UV filter in certain regions and continues to be used in niche skincare and dermatological applications.
In some cases, Menthyl anthranilate has been included in pharmaceutical preparations designed for individuals who are prone to photosensitivity disorders, as it helps reduce skin reactions triggered by UV exposure.
Although Menthyl anthranilate is less commonly found in mainstream sunscreens today, its history and continued presence in select formulations highlight its importance as one of the early chemical filters used to protect against UV-A radiation.
With the increasing focus on photoprotection and anti-aging skincare, Menthyl anthranilate remains a compound of interest for researchers and formulators who aim to develop safer and more effective sun protection solutions.
Menthyl anthranilate has also been explored for its potential antioxidant properties, as studies suggest that it may help neutralize free radicals generated by UV exposure and environmental pollutants.
This makes Menthyl anthranilate a potential ingredient in anti-aging skincare, where oxidative stress is a major contributing factor to wrinkles, loss of elasticity, and uneven skin tone.
Some cosmetic formulations, including moisturizers, foundations, and tinted sunscreens, incorporate Menthyl anthranilate not only for its UV-A protection but also for its skin-conditioning benefits.
Menthyl anthranilate is also included in some lip balms, after-sun care products, and specialized dermatological treatments for individuals with heightened sensitivity to UV radiation.
Despite its benefits, the use of Menthyl anthranilate in sunscreen formulations has declined in recent years due to the growing demand for more advanced and broad-spectrum UV filters.
Regulatory agencies such as the U.S. Food and Drug Administration (FDA) have approved Menthyl anthranilate for use in over-the-counter sunscreens at concentrations of up to 5%, but it has become less common in mainstream sun care products due to the development of newer, more efficient alternatives like avobenzone, Tinosorb S, and Mexoryl SX.
In some regions, regulatory changes and consumer preferences have led to a decrease in its usage, as modern sunscreens aim to offer superior stability and photoprotective efficacy.
However, Menthyl anthranilate continues to be recognized as a safe and effective ingredient in certain specialized applications.
Menthyl anthranilate is sometimes included in pharmaceutical sunscreens prescribed for individuals with medical conditions that make them highly sensitive to UV exposure, such as lupus, rosacea, and certain photodermatoses.
Additionally, Menthyl anthranilate remains a component in some legacy formulations where its mild nature and compatibility with other ingredients make it a useful addition to sunscreen blends.
As research into sunscreen technology advances, there is ongoing interest in improving the stability, photostability, and efficacy of existing UV filters, including Menthyl anthranilate.
Some studies have explored ways to enhance Menthyl anthranilate's performance through encapsulation in nanocarriers, combination with stabilizing agents, or incorporation into multi-functional skincare products that offer both sun protection and anti-aging benefits.
While its prominence in commercial sunscreens may have diminished, Menthyl anthranilate remains a valuable compound in the field of photoprotection, with potential applications in both dermatological and cosmetic science.
With growing concerns about the impact of chemical sunscreens on marine ecosystems, particularly coral reefs, certain UV filters such as oxybenzone and octinoxate have been banned in places like Hawaii and Palau due to their toxic effects on coral reefs.
While Menthyl anthranilate has not been extensively studied in relation to coral reef damage, there is no strong evidence suggesting that it has significant environmental toxicity.
However, because Menthyl anthranilate is an organic UV filter, further research is needed to fully assess its potential impact on marine life.
Market Overview of Menthyl Anthranilate:
While specific market data for Menthyl anthranilate is scarce due to its limited use compared to mainstream UV filters, it falls under the broader UV‑absorbing chemicals for cosmetics category.
This market offers insight into Menthyl anthranilate's trends and potential:
The global UV‑absorbing chemicals market—which covers categories like benzophenones (Menthyl anthranilate’s class), salicylates, cinnamates, anthranilates, and mineral filters—was valued at approximately USD 547 million in 2023 and is projected to grow to around USD 1.1 billion by 2034, achieving a CAGR of 6.2% between 2024 and 2034.
Within the wider sun‑protection active ingredients landscape, the market was estimated at USD 816 million in 2023, expected to expand to USD 1.37 billion by 2033, with a 5.3% CAGR.
The overall suncare products market, where Menthyl anthranilate is utilized in formulations, is forecasted to rise from USD 15.43 billion in 2025 to USD 28.96 billion by 2035, with strong demand across sunscreens and skincare lines.
Key Takeaways for Menthyl anthranilate:
Market Position:
Menthyl anthranilate is a niche UVA filter within a rapidly growing UV-filter ingredient market.
Growth Drivers:
Rising awareness about UV protection and demand for multi-functional, photostable, and eco-conscious formulants.
Significance:
While Menthyl anthranilate itself may represent a small share, it belongs to a sector poised to double in size over the next decade.
Uses of Menthyl Anthranilate:
Menthyl anthranilate is the only FDA-approved liquid sunscreen chemical with uVA-absorption capabilities.
Menthyl anthranilate has an approved usage level of 3.5 to 5 percent.
This is a stable ingredient and can be combined with other sunscreen chemicals to increase SPF while providing uVA protection.
Menthyl anthranilate is a weak UVB filter and with absorption mainly in the near UVA portion of the spectrum.
They are less effective than benzophenones in this range and are less widely used.
Menthyl anthranilate is used as a UV filter in skin care formulations.
Sunscreens are used to protect the skin from the harmful effects of the sun.
They help to prevent sunburn and premature aging (such as wrinkles, leathery skin).
Sunscreens also help to decrease the risk of skin cancer and also of sunburn-like skin reactions (sun sensitivity) caused by some medications (including tetracyclines, sulfa drugs, phenothiazines such as chlorpromazine).
The active ingredients in sunscreens work either by absorbing the sun's ultraviolet (UV) radiation, preventing it from reaching the deeper layers of the skin, or by reflecting the radiation.
Wearing sunscreen does not mean that you can stay out longer in the sun. Sunscreens cannot protect against all of the sun's radiation.
There are various types of sunscreens available in many forms (such as cream, lotion, gel, stick, spray, lip balm).
Menthyl anthranilate serves multiple purposes across the fields of sun protection, skincare, and dermatology.
Menthyl anthranilate's ability to absorb UV-A radiation makes it a key ingredient in sunscreens, daily skincare products, and cosmetics designed to prevent photoaging and sun damage.
Additionally, Menthyl anthranilate's mild nature and compatibility with sensitive skin make it a valuable component in pharmaceutical and dermatological preparations aimed at individuals with photosensitivity conditions.
While its use has become less widespread due to the introduction of newer UV filters, Menthyl anthranilate remains an effective and approved option for sun protection, particularly in specialized formulations where its unique benefits continue to be recognized.
Menthyl anthranilate has several uses primarily related to its ability to absorb ultraviolet A (UV-A) radiation, making it a valuable ingredient in sunscreen formulations.
Menthyl anthranilate's primary function is to protect the skin from the harmful effects of long-wave UV-A rays, which are known to penetrate deeper into the skin than UV-B rays and contribute to premature aging, DNA damage, and an increased risk of skin cancer.
By acting as a chemical UV filter, Menthyl anthranilate absorbs UV-A radiation and converts it into less harmful heat energy, preventing it from reaching the deeper layers of the skin where it can cause cellular damage.
One of the most common applications of Menthyl anthranilate is in sunscreen products, where it is often combined with other UV filters to provide a broader spectrum of sun protection.
Since Menthyl anthranilate primarily absorbs UV-A rays but offers limited protection against UV-B radiation, it is frequently formulated alongside ingredients such as zinc oxide, titanium dioxide, avobenzone, and octinoxate to ensure comprehensive protection against both UV-A and UV-B exposure.
This combination helps prevent sunburn, skin discoloration, and long-term damage such as collagen breakdown and wrinkles.
In addition to its use in traditional sunscreens, Menthyl anthranilate is also found in various skincare and cosmetic products that offer sun protection.
Many moisturizers, foundations, tinted sunscreens, lip balms, and anti-aging creams contain Menthyl anthranilate as an active ingredient to provide daily UV defense while also delivering hydration, skin-conditioning benefits, and antioxidant protection.
By incorporating UV filters like Menthyl anthranilate into everyday skincare and makeup products, manufacturers help consumers maintain consistent sun protection throughout the day without relying solely on stand-alone sunscreens.
Beyond Menthyl anthranilate's cosmetic applications, Menthyl anthranilate is also used in pharmaceutical and dermatological formulations designed for individuals with heightened sensitivity to UV radiation.
Some people with medical conditions such as lupus, rosacea, polymorphous light eruption (PMLE), and other photosensitivity disorders require specialized sun protection to prevent skin flare-ups and irritation caused by UV exposure.
Menthyl anthranilate’s ability to absorb UV-A rays while being gentle on the skin makes it a useful ingredient in sunscreens formulated for these individuals, as it minimizes the risk of adverse reactions while offering effective protection against the sun’s damaging effects.
Additionally, Menthyl anthranilate has been explored for its mild antioxidant properties, which may help neutralize free radicals produced by UV exposure and environmental pollutants.
Free radicals contribute to oxidative stress, which is a major factor in premature aging, skin inflammation, and even some skin diseases.
By incorporating Menthyl anthranilate into skincare formulations, manufacturers can enhance the protective benefits of their products and support overall skin health.
This is particularly beneficial in anti-aging skincare lines, where ingredients that combat oxidative damage and support the skin’s natural repair mechanisms are highly valued.
Although Menthyl anthranilate has historically been a popular sunscreen ingredient, its usage has declined in some regions due to the growing preference for newer, more photostable UV filters with broader-spectrum protection.
However, Menthyl anthranilate is still approved for use by regulatory agencies such as the U.S. Food and Drug Administration (FDA), which allows its inclusion in over-the-counter sunscreen formulations at concentrations of up to 5%.
In certain niche applications, such as specialized dermatological sunscreens, after-sun care products, and formulations intended for sensitive skin, Menthyl anthranilate continues to be used due to its mild nature and UV-A protective properties.
Moreover, ongoing research in sunscreen technology has led to new formulation techniques that aim to improve the effectiveness and stability of UV filters like Menthyl anthranilate.
Some studies have investigated methods such as encapsulation in nanocarriers, combination with stabilizing agents, and integration into hybrid formulations that combine chemical and physical UV blockers.
These advancements may enhance Menthyl anthranilate’s role in future sun protection products and skincare applications, ensuring that it remains a viable option for those seeking targeted UV-A defense and gentle, skin-friendly formulations.
Sunscreens and Skincare:
Menthyl anthranilate is primarily used as a UVA sunscreen agent, protecting skin against long-wave UVA radiation (320–400 nm) that contributes to photoaging, hyperpigmentation, and skin cancers.
Menthyl anthranilate is often combined with UVB filters (like octocrylene or homosalate) to create broad-spectrum protection.
Cosmetic Formulations:
Menthyl anthranilate added to lotions, creams, lip balms, and makeup products to provide invisible UVA protection while maintaining smooth texture and good skin compatibility.
Personal Care Products:
Menthyl anthranilate is sometimes used in daily moisturizers and hair care formulations to protect hair and scalp from UV-induced damage, dryness, and color fading.
Industrial and Material Applications:
Menthyl anthranilate beyond cosmetics, Menthyl anthranilate’s UV-absorbing ability makes it useful in plastics, coatings, and adhesives to prevent photodegradation, discoloration, and brittleness caused by sunlight exposure.
Pharmaceutical Topicals:
Menthyl anthranilate can be incorporated into dermatological creams and ointments to shield sensitive or healing skin areas from UVA-related stress and damage.
Benefits of Menthyl Anthranilate:
UVA Protection:
Menthyl anthranilate provides strong absorption in the long-wave UVA spectrum (320–400 nm), offering protection against photoaging, pigmentation, and skin cancer risks.
Gentle on Skin:
Menthyl anthranilate compared to some chemical UV filters, Menthyl anthranilate is considered low-irritant and non-sensitizing, making it suitable for sensitive skin and daily-use products.
Cosmetic Compatibility:
Menthyl anthranilate's oil-soluble nature allows easy incorporation into lotions, creams, sprays, and makeup products without leaving a visible residue or altering texture.
Photostability:
Menthyl anthranilate is relatively stable under sunlight, helping to maintain long-lasting UVA protection and improving the performance of broad-spectrum sunscreen formulations.
Synergistic Effect:
When combined with UVB filters (e.g., octocrylene, homosalate, or octinoxate), Menthyl anthranilate enhances broad-spectrum coverage, creating more effective sun protection systems.
Material Protection:
Beyond skincare, Menthyl anthranilate’s UV-absorbing property helps protect plastics, coatings, and adhesives from degradation, extending the lifespan of consumer and industrial products.
Production of Menthyl Anthranilate:
Menthyl anthranilate is produced mainly for use in sunscreens and cosmetic formulations as a UVA filter.
Industrial production typically starts with natural menthol, which is obtained from peppermint oil or synthesized from thymol.
Menthol serves as the alcohol component for the esterification process.
The other key raw material is anthranilic acid (o-aminobenzoic acid), which functions as the acid component.
In large-scale production, anthranilic acid is often converted into a more reactive intermediate such as anthraniloyl chloride.
This intermediate is then reacted with menthol under controlled conditions, usually in the presence of an acid catalyst or coupling agent, to form the ester menthyl anthranilate (Menthyl anthranilate).
The resulting product is then purified through crystallization or distillation to remove impurities and ensure cosmetic-grade quality.
The final Menthyl anthranilate is an oil-soluble, stable crystalline compound suitable for incorporation into sunscreen creams, lotions, and sprays.
History of Menthyl Anthranilate:
Menthyl anthranilate was first synthesized in the early 20th century as part of research into aromatic ester derivatives of anthranilic acid, which had been studied for their pleasant fragrance and stability in perfumery.
By the mid-1900s, scientists discovered that certain anthranilate esters exhibited strong absorption in the ultraviolet A (UVA) range, making them useful as sun-protective agents.
Menthyl anthranilate was introduced into cosmetic formulations in the 1960s and 1970s, during a period when the sunscreen industry was shifting focus from preventing sunburn (primarily UVB protection) to addressing photoaging and deeper UVA damage.
Menthyl anthranilate's oil-soluble, stable structure allowed formulators to combine it with UVB filters, creating broader-spectrum protection.
In the 1980s and 1990s, Menthyl anthranilate was officially listed and approved as an active sunscreen ingredient by the U.S. Food and Drug Administration (FDA) at concentrations up to 5%, and later recognized in various international pharmacopeias.
Although its usage has declined in favor of newer UVA filters such as avobenzone, Menthyl anthranilate remains a historically significant agent, marking an important step in the development of modern multi-spectrum sunscreens.
Today, Menthyl anthranilate is still included in select sunscreen and personal care products, especially in regions that maintain its regulatory approval, and it is studied both for its photoprotective qualities and its role as an early example of anthranilate-based UV filters.
Handling and Storage of Menthyl Anthranilate:
Handle Menthyl anthranilate in accordance with good industrial hygiene and safety practices.
Avoid direct contact with eyes, skin, and clothing; use protective gloves and safety goggles when handling.
Store in a cool, dry, and well-ventilated area, away from direct sunlight and sources of heat.
Keep container tightly closed to prevent contamination and degradation.
Recommended storage temperature:
below 25 °C, protected from moisture.
Stability and Reactivity of Menthyl Anthranilate:
Menthyl anthranilate is generally stable under normal storage and handling conditions.
Avoid exposure to high temperatures, strong oxidizing agents, and strong acids or bases, which may cause decomposition.
Thermal decomposition may release irritating fumes such as carbon oxides (CO, CO₂) and nitrogen oxides (NOx).
Photostability:
Relatively stable but prolonged UV exposure can reduce efficiency.
First Aid Measures of Menthyl Anthranilate:
Inhalation:
Move the affected person to fresh air.
Seek medical attention if symptoms (cough, dizziness) occur.
Skin Contact:
Wash with soap and water.
Remove contaminated clothing.
Seek medical advice if irritation persists.
Eye Contact:
Rinse cautiously with water for several minutes.
Remove contact lenses if present.
Seek immediate medical attention if irritation continues.
Ingestion:
Rinse mouth with water.
Do not induce vomiting unless directed by medical personnel.
Seek medical attention immediately.
Firefighting Measures of Menthyl Anthranilate:
Suitable extinguishing media:
Water spray, dry chemical powder, foam, or carbon dioxide (CO₂).
Fire hazards:
Combustion may produce hazardous gases such as carbon monoxide, carbon dioxide, and nitrogen oxides.
Firefighters should wear self-contained breathing apparatus (SCBA) and protective clothing.
Prevent fire-extinguishing water from entering drains or surface waters.
Accidental Release Measures of Menthyl Anthranilate:
Avoid inhalation of vapors/dust and contact with skin or eyes.
Use appropriate personal protective equipment (PPE) such as gloves, goggles, and protective clothing.
Absorb spill with inert material (e.g., sand, vermiculite) and place in a suitable container for disposal.
Clean area thoroughly with water and detergent to remove residues.
Prevent release into the environment, especially waterways.
Exposure Controls / Personal Protection of Menthyl Anthranilate:
Engineering Controls:
Ensure adequate ventilation, preferably with local exhaust systems in production areas.
Personal Protective Equipment (PPE):
Respiratory Protection:
Not required under normal conditions; use mask if dust/vapor concentrations exceed exposure limits.
Skin Protection:
Wear protective gloves (nitrile or neoprene).
Eye Protection:
Safety glasses or chemical splash goggles.
Body Protection:
Protective clothing or lab coat.
Maintain good industrial hygiene practices:
Wash hands before breaks and after handling; do not eat, drink, or smoke in work areas.
Identifiers of Menthyl Anthranilate:
Common Name: Menthyl anthranilate
IUPAC Name: 3-(menthoxycarbonyl)aniline (or menthyl 2-aminobenzoate)
CAS Number: 865-47-4
EC Number (EINECS): 212-718-0
Molecular Formula: C₁₈H₂₅NO₂
Molecular Weight: 287.40 g/mol
Chemical Class: Aromatic ester (anthranilic acid ester of menthol)
UNII (FDA Unique Ingredient Identifier): A27T6M9L25
INCI Name: Menthyl anthranilate
Appearance: Pale yellow to amber viscous liquid or semi-solid
Odor: Mild, menthol-like with a floral note
CAS Number: 865-47-4
EC Number (EINECS): 212-718-0
PubChem CID: 24551
ChemSpider ID: 22947
ChEMBL ID: ChEMBL2106223
UNII (FDA Unique Ingredient Identifier): A27T6M9L25
KEGG ID: C14146
InChI: InChI=1S/C18H25NO2/c1-12-8-7-11(9-13(12)2)15(3)10-16(14-5-4-6-19-17(14)20)21-18(12)22/h4-6,11,15-16,18-19H,7-10H2,1-3H3,(H,20,22)/t11-,12-,15-,16+,18-/m1/s1
InChI Key: UIWBRKPLZZOWIH-VIFPVBQESA-N
SMILES: CC1CCC(C(C1)C(C)C)OC(=O)C2=CC=CC=C2N
Properties of Menthyl Anthranilate:
Molecular Formula: C₁₈H₂₅NO₂
Molar Mass: 287.40 g/mol
Appearance: Colorless to pale yellow oil-like liquid or viscous ester
Odor: Mild, faintly aromatic / menthol-like
Taste: Slightly bitter, aromatic
Density: ~ 1.07 g/cm³ (at 20 °C)
Melting Point: –12 °C to –10 °C (liquid at room temperature)
Boiling Point: ~ 150–152 °C at 1.5 mmHg (decomposes at higher temps under normal pressure)
Refractive Index: n²⁰D ~ 1.525–1.535
Flash Point: > 150 °C (closed cup)
Vapor Pressure: Very low (negligible at 25 °C)
Solubility:
Water: Practically insoluble (< 0.1 g/L at 25 °C)
Soluble in: Organic solvents such as ethanol, isopropanol, acetone, chloroform, and oils
Lipophilicity (LogP): ~ 5.6 (highly lipophilic)
Melting point: 62.5-63.5°
Boiling point: 177-179 °C (3 mm Hg, lit.)
Density: 1.04 g/mL at 25 °C (lit.)
Refractive index: n20/D 1.542 (lit.)
Flash point: >230 °F
Storage temp.: 2-8°C
Form: Liquid
pKa: 2.17±0.10 (Predicted)
Odor: At 100.00%: grape menthol
Odor Type: Fruity
LogP: 6.085 (est)
Molecular Formula: C₁₈H₂₅NO₂
Molecular Weight: 287.40 g/mol
Monoisotopic Mass: 287.1885 g/mol
Structure: Ester formed from menthol (a cyclic monoterpene alcohol) and anthranilic acid (o-aminobenzoic acid).
State at Room Temperature: Viscous liquid to semi-solid
Color: Pale yellow to colorless
Odor: Mild, slightly mentholated and aromatic
Density: ~ 1.07–1.08 g/cm³ (at 20 °C)
Refractive Index (n²⁰D): ~ 1.525–1.535
Melting Point: –12 to –10 °C
Boiling Point: ~ 150–152 °C (at 1.5 mmHg vacuum distillation)
Flash Point: > 150 °C (closed cup)
Viscosity: High (oil-like consistency)
