Methyl anthranilate

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Methyl anthranilate
Methyl anthranilate.svg
Methyl anthranilate-3D-balls.png
Names
Preferred IUPAC name
Methyl 2-aminobenzoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.667 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-132-4
KEGG
PubChem CID
UNII
  • InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3 X mark.svgN
    Key: VAMXMNNIEUEQDV-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
    Key: VAMXMNNIEUEQDV-UHFFFAOYAV
  • COC(=O)c1c(N)cccc1
Properties
C8H9NO2
Molar mass 151.165
Appearancecolorless liquid
Odor grape-like
Density 1.168 g/cm3
Melting point 24 °C (75 °F; 297 K)
Boiling point 256 °C (493 °F; 529 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H319
P264, P280, P305+P351+P338, P337+P313
Flash point 104 °C (219 °F; 377 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Methyl anthranilate, also known as MA, methyl 2-aminobenzoate, or carbomethoxyaniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2. It has a strong and fruity grape smell, and one of its key uses is as a flavoring agent.

Contents

Chemical properties

It is a colorless to pale yellow liquid with melting point 24 °C and boiling point 256 °C. It has a density of 1.168 g/cm3 at 20 °C. [1] It has a refractive index of 1.583 at 589 nm of wavelength and 20 °C. [2] It shows a light blue-violet fluorescence. It is very slightly soluble in water, and soluble in ethanol and propylene glycol. It is insoluble in paraffin oil. It is combustible, with flash point at 104 °C. Pure, it has a fruity grape smell; at 25 ppm it has a sweet, fruity, Concord grape-like smell with a musty and berry nuance. [3] [4]

Uses

Methyl anthranilate acts as a bird repellent by irritating sensory receptors. [5] Dimethyl anthranilate (DMA) has a similar effect. It is also used for part of the flavor of grape Kool-Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), fruit (e.g. Grāpples), chewing gum, and nicotine products. [6]

Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery. [3] [7] It is also used to produce Schiff bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol, [8] produced by combining methyl anthranilate and hydroxycitronellal. [9]

In organic synthesis, methyl anthranilate can be used as a source of the highly reactive aryne, benzyne. It is obtained by diazotization of the amine group using sodium nitrite which eliminates nitrogen and CO2 giving benzyne as an intermediate for Diels-Alder addition or other substitution at the ring. [10]

Occurrence

Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes and hybrids thereof, and in bergamot, black locust, champak, gardenia, jasmine, lemon, mandarin orange, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal, and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate. [11]

Related Research Articles

<span class="mw-page-title-main">Flavoring</span> Food additive used to change its aroma or taste

A flavoring, also known as flavor or flavorant, is a food additive used to improve the taste or smell of food. It changes the perceptual impression of food as determined primarily by the chemoreceptors of the gustatory and olfactory systems. Along with additives, other components like sugars determine the taste of food.

Perfume is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Perfumes can be defined as substances that emit and diffuse a pleasant and fragrant odor. They consist of manmade mixtures of aromatic chemicals and essential oils. The 1939 Nobel Laureate for Chemistry, Leopold Ružička stated in 1945 that "right from the earliest days of scientific chemistry up to the present time, perfumes have substantially contributed to the development of organic chemistry as regards methods, systematic classification, and theory."

<i>Cananga odorata</i> Species of tree

Cananga odorata, known as ylang-ylang or cananga tree, is a tropical tree that is native to the Philippines, Malaysia, Indonesia, New Guinea, the Solomon Islands, and Queensland, Australia. It is also native to parts of Thailand and Vietnam. It is valued for the essential oils extracted from its flowers, which has a strong floral fragrance. Ylang-ylang is one of the most extensively used natural materials in the perfume industry, earning it the name "Queen of Perfumes".

<span class="mw-page-title-main">Ethyl butyrate</span> Chemical compound

Ethyl butyrate, also known as ethyl butanoate, or butyric ether, is an ester with the chemical formula CH3CH2CH2COOCH2CH3. It is soluble in propylene glycol, paraffin oil, and kerosene. It has a fruity odor, similar to pineapple, and is a key ingredient used as a flavor enhancer in processed orange juices. It also occurs naturally in many fruits, albeit at lower concentrations.

<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.

<span class="mw-page-title-main">Castoreum</span> Fluid produced by beavers

Castoreum is a yellowish exudate from the castor sacs of mature beavers. Beavers use castoreum in combination with urine to scent mark their territory. Both beaver sexes have a pair of castor sacs and a pair of anal glands, located in two cavities under the skin between the pelvis and the base of the tail. The castor sacs are not true glands on a cellular level, hence references to these structures as preputial glands, castor glands, or scent glands are misnomers.

<span class="mw-page-title-main">Neroli</span> Essential oil of the bitter orange blossom

Neroli oil is an essential oil produced from the blossom of the bitter orange tree. Its scent is sweet, honeyed and somewhat metallic with green and spicy facets. Orange blossom is also extracted from the same blossom and both extracts are extensively used in perfumery. Orange blossom can be described as smelling sweeter, warmer and more floral than neroli. The difference between how neroli and orange blossom smell and why they are referred to with different names, is a result of the process of extraction that is used to obtain the oil from the blooms. Neroli is extracted by steam distillation and orange blossom is extracted via a process of enfleurage or solvent extraction.

<span class="mw-page-title-main">Ethyl salicylate</span> Chemical compound

Ethyl salicylate is the ester formed by the condensation of salicylic acid and ethanol. It is a clear liquid that is sparingly soluble in water, but soluble in alcohol and ether. It has a pleasant odor resembling wintergreen and is used in perfumery and artificial flavors.

2-Undecanone, also known as methyl nonyl ketone and IBI-246, is the organic compound with the formula CH3C(O)C9H19. It a colorless oil. It is usually produced synthetically, but it can also be extracted from various plant sources, including from essential oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial leaf vegetable Houttuynia cordata.

<span class="mw-page-title-main">Orris oil</span> Oil obtained from the root of iris × germanica

Orris oil is an essential oil derived from irises, particularly Iris germanica. It is sometimes used as a flavoring agent and as an ingredient in perfume production. It can also have uses in body lotions.

<span class="mw-page-title-main">Manzanate</span> Chemical compound

Ethyl 2-methylvalerate (systematically ethyl 2-methylpentanoate, commonly referred to as manzanate) is the organic compound with the formula CH3CH2CH2(H3C)CHCO2CH2CH3. This colorless liquid has a fruity apple smell and with aspects of cider and sweet pineapple. It is commonly used as a flavoring agent, but has a wide range of applications. 2-Methylpentanoic acid esters have at least 2 enantiomers. It is common for enantiomers to have distinct or similar smells.

Grape drinks are sweetened drinks with a grape flavor and a deep purple color. They may be carbonated or not.

Ethyl decadienoate, also known as pear ester, is an organic chemical compound used in flavors and perfumery for its pear-like taste and odor.

<span class="mw-page-title-main">Methyl propionate</span> Chemical compound

Methyl propionate, also known as methyl propanoate, is an organic compound with the molecular formula CH3CH2CO2CH3. It is a colorless liquid with a fruity, rum-like odor.

Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C(CH
2
)
k
CH=CH(CH
2
)
7-k
–H, where k is between 0 and 7 inclusive.

Anthranilate-based insect repellents include methyl anthranilate, N,N-dimethylanthranilic acid (DMA), ethyl anthranilate (EA), and butyl anthranilate (BA). Chemically, they are esters of anthranilic acid. While the United States Food and Drug Administration (FDA) has approved some of these compounds for use as food additives, cinnamyl anthranilate is banned by the FDA. The compounds repel both fruit flies and mosquitos, and target the same neurons that respond to DEET. The receptors are located on part of the antennae known as the Sacculus.

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers. It is used in the creation of synthetic fruity scents.

References

  1. Kováts, Kugler (1963). "Zur Kenntnis ätherischer Öle. 1. Mitteilung. Zur Kenntnis des Mandarinenschalen-Öls (Citrus reticulata BLANCO, bzw. Citrus nobilis var. deliciosa SWINGLE "Mandarin")". Helvetica Chimica Acta. 46 (5): 1480–1513. doi:10.1002/hlca.19630460506.
  2. Halama; Pytela (1996). "Steric Effects in Acid-Catalyzed Decomposition and Base-Catalyzed Cyclization of 1-(2-Alkoxycarbonylphenyl)-3-phenyltriazenes". Collection of Czechoslovak Chemical Communications. 61 (5): 751. doi:10.1135/cccc19960751.
  3. 1 2 The Good Scents Company: Methyl anthranilate
  4. The Japan Food Chemical Research Foundation
  5. Ahmad, Shahzad, et al. "Effectiveness of methylanthranilate and anthraquinone as repellent against house crows (Corvus splendens) on wheat seeds and seedlings in captivity." Pakistan Journal of Zoology 48.5 (2016).
  6. Brown, Jessica E.; Luo, Wentai; Isabelle, Lorne M.; Pankow, James F. (2014). "Candy Flavorings in Tobacco". New England Journal of Medicine. 370 (23): 2250–2252. doi: 10.1056/NEJMc1403015 . PMID   24805984.
  7. An Introduction to Perfumery by Curtis & Williams 2nd Edition, 2009, ISBN   978-0-9608752-8-3, ISBN   978-1-870228-24-4
  8. The Chemistry of Fragrances: From Perfumer to Consumer, ed. Charles Sell, ISBN   0-85404-824-3, ISBN   978-085404-824-3
  9. Good Scents Company Page for Aurantiol
  10. Tadross, Pamela M.; Stoltz, Bryan (2012). "A Comprehensive History of Arynes in Natural Product Total Synthesis". Chem. Rev. 112 (6): 3550–3577. doi:10.1021/cr200478h. PMID   22443517 . Retrieved 20 November 2022.
  11. Daniele Fraternale, Donata Ricci, Guido Flamini and Giovanna Giomaro. Volatiles Profile of Red Apple from Marche Region (Italy). Rec. Nat. Prod. (2011), 5:3; 202-207. pdf