COUMARIN
Coumarin is a naturally occurring aromatic organic compound belonging to the benzopyrone chemical class, widely found in plants such as tonka beans, cinnamon, vanilla, sweet clover, and various other botanicals.
Coumarin is extensively used in perfumes, cosmetics, and household products due to its sweet, vanilla-like fragrance, while also serving as a precursor to anticoagulant drugs like warfarin.
Despite its valuable applications, coumarin’s direct use in food products is restricted in many countries due to concerns over its potential hepatotoxicity and regulatory safety limits.
CAS Number: 91-64-5
EC Number: 202-086-7
Chemical Formula: C9H6O2
Molar Mass: 146.145 g·mol−1
Synonyms: coumarin, 91-64-5, 2H-Chromen-2-one, 2H-1-Benzopyran-2-one, cumarin, 1,2-Benzopyrone, chromen-2-one, Rattex, Coumarinic anhydride, Tonka bean camphor, Coumarine, cis-o-Coumarinic acid lactone, Coumarinic lactone, o-Hydroxycinnamic acid lactone, Benzo-alpha-pyrone, o-Hydroxycinnamic lactone, 2-Oxo-1,2-benzopyran, Kumarin, Benzo-a-pyrone, 2H-Benzo(b)pyran-2-one, 5,6-Benzo-2-pyrone, 2H-1-Benzopyran, 2-oxo-, Kumarin [Czech], o-Hydroxyzimtsaure-lacton, 5,6-Benzo-alpha-pyrone, 2H-Benzo[b]pyran-2-one, Coumarinum, 1-Benzopyran-2-one, NCI C07103, 103802-83-1, Caswell No. 259C, o-Coumaric acid lactone, NSC 8774, CCRIS 181, cis-o-Coumaric acid anhydride, chromenone, EPA Pesticide Chemical Code 127301, DTXSID7020348, CHEBI:28794, BRN 0383644, HSDB 1623, 2-oxo-2H-1-benzopyran, o-Hydroxyzimtsaure-lacton [German], AI3-00753, UNII-A4VZ22K1WT, NSC-8774, EINECS 202-086-7, A4VZ22K1WT, Nci-c07103, MFCD00006850, 2-Propenoic acid, 3-(2-hydroxyphenyl)-, delta-lactone, 3-(2-Hydroxyphenyl)-2-propenoic delta-lactone, Benzo-.alpha.-pyrone, Cinnamic acid, o-hydroxy-, delta-lactone, Coumarin (prohibited), NSC8774, o-hydroxycinnamic acid delta-lactone, CHEMBL6466, 2-Propenoic acid, 3-(2-hydroxyphenyl)-delta-lactone, DTXCID50348, MLS000028741, EC 202-086-7, 5-17-10-00143 (Beilstein Handbook Reference), NCGC00091502-01, Coumarin, >=98%, SMR000059040, COUMARIN (IARC), COUMARIN [IARC], COUMARIN (MART.), COUMARIN [MART.], 2h-chromene-2-one, 2-Propenoic acid, 3-(2-hydroxyphenyl)-, d-lactone, 2-Propenoic acid, 3-(2-hydroxyphenyl)-, .delta.-lactone, benzopyranone, coumarinac lactone, CAS-91-64-5, Coumarin [NF], COU, 2H-Benzopyran-2-one, SR-01000721887, chromen-one, a coumarin, coumarin-, d-lactone, Venalot mono, Coumarin Phenolic, Rattex Rodenticide, benzopyrylium olate, Coumarin (DCF), Coumarin1513, 1, 2-Benzopyrone, a 1,2-benzopyrone, Coumarin (Standard), Venalot mono (TN), Spectrum_001336, ST023509, COUMARIN [HSDB], Opera_ID_268, 2H-Chromen-2-one #, 3-(2-hydroxyphenyl)-, COUMARIN [MI], 2H-1-benzopyran-2-on, Spectrum2_000303, Spectrum3_001772, Spectrum4_001818, Spectrum5_000555, COUMARINUM [HPUS], bmse000077, COUMARIN [WHO-DD], Epitope ID:114082, SCHEMBL6252, WLN: T66 BOVJ, BSPBio_003263, KBioGR_002460, KBioSS_001816, MLS001148422, MLS002454395, {2H-Benzo[b]pyran-2-one}, BIDD:ER0667, SPECTRUM1400208, SPBio_000266, Cinnamic acid, .delta.-lactone, Coumarin, >=99% (HPLC), BDBM12342, HY-N0709R, KBio2_001816, KBio2_004384, KBio2_006952, KBio3_002764, GLXC-19130, HMS1923M11, HMS2091E19, HMS2232H18, HMS3369L08, HMS3652B05, HMS3885D09, Pharmakon1600-01400208, HY-N0709, Tox21_111141, Tox21_202427, Tox21_300057, CCG-38580, NSC755852, s4170, STK066167, COUMARIN (PROHIBITED) [FHFI], AKOS000120175, Tox21_111141_1, 2H-chromen-2-one (ACD/Name 4.0), CR-0048, CS-8148, DB04665, FC20572, NSC-755852, SDCCGMLS-0066912.P001, USEPA/OPP Pesticide Code: 127301, NCGC00091502-02, NCGC00091502-03, NCGC00091502-04, NCGC00091502-05, NCGC00091502-06, NCGC00091502-07, NCGC00091502-08, NCGC00091502-09, NCGC00091502-11, NCGC00091502-12, NCGC00091502-16, NCGC00254092-01, NCGC00259976-01, Coumarin 1000 microg/mL in Acetonitrile, NCI60_041938, SBI-0061760.P002, DB-057267, DB-261057, Cinnamic acid, o-hydroxy-, .delta.-lactone, Coumarin, Vetec(TM) reagent grade, >=99%, NS00002381, SW220278-1, EN300-18115, BIM-0061760.0001, C05851, D07751, D81844, AB00375898_11, AB00375898_12, AP-123/40186862, Coumarin, primary pharmaceutical reference standard, Q111812, CU-01000013121-2, SR-01000721887-2, SR-01000721887-3, BRD-K23913458-001-02-5, BRD-K23913458-001-13-2, BRD-K23913458-001-19-9, BRD-K23913458-001-20-7, Coumarin, certified reference material, TraceCERT(R), Z57169486, Coumarin, European Pharmacopoeia (EP) Reference Standard, F3096-1712, 2H-1-Benzopyran-2-one;1,2-Benzopyrone;5,6-Benzo-2-pyrone, COUMARIN (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC], COUMARIN (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC], D3E956C4-9541-4F57-9435-7D915C38E19E, InChI=1/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6, 202-086-7, 2h-1-benzopyran-2-one;coumarin;2h-chromen-2-one;coumarin ;coumarin (2h-1-benzopyran-2-one) (chromen-2-one);2h-1-benzopyran-2-one coumarin 2h-chromen-2-one coumarin coumarin (2h-1-benzopyran-2-one) (chromen-2-one)
Coumarin is a naturally occurring aromatic organic compound belonging to the benzopyrone chemical class, widely found in plants such as tonka beans, cinnamon, vanilla, sweet clover, and various other botanicals.
Coumarin is known for its sweet, pleasant, and vanilla-like fragrance, which has led to its extensive use in perfumes, cosmetics, and flavoring agents, although its direct use in food products is restricted in some countries due to potential health concerns.
Coumarin serves as a precursor to several anticoagulant medications, most notably warfarin, which is used to prevent blood clotting disorders.
While coumarin itself is not an anticoagulant, its derivatives function by inhibiting vitamin K-dependent clotting factors.
Additionally, Coumarin has been investigated for its antifungal, antibacterial, anti-inflammatory, and anticancer properties, though its high doses have been linked to hepatotoxicity in animal studies.
Due to these concerns, regulatory bodies such as the FDA have set limits on its use in consumable products.
Despite this, coumarin remains a valuable compound in various industries, particularly in fragrance production, where it provides a warm, spicy, and slightly herbaceous scent that enhances the depth and complexity of perfumes.
Beyond industrial applications, Coumarin plays a crucial ecological role, as it acts as a natural defense mechanism in plants, deterring herbivores and insects.
Coumarin's presence in certain grasses and forage plants has been associated with sweet-smelling hay and, in some cases, has contributed to livestock poisoning when ingested in large amounts.
Ongoing research continues to explore the potential pharmacological benefits of coumarin and its derivatives, aiming to harness its medicinal properties while minimizing toxicity concerns.
Coumarin is an aromatic organic chemical compound with formula C9H6O2.
Coumarin's molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by an unsaturated lactone ring −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring.
Coumarin belongs to the benzopyrone chemical class and considered as a lactone.
Coumarin is a colorless crystalline solid with a sweet odor resembling the scent of vanilla and a bitter taste.
Coumarin is found in many plants, where it may serve as a chemical defense against predators.
While coumarin is not an anticoagulant, its 3-alkyl-4-hydroxy derivatives, such as the fungal metabolite dicoumarol, inhibit synthesis of vitamin K, a key component in blood clotting.
A related compound, the prescription drug anticoagulant warfarin, is used to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism.
Coumarin appears as colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.
Coumarin is a chromenone having the keto group located at the 2-position.
Coumarin has a role as a fluorescent dye, a plant metabolite and a human metabolite.
Coumarin is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.
Coumarin is used by consumers, by professional workers (widespread uses), in formulation or re-packing and at industrial sites.
Coumarin is a naturally occurring benzo-α-pyrone compound that is most often used as a fragrance ingredient, where it functions as a fragrance, as a fragrance enhancer, and as a stabilizer.
Coumarin is widely used in perfumes, hand soaps, detergents, and lotions at concentrations from 0.01% to 2.4%.
Coumarin is used to give pleasant aromas to household products or to mask unpleasant odors.
The conservative estimate for systemic exposure of humans by using cosmetic products is 0.13 mg kg−1 day−1, disregarding any corrections that should be made for absorption that is <100%.
Coumarin is used as a pharmaceutical for the treatment of high protein lymphedema, for improved venous circulation, and has been in clinical trials as an antineoplastic.
Unlike coumadin (or warfarin), coumarin has no anticoagulant activity and is not used clinically as an anticoagulant or as a rodenticide.
Coumarin is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants.
Coumarin is found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs.
Although coumarin's use in foods is allowed via naturals such as cinnamon, at the present time coumarin is not permitted for use as a direct food additive, although it is used as a tobacco flavor.
Coumarin is also used in the electroplating industry.
Coumarin is a naturally occurring benzopyrone compound with a distinctive sweet, vanilla-like fragrance, commonly found in a variety of plants such as tonka beans, cassia cinnamon, sweet woodruff, and lavender.
Coumarin plays a significant role in the perfume, pharmaceutical, and food industries due to its aromatic and biological properties.
As an organic compound, coumarin has been widely utilized in the synthesis of anticoagulant drugs like warfarin, which are essential in preventing blood clot formation in patients with cardiovascular conditions.
While coumarin itself does not possess direct anticoagulant properties, its metabolic derivatives inhibit vitamin K epoxide reductase, disrupting the coagulation cascade.
Despite its widespread use in fragrances, cosmetics, and even tobacco products, coumarin's direct consumption is regulated due to concerns about its hepatotoxicity, particularly its potential to cause liver damage when ingested in high doses over prolonged periods.
Regulatory agencies such as the FDA and the European Food Safety Authority (EFSA) have imposed restrictions on Coumarin's use in food products, especially in items like cinnamon-flavored pastries and beverages where its concentration may exceed safe limits.
Coumarin’s presence in cinnamon, particularly cassia cinnamon, has led to concerns about excessive consumption, as it is a common ingredient in many diets worldwide.
Beyond its industrial and medicinal applications, coumarin serves important ecological functions, acting as a plant defense mechanism by deterring herbivores and inhibiting fungal and bacterial growth.
This phytochemical has been extensively studied for Coumarin's pharmacological potential, showing promise in areas such as anti-inflammatory, antimicrobial, antioxidant, and anticancer research.
Several synthetic and semi-synthetic derivatives of coumarin are being explored for their therapeutic potential in treating various diseases, including neurodegenerative disorders, infectious diseases, and metabolic conditions.
In traditional medicine, plant extracts containing coumarin have been used for centuries to alleviate ailments such as edema, inflammation, and circulatory disorders, highlighting its long-standing medicinal significance.
However, safety concerns remain, particularly in relation to coumarin’s metabolism in the liver, where it is converted into toxic metabolites such as 3,4-coumarin epoxide, which can lead to hepatotoxicity and potential carcinogenic effects in high doses.
Despite these concerns, coumarin continues to be a valuable compound in modern applications.
In perfumery, Coumarin contributes warm, sweet, and slightly spicy notes to fragrances, often enhancing the complexity of floral and oriental scents.
Coumarin is also used in soaps, detergents, and household products to impart a pleasant aroma.
In the agricultural sector, coumarin-derived compounds have been investigated for their role as natural pesticides and plant growth regulators.
Ongoing research aims to develop safer derivatives with enhanced therapeutic benefits while minimizing toxicity.
The balance between its beneficial properties and potential health risks continues to be a topic of scientific and regulatory interest, making coumarin a compound of both historical and modern significance across multiple industries.
Uses of Coumarin:
Coumarin is widely used across various industries due to its aromatic, medicinal, and biological properties.
In the fragrance and cosmetics industry, Coumarin is a key ingredient in perfumes, colognes, lotions, and scented personal care products, providing a warm, sweet, and slightly spicy aroma.
Coumarin is also used in household items such as air fresheners, soaps, and detergents to enhance their scent.
In pharmaceuticals, coumarin serves as a precursor for anticoagulant drugs like warfarin, which are essential in preventing blood clot-related conditions.
Additionally, Coumarin has been studied for its potential anti-inflammatory, antioxidant, antimicrobial, and anticancer properties, showing promise in various medical applications.
Although once used as a flavoring agent in food and beverages due to Coumarin's vanilla-like taste, direct use is now restricted in many countries due to concerns over liver toxicity.
However, Coumarin is still naturally present in ingredients like cassia cinnamon and tonka beans, which are used in some culinary applications.
In agriculture, coumarin plays a role in pest control, as it is a key component in certain rodenticides and serves as a natural plant defense mechanism against herbivores, fungi, and bacteria.
The tobacco industry has also utilized coumarin to enhance the aroma and taste of tobacco products.
Furthermore, Coumarin's fluorescent properties make it valuable in scientific research, particularly in medical imaging and drug development.
Despite regulatory limitations, coumarin remains a crucial compound in numerous fields, with ongoing research exploring its potential therapeutic benefits and industrial applications.
Coumarin is often found in artificial vanilla substitutes, despite having been banned as a food additive in numerous countries since the mid-20th century.
Coumarin is still used as a legal flavorant in soaps, rubber products, and the tobacco industry, particularly for sweet pipe tobacco and certain alcoholic drinks.
Coumarin is most often used as a fragrance ingredient, where it functions as a fragrance, as a fragrance enhancer, and as a stabilizer.
Coumarin is widely used in perfumes, hand soaps, detergents, and lotions at concentrations from 0.01 to 2.4%.
Coumarin is used to give pleasant aromas to household products or to mask unpleasant odors.
The conservative estimate for systemic exposure of humans by using cosmetic products is 0.13 mg kg−1 day−1, disregarding any corrections that should be made for absorption that is <100%.
Coumarin is used as a pharmaceutical for the treatment of high-protein lymphedema and for improved venous circulation, and has been tested in clinical trials as an antineoplastic.
Although coumarin's use in foods is allowed via naturals such as cinnamon, at the present time, coumarin is not permitted for use as a direct food additive; however, Coumarin is used as a tobacco flavor.
Coumarin is also used in the electroplating industry.
Coumarin is a naturally occurring benzo-α-pyrone compound that is most often used as a fragrance ingredient, where it functions as a fragrance, as a fragrance enhancer, and as a stabilizer.
Coumarin is widely used in perfumes, hand soaps, detergents, and lotions at concentrations from 0.01% to 2.4%.
Coumarin is used to give pleasant aromas to household products or to mask unpleasant odors.
The conservative estimate for systemic exposure of humans by using cosmetic products is 0.13 mg kg−1 day−1, disregarding any corrections that should be made for absorption that is <100%.
Coumarin is used as a pharmaceutical for the treatment of high protein lymphedema, for improved venous circulation, and has been in clinical trials as an antineoplastic.
Unlike coumadin (or warfarin), coumarin has no anticoagulant activity and is not used clinically as an anticoagulant or as a rodenticide.
Coumarin is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants.
Coumarin is found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs.
Although coumarin's use in foods is allowed via naturals such as cinnamon, at the present time coumarin is not permitted for use as a direct food additive, although it is used as a tobacco flavor.
Coumarin is also used in the electroplating industry.
Coumarin has a wide range of applications across various industries due to its aromatic, medicinal, and biological properties.
Some of Coumarin's key uses include:
Perfumery and Fragrance Industry:
Coumarin is a widely used fragrance compound in perfumes, colognes, and scented personal care products such as lotions, shampoos, and soaps.
Coumarin imparts a warm, sweet, and slightly spicy scent, often enhancing the depth of floral and oriental fragrances.
Coumarin is used in air fresheners, detergents, and cleaning products for its pleasant aroma.
Pharmaceuticals and Medicine:
Coumarin serves as a precursor for the synthesis of anticoagulant drugs such as warfarin, acenocoumarol, and dicoumarol, which are used to prevent blood clots in patients with cardiovascular conditions.
Investigated for Coumarin's potential anti-inflammatory, antioxidant, antimicrobial, antifungal, and anticancer properties.
Some coumarin derivatives are studied for their possible use in treating neurodegenerative diseases, such as Alzheimer’s and Parkinson’s disease.
Coumarin found in traditional medicine, where plant extracts containing coumarin have been used to treat circulatory disorders, edema, and inflammation.
Flavoring Agent (Restricted Use in Foods and Beverages):
Historically used as a flavoring in food products due to Coumarin's vanilla-like and slightly bitter taste.
Found naturally in cassia cinnamon, tonka beans, sweet clover, and certain teas, sometimes contributing to their flavor.
Due to Coumarin's potential hepatotoxicity, its direct use as a food additive is banned in some countries, including the United States.
Some beverages and confectionery items still contain naturally occurring coumarin in regulated amounts.
Agriculture and Pest Control:
Coumarin is used in rodenticides and pesticides, particularly in the production of anticoagulant-based rat poisons.
Functions as a natural plant defense compound, deterring herbivores and protecting plants from fungal and bacterial infections.
Tobacco and Alcohol Industry:
Coumarin is used as an additive in tobacco products, such as cigarettes and pipe tobacco, to enhance their aroma and flavor.
In some cases, coumarin-rich extracts are used in alcoholic beverages to impart unique sweet, spicy, or herbal notes.
Cosmetics and Skincare:
Added to body lotions, creams, deodorants, and bath products for Coumarin's fragrance and mild antimicrobial properties.
Coumarin is sometimes used in sunscreens and anti-aging creams due to its potential antioxidant effects.
Scientific and Industrial Research:
Investigated for Coumarin's fluorescent properties, making it useful in biochemical and medical imaging applications.
Studied in nanotechnology and drug delivery systems to develop targeted therapeutic agents.
Despite its widespread applications, coumarin's potential toxicity requires careful regulation, particularly in food and pharmaceutical products.
However, Coumarin's role in fragrance, medicine, and industry remains significant, making it a highly valuable compound across multiple fields.
Industry Uses:
Odor agents
Fragrance
Consumer Uses:
Coumarin is used in the following products: perfumes and fragrances, cosmetics and personal care products, adhesives and sealants, air care products, biocides (e.g. disinfectants, pest control products), pharmaceuticals, polishes and waxes, textile treatment products and dyes and washing & cleaning products.
Other release to the environment of Coumarin is likely to occur from: indoor use as processing aid and outdoor use as processing aid.
Other Consumer Uses:
Processing aids not otherwise specified
Odor agents
Fragrance
Widespread uses by professional workers:
Coumarin is used in the following products: perfumes and fragrances and cosmetics and personal care products.
Other release to the environment of Coumarin is likely to occur from: indoor use as processing aid and outdoor use as processing aid.
Uses at industrial sites:
Coumarin is used in the following products: pH regulators and water treatment products, laboratory chemicals, washing & cleaning products, water treatment chemicals, perfumes and fragrances and cosmetics and personal care products.
Coumarin has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of Coumarin can occur from industrial use: in processing aids at industrial sites and as an intermediate step in further manufacturing of another substance (use of intermediates).
Natural Occurrence of Coumarin:
Coumarin is found naturally in many plants.
Freshly ground plant parts contain higher amount of desired and undesired phytochemicals than powder.
In addition, whole plant parts are harder to counterfeit; for example, one study showed that authentic Ceylon cinnamon bark contained 0.012 to 0.143 mg/g coumarin, but samples purchased at markets contained up to 3.462 mg/g, possibly because those were mixed with other cinnamon varieties.
Vanilla grass (Anthoxanthum odoratum)
Sweet woodruff (Galium odoratum)
Sweet grass (Hierochloe odorata)
Sweet-clover (genus Melilotus)
Meranti trees (genus Shorea)
Tonka bean (Dipteryx odorata)
Cinnamon; a 2013 study showed different varieties containing different levels of coumarin:
Ceylon cinnamon or true cinnamon (Cinnamomum verum): 0.005 to 0.090 mg/g
Chinese cinnamon or Chinese cassia (C. cassia): 0.085 to 0.310 mg/g
Indonesian cinnamon or Padang cassia (C. burmannii): 2.14 to 9.30 mg/g
Saigon cinnamon or Vietnamese cassia (C. loureiroi): 1.06 to 6.97 mg/g
Deertongue (Carphephorus odoratissimus)
Tilo (Justicia pectoralis)
Mullein (genus Verbascum)
Many cherry blossom tree varieties (of the genus Prunus).
Related compounds are found in some but not all specimens of genus Glycyrrhiza, from which the root and flavour licorice derives.
Coumarin is found naturally also in many edible plants such as strawberries, black currants, apricots, and cherries.
Coumarins were found to be uncommon but occasional components of propolis by Santos-Buelga and Gonzalez-Paramas 2017.
Biological function:
Coumarin has appetite-suppressing properties, which may discourage animals from eating plants that contain it.
Though Coumarin has a pleasant sweet odor, it has a bitter taste, and animals tend to avoid it.
Metabolism:
The biosynthesis of coumarin in plants is via hydroxylation, glycolysis, and cyclization of cinnamic acid.
In humans, the enzyme encoded by the gene UGT1A8 has glucuronidase activity with many substrates, including coumarins.
Production of Coumarin:
Coumarin can be produced through both natural extraction and synthetic chemical synthesis.
Naturally, Coumarin is found in various plants, including tonka beans, cassia cinnamon, sweet clover, and lavender, where it exists as a secondary metabolite.
The extraction process involves solvent extraction or steam distillation, followed by purification through crystallization or chromatography.
However, due to regulatory restrictions and the high cost of natural extraction, most commercial coumarin is now produced synthetically.
The synthetic production of coumarin is typically carried out through the Perkin reaction, a chemical process developed in the 19th century.
This reaction involves the condensation of salicylaldehyde and acetic anhydride in the presence of a base, such as sodium acetate, resulting in coumarin formation.
Other synthetic methods include the Pechmann condensation, which uses phenols and β-ketoesters under acidic conditions, and the Knoevenagel reaction, which allows for further modification of coumarin derivatives.
These synthetic routes provide a cost-effective and scalable way to produce high-purity coumarin for use in perfumes, pharmaceuticals, and industrial applications.
Once synthesized, coumarin undergoes further refinement and quality control testing to ensure its purity and compliance with safety regulations.
In the fragrance industry, coumarin is blended with other aromatic compounds, while in pharmaceuticals, its derivatives undergo modifications to enhance therapeutic effects and reduce toxicity.
Despite Coumarin's widespread use, strict regulations govern its production and application due to concerns about its potential hepatotoxicity at high concentrations.
However, advances in biotechnology and green chemistry continue to explore more sustainable and safer production methods, including microbial biosynthesis and enzymatic pathways, to reduce environmental impact and improve efficiency.
General Manufacturing Information of Coumarin:
Industry Processing Sectors:
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Plastics Material and Resin Manufacturing
All Other Chemical Product and Preparation Manufacturing
Wholesale and Retail Trade
Miscellaneous Manufacturing
Other (requires additional information)
All Other Basic Organic Chemical Manufacturing
Synthesis of Coumarin:
Coumarin can be prepared by a number of name reactions, with the Perkin reaction between salicylaldehyde and acetic anhydride being a popular example.
The Pechmann condensation provides another route to coumarin and its derivatives starting from phenol, as does the Kostanecki acylation, which can also be used to produce chromones.
Biosynthesis:
From lactonization of ortho-hydroxylated cis-hydroxycinnamic acid.
Human Metabolite Information of Coumarin:
Cellular Locations:
Cytoplasm
Extracellular
Membrane
Derivatives of Coumarin:
Coumarin is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals similar to dicoumarol.
4-hydroxycoumarins are a type of vitamin K antagonist.
They block the regeneration and recycling of vitamin K.
These chemicals are sometimes also incorrectly referred to as "coumadins" rather than 4-hydroxycoumarins.
Some of the 4-hydroxycoumarin anticoagulant class of chemicals are designed to have high potency and long residence times in the body, and these are used specifically as rodenticides ("rat poison").
Death occurs after a period of several days to two weeks, usually from internal hemorrhaging.
Etymology of Coumarin:
Coumarin is derived from coumarou, the French word for the tonka bean, from the Old Tupi word for its tree, kumarú.
History of Coumarin:
Coumarin was first isolated from tonka beans in 1820 by A. Vogel of Munich, who initially mistook it for benzoic acid.
Also in 1820, Nicholas Jean Baptiste Gaston Guibourt (1790–1867) of France independently isolated coumarin, but he realized that it was not benzoic acid.
In a subsequent essay he presented to the pharmacy section of the Académie Royale de Médecine, Guibourt named the new substance coumarine.
In 1835, the French pharmacist A. Guillemette proved that Vogel and Guibourt had isolated the same substance.
Coumarin was first synthesized in 1868 by the English chemist William Henry Perkin.
Coumarin has been an integral part of the fougère genre of perfume since it was first used in Houbigant's Fougère Royale in 1882.
Handling and Storage of Coumarin:
Handling:
Use in a well-ventilated area to avoid inhalation of dust or vapors.
Avoid direct skin and eye contact; wear protective gloves and goggles.
Do not ingest or inhale; if handling in large quantities, use a respirator.
Wash hands thoroughly after handling.
Keep away from strong acids, bases, and oxidizing agents.
Storage:
Store in a cool, dry, and well-ventilated area.
Keep container tightly closed and away from heat, moisture, and direct sunlight.
Store separately from food and beverages.
Recommended storage temperature: Below 25°C (77°F).
Stability and Reactivity of Coumarin:
Stability:
Stable under normal temperature and pressure conditions.
Sensitive to strong acids and bases, which may cause hydrolysis.
Reactivity:
Reacts with oxidizing agents, leading to decomposition.
Can undergo electrophilic aromatic substitution and hydrolysis under alkaline conditions.
Avoid exposure to strong reducing or oxidizing chemicals.
Decomposition Products:
Can release toxic fumes, including carbon monoxide (CO) and carbon dioxide (CO₂), when burned or decomposed at high temperatures.
First Aid Measures of Coumarin:
Inhalation:
Move the affected person to fresh air immediately.
If breathing is difficult, administer oxygen and seek medical attention.
If respiratory irritation occurs, seek medical advice.
Skin Contact:
Wash affected area with soap and water.
Remove contaminated clothing and wash before reuse.
If irritation persists, seek medical attention.
Eye Contact:
Rinse thoroughly with water for at least 15 minutes, lifting eyelids occasionally.
Seek medical attention if irritation or redness persists.
Ingestion:
Do not induce vomiting.
Rinse mouth with water.
If swallowed in large amounts, seek medical attention immediately.
Do not give anything by mouth to an unconscious person.
Firefighting Measures of Coumarin:
Flammability:
Coumarin is combustible but not highly flammable.
Flash point:
150°C (302°F) (closed cup).
Extinguishing Media:
Use dry chemical powder, carbon dioxide (CO₂), foam, or water spray.
Do not use a direct water jet, as Coumarin may spread the fire.
Special Firefighting Procedures:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear.
Use water spray to cool exposed containers and prevent overheating.
Avoid inhaling combustion fumes, which may contain toxic gases such as carbon monoxide (CO) and carbon dioxide (CO₂).
Accidental Release Measures of Coumarin:
Personal Precautions:
Avoid inhalation of dust or vapors; wear a mask if necessary.
Use personal protective equipment (PPE) such as gloves, goggles, and protective clothing.
Ensure adequate ventilation in spill areas.
Environmental Precautions:
Do not allow Coumarin to enter drains, soil, or waterways.
Inform local authorities if significant quantities have been spilled.
Cleanup Methods:
Small Spills:
Sweep up or vacuum material carefully and place in a sealed container for disposal.
Large Spills:
Contain the spill with absorbent materials (e.g., sand or vermiculite) and dispose of according to local regulations.
Exposure Controls / Personal Protection of Coumarin:
Exposure Limits:
Occupational exposure limits are not well established but should be minimized due to potential toxicity.
Engineering Controls:
Ensure proper ventilation or use fume hoods when handling large amounts.
Use local exhaust ventilation if airborne concentrations are high.
Personal Protective Equipment (PPE):
Respiratory Protection:
Use an appropriate mask or respirator if dust or vapors are present.
Eye Protection:
Wear safety goggles or face shields to prevent eye contact.
Skin Protection:
Use chemical-resistant gloves and protective clothing.
Hygiene Measures:
Wash hands and exposed skin thoroughly after handling.
Identifiers of Coumarin:
CAS Number: 91-64-5
Beilstein Reference: 383644
ChEBI: CHEBI:28794
ChEMBL: ChEMBL6466
ChemSpider: 13848793
DrugBank: DB04665
ECHA InfoCard: 100.001.897
EC Number: 202-086-7
Gmelin Reference: 165222
KEGG: D07751
PubChem CID: 323
RTECS number: GN4200000
UNII: A4VZ22K1WT
CompTox Dashboard (EPA): DTXSID7020348
InChI: InChI=1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
InChI=1/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H
Key: ZYGHJZDHTFUPRJ-UHFFFAOYAC
SMILES: O=C1C=Cc2ccccc2O1
IUPAC Name: 2H-1-Benzopyran-2-one
Common Name: Coumarin
Chemical Formula: C₉H₆O₂
Molecular Weight: 146.15 g/mol
CAS Number: 91-64-5
PubChem CID: 323
EINECS Number: 202-086-7
UNII (FDA Identifier): A4VZ22K1WT
SMILES Representation: O=C1OCc2ccccc2C1
InChI: InChI=1S/C9H6O2/c10-9-5-3-7-2-1-4-8(11)6-7-9/h1-6H
IUPAC Name: 2H-1-Benzopyran-2-one
Systematic Name: 1-Benzopyran-2-one
Common Names: Coumarin, 2H-Chromen-2-one, Benzopyrone
Molecular Formula: C₉H₆O₂
Molecular Weight: 146.15 g/mol
Density: ~0.935 g/cm³
Vapor Pressure: 0.0025 mmHg at 25°C
Refractive Index: 1.597
Dipole Moment: 2.6 D
CAS Number: 91-64-5
EC Number: 202-086-7
Beilstein Reference: 190757
Gmelin Number: 521855
ChemSpider ID: 313
SMILES: O=C1OCc2ccccc2C1
InChI: InChI=1S/C9H6O2/c10-9-5-3-7-2-1-4-8(11)6-7-9/h1-6H
InChI Key: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Properties of Coumarin:
Chemical formula: C9H6O2
Molar mass: 146.145 g·mol−1
Appearance: colorless to white crystals
Odor: pleasant, like vanilla beans
Density: 0.935 g/cm3 (20 °C (68 °F))
Melting point: 71 °C (160 °F; 344 K)
Boiling point: 301.71 °C (575.08 °F; 574.86 K)
Solubility in water: 0.17 g / 100 mL
Solubility: very soluble in ether, diethyl ether, chloroform, oil, pyridine
soluble in ethanol
log P: 1.39
Vapor pressure: 1.3 hPa (106 °C (223 °F))
Magnetic susceptibility (χ): −82.5×10−6 cm3/mol
IUPAC Name: 2H-1-Benzopyran-2-one
Molecular Formula: C₉H₆O₂
Molecular Weight: 146.15 g/mol
Chemical Structure: Benzopyrone (lactone of o-hydroxycinnamic acid)
Functional Groups: Lactone, Aromatic Ring
2. Physical Properties
Appearance: White to colorless crystalline solid
Odor: Sweet, vanilla-like, with a slightly bitter undertone
Taste: Slightly bitter with a characteristic almond-vanilla flavor
Density: ~0.935 g/cm³
Melting Point: 68-74°C (154-165°F)
Boiling Point: 302°C (576°F)
Solubility in Water: Slightly soluble (~0.17 g/L at 25°C)
Solubility in Organic Solvents: Highly soluble in ethanol, methanol, ether, benzene, chloroform, and acetone
Vapor Pressure: 0.0025 mmHg at 25°C
Flash Point: 150°C (302°F) (closed cup)
Refractive Index: 1.597
Log P (Octanol-Water Partition Coefficient): 1.39 (moderately lipophilic)
Molecular Weight: 146.14 g/mol
XLogP3: 1.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 146.036779430 Da
Monoisotopic Mass: 146.036779430 Da
Topological Polar Surface Area: 26.3 Ų
Heavy Atom Count: 11
Complexity: 196
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Structure of Coumarin:
Crystal structure: orthorhombic
Related compounds of Coumarin:
Chromone
2-Cumaranone
Names of Coumarin:
Regulatory process names:
2H-1-Benzopyran-2-one
Coumarin
Coumarin
coumarin
Trade names:
COUMARIN
Coumarin
Coumarine
O-HYDROXYCINNAMIC ACID LACTONE
Rattex
TONKA BEAN CAMPHOR
Tonka bean camphor
IUPAC names:
(2H)-1-Benzopyran-2-one
- chromen-2-one
1,2-benzopyran-2-one
1,2-benzopyrone
1-Benzopyran-2-one
1-benzopyran-2-one
1-benzopyrane-2-one
2H Chromen-2-one
2H-1-Benzopyran-2-on
2H-1-Benzopyran-2-one
2H-Chromen-2-one
2H-chromen-2-one
Chromen-2-one
chromen-2-one
COUMARIN
Coumarin
coumarin
Coumarin
coumarin
Coumarin; 2H-1-Benzopyran-2-one
cumarin
Cumarina
Preferred IUPAC name:
2H-1-Benzopyran-2-one
Other name:
1-Benzopyran-2-one
Other identifier:
91-64-5
MeSH Entry Terms of Coumarin:
1,2-benzopyrone
5,6-benzo-alpha-pyrone
coumarin
