Coumarin (CAS 91-64-5) — formula C9H6O2, molecular weight 146.14; category pharmaceutical intermediates and APIs.
| CAS Number | 91-64-5 |
|---|---|
| Molecular Formula | C9H6O2 |
| Molecular Weight | 146.14 |
| Melting Point | 154 to 158 °F (NTP, 1992) |
| Boiling Point | 568 °F at 760 mmHg (NTP, 1992) |
| LogP | 1.4 |
| Applications | Uses: Occurs naturally in the tonka beans, Cassia, and lavender oils, [Marks, p. 172] Used in soaps, tobacco, pharmaceuticals, and rubber products, Also used in the fragrance industry and in the electroplating industry to polish chrome-plated steel, Coumarin banned in US since 1954 as a flavor in food, it may contaminate vanilla imported from Mexico and Caribbean countries, [HSDB] The anticoagulant warfarin (Coumadin) is synthesized from 4-hydroxycoumarin and benzalacetone with pyridine as a catalyst, Many coumarins are effective laser dyes, [Ullmann], Electroplating [Category: Plate], For Coumarin (USEPA, OPP Pesticide Code: 127301) there are 0 labels match., SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses., Formerly important as a flavor and perfume in foods and pharmaceuticals., As deodorizing and odor enhancing agent in soaps, tobacco and rubber products., Pharmaceutic aid (flavor)., For more Uses (Complete) data for COUMARIN (10 total), please visit the HSDB record page., Use (kg, approx.) in Germany (2009): >75, Consumption (g per capita, approx.) in Germany (2009): 0.000916, Calculated removal (%): 92.1, Coumarin is a chemical compound, poison found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. The parent compound, coumarin, occurs naturally in many plants, natural spices, and foods such as tonka bean, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, wine, and other foodstuffs. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% to 6.4% in fine fragrances to <0.01% in detergents. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity, carcinogenicity and its human relevance. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. However, at low doses (typically 7 to 10 mg, day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema of various etiologies., Use Classification: Fragrance Ingredients, Cosmetics -> Masking, Pharmaceuticals -> Animal Drugs -> Approved in Taiwan, Industry Uses: Plating agent, Other, Fragrance, Consumer Uses: Fragrance, Household Products: Cosmetics product ingredient: 2H-1-Benzopyran-2-one (COUMARIN), Coumarin is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223, 2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)., For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:, https:, www.cdph.ca.gov, Programs, CCDPHP, DEODC, OHB, CSCP, Pages, FragranceAllergens.aspx, Product count: 17711, Information on 416 consumer products that contain Coumarin in the following categories is provided:, • Auto Products, • Commercial, Institutional, • Inside the Home, • Personal Care, • Pesticides, • Pet Care, Methods of Manufacturing: ...Made synthetically by heating salicylic aldehyde, sodium acetate, and acetic acid anhydride., From o-cresol and carbonyl chloride followed by chlorination of the carbonate and fusion with a mixture of alkali acetate, acetic anhydride, and a catalyst., Synthesis from salicyladehyde by the Perkin reaction. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperatures., Synthesis from o-cresol by the Raschig process. The hydroxyl group of o-cresol is protected by a carbonate or phosphate group, and the ester can be converted into the corresponding benzal chloride derivative by chlorination of the methyl group. Reaction of this intermediate with acetic anhydride yields o-acetylsalicylaldehyde and acetyl chloride. Ring closure of the aldehyde with acetic anhydride gives coumarin., IFRA Fragrance Standards: Coumarin, 2H-1-Benzopyran-2-one, 2H-chromen-2-one, 1, 2-Benzopyrone, cis-o-Coumaric acid lactone, Coumarinic anhydride, 2-Oxo-1, 2-benzopyran, Tonka bean camphor, IFRA_STD_023.pdf, 49, IFRA 51st Amendment - Guidance for the use of IFRA Standards, Restriction: This material should be used only in the limited quantity as stated in the Standard, DERMAL SENSITIZATION AND SYSTEMIC TOXICITY, Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards., Restriction Limits in the Finished Product (%): 0.089 [Products applied to the lips], 0.08 [Products applied to the axillae], 0.089 [Products applied to the face, body using fingertips], 1.5 [Produc |
| Category | Pharmaceutical Intermediates |
Documented applications: Uses: Occurs naturally in the tonka beans, Cassia, and lavender oils, [Marks, p. 172] Used in soaps, tobacco, pharmaceuticals, and rubber products, Also used in the fragrance industry and in the electroplating industry to polish chrome-plated steel, Coumarin banned in US since 1954 as a flavor in food, it may contaminate vanilla imported from Mexico and Caribbean countries, [HSDB] The anticoagulant warfarin (Coumadin) is synthesized from 4-hydroxycoumarin and benzalacetone with pyridine as a catalyst, Many coumarins are effective laser dyes, [Ullmann], Electroplating [Category: Plate], For Coumarin (USEPA, OPP Pesticide Code: 127301) there are 0 labels match., SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses., Formerly important as a flavor and perfume in foods and pharmaceuticals., As deodorizing and odor enhancing agent in soaps, tobacco and rubber products., Pharmaceutic aid (flavor)., For more Uses (Complete) data for COUMARIN (10 total), please visit the HSDB record page., Use (kg, approx.) in Germany (2009): >75, Consumption (g per capita, approx.) in Germany (2009): 0.000916, Calculated removal (%): 92.1, Coumarin is a chemical compound, poison found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. The parent compound, coumarin, occurs naturally in many plants, natural spices, and foods such as tonka bean, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, wine, and other foodstuffs. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% to 6.4% in fine fragrances to <0.01% in detergents. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity, carcinogenicity and its human relevance. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. However, at low doses (typically 7 to 10 mg, day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema of various etiologies., Use Classification: Fragrance Ingredients, Cosmetics -> Masking, Pharmaceuticals -> Animal Drugs -> Approved in Taiwan, Industry Uses: Plating agent, Other, Fragrance, Consumer Uses: Fragrance, Household Products: Cosmetics product ingredient: 2H-1-Benzopyran-2-one (COUMARIN), Coumarin is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223, 2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)., For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:, https:, www.cdph.ca.gov, Programs, CCDPHP, DEODC, OHB, CSCP, Pages, FragranceAllergens.aspx, Product count: 17711, Information on 416 consumer products that contain Coumarin in the following categories is provided:, • Auto Products, • Commercial, Institutional, • Inside the Home, • Personal Care, • Pesticides, • Pet Care, Methods of Manufacturing: ...Made synthetically by heating salicylic aldehyde, sodium acetate, and acetic acid anhydride., From o-cresol and carbonyl chloride followed by chlorination of the carbonate and fusion with a mixture of alkali acetate, acetic anhydride, and a catalyst., Synthesis from salicyladehyde by the Perkin reaction. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperatures., Synthesis from o-cresol by the Raschig process. The hydroxyl group of o-cresol is protected by a carbonate or phosphate group, and the ester can be converted into the corresponding benzal chloride derivative by chlorination of the methyl group. Reaction of this intermediate with acetic anhydride yields o-acetylsalicylaldehyde and acetyl chloride. Ring closure of the aldehyde with acetic anhydride gives coumarin., IFRA Fragrance Standards: Coumarin, 2H-1-Benzopyran-2-one, 2H-chromen-2-one, 1, 2-Benzopyrone, cis-o-Coumaric acid lactone, Coumarinic anhydride, 2-Oxo-1, 2-benzopyran, Tonka bean camphor, IFRA_STD_023.pdf, 49, IFRA 51st Amendment - Guidance for the use of IFRA Standards, Restriction: This material should be used only in the limited quantity as stated in the Standard, DERMAL SENSITIZATION AND SYSTEMIC TOXICITY, Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards., Restriction Limits in the Finished Product (%): 0.089 [Products applied to the lips], 0.08 [Products applied to the axillae], 0.089 [Products applied to the face, body using fingertips], 1.5 [Produc.
Coumarin is a pharmaceutical intermediate or API compound with CAS registry number 91-64-5 and molecular formula C9H6O2 (molecular weight 146.14), belonging to the pharmaceutical intermediates and APIs segment of chemical raw materials.
CAS number: 91-64-5
Its molecular formula C9H6O2 comprises 9 C, 6 H, 2 O atoms.
Also known as: Coumarin · 香豆素
Category: pharmaceutical intermediates and APIs
The CAS registry number of Coumarin is 91-64-5.
Molecular formula C9H6O2, molecular weight 146.14.
It is also registered under: Coumarin, 香豆素.
Recorded applications: Uses: Occurs naturally in the tonka beans, Cassia, and lavender oils, [Marks, p. 172] Used in soaps, tobacco, pharmaceuticals, and rubber products, Also used in the fragrance industry and in the electroplating industry to polish chrome-plated steel, Coumarin banned in US since 1954 as a flavor in food, it may contaminate vanilla imported from Mexico and Caribbean countries, [HSDB] The anticoagulant warfarin (Coumadin) is synthesized from 4-hydroxycoumarin and benzalacetone with pyridine as a catalyst, Many coumarins are effective laser dyes, [Ullmann], Electroplating [Category: Plate], For Coumarin (USEPA, OPP Pesticide Code: 127301) there are 0 labels match., SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses., Formerly important as a flavor and perfume in foods and pharmaceuticals., As deodorizing and odor enhancing agent in soaps, tobacco and rubber products., Pharmaceutic aid (flavor)., For more Uses (Complete) data for COUMARIN (10 total), please visit the HSDB record page., Use (kg, approx.) in Germany (2009): >75, Consumption (g per capita, approx.) in Germany (2009): 0.000916, Calculated removal (%): 92.1, Coumarin is a chemical compound, poison found in many plants, notably in high concentration in the tonka bean, woodruff, and bison grass. The parent compound, coumarin, occurs naturally in many plants, natural spices, and foods such as tonka bean, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, wine, and other foodstuffs. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% to 6.4% in fine fragrances to <0.01% in detergents. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity, carcinogenicity and its human relevance. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. However, at low doses (typically 7 to 10 mg, day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema of various etiologies., Use Classification: Fragrance Ingredients, Cosmetics -> Masking, Pharmaceuticals -> Animal Drugs -> Approved in Taiwan, Industry Uses: Plating agent, Other, Fragrance, Consumer Uses: Fragrance, Household Products: Cosmetics product ingredient: 2H-1-Benzopyran-2-one (COUMARIN), Coumarin is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223, 2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)., For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:, https:, www.cdph.ca.gov, Programs, CCDPHP, DEODC, OHB, CSCP, Pages, FragranceAllergens.aspx, Product count: 17711, Information on 416 consumer products that contain Coumarin in the following categories is provided:, • Auto Products, • Commercial, Institutional, • Inside the Home, • Personal Care, • Pesticides, • Pet Care, Methods of Manufacturing: ...Made synthetically by heating salicylic aldehyde, sodium acetate, and acetic acid anhydride., From o-cresol and carbonyl chloride followed by chlorination of the carbonate and fusion with a mixture of alkali acetate, acetic anhydride, and a catalyst., Synthesis from salicyladehyde by the Perkin reaction. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperatures., Synthesis from o-cresol by the Raschig process. The hydroxyl group of o-cresol is protected by a carbonate or phosphate group, and the ester can be converted into the corresponding benzal chloride derivative by chlorination of the methyl group. Reaction of this intermediate with acetic anhydride yields o-acetylsalicylaldehyde and acetyl chloride. Ring closure of the aldehyde with acetic anhydride gives coumarin., IFRA Fragrance Standards: Coumarin, 2H-1-Benzopyran-2-one, 2H-chromen-2-one, 1, 2-Benzopyrone, cis-o-Coumaric acid lactone, Coumarinic anhydride, 2-Oxo-1, 2-benzopyran, Tonka bean camphor, IFRA_STD_023.pdf, 49, IFRA 51st Amendment - Guidance for the use of IFRA Standards, Restriction: This material should be used only in the limited quantity as stated in the Standard, DERMAL SENSITIZATION AND SYSTEMIC TOXICITY, Due to the possible ingestion of small amounts of fragrance ingredients from their use in products in Categories 1 and 6, materials must not only comply with IFRA Standards but must also be recognized as safe as a flavoring ingredient as defined by the IOFI Code of Practice (www.iofi.org). For more details see chapter 1 of the Guidance for the use of IFRA Standards., Restriction Limits in the Finished Product (%): 0.089 [Products applied to the lips], 0.08 [Products applied to the axillae], 0.089 [Products applied to the face, body using fingertips], 1.5 [Produc.
Category: Pharmaceutical Intermediates.
Independent reference data for Coumarin (CAS 91-64-5), compiled from public chemistry databases.
| CAS Registry Number | 91-64-5 |
|---|---|
| PubChem CID | 323 |
| Molecular formula | C9H6O2 |
| IUPAC name | chromen-2-one |
| UNII (FDA) | A4VZ22K1WT |
| Molecular Weight | 146.14 |
|---|---|
| XLogP3 | 1.4 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 0 |
| Exact Mass | 146.036779430 |
| Monoisotopic Mass | 146.036779430 |
| Topological Polar Surface Area | 26.3 |
| Heavy Atom Count | 11 |
| Boiling Point | 568 °F at 760 mmHg (NTP, 1992) |
|---|---|
| Boiling Point | 301.71 °C |
| Boiling Point | 297.00 to 301.00 °C. @ 760.00 mm Hg |
| Boiling Point | 297-299 °C |
| Melting Point | 154 to 158 °F (NTP, 1992) |
| Melting Point | 71 °C |
| Melting Point | 68-70 °C |
| Flash Point | 304 °F (NTP, 1992) |
| Flash Point | 150 °C |
| Solubility | In water, 1,900 mg/l @ 20 °C |
coumarin; 91-64-5; 2H-Chromen-2-one; 2H-1-Benzopyran-2-one; cumarin; 1,2-Benzopyrone; chromen-2-one; Tonka bean camphor; Rattex; Coumarinic anhydride; Coumarine; cis-o-Coumarinic acid lactone; Coumarinic lactone; o-Hydroxycinnamic acid lactone; Benzo-alpha-pyrone; 5,6-Benzo-2-pyrone
| Regulatory & Food Contact | FDA Substance added to food: FLAVORING AGENT OR ADJUVANT COUMARIN--PROHIBITED CIR / INCI: Cosmetics ingredient -> Base; Flavor; Fragrance; Moisturizing/Humectant; Other (Specify) |
|---|---|
| GHS notification summary | 1.5% (43 / 2825) |
| GHS notification summary | 1.5% (43 / 2825) |
|---|---|
| Reported hazard statements | H301 (12.1%), H302 (84.5%), H317 (92.9%), H373 |
This chemical does not meet GHS hazard criteria for 1.5% (43 of 2825) of reports.
H301 (12.1%): Toxic if swallowed [Danger Acute toxicity, oral]
Phenolic · CAS 91-64-5 · C9H6O2. UNII A4VZ22K1WT. Boiling Point: 568 °F at 760 mmHg (NTP, 1992); Boiling Point: 301.71 °C; Boiling Point: 297.00 to 301.00 °C. @ 760.00 mm Hg.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: 香豆素