COUMARIN
What is coumarin?
Synthetic Ingredient For Perfumery Overview
Coumarin (/ˈkuːmərɪn/) or 2H-chromen-2-one is an aromatic organic chemical compound with formula C9H6O2. Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain −(CH)=(CH)−(C=O)−O−, forming a second six-membered heterocycle that shares two carbons with the benzene ring. It can be placed in the benzopyrone chemical class and considered as a lactone.
It is found in many plants, where it may serve as a chemical defense against predators. By inhibiting synthesis of vitamin K, a related compound is used as the prescription drugwarfarin – an anticoagulant – to inhibit formation of blood clots, deep vein thrombosis, and pulmonary embolism.
Discovery
Coumarin was first isolated from tonka beans in 1820 by A. Vogel of Munich, who initially mistook it for benzoic acid.
Profile
📂 CAS N° — 91-64-5
⚖️ MW — 146.14 g/mol
📝 Odor Type — Almondy \ Coumarinic
📈 Odor Strength — Medium, Consider smelling in 10% sol
👃🏼 Odor Profile — Powdery, sweet, almondy, hay like, sweet herbaceous.
👅 Flavor Profile — Bitter taste, except when highly diluted, then sweet-herbaceous, haylike, nutlike.
⚗️ Uses — Extensively used in perfumery to support herbaceous odors, Lavender, Lavandin, Rosemary, Citrus oils, Oakmoss, etc., and as a fixative in numerous types of fragrances, Almost a standard ingredient in Fougere types with Amylsalicylate and Lavender notes, with or without Oakmoss.
Important product for Fougere accord specially in oriental fougere
Coumarin is derived from coumarou, the French word for the tonka bean. The word tonka for the tonka bean is taken from the Galibi (Carib) tongue spoken by natives of French Guiana (one source for the plant); it also appears in Old Tupi, another language of the same region, as the name of the tree. The old genus name, Coumarouna, was formed from another Tupi name for tree, kumarú.
A classical masking agent for lodoform odor, Phenolic odors, Quinoline odors, etc.
Not permitted for food use in the U.S.A., Also banned from food flavorings in a number of other countries. However, extracts of certain botanical materials, rich in Coumarin, are still in use as Tobacco flavoring agents and in other flavors.
The hazardous level of Coumann is estimated at 3 grams per day for adult human beings.
Note — Coumarin is the main ingredient of tonka bean
Appereance — Coumarin appears as colorless crystals, flakes or colorless to white powder.
Production
from salicylic aldehyde + Acetic Anhydride + Anhydrous sodium acetate
From ortho cresol + carbonyl chloride, followed by chlorination of the resulting carbonate, fusion of the Dichlorocresol with alkali acetate and acetic anhydride plus a catalyst.
Some useful links
SOURCES AND INFORMATION
National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 323, Coumarin. Retrieved December 1, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/Coumarin.
Coumarins and indandiones, https://www.drugs.com/drug-class/coumarins-and-indandiones.html
Wikipedia contributors. (2020, November 13). Coumarin. In Wikipedia, The Free Encyclopedia. Retrieved 16:40, December 1, 2020, from https://en.wikipedia.org/w/index.php?title=Coumarin&oldid=988442806
Vogel, A. (1820). "Darstellung von Benzoesäure aus der Tonka-Bohne und aus den Meliloten- oder Steinklee-Blumen" Annalen der Physik (in German). 64 (2): 161–166. Bibcode:1820AnP....64..161V. doi:10.1002/andp.18200640205.
Vogel, A. (1820). "De l'existence de l'acide benzoïque dans la fève de tonka et dans les fleurs de mélilot"
Perfume and flavor chemicals, S. Arctander, Denmark 1969.