Tonka bean

C, b.p. 290 C. Occurs in the Tonka bean, of which it is the odorous ingredient. Prepared synthetically by heating salicylaldehyde with elhanoic anhydride and sodium elhanoate. It... 

Until the late 1890s, coumarin was obtained commercially from only natural sources by extraction from tonka beans and deer tongue. Then synthetic methods of preparation and industrial manufacturing processes were discovered and developed starting principally from o-cresol, phenol, and sahcylaldehyde. Various methods can be used to obtain coumarin from each of these starting materials. 

Coumarin, or extract of Tonka beans, which contain coumarin, may be detected as follows A small quantity of the essence is evaporated to dryness, the residue fused with caustic potash, saturated with hydrochloric acid and treated with a drop of ferric chloride solution. If coumarin be present, a violet colour due to the formation of salicylic acid, will be produced. 

Tonka bean absolute is prepared by solvent extraction either directly from so-called Tonka beans or via the concrete. Tonka beans are the seeds of fruits from Dipteryx odorata (Aubl.) Willd. (Fabaceae). 

Tonka bean absolute is a solid or crystalline mass with a sweet, caramel-like odor, reminiscent of coumarin, which is the main constituent of the volatile part of... 

Coumarin 162 (Structure 4.49) is a naturally occurring lactone in crystal form found in hay and tonka beans. It is one of the most used fragrance materials and is responsible for spicy green notes. Dihydrocoumarine 163 is also present in various essential oils with a characteristic sweet herbal odour. Umbellif-erone 164, scopoletin 165, bergaptene 166 and coumarin are found in Rutaceae, Apiaceae, Lamiaceae and Asteraceae oils. Nepetalactones 167 are confined to the oils of Nepeta species [1,3, 21-23, 63]. 

Coumarin was first isolated by Vogel in 1820 by extraction from tonka beans (Dipteryx odorata). It was subsequently identified in a large number of plants belonging to many different families. Its better known occurrences are in sweet clover (Melilotus alba and M. officinalis), sweet woodruff (Asperula odorata), vanilla leaf (Trilisa odoratissima), vanilla beans (Vanillaplanifolia), cassia (Cinnamorum cassia), lavender (Lavendula officinalis) and balsam of Peru (Myroxylon pereirae) (Perone, 1972 Maries et al, 1987 Boisde Meuly, 1993 Budavari, 1998). 

Food containing any added coumarin as such or as a constituent of tonka beans or tonka extract is deemed to be adulterated under the act , based upon an order published in the Federal Register of 5 March 1954 (19 FR 1239) (Food and Drug Administration, 1999). 

Everything expensive gets adulterated and faked - vanilla is no exception. Synthetic vanillin is an obvious choice to spice up beans of low quality, or beans that have been extracted to yield the expensive vanilla extract (obtained by macerating vanilla pods in a mixture of water and alcohol). Synthetic vanillin could appear in the extract itself. Tonka bean extract features regularly in vanilla extract, especially in Mexico. 

Tonka beans 33. Sweet woodruff 34. Tamarind 35. Umbelliferae 36. Willow 37. Woodruff... 

Coumarin constituents (black cohosh, chamomile, fenugreek, horse chestnut, sweet melilot, tonka beans, sweet woodruff). Naturally occurring coumarins are only weakly anticoagulant, but improper storage causes the production of dicoumarol by microbial transformation. Woodruff may contain constituents of warfarin... 

Coumarin, a naturally occurring compound isolated from lavender, sweet clover, and tonka bean, is made in the laboratory from o-hydroxybenzaldehyde by the reaction depicted below. Draw a stepwise mechanism for this reaction. Coumarin derivatives are useful synthetic anticoagulants. 

Coumarin. New-mown Hay.—Coumarin is a pleasant smelling compound, and is the odoriferous constituent of the plant Asperula odorata or wood ruff, and also of new-mown hay. It is also present in Tonka beans the extract of which is used as a substitute for vanilla. 

The seeds of Dipteryx odorata (Dutch tonka bean) and Dipteryx oppositofolia (EngUsh tonka bean) are said to yield 1-3% of the non-anticoagulant coumarin, which is covered in a separate monograph. 

Cytisus scoparius (Scotch broom) D/jpferyx species (tonka beans) Genista tinctoria (dyer s broom) Glycyrrhiza glabra (liquorice)... 

Dionaea muscipuia (Venus fiytrap) D/pferyxspecies (tonka beans) Dryopteris fiiix-mas (maie fern)... 

Juniper Juniperus communis Tonka beans Dipteryx species... 

Coumarin occurs in lavender, woodruff [Asperula), tonka beans, and sweet clover (Melilotus). Coumarin can be extracted from sweet clover with hot water. Reference (Sethna 1945)... 

Synonyms Coumarin 2f-f-l-Benzopyran-2-one 1,2-Benzopyrone cfs-o-Coumaric acid lactone Coumarinic anhydride 2-Oxo-l,2-benzopyran Tonka bean camphor note coumadin and warfarin are not synonyms for coumarin) Chemical/Pharmaceutical/Other Class Benzo-a-pyrone... 

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. It is found in edible plants such as strawberries, cinnamon, peppermint, green... 

Coumarin is a white crystalline solid. Its odor has been described both as vanilla-like and as having a note of newly mown hay . Odor thresholds of 0.33-2 ppb have been reported. Coumarin occurs naturally in many plants such as tonka beans, lavender, and cassia and in many natural food stuffs such as cinnamon, green tea, peppermint, and sweet clover honey. Concentrations range from 87 000 ppm in cassia and 40 000 ppm in cinnamon to 20 ppm in peppermint and 5 ppb in tangerines. 

CIC Vanillin, the main component in vanilla flavour is the basic key ingredient for the creamy, sweet character. All other volatile flavouring compounds have been identified only in small traces. Among them 2-methoxy phenol and 2-methoxy-4-vinyl phenol are responsible for the phenolic, smoky odour. 4-Methoxy benzalde-hyde, 3,4-methylene-dioxy-benzaldehyde, methyl benzoate and methyl ciimamate impart the warm, powdery, aromatic floral character. Vitispirane adds a fruity, floral topnote. Natural vanilla extract blends very well with other flavourings and it has been modified in different directions ethyl vanillin is used to increase the sweet, creamy vanillin aspect. Tonka beans and coumarin add a full, dried hay, slightly caramel-like custard aspect, supported by the butter notes of diacetyl and 4-hydroxy-decanolide. 

Coumarm Tonka beans a. other nat. origin., syn. distinguish nat., syn. possible [365]... 

The use of coumarin, tonka bean, safrole, sassafras oil, dihydrosafrole, isosafrole, agaric acid, nitrobenzene, dulcamara, pennyroyal oil, oil of tansy, rue oil, birch tar oil, cade oil, volatile bitter almond oil containing hydrocyanic acid, and male fern as flavouring agents is prohibited. 

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