Jasmin flowers

Many cycHc ketones occur in natural oils. Jasmone [488-10-8] (3-meth5l-2-(2-pentyl)-2-cyclopenten-l-one) (4) is an odoriferous component of the oil obtained from jasmine flowers. /-Menthone [14073-97-3] (5) is the most frequently occurring of four optically active isomers, and is a colorless Hquid with a minty odor obtained from Mentha species of plants. Muscone [541-91-3] (6) and civetone [542-46-1] (7) are expensive animal products. 

In an important next step, it has been found that flowers and other plant parts can be analyzed by using head space techniques without removing them from the living plant (3). It was immediately observed that there are remarkable differences in the volatile compositions observed from Hve and picked flowers. This is exemplified for jasmine flowers in Table 3. Reconstitutions produced from this information have provided perfumers with novel and fresh notes for use in their creations. This technique continues to be appHed to many kinds and varieties of flowers, leaves (herbs, spices), and fmits. The reasons for the remarkable differences observed are not known. 

Table 3. Head Space Constituents of Jasmine Flowers...

Minor Varieties. Brick teas are prepared in the former Soviet Union and in parts of the People s RepubHc of China (82). These products are often cooked as a soup with butter or other fats. Flavorants such as jasmine flowers maybe added during processing. Oil of bergamot is used to prepare Ead Grey tea. 

Indol, CgH N, is the mother substance of the indigo group of compounds. It exists in various essential oils including neroli oil and oil of jasmin flowers. It is a crystalline compound, melting at 52° and boiling at 253° to 254°. Its odour is powerful and disagreeable, being distinctly faecal in character. Its constitution is as follows —... 

Jasmine flowers are sometimes added to manufactured green tea in the country of origin and they impart characteristic floral notes. 

Source Indole was detected in jasmine flowers Jasminum officinale), licorice [Glycyrrhiza glabra), kohlrabi stems [Brassica oleraceavAT. gongylodes), and hyacinth flowers Hyacinthus orientalid at concentrations of 42 to 95, 2, 1.33, and 0.24 to 3.45 ppm, respectively. Indole also occurs in tea leaves, black locust flowers, corn leaves, petitgrain, and yellow elder (Duke, 1992). 

C13H20O3, Mr 224.30, is a volatile component of jasmin flower absolute. It is a colorless to pale yellow liquid, Z>po.25kPa 116-118°C, 1.022-1.028, 1.473-... 

Jasminum samba (L.) Aiton Mo Li Hua (Arabian jasmine) (flower, root) Formic acid, benzoic acid, acetic acid, anthranil acid, sesquiterpene, sesquijasmine.60 This herb (root) is toxic. Sedative, anesthetic, vulnerary properties. For congestive headache, lactifuge. 

Neither No. 128 nor 129 is bright enough to make much of a show if the colored fire is also burning. When they bum to an end, the fire is communicated to the colored composition at the same time the bright diamond composition, either No. 149 or 152, commences to bum. No. 149 produces a splendid aureole of silver-white flowers. These flowers are less developed than those produced by steel wool and make a different effect from the latter. 40 No. 152 produces a splendid effect—no inflamed disc, no reddish sparks—numerous jasmine flowers of all dimensions forming a vast aureole of a striking white. 41... 

Jasmine flowers for the production of essences are picked at night as the plants him hemu al reactions cause odorous compounds to be at their most intense after dark. It is an expensive essential oil to produce and this is reflected in the price of a good quality product. 

The organic compounds available to us today are those present in living things and those formed over millions of years from dead things. In earlier times, the organic compounds known from nature were those in the essential oils that could be distilled from plants and the alkaloids that could be extracted from crushed plants with acid. Menthol is a famous example of a flavouring compound from the essential oil of spearmint and ds-ja.smone an example of a perfume distilled from jasmine flowers. 

The first of these is impressive for the high yield and the lack of interference by the carboxylic acid group. The second is important because the product is the perfumery compound a s-jasmone found naturally in jasmine flowers, and is formed in good yield with no change in the position or geometry of the Z double bond. 

Figure 1 Coexistence of the past and present techniques in F F industry classical enfleurage process (photo on the left) and a supercritical carbon dioxide extraction facility as modern factory equipment (on the right). The photo on the left shows a stock of jasmine flowers in the basket (center) that are spread upon a wooden frame (chassis) that secures a glass plate coated with fat. The chassis is then piled to allow diffusion of fragrant components (note that the fat is applied on both sides of the glass plate to gain access to the headspace volume made by the chassis underneath). Enfleurage process photo reproduced from E. Guenther, The Essential Oils with permission from Krieger Publishing Company Melbourne, FL, USA, 1948 (reprinted 2006) Vol. 1, p 192.

O-Jasmone (= 3- Vitis vinifera (Vitaceae) (wine) Jasminum officinale (jasmine flower) OD-R (jasmine odour)... 

Methyl anthranilate occurs in oil of orange blossoms (neroli oil), oil of orange peel, and in the essential oil of jasmine flowers, and is extensively used in perfumery. 

ProbiGm 12.10 What is the structute of c/s-jasmone, a natural product isolated from jasmine flowers, formed by treatment of alkyne A with H2 in the presence of the Lindlar catalyst ... 

Extraction (enfleura e method), A method, used since classical antiquity, where the fresh plant material (often flowers, e.g. jasmine flowers, passion flower) is introduced into fat, which is spread over large plates. After some days the essential oil in the fat is extracted with alcohol. Short extraction of the fat at 50-80°C is used for flowers of roses, hyacinths and carnations. 

Figure 3.2 Still charged with jasmine flowers...

Before this century, perfumes commanded such a price that only the wealthiest people could afford them. This is because perfumers relied on natural sources for their ingredients. Most of these ingredients are in limited supply and are expensive to produce. For instance, it takes about 7 000 000 jasmine flowers to produce 1 kg of oil. The flowers have to be picked by hand (no-one has yet devised a mechanical method of harvesting jasmine) in the first few hours of the day when their oil content is at its highest (Figure 3.3). In view of the costs of cultivation and extraction, it is not surprising to find that jasmine oils cost in the region of 2000/kg. 

The synthesis of the macrocyclic lactone 131 found in jasmine flowers illustrates the use of naked enolates. Lactone disconnection to 132 and the usual Michael-based three-component... 

Jasmone. 3-Methyi-2-(2-pentenyl)-2-cyclopcnten-1-ene. C,HlsO mol wt 164.24. C 80.44%. H 9.82%, O 9.74%. Found in the volatile portion of oil from jasmine flowers. Natural jasmone is the eis-ketone. Isoln and structure Ruzicka, Pfeiffer, Heh. Chim. Acta 16, 1208 (1933). 

Determine the structure for a compound with formula Ci iHieO. This compound is isolated from jasmine flowers. The infrared spectrum shows strong bands at 1700 and 1648 cm The proton NMR spectrum, with expansions, along with the HETCOR, COSY, and DEPT spectra are provided in this problem. The DEPT-90 spectmm is not shown, but it has peaks at 125 and 132 ppm. This compound is synthesized from 2,5-hexanedione by monoaUcylation with (Z)-l-chloro-2-pentene, followed by aldol eondensation. Assign all of the protons and carbons for this compound. 

---