Jasmine odor

Of the 11 compounds which constitute approximately 86% of jasmin volatiles, only benzyl acetate, i7t-jasmone (18), and methyl jasmonate possess the characteristic odor of jasmin. Trace components including i7t-j asrnin lactone [34686-71-0] (20) (0.9%) andmethyl ( /-jasmonate (6) (0.1%) are the key contributors to the jasmin odor. 

Of the four possible optical isomers, the (+)-( I )-cw-isomer possesses the most characteristic jasmin odor. Methyl dihydrojasmonate is prepared by Michael addition of malonic acid esters to 2-pentyl-2-cyclopenten-l-one, followed by hydrolysis and decarboxylation of the resulting (2-pentyl-3-oxocyclopentyl) malonate, and esterification of the (2-pentyl-3-oxocyclopentyl)acetic acid [136]. 

Jasmin absolute is obtained by solvent extraction, via the concrete, from the flowers of Jasminum grandiflorum L. (Oleaceae), cultivated in Egypt, Italy, Morocco, and India, and of J. sambac (L.) Ait. from China and India. The concrete is usually a brown to dark brown waxy mass, with a characteristic jasmin odor. 

The absolute is generally a reddish-brown liquid with a delicate jasmin odor the color deepens on storage. 

Aldehydes and ketones are also important components of many fragrances and flavors. For example, butanal (butyraldehyde) is used to impart a buttery flavor to margarine and other foods. Because aldehydes are slowly oxidized to carboxylic acids by the oxygen of air, it is readily apparent how the odor of rancid butter arises. Although a-pentylcinnamaldehyde does not occur naturally, it has been found to have a powerful jasmine odor and is used in many perfumes and soaps, a-lonone is a naturally oc-... 

The most consistently accurate structure/odor model is Amoore s camphor model (48). As shown in Fig. 3, the model indicates that hydrophobic molecules with an ellipsoidal shape that have a long axis of 9.5 A and a short axis of 7.5 A will possess a camphoraceous odor. Another example of a simple but effective model is Boelens s model for jasmine odorants (51). Shown in Fig. 4, this model proposes that, to possess a jasmine odor, a molecule should contain a central carbon atom surrounded by a strongly polar group, a weakly polar group, and an alkyl chain. 

CnHigO, Mt 166.26, bp2j kPa 87-88 °C, d25 0.9157, n 1.4771, is a colorless, slightly viscous liquid with a typical jasmine odor, resembling that of the naturally occurring c/s-jasmone. Dihydrojasmone can be synthesized by various routes. A preferred method is intramolecular aldol condensation of 2,5-undecanedione, which can be prepared from heptanal and 3-buten-2-one in the presence of a thiazolium salt, such as 5-(2-hydroxyethyl)-4-methyl-3-benzylthiazolium chloride [120] ... 

ChHi60, Mr 164.25, bpi kPa 78-79 °C, tfi° 0.9423, n 1.4989 occurs in jasmine absolute and contributes to its typical jasmine odor. It is a pale yellow, viscous liquid with a strong jasmine odor. Various stereospecific syntheses for c/s-jasmone have been reported. A patented method involves alkylation of 3-methyl-2-cyclopen-ten-l-one with cz. y-2-pentenyl chloride in an alkaline medium in the presence of a phase-transfer catalyst (e.g., tricaprylmethylammonium chloride) [121] ... 

Of all possible isomers, the (+)-(lR)-cis isomer possesses the most characteristic and intensive jasmine odor. Therefore, an industrially feasible process for the production of a methyl dihydrojasmonate with a high portion of this isomer has been developed. The process comprises the catalytic hydrogenation of the corresponding cyclopenteneacetic acid in the presence of a ruthenium(II) complex with chiral ligands and subsequent esterification [138]. 

R = CH3, C9H10O2, Mt 150.18, fepiookPa 215 °C, 4° 1.0550, reg1 1.5232, is the main component of jasmine absolute and gardenia oils. It occurs as a minor component in a large number of other essential oils and extracts. It is a colorless liquid with a strong, fruity, jasmine odor. Benzyl acetate is prepared by esterification of benzyl alcohol with acetic anhydride (e.g., with sodium acetate as a catalyst) or by reaction of benzyl chloride with sodium acetate. In terms of volume, benzyl acetate is one of the most important fragrance and flavor chemicals. 

It is characterized by a naphthalenic flavor and a jasmine odor (Chemisis, 1963). 

It is described as having a fruity, estery taste and a light jasmine odor (Chemisis, 1962). It is characterized by a solvent, acetate-like taste (Winter et al., 1975a). 

Properties Colorless liq., lily-jasmine odor, spicy taste sol. in alcohol almost insol. in water m.w. 178.23... 

Properties Colorless liq. balsamic fruity jasmine odor misc. with alcohol, ether insol. in water m.w. 220.27 dens. 1.036 b.p. 276 C flash pt. > 230 F... 

Once the chemical natures of these natural compounds had been determined, chemists could start artificially making similar compounds and modifying the natural compounds. That is what synthetic organic chemists excel at. Perfumes used to be made from naturally occurring compounds such as those mentioned above. Today, however, artificially synthesized compounds are used in conjunction with natural ones. Some synthesized compounds have no resemblance in structures to natural compounds, but imitate the olfactory impressions of natural ones. For example, a-amylcinnamaldehyde reminds us of the jasmine odor, and 4-rcrt-butylcyclohexyl acetate imitates woody, violet odor. 

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