Raspberry odor

Hydroxybenzaldehyde has an agreeable aromatic odor, but is not itself a fragrance. It is, however, a useful intermediate in the synthesis of fragrances. The methyl ether of -hydroxybenzaldehyde, ie, -anisaldehyde, is a commercially important fragrance. Anisaldehyde can be made in a simple one-step synthesis from hydroxybenzaldehyde and methyl chloride. Another important fragrance, 4-(p-hydroxyphenyl)butanone, commonly referred to as raspberry ketone, can be prepared from the reaction of -hydroxybenzaldehyde and acetone, followed by reduction (see Flavors and spices). 

Odor. Olfaction is an important part of the flavor sensation which allows the individual to distinguish its quality, i.e. raspberry vs lemon. However, not eveiy individual experiences the same olfactory sensations due to specific anosmias, the olfactory equivalent of color-blindness. Specific anosmia occurs when an individual... 

Red cabbage as a colorant source has been studied for many years. As of 1990 at least one firm has introduced San Red RC, the first commercially available food color derived from red cabbage. The color can be used alone or in combination with other colors to create strawberry, cherry, raspberry, and blueberry tones. By way of proprietary technology, the new dye is claimed to be free of flavor and odor defects, which in the past have been associated with red cabbage. The dye is pH dependent. The color tones move toward blue-red as the pH value increases. San Red RC ranks between cochineal and grape juice in percent or color retention. 

Place the test tubes in a warm water bath at 60°C for 15 min. Remove the test tubes from the water bath, cool, and add 2 mL of water to each. Note that there is a layer on top of the water in each test tube. With a Pasteur pipet, take a few drops from this top layer and place on a watch glass. Note the odor. Match the ester from each test tube with one of the following odors banana, peach, raspberry, nail polish remover, wintergreen. 

Oxidation of pentynediol 119 by Mn02 followed by interaction with p-TSA led to acetylenic derivative 120 that possesses extremely strong and diffusive violet and freesia, raspberry, woody, odors similar to )S-ionone. But the odor of allene derivative 122, also prepared from diol 119 by dehydration with LiAIH4 and further oxidation with Mn02, was rather unpleasant (85LA950). 

Several Ci 3-norisoprenoids, including p-damascenone, p-ionone, and 1,1,6-trimethyl-1,2-dihydronaphtalene (TON), are powerful odorant in wine. P-Damascenone, which can be present in young wine at up to 180 times its odour threshold of 0.05 (Jig/L, has a stewed apple, rose, honey aroma (Francis and Newton 2005). P-Ionone, which has violet, flower, and raspberry aroma, is typically present at higher concentration in red wines. TDN develops a kerosene-like odour in aged whites, particularly Riesling (Francis and Newton 2005). 

Forms colorless crystals (mp 82-83° C) with a sweet-fruity odor strongly reminiscent of raspberries. 

Compounds include alcohols, acids, esters, carbonyls, ketones, and other hydrocarbons. However, a particular ketone l-(4-hydroxy phenyl)-3-butanone has an odor very much like raspberry [7,30]. This particiilar ketone, i.e., raspberry ketone, is sold under trade names Frambinon (Dragoco) and Oxyphe-nylon (IFF). In Hawai, the acetate of raspberry ketone is used under the trade name of Cue-Lure CAS No. [3572-06-3] to attract the harmhil melon-fly, Dacus Curcurbitae. 

It may not be out of place to mention that ketones are partly or wholly responsible for the odor of many natural products such as camphor, raspberries, coffee, musk, caraway, butter, rue, and jasmine. 

C10H12O2, Mr 164.20, is a highly characteristic component of raspberry aroma. It forms colorless crystals (mp 82-83 °C) with a sweet-fruity odor strongly reminiscent of raspberries. 

Raspberry ketones prevent obesity or counteract a constitutional tendency toward obesity by promoting the decomposition of lipids accumulated in the adipose tissues. But these ketones are poorly soluble in water and have a characteristic aroma even at an extremely low concentration, so it was impossible to add an amount capable of exerting a lipolytic or anti-obese effect to cosmetics, drinks, or pet foods [29]. Flowever, by including raspberry ketones into CyDs the solubility is increased and the specific odor is reduced, resulting in a marked improvement of the taste and stabUity. Importantly, the lipolytic and anti-obese effects are not affected by the complexation. 

C13H20O, Mr 192.30, isomers of ionone which differ only in the position of the ring double bond (a-, /3-, Y-, S-, and c-damascone). The name damascones or rose ketones is derived from their occurrence in the essential oil of damask rose (Rosa damascena). a-D. bp. 77-80°C (0.13 Pa), [alg +487° (CHCI3) /5-D. bp. 52 °C (0.13 Pa). D. possess the common olfactory feature of a narcotic-herby odor of exotic flowers with an undertone resembling black currents. Although a- and /3-D. in rose oil have a combined content of merely ca. 0.15%, they determine the basic odor of the oil (olfactory threshold 0.009 ppb). D. occur in other flower oils as well as in tea, certain tobacco, and fruit aromas, e.g., apples and raspberries, a- and /3-D. are in-... 

CsHgOj, Mr 128.13 cryst., mp. 79-80 °C odor resembling caramel, in dilute solution pineapple- and straw-berry-like olfactory threshold in water 40 ppt. LD50 (rat p.o.) 1660mg/kg. An important flavor compound, occurring naturally in pineapples, strawberries, raspberries, etc., sometimes as the glucoside. It is also formed thermally from deoxyhexoses, e. g., in coffee. For production, see... 

The precursors of some phenylpropanoid odor/flavor components of raspberry fruit occur as the 4 -0-p-D-gluco-pyranoside of 4-(4 -hydroxyphenyl)butan-2-one (raspberry ketone) and the S -O-p-o-glucopyranoside of 4-(3, 4 -dihy-droxyphenyl)butan-2-one (Pabst et al., 1990). 

Cichorium intybus) are also quite common in plants. Vanillin, the odor principle occurring in Vanilla pods, is certainly of very widespread origin [42, 44]. Ellagic acid has been reported to be present in berries, particularly raspberries Rubus idaeus), strawberries, and blackberries. However, free ellagic acid is normally present in low levels in berries that more commonly contain ellagitaimins [38,45]. 

Precise odor descriptions for other 5-lactones exist in the literature (162). 8-Lactones play an outstanding role in many dairy products (725, 162). They were also isolated from depot animal fat (50, 727, 342, 683, 684, 686), and furthermore found in certain products of vegetable origin such as coconut 14, 344), pineapple (94, 408), passion fruit (777), apricot (623), peach (729, 268), strawberry (755, 661), raspberry (705), roasted filberts (507), black tea (79, 50), and in beverages produced by alcoholic fermentation such as beer (584), rum (343) and whisky (277). 

Propose a structure of compound C (molecular formula C10H12O) consistent with the following data. C is partly responsible for the odor and flavor of raspberries. 

Esters are responsible for the pleasant odors and unique flavors of many fruits. For example, pentyl acetate is found in bananas, octyl acetate is found in oranges, and isobutyl formate is found in raspberries. 

The character impact compound is the raspberry ketone , i. e. l-(p-hydroxyphenyl)-3-butanone (Vn). Its concentration is 2mg/kg and its odor threshold is 5 pg/kg (water). The starting point for the biosynthesis of VII is the condensation reaction of p-cumaroyl-CoA with malonyl-CoA (cf. Formula 18.38). Additional aroma notes are provided by (Z)-3-hexenol, a- and P-ionone. 

Ionone (334) is also very widespread in nature being found in, among others, rose, osmanthus, raspberries, cherries, tobacco, carrots, and capsicums. It has a warm woody, dry, and fruity odor and is greener than a-ionone. However, it is less useful than the latter and is used particularly in woody perfumes. In production terms, it is the most important of all the ionones because of its use in vitamin manufacture. 

P-Damascenone (343) is present in Bulgarian rose oil at a level of only 0.05%, but is a major contributor to the overall odor of the oil. Not surprisingly, it is used in reconstitutions of rose oil. It is also found in rose, apricot, beer, grape, mango, tomato, wine, rum, raspberries, passionfruit, and blackberries. Its detection threshold is one-tenth those of a- or p-damascone. 

Green-note compounds are responsible of the fresh, green odor of cut leaves and are important components of the flavor of fruits and vegetables, such as apples, cherries, kiwifruits, raspberries, strawberries, and tomatoes. They include six-carbon aldehydes and alcohols, such as (2 )-hexenal (leaf aldehyde) and (3Z)-hexenol (leaf alcohol). Nine-carbon aldehydes and alcohols, which are found in the aroma of cucumbers and melons, are also considered green-note compounds. 

The aroma substances that comprise flavors are found in nature as complex mixtures of volatile compounds. A vast majority of volatile chemicals that have been isolated from natural flavor extracts do not provide aroma contributions that are reminiscent of the flavor substance. For instance, n-hexanal is a component of natural apple flavor (1) however, when smelled in isolation, its odor is reminiscent of green, painty, rancid oil. Similarly, ethyl butyrate has a nondescript fruity aroma although it is found in strawberries, raspberries, and pears, it does not uniquely describe the aroma quality of any of these individual fruits. It has long been the goal of flavor chemists to elucidate the identity of pure aroma chemicals that have the distinct character impact of the natural fruit, vegetable, meat, cheese, or spice that they were derived from. Often, these are referred to as character impact compounds (2). 

In addition to the character impact compound of raspberry, 4-(4-hydroxy-phenyl)-butan-2-one (raspberry ketone), alpha- and beta-ionone, geraniol, and linalool were concluded to be of importance in raspberry aroma (30). Its odor threshold was measured at 1-10 ig/kg. The ionones have chemical stracture similarities and potencies comparable to P-damascenone (11). 

M. Larsen and L. Poll, Odor thresholds of some important aroma compounds in raspberries, Z. Lebensm. Unters. Forsch. 191 129 (1990). 

---