Ambrette seeds

Famesol is manufactured from nerohdol by isomerization over a vanadium catalyst (55). Famesol occurs in several essential oils, such as ambrette seed, neroh, rose, cyclamen, and jasmine it is also used in floral and oriental fragrances. 

Farnesol, CjsH gO, is an aliphatic sesquiterpene alcohol, which occurs in ambrette seed oil, and flower oils of the type of acacia, lime flowers, mignonette, and lilac flowers. 

This alcohol is almost invariably present in those essential oils which contain aliphatic terpene alcohols, but in most of these it is present in very small amount, and it is only from ambrette seed oil that any quantity has been prepared. Ambrette seeds contain about 0-1 per cent, of this alcohol, which, when freed from decylic alcohol which is also present, has the following characters —... 

Of the four possible isomers (due to the double bonds in the 2- and 6-positions), the trans-trans isomer is the most common in nature and occurs, for example, in ambrette seed oil. 2-cis-6-trans-Fsinieso has been identified in petitgrain oil Bigarade. 

C16H28O2, Mr 252.40, is not reported as being found in nature in contrast to Z)-l-hexadecen-16-olide which occurs in ambrette seed oil (see p. 172) and which is also... 

Raw materials derived from intensive agricultural cultivation are usually relatively inexpensive. However, the prices of some natural materials may exceed 1000 per kilogram because cultivation and harvesting of these plants are tedious and product yields are very low. Examples of extremely valuable ingredients of fragrance and flavor creations include rose oil, jasmine absolute, tuberose absolute, orris root oil, ambrette seed oil, angelica root oil, and orange flower oil [220]. 

Ambrette seed oil is obtained by steam distillation of the dried, crushed seeds of Ambelmoschus moschatus Medik. Hibiscus abelmoschus L., Malvaceae), a flowering shrub growing in tropical areas. Due to its content of long-chain fatty acids, the crude product is a waxy mass and, therefore, also called Ambrette beurre. Removal of the fatty acids with alkali gives a clear yellow to amber liquid with the strong, musky odor of ambrettolide. 

Other components are acyclic aliphatic esters and terpenes, such as farnesol and farnesyl acetate [237-239a]. Ambrette seed oil is one of the most expensive essential oils and, thus, is used mainly in fine fragrances and in alcoholic beverages. FCT 1975 (13) p.705 [8015-62-1], [84455-19-6]. 

Macrocyclic lactones like ambrettolide (7-hexadecen-l,16-olide) 158, 15-pentadecanolide (cyclopentadecanolide) 159, hexadecanolide (cyclohexa-decanolide) 160 and cyclohexadec-7-enolide 161 (Structure 4.48) are called musks. They are found in a variety of essential oils, e.g. ambrette seed oil and angelica root oil [1-4, 21-23, 62]. 

Ambrette seed Hibiscus abelmoschus L. (Z)-7-Hexadecan-16-olide, ambret-tolide (8-9), 5-tetradecen-14-olide, (2f ,6f )-farnesyl acetate (39-59)... 

Higher oxygenated terpenes include the sesquiterpene alcohol, famesol, which has a lily-of-the-valley odor and occurs in ambrette-seed oil. On acid dehydration it gives a-farnesene (Table 30-1) under some conditions, and bis-abolene (a component of oil of bergamot) under others ... 

Although natural flower absolutes are less important than in Chanel No. 5 and Arpege in establishing the essential character of the fragrance, rose, jasmin, and tuberose may be added, together with tonka, to back up the coumarin (1.5%), and a trace of natural vanilla. A trace also of ambrette seed can give a wonderful smoothness to the composition, working particularly well as part of the rose accord. 

Ambrette Seed Oil occurs as a clear yellow to amber liquid with the strong, musky odor of ambrettolide. It is a volatile oil obtained by steam distillation from the partially dried and crushed seeds of the plant Abeltnoschus moschatus Moench, syn. Hibiscus abeltnoschus L. (Fam. Malvaceae). It is refined by solvent extraction to remove fatty acids or by precipitation of the fatty acid salts. It is soluble in most fixed oils and in mineral oil, often with cloudiness, but relatively insoluble in glycerin and in propylene glycol. 

Ambrette Seed Oil 649 Butadiene-Styrene 50/50 Rubber Citronellyl Isobutyrate... 

Aluminum Identification Test, 753 Aluminum Magnesium Silicate, 41 Aluminum Potassium Sulfate, 21 Aluminum Sodium Sulfate, 21 Aluminum Sulfate, 22 Ambrette Seed Liquid, 23 Ambrette Seed Oil, 23, 596 Aminoacetic Acid, 186 A-[4-[[(2-Amino-l,4-dihydro-4-oxo-6-pteridinyl)methyl] amino] benzoyl] -l-glutamic Acid, 157 3 - Amino-7-dimethylamino-2-methylphenazine Chloride, 861 L-2-Aminoglutaramic Acid, 175 L-2-Amino-5-guanidinovaleric Acid, 32, (S3)5... 

Properties Colorless liquid having powerful musklike odor. Found in ambrette-seed oil. 

Derivation Found in nature in many flowers and essential oils such as cassia, neroli, cananga, rose, balsams, ambrette seed. 

Yellow crystals with an intense ambrette-seed odor. 

Ci6H2g02, Mt 252.40, is not reported as being found in nature, in contrast to (Z)-7-hexadecen-16-olide, which occurs in ambrette seed oil (see p. 182) and which is also referred to as ambrettolide. It is a colorless to slightly yellow liquid, re 0 0.949 -0.957, re 0 1.477-1.482, with an intense and powerful musk odor. It is prepared by treating aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) with trimethyl... 

Musk Ketone and Musk Ambrette. Musk Ketone is considered to have the closest odour to that of natural musk, and Musk Ambrette, as its name implies, has an odour reminiscent of ambrette seeds. Other nitromusks, which were discovered later, include Musk Tibetine and Moskene. The structures of these, together with the synthetic routes to Musk Xylene and Musk Ketone, are shown in Figure 4.51. Both of these are prepared from m-xylene through initial f-butylation. Nitration of the z-butyldimethylbenze ne thus produced gives Musk Xylene, and acetylation followed by nitration gives Musk Ketone. The other nitromusks are prepared by similar combinations of classical aromatic reactions. 

Maurer, B., and Grieder, A. (1977). (Z)-5-Tetradecen-14-olide, a new macrocyclic lactone, and two unsaturated straight chain acetates from ambrette seed absolute. Helv. Chim. Acta 60, 1155-1160. 

Ambrette seed oil. Pasty yellow mass, often also called ambrette butter or concrete, consisting mostly of palmitic acid. The actual oil (also known as ambrette absolute) is obtained by treatment with alkali or pre-... 

D. 0.958, n 1.4816, bp. (0.13 kPa) 154-156 °C, LD50 (rat orally) >5 g/kg. Kerschaum identified A. in ambrette seed oil as origin of the musk-like odor. Its synthesis is rather laborious so that A. still belongs to the more expensive musk fragrances. Its main use is in fine perfumery. 

Faraesyl acetate see ambrette seed oil. Fascaplysln(e) see oxindole alkaloids. 

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