From sandalwood oil

Schimmel Co. have isolated a hydrocarbon of the formula CjjHj from sandalwood oil. This body is completely saturated and is unaffected by potassium permanganate at ordinary temperatures. 

It is probable that the tricyclic hydrocarbon from sandalwood oil is identical with, or at least closely allied to, Semmler s nor-tric /cZoeksanta-lane. 

Teresantalol is an alcohol of the formula Cj jgO, which was isolated from sandalwood oil by Schimmel Co. It has been prepared artificially by Semmler and Bartelt, by reducing teresantalic acid with sodium. 

Santalol, the alcohol or mixtiire of alcohols obtained from sandalwood oil. Its specific gravity at 15° 0. is 0 9795 optical rotation, -18° and refractive index at 20° 0., 1 507. 

Sandalwood Oil, East Indian. The use of sandalwood oil for its perfumery value is ancient, probably extending back some 4000 years. Oil from the powdered wood and roots of the tree Santalum album L. is produced primarily in India, under government control. Good quaUty oil is a pale yellow to yellow viscous Hquid characterized by an extremely soft, sweet—woody, almost ariimal—balsarnic odor. The extreme tenacity of the aroma makes it an ideal blender—fixative for woody-Oriental—floral fragrance bases. It also finds extensive use for the codistillation of other essential oils, such as rose, especially in India. There the so-called attars are made with sandalwood oil distilled over the flowers or by distillation of these flowers into sandalwood oil. The principal constituents of sandalwood oil are shown in Table 11 (37) and Figure 2. 

OC-Santalol. Sandalwood oil is comprised of mainly (90%) a- and P-santalol, which gives the oil the woody, tenacious sandalwood odor. An impure a-santalol [115-71 -9] (100) can be isolated by the distillation of the oil. P-Santalol [77-42-9] (101) is also isolated but ia much smaller amounts. The price of sandalwood oil, E. Indian, ia 1995 was 286/kg, and the oil from Indonesia was 187/kg (69). The high price of these oils has created the need to synthesize new materials with the sandalwood odor. The terpenophenols are manufactured by condensation of camphene with phenoHc compounds followed by hydrogenation to the cycloaUphatic alcohols (194). 

Santene has also been examined by Aschan. The following are the characters of the purest specimens which have been isolated from sandalwood and Siberian nine oils —... 

The fraction of oil of cade boiling at 260° to 280° is converted into cadinene dihydrochloride by saturating its solution in dry ether with dry hydrochloric acid gas. The hydrochloride is separated, dried, and leorystallised, and the hydrochloric acid removed by heating it with aniline or with sodium acetate in glacial acetic acid. The liberated cadinene is rectified in a current of steam. Cadinene from oil of cade is highly laevo-rotatory, the dextro-rotatory variety being obtained from Atlas cedar oil and West Indian sandalwood oil. 

By the dehydration of the isomeric santalols contained in sandalwood oil, Guerbet obtained two sesquiterpenes, which he designates u-isosantalene and /3-isosantalene, according to the santalol from which they are respectively obtained. He assigns to them the following characters —... 

There exist in sandalwood oil (from Santalum album) two isomeric sesquiterpene alcohols, of the formula CjjHg O. They are both primary UDSaturated alcohols, one being bicyclic, the other tricyclic. These two alcohols are termed a-santalol and /3-santalol. a-santalol has the following characters —... 

The specific gravity, refractive index, and specific rotation given above are those recorded by Paolini and Divizia and are probably accurate since the a-santalol was prepared by regeneration from its strychnine phthalate. The values recorded for commercial santalol, prepared by fractional distillation, are as follows, and are the average values for the mixed santalols as they occur in sandalwood oil... 

The alcohols of the so-called West Indian sandalwood oil, which is distilled from a species of Amyris, are known under the name of amyrol. It is, in all probability a mixture of two alcohols of the formulae CjjHjjO Its characters are as follows —... 

The oil is sometimes incorrectly called West Indian sandalwood oil. However, its composition and odor are different from those of the oils obtained from sandalwood species. The major components of amyris oil are sesquiterpenoids such as elemol [639-99-6], /3-eudesmol [473-15-4], and epi-7-eudesmol [15051-81-7] [241-244]. 

REPELLENT. 1. A substance that causes and insect of animal to turn away from it or reject it as food. Repellents may be in the form of gases (olfactory), liquids, or solids (gustatory). Standard repellents for mosquitos, ticks, etc., arc dtronella oil, dimethyl phthalatc, w-butylmcsityl oxide oxalate, DEET, and 2-ethyl hexanediol-1,3. Actidione is the most effective rodent repellent, but is too toxic and too costly to use. Copper naphthenate and lime/sulfnr mixtures protect vegetation against rabbits and deer. Shark repellents are copper acetate or formic acid mixed with ground asbestos. Bird repellents are chiefly based on taste, but this sense varies widely with the type of bird so that generalization is impossible. G -Naphthol, naphthalene, sandalwood oil, quinine, and ammonium compounds have been used, with no uniformity or result. 

Sandalwood Oil, East Indian Type, occurs as a pale yellow to yellow, somewhat viscous, oily liquid with a strong, persistent, characteristic odor. It is the volatile oil obtained by steam distillation from the dried, ground roots and wood of Santalum album L. (Fam. Santalaceae). It is soluble in most fixed oils, in propylene glycol, and in mineral oil, sometimes with haziness. It is insoluble in glycerin. 

An extensive examination of the minor components of East Indian sandalwood oil has revealed as one component (177), ° which is also synthesized from teresantalic acid by oxidative decarboxylation and cyclopropylmethylhomoallylic rearrangement. 

C12 hydrocarbon (271)135 by a similar route but this compound is not identical to a tricyclic hydrocarbon isolated from East Indian sandalwood oil and reported to have this structure. (+)-Copacamphor (272) and (+)-copaborneol (273) have been isolated from Espeltiopsis guacharaca.136 The interesting sinularene derivative (274) and the acetoxycyclosinularane (275) have been isolated from the marine source, Clavularia inflata.137 These compounds, together with an aromadendrane derivative (see p. 181) are the first sesquiterpenoids from Octocorallia of the order Stolonifera. 

Heissler, D., and Riehl, J.-J., Synthesis with benzenesulfenyl chloride. On the structure of a ( 12IIis hydrocarbon from East Indian sandalwood oil. Tetrahedron Lett., 21, 4711, 1980. 

Sandalwood oil is obtained by distillation of the parasitic tree Santa-lum album. The major components of the oil are the santalols (27, 28). Many syntheses of these and related chemicals have been reported but, elegant as they are, none compete economically with the oil itself. The synthetic sandalwood materials fall into two main classes, the so-called terpenophenols and the materials derived from campholenic aldehyde. 

Oil of Santal. Sandalwood oil arheol East Indian sandalwood oil. Volarile oil from dried heart wood of Sonfci-lum album L, Santalaceae, Constit. At least 90% total alcohols calculated as santalo], about 2-4% santalol as esters. 

Pale yellow somewhat viscid liquid characteristic sandalwood odor and taste. dg 0.965-0 980. aas —15 to —20 . njj 1.500-1 510. Very slightly sol in warer sol in 5 vols 70% alcohol. Keep well closed, cool and protected from light, Note West Indian sandalwood oil is derived from Amyris balsamifera and is not official. Its rotation is +24 to +29 . ll is less sol in 70% a]c than the East Indian, therap CAT Urinary anti-infective. 

Production Even today many aroma chemicals are still isolated from essential oils, others are prepared semisynthetically from the components of the oils or from other suitable oiganic compounds. The proportion of natural and nature identical aroma chemicals used in the perfume industry is ca. 70%. The aroma chemicals not occurring in nature are often structural analogues of natural products that are difficult to synthesize, e.g., the sandalwood aroma chemicals prepared from campholene aldehyde or camphene and guaiacol as substitutes for the expensive sandalwood oil or santalols. 

Occurrence Tricyclene in juniper oil (Juniperus communis, Cupressaceae) and in the essential oil of the fir Abies balsamea (Pinaceae) ca. 1.3%. Teresantalol, ter-santalal, and teresantalic acid are isolated from East Indian sandalwood oil. sandalwood oil (Santalum album, Santalaceae). 

An additional bond from C-2 to C-4 of campherenane formally leads to tricyclic a-santalane, the basic skeleton of some constituents found in sandalwood oil (oil of santal) with a woody, sweet, balsamic odor, used in perfumery and as a urinary antiinfective obtained from dried heartwood of the tree Santalum album (San-talaceae) grown in east India. Examples include (+)-( -a-santalol with a slight woody odor similar to cedar wood oil and (+)-(Ej-a-santalal, with a strong woody odor. 

Synonyms Amyris balsamifera Amyris balsamifera oil Amyris oil Amyris oil. West Indian type Sandalwood oil Sandalwood oil. West Indian West Indian rosewood oil West Indian sandalwood oil Definition Produced by steam distillation of wood from Amyris balsamifera tree, contg. caryophyllene, cadinene, cadinol Properties Pale-yel. liq. sandalwood odor burning taste sol. in alcohol dens. 0.96 kg/l (20 C) ref. index 1.5035-1.5120(20 C)... 

The East Indian sandalwood oil probably represents one of the most precious perfumery natural raw materials because of the rarity of the natural plants from which it is extracted. As until recently [36] since no industrially viable process existed for production of (Z)-beta-santalol, the main olfactive constituent of Indian sandalwood (see Fig. 6), the focus was directed toward the search for cheaper synthetic analogs in order to also prevent resource depletion. Alpha-campholenic aldehyde derivatives are clearly affording the best, and most often used substitutes for such a natural resource [37]. 

Other terpene alcohols include geraniol, citronellol from rose oil, Rosa gallica (Rosaceae), and scented geraniums Pelargonium spp. (Geraniaceae). Nerol is a stereoisomer of geraniol. Borneol is found in rosemary oil—Rosmarinus officinalis (Lamiaceae). Santalol from heartwood of sandalwood—Santalum album, S. spicatum (Santa-laceae)—is a sesquiterpene alcohol. 

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