BALSAM TOLU

Compounds related to benzene were obtained from similar plant extracts Eor example a pleasant smelling resin known as tolu balsam was obtained from the South American tolu tree In the 1840s it was discovered that distillation of tolu balsam gave a methyl derivative of benzene which not surprisingly came to be named... 

Essential oils are isolated from various plant parts, such as leaves (patchouH), fmit (mandarin), bark (cinnamon), root (ginger), grass (citroneUa), wood (amyris), heartwood (cedar), gum (myrrh oil), balsam (tolu balsam oil), berries (pimento), seeds (diU), flowers (rose), twigs and leaves (thuja oil), and buds (cloves). 

Benzoic acid in the free state, or in the form of simple derivatives such as salts, esters, and amides, is widely distributed in nature. Gum benzoin (from styrax ben in) may contain as much as 20% benzoic acid in the free state or in combinations easily broken up by heating. Acaroid resin (from anthorrhoca haslilis) contains from 4.5 to 7%. Smaller amounts of the free acid are found in natural products including the scent glands of the beaver, the bark of the black cherry tree, cranberries, pmnes, ripe cloves, and oil of anise seed. Pern and Tolu balsams contain benzyl benzoate the latter contains free benzoic acid as well. The urine of herbivorous animals contains a small proportion of the glycine derivative of benzoic acid, hippuric acid [495-69-2] (CgH CONHCH2COOH). So-called natural benzoic acid is not known to be available as an item of commerce. 

Ben /ben ate [120-51-4] CgH COOCH2CgH, mp, 21°C, cff , 1.118 bp, 323—324°C at 101.3 kPa , 1.5681. This is a colorless, oily liquid with a faiat, pleasant aromatic odor and a sharp, burning taste. It occurs naturally iu Pern and Tolu balsams, is spariugly volatile with steam, and is iusoluble iu water. Benzyl benzoate is prepared commercially by the direct esterification of benzoic acid and benzyl alcohol or by reaction of benzyl chloride and sodium benzoate. The pleasant odor of benzyl benzoate, like other benzoic esters, has long been utilized iu the perfume iadustry, where it is employed as a solvent for synthetic musks and as a fixative. It has also been used iu confectionery and chewing gum flavors. 

Phenyl-2-propenoic acid [621 -82-9] commonly referred to as cinnamic acid, is a white crystalline soHd having a low intensity sweet, honeylike aroma. It has been identified as a principal constituent in the botanical exudates from Styrax IJquidamber orientalis) Benzoin Styrax ben in Pern Balsam [Myroxylon pereirae and Tolu Balsam (]Ayro>ylon balsamum) (4,5). In these, as well as numerous other natural products, it exists both as the free acid and in the form of one or more of its esters, as for example, methyl cinnamate, ben2yl cinnamate [103 1 -3] and cinnamyl cinnamate. 

In the early days of organic chemistry, the word aromatic was used to describe such fragrant substances as benzaldehyde (from cherries, peaches, and almonds), toluene (from Tolu balsam), and benzene (from coal distillate). It was soon realized, however, that substances grouped as aromatic differed from most other organic compounds in their chemical behavior. 

Tolu balsam resinoid is produced by extraction of the balsam of Myroxylon balsamum (L.) Harms (Fabaceae). It is a dark orange brown mass with a sweet, resinous, long-lasting odor, reminiscent of hyacinth. An essential oil is also distilled from the balsam. 

Tolu balsam resinoid contains a fairly large amount of benzyl and cinnamyl esters of benzoic and cinnamic acid [284a, 800-800b]. 

Phenylpropanoids are widespread in higher plants, especially in the plants that produce essential oils, e.g. plants of the families, Apiaceae, Lamiaceae, Lauraceae, Myrtaceae and Rutaceae. For example, Tolu balsam (Myroxylon balsamum, family Fabaceae) yields a high concentration of cinnamic acid esters, cinnamon (Cinnamomum verum, family Lauraceae) produces cinnamaldehyde, fennel (Foeniculum vulgare, family Apiaceae) is a good... 

Toluene is a clear, flammable, aromatic hydrocarbon liquid with a smell similar to benzene. It is also called methylbenzene, indicating that a methyl group has been added to one of benzenes carbon atoms. Toluene was first isolated by Pierre-Joseph Pelletier (1788—1842) and Philippe Walter (1810—1847) in 1837. The name toluene comes from the South American tree Toluifera balsamum. Henri-Etienne Sainte-Claire Deville (1818—1881) isolated toluene from the tree s gum, Tolu balsam, in 1841. 

Charge Tolu balsam tincture into mixing tank and add magnesium carbonate. 

Toluol.—When tolu balsam is distilled, there passes over a large quantity of benzoic, mixed with a little cinnamic acid, and a yellow liquid, which is a mixture of toluol and benzoic ether. By redistilling this, so as only to collect the portions which pass over hetweas 265° and 285°, a distillate is obtained, which, when deprived of benzole acid by distillation with solid caustic potaaaa, possesses the properties which belong to toluol. 

Botany Bay Resin, said to be the produco of acaroie resinifem, is of a yellow hue, brittle, and of a slightly astringent taste. -It exhales a fragrant odor when heated, and dissolves In aloohol and ether. It resembles tolu balsam in containing cinnamic, and a small quantity of benzoio add. 

Even when smelling a complicated blend of materials experienced perfumers are readily able to recognize the presence of certain natural ingredients. They do not need to think of the hundreds of possible individual components each may contain. The specific combinations form an olfactory pattern that perfumers are immediately able to identify as, for instance, patchouli, geranium, or tolu balsam. 

Octotillone (56), from commerical tolu balsam, differs from the previously described 20/ -octotillone and is therefore its 24-epimer. The callus cells of Panax gingseng have been reported to produce panaxatriol (57). The full paper on gingsenoside Rg has appeared. 

Benzyl Alcohol.—The simplest aromatic alcohol is the hydroxyl derivative of toluene and is known as benzyl alcohol, CeHs—CH2—OH. The radical, (CeHs—CH2—), is termed benzyl as in the alcohol and chloride above. The alcohol occurs as an ester in Peru balsam, in storax, a resin obtained from a plant sty rax, and in Tolu balsam from which the mother hydrocarbon toluene derives its name. On hydrolysis of the balsam benzyl alcohol is obtained. It is a liquid, b.p. 206.5°, slightly soluble in water and soluble in alcohol or ether. It may be prepared by those syntheses just given which yield primary alcohols. It may also be prepared by the reduction of the corresponding aldehyde, known as benzoic aldehyde or benzaldehyde (p. 655). On oxidation it yields the aldehyde and then an acid, benzoic acid. 

Occurrence.—Benzoic acid is a naturally occurring substance being found both free and as esters in gum benzoin Peru and Tolu balsams huckleberries, the flower, dragon s blood, etc. It also occurs in combina-... 

Which of the two is the cis form and which the trans form has not been determined. A third cinnamic acid, viz., iso-cinnamic acid, is also known, but the constitution of it has not been established. Cinnamic acid is found in nature in the resin storax both as the free acid and as the cinnamic alcohol ester, styrin. It is also found in Peru and Tolu balsams as the free acid and as the benzyl alcohol ester, the benzoic acid ester of benzyl alcohol being present also. Thus benzyl alcohol, benzoic acid, cinnamic alcohol and cinnamic acid are all constituents of esters present in these plant resins. Allo-cinnamic acid, the geometric isomer, is obtained from coca leaves from which the alkaloid cocaine is also obtained (p. 896). When cinnamic acid is heated with lime it loses carbon dioxide and yields the unsaturated side-chain hydrocarbon st3rrene, or phenyl ethylene, CeHs—CH = CH2. On reduction it yields first cinnamic aldehyde, found in oil of cinnamon (p. 842) and then cinnamic alcohol. Both cinnamic acid and allo-cinnamic acid yield anhydrides. 

Benzyl Alcohol, NF. Ben/yl alcohol (phenylcarbinol. phenylmethanol) occurs naturally as the unesteriried form in oil of jasmine and in esters of acetic, cinnamic, and benzoic acids in gum benzoin,. storax re.sin. Peru balsam, tolu balsam, and some volatile oils. It is. soluble in water and alcohol and is a clear liquid with an aromatic odor. 

Benzoic Add, USP. Benzoic acid and its esters occur naturally in gum benzoin and in Peru and tolu balsam.s. It is found as a white crystalline solid that slowly sublimes at room temperature and is steam distillable. It is slightly soluble in water (0.3%) but more. soluble in alcohol and in other polar organic. solvents. It has a pK of 4.2. Benzoic acid is used externally as an antiseptic in lotions, ointment.s. and mouthwashes. It is mure effective as a preservative in foods and pharmaceutical products at low pH (Ic.ss than the pK ). When used as a preservative in emulsions, its effectiveness depends on both pH and distribution into the two pha.scs. ... 

Tolu balsam, a plastic solid, is derived from a related tree in Colombia. Its uses are similar to Peru balsam. Source of tolu oil. Odorless. 

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