Vanillin benzoin

In detergent perfumes, the stabiUty of vanillin is not always certain. It depends on the association made with other raw materials, eg, with patchouli, frankincense, cloves, most of the animal notes, and such chemicals as amyl saUcylate, methyl ionones, heflotropin, gamma undecalactone, linalool, methyl anthrarulate, benzyl acetate, phenyl ethyl alcohol, cedar wood derivatives, oak mosses, coumarin, benzoin. Pern balsam, and cistus derivatives. In some cases, these mixtures can cause discoloration effects. 

Vanillin, CgHgOj, is one of the most important synthetic perfumes. It is the active odorous ingredient of the vanilla pod, in which it occurs to the extent of about 2 per cent., appearing on the surface of the bean as a fine white crystalline efflorescence. It occurs naturally also in Sumatra benzoin (about 1 per cent.), Siam benzoin (15 per cent.), and the balsams of Tolu and Peru (traces). Numerous other bodies have been recorded as containing it, such as asafoetida, beetroot and asparagus, the seeds of Lupinus albus, the seeds of Sosa canina, etc. 

Styrax tonkinensis Pierre. S. benzoin Dryand An Xi Xian (Styrax) (leaf) Sumaresinolic acid, coniferyl cinnamate, styracin, vanillin, alpha-phenylpropyl cinnamyl cinnamate, balsamic acid.33-50 As an aromatic stimulant, for aphrodisiac, an astringent. 

N.A. Styrax benzoin Dryander Cinnamic, benzoic, sumaresinolic acid esters, benzoic acid, benzaldehyde, vanillin.99 Antiseptic, astringent. Externally for wounds and ulcers, internally to settle cramps, stimulate coughing, disinfect the urinary tract. 

At the time when Shalimar was made it was customary to use a high proportion of the alcoholic tinctures made from natural products, rather than the concentrated absolutes and resins. These would have included such products as vanilla, benzoin, and tonka to give naturalness to the ethyl vanillin and coumarin, as well as tinctures of civet, castoreum, ambergris, and musk. Such products retain more of the most volatile components of the starting material, giving a wonderful quality and life to the finished product. 

Other aspects of the perfume are its balsamic notes such as benzoin which, with castoreum and a costus note (the natural product can no longer be used), combine with the isobutyl quinoline to give the leather character. As we have seen before, spices such as cinnamon and clove work well with leather notes, and these are again present, backed up by a carnation accord of eugenol, heliotropin, and vanillin. 

Protocatechuic Acid.—One of the di-hydroxy benzoic acids is related to vanillin, which we have already studied. The acid is known as protocatechuic acid, and derives its name from the fact that it may be obtained from a gum or resin, known as gum catechin by fusion with potash, i.e. by heat and oxidation in presence of an alkali. A large variety of plant products including alkaloids essential oils, gums, resins and tannins yield this acid. The following may be mentioned gum catechin, gum benzoin, guaiac resin, myrrh, piperine or piperic acid, vanillin, cafe-tannic acid. These natural sources at once suggest a relationship to vanillin (p. 661) and heliotropin (p. 662). It is the acid corresponding to protocatechuic aldehyde, 3-4-di-hydroxy benzal-dehyde (p. 661), which explains the relationship just mentioned. Its constitution, is then ... 

Benzoin, or gum benzoin, is a resinous secretion obtained from cuts made in the trunk or branches of the Styrax benzoin tree. It contains coniferyl benzoate, benzoic acid, benzyl cinnamate, vanillin (a phenol aldehyde) and a number of triterpenes. ... 

Benzoe Sumatra resinoid is obtained by solvent extraction of the resin from Styrax benzoin Dryand., a tree growing predominantly on the island of Sumatra. Benzoe Sumatra resinoid is a dark brown, viscous liquid with a warm, powdery, sweet-balsamic odor. Its main volatile, odor-determining components are derivatives of benzoic and cinnamic acids and vanillin [284]. 

Benzoe tonkinensis Siam-benzoin, gum benjamin Styrax tonkinensis (PIERRE) CRAIB t x HARTWICH Styracaceae Ph. Eur. Ill, OAB 90. Helv VII, USP XXtl, MD 25% free or combined adds, determined as benzoic acid (Ph. Eur. 111). Coniferyi benzoate (60%-80°/li), coumaryl benzoate (10-15%), benzoic acid (10%-20%), vanillin (about 0.3%), a-siaresinolk acid ( = 19-hydroxyoleanolic acid)... 

Benzoc Sumatra Sumatra-benzoin Styrax benzoin DRY AND.. Styracaceae BP 93, USP XXII, MD Ciimanioyl benzoate and coniferyi benzoate (70%-80%), cinnamic acid esters, styracin, cinnamic acid (about 10%), cinnamic acid pheiiylpropy] CvSter (about L%), vanillin (about 1%), sumaresinolic acid (= 6-hydroxyoleanolic acid)... 

Gum Benzoin. Resin benzoin resin benjamin gum benjamin. Balsamic resin from Styrax benzoin Dryand., known as Sumatra benzoin, or from S. tonkinensis (Pierre) Craib, Styracaceae, or other species of Styrax known as Siam benzoin. Habit. Thailand, Cambodia, S. Vietnam, Sumatra, Java, and Sunda Islands. Constit. Ethereal oil, free and combined benzoic and cinnamic acids up to 39%, vanillin, coniferyl benzoate, resin (a mixture of benzoresino] and ben-zoresinotannol) ester fled with benzoic acid, styrol, styradn. Not less than 90% of Siam and not less than 75% of Sumatra benzoic is sol in ale (U.S.F.), Ref Reinitzer, Arch. Pharm. 264, 131 (1926) Brans, Pharm. Weekbl. 73, 374 (1936) Freudenberg, Bittner, Ber. 83, 600 (1950). 

Note to the instructor Possible pairs of compounds are given in the following list. The two compounds to be resolved are given first, followed by the three developing solvents to try (1) benzoin and benzil acetone, methylene chloride, hexane (2) vanillin and vanillyl alcohol acetone, 50% toluene-50% ethyl acetate, hexane (3) diphenylmethanol and benzophenone acetone, 70% hexane-30% acetone, hexane. Each compound in a pair should be prepared individually and as a mixture of the two compounds. Prepare all of them as 1% solutions in acetone. 

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