Benzyl alcohol storax

Benzyl Ginnamate.—The cinnamic acid ester of benzyl alcohol is a natural constituent of storax, tolu, and Peru balsams. It is a crystalline Bubstance with a characteristic sweet balsamic odour. It may be prepared by heating sodium cinnamate, alcohol, and benzyl chloride together under a reflux condenser. It is a useful ester where a sweet balsamic odour is required to be introduced into a perfume, especially cf the heavy type. It forms white, glistening prisms, which melt at 39°, and.decompose when heated to 350°. The best commercial specimens have the following characters —... 

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. 

Homologues.—The homologues of benzyl alcohol result from substitution of the hydroxyl group in one of the methyl groups of xylene, mesitylene, etc., or, as in the examples previously given of secondary and tertiary aromatic alcohols, by the substitution of hydroxyl in a poly-carbon side chain either saturated or unsaturated. These need not be discussed further except to mention that both phenyl propanol, CeHs—CH2—CH2—CH2OH, and phenyl propenol, CeHs—CH = CH— CH2OH, are also found as cinnamic acid esters in storax. 

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. 

Benzoin tincture contains 10% benzoin in alcohol, while the compound formulation also contains 2% aloes, 8% storax, and 4% tolu balsam in alcohol. Occasionally, allergic contact dermatitis occurs to these preparations or derivatives in Ar-ning s tincture (besides benzoin, tumenol ammonium, anthrarobin, and ether), adhesives, water repellent barrier creasms, lozenges, and cosmetics (Spott and Shelley 1970). Cross-reactions occur to balsam of Peru, storax, eugenol, vanilla, a-pinene, benzyl alcohol, and benzyl cinnamate (Hjorth 1961). 

Properties Dk. brn. vise, liq., pleasant vanilla odor sol. in fixed oils si. sol. in propylene glycol insol. in water, glycerin dens. 1.150-1.170 Toxicology LD50 (oral, rat) > 5 g/kg, (skin, rabbit) >10 g/kg low toxicity by ing. and skin contact skin irritant mild allergen can cause contact dermatitis and stuffy nose common sensitizer may cross react with benzoin, rosin, benzoic acid, benzyl alcohol, cinnamic acid, essential oils, storax, etc. TSCA listed Precaution Combustible when heated Hazardous Decomp. Prods. Heated to decomp., emits acrid smoke and irritating fumes... 

Compounds present in storax oil include styrene, phenylpropyl alcohol, cinnamic alcohol, benzyl alcohol, ethyl alcohol, and vanillin (karrer list and horhammer). 

Phenyl-propyl alcohol, CgH. CHj. CH.2. CHj. OH, is the next highest homologue of phenyl-ethyl alcohol, and is also known as hydro-cinnamyl alcohol. Like the last described bodies it has been known for many years, its first preparation being described in the Aivnalen (188, 202). It occurs as a cinnamic acid ester in storax, and as an acetic ester in cassia oil. It is prepared synthetically by the reduction of cinnamyl alcohol with sodium amalgam and water, or by the reduction of cinnamic or benzyl acetic esters with sodium and absolute alcohol. It has the following characters —... 

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