Nopol acetate

Nopol acetate. See Nopyl acetate Nopol (terpene). See Nopol Nopyl acetate... 

CAS 128-51-8 EINECS/ELINCS 204-891-9 Synonyms 2-(2-Acetoxyethyl)-6,6-dimethylnorpin-2-ene 6,6-Dimethylbicyclo [3.1.1] hept-2-ene-2-ethanol acetate 6,6-Dimethylbicyclo (3.1.1.)-2-heptene-2-ethyl acetate 2-(6,6-Dimethylbicyclo [3,1,1] hept-2-en-2-yl) ethyl acetate 6,6-Dimethyl-2-norpinene-2-ethanol acetate Lignyl acetate Nopol acetate 2-Norpinene-2-ethanol, 6,6-dimethyl-, acetate 2-Pinene-10-methyl acetate Classification Organic compd. 

The acetate is also usehil commercially and can be made by direct esterification of Nopol. The products are usehil in soaps, detergents, poHshes, and other household products. 

Pinene is similar to a-pinene in its reactions. Pyrolytic cleavage to myrcene, the starting material for acyclic terpenes, is used on an industrial scale. Addition of formaldehyde results in the formation of nopol nopyl acetate is used as a fragrance material. /3-Pinene is produced in large quantities by distillation of turpentine oils. It is used as a fragrance material in household perfumery. However, most /3-pinene is used in the production of myrcene. 

Another bicyclic monoterpene of use in perfumery is nopyl acetate, which has a sweet woody-fruity odour. Prins reaction of /Tpinene with formaldehyde gives nopol which is easily esterified to the acetate (Scheme 4.27). 

Formaldehyde undergoes thermal ene reactions with reactive 1,1-disubstituted and trisubstituted alk-enes at 180-220 °C. 3-Pinene, a particularly reactive ene component, reacts with formaldehyde at 180 C to give nopol in 95% yield (equation 5). Methylenecyclohexane reacts similarly. Blomquist extended the scope of these reactions by using acetic acid-acetic anhydride as solvent at 180-190 °C. °... 

Ci3H2o02 Mr 208.30, bph5 122 °C, df 0.9811, rag0 1.4733, [a]D -30.9°, is not found in nature and has a fresh-fruity-woody odor. It is prepared by acetylation of (-)-nopol with acetic anhydride. (-)-Nopol is obtained from (- )-/ -pinene and paraformaldehyde in a Prins reaction. 

P-pinene with formaldehyde gives nopol which is easily esterified to the acetate as shown in Figure 4.31. 

Methyl a-naphthyl ketone Methyl 2-nonynoate Methyl 2-octynoate Myrcenyl acetate Nopol Phenoxyethyl propionate Piperonyl acetone Prenyl benzoate Propenylguaethol a-Terpineol... 

Saccharin sodium anhydrous Saccharin sodium dihydrate Sherbrite 30 Sherbrite 85 Sweet-Chew 30 Sweet-Chew 85 Sweet-Chew 95 Sweet-Chew 99 Syncal GS Syncal GSD Syncal S Syncal SDS Syncal US Unisweet SOSAC 204-890-3 Nopol 204-891-9 Nopyl acetate 204-909-5 Cl 61565 D C Green No. 6 Macrolex Green 5B Solvent green 3 204-927-3 Pyrene 204-932-0... 

Prins reaction of P-pinene with formaldehyde gives the alcohol nopol (39) and its acetate [35836-72-7] (40) is used as a fragrance ingredient. Base-catalyzed addition of dieth-ylamine to myrcene gives geranyl diethyl amine (41), which is converted to menthol (42) as described below. 

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