Turpentine, Indian

Turpentine Oil. The world s largest-volume essential oil, turpentine [8006-64-2] is produced ia many parts of the world. Various species of piaes and balsamiferous woods are used, and several different methods are appHed to obtain the oils. Types of turpentines include dry-distiUed wood turpentine from dry distillation of the chopped woods and roots of pines steam-distilled wood turpentine which is steam-distilled from pine wood or from solvent extracts of the wood and sulfate turpentine, which is a by-product of the production of sulfate ceUulose. From a perfumery standpoint, steam-distilled wood turpentine is the only important turpentine oil. It is rectified to yield pine oil, yellow or white as well as wood spirits of turpentine. Steam-distilled turpentine oil is a water-white mobile Hquid with a refreshing warm-balsamic odor. American turpentine oil contains 25—35% P-pinene (22) and about 50% a-pinene (44). European and East Indian turpentines are rich in a-pinene (44) withHtfle P-pinene (22), and thus are exceUent raw materials... 

Turpentine from the western United States is different from that of the southern states in that it contains 3-carene ranging from 12—43%, depending on the species of pine tree. Indian turpentine also contains about 60% 3-carene and about 15% of the sesquiterpene longifolene. Turpentine from Sweden, Finland, CIS, and Austria all contain 3-carene however, a- and P-pinene are commercially the most important components of the turpentines. 

Garyophyllene. (-)-CaryophyUene can be isolated from Indian turpentine and has been used to prepare a number of woody aroma products. The epoxides are produced by reaction with peracids. Acetylation of caryophyUene also gives a usehil methyl ketone (180) (Fig. 8). Acid-catalyzed rearrangement of caryophyUene in the presence of acetic acid gives a mixture of esters, which are related to caryolan-l-ol and clovan-2-ol (181). 

This terpene has been isolated by Simonsen from Indian turpentine oil, from Pinus longifolia. It is identical with the terpene previously described by Robinson as a terpene yielding sylvestrene hydrochloride when treated with hydrogen chloride. Its characters are as follows —... 

Menthol from (+)-3-Carene. An Indian manufacturing process for (—)-menthol starts from 3-carene, the major component of Indian turpentine oil (55-65%). (+)-3-Carene isomerizes to (+)-2-carene, which can be pyrolyzed to (+)-tra s-2,8-/ -menthadiene. Isomerization of the latter yields (+)-isoterpi-nolene, which is hydrogenated to give >50% (+)-3-/ -menthene. Epoxidation and subsequent rearrangement lead to a menthone isomenthone mixture,... 

Also syntheses based on 3-carene from Indian turpentine and on D-pulegone from pennyroyal oil have been practised on a commercial scale in the past, but these approaches have been abandoned, because they were considered uneco-... 

A review of the class635 and a detailed conformational analysis of the carane-2,3-diols636 have appeared. No new naturally occurring carane derivatives, or any unusual sources of known compounds, have been reported, but much detailed chemistry based on (+ )-car-3-ene has been carried out directed towards the commercial exploitation of this major component of Indian turpentine. Syntheses of car-2-, car-3-, and car-3(10)-enes from cyclohex-3-en-l-one have been developed.637... 

Longifolene is present in Indian turpentine, which is obtained from the species Pinus longifolia. This hydrocarbon also has a strained skeleton and treatment with acid causes rearrangement to isolongifo-lene. Treatment of this with a peracid under acidic catalysis gives... 

Indian turpentine is rich in 3-carene and this can be used as a starting material for synthesis of menthol. The overall scheme is shown in Figure 4.23. 

SiMONSEN, J. L. The Constituents of Indian Turpentine from Pinus longifolia Roxb. J. Chem. Soc. (London) 117, 570 (1920). 

Longifolene is primarily found in Indian turpentine oil, which is commercially extracted from Pinus roxburghii (chir pine) (Bornscheuer et al., 2014). In rabbits, longifolene is metabolized as follows attack on the exo-methylene group from the endo-face to form its epoxide followed by isomerization of the epoxide to a stable mrfo-aldehyde. Then rapid CYP-catalyzed hydroj lation of this enr/o-aldehyde occurs (Asakawa et al., 1986) (Figure 9.30). 

Because of the presence of three asymmetric C-atoms in its structure, menthol occurs in four pairs of optical isomers, (—)- and (+)-menthol, (+)- and (—)-neomenthol, (+)- and (—)-isomenthol, and (+)- and (—)-neoisomenthol. (—)-Menthol is the isomer that mostly occurs in nature and, besides its characteristic odor, it possesses a cooling effect on the skin and mucosa. It can be obtained synthetically or from peppermint or other mint oils, or from essential oils such as citronella oil, eucalyptus oil, and Indian turpentine oil. Due to its minty smell and flavor, it is used in pharmaceuticals, soaps, hygiene products like toothpaste, cosmetics, chewing gum, teas, sweets, and tobacco products [40, 41]. 

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