Limonene degradation

Cold pressed orange oil contains over 95 by weight monoterpene hydrocarbons. The principal constituent, d-limonene, ranges from 83-97 percent (9), Limonene degradation has been well docu-meted in the literature (LO, 1 1). Anandaraman identified limonene-1,2-epoxide and carvone as two of the earliest degradation products of d-limonene (12, 13). 

LEH originates from the bacterium Rhodococcus erythropolis DCL14." ° LEH is part of a limonene degradation pathway where it catalyzes the conversion of limonene-1,2-epoxide to limonene-1,2-diol (Scheme... 

Biological oxygen uptake of the isolates grown on (+)-limonene with potential intermediates of limonene degradation (activities in nmol 02-min -[mg protein] )... 

This strain was identified by the NCIMB as a Rhodococcus sp. Enzyme activities involved in limonene degradation were determined in cell extracts of limonene grown cells (Table 2). 

Chang, H.C. and P. Oriel (1994) Cloning and expression of a limonene degradation pathway from Bacillus stearothermophilus in Escherichia coli. J. Food Sci. 59 660-662. 

KAM 07] Kamphoff M., Thiele T., Kunz B., Influence of different extraction parameter on a solid-phase dynamic extraction for the gas chromatographic determination of d-limonene degradation products by using a fractional factorial design . Journal ofAOACInternational, vol. 90, pp. 1623-2627, 2007. 

Used tires create serious environmental problems, because they do not degrade easily and they release noxious contaminants when they bum. Recently, a process has been developed that breaks tires down into a polyisoprene oil that can then be further decomposed into limonene. The yield of limonene is only a few percent, but if this process can be made more efficient it may become possible to turn ugly, smelly old tires into fragrant oil of lemon. 

Degradation of many terpenes has been examined including p-pinene, o-limonene, and trani-caryophyllene (Grosjean et al. 1993c). 

Van der Werf Ml, HJ Swarts, JAM de Bont (1999) Rhodococcus erythopolis DCL14 contains a novel degradation pathway for limonene. Appl Environ Microbiol 65 2092-2102. 

Hydroxylation and Baeyer-Villiger reactions carried out by monooxygenation are important in the degradation of a range of terpenoids and steroids. The aerobic degradation of limonene can take place by a number of reactions several of which involve hydroxylation at allylic positions... 

Terpene resins are most commonly used in adhesive production, where they confer very strong tackifying properties. The terpene resins improve the resistance of adhesives to oxidative degradation. These resins are normally produced from p-pinene and are light yellow in colour. Polymers of dipentene and limonene are also available as resins. 

The two extrusion products, Reg and SF Duraromes, exhibited the lowest rates of limonene-1,2-epoxide formation. After 6 months storage at temperatures of 25 and 37 C, these products contained epoxide levels of < 0.20 mg/g orange oil. At 50 C, the Reg Durarome showed levels 0.50 mg/g orange oil. Epoxide degradation may also have been a factor similar to that seen with beta-cyclodextrin. 

Fig. (15). Pathways for the degradation of limonene by a soil Pseudomonad (after [68])...

The same group has also isolated a strain of Pseudomonas putida-arvilla (PL-strain) from limonene and (+)-a-pinene as the sole carbon source that was capable of growing on (+)-limonene, (+)-a-pinene, (-)-a-pinene, / -pinene, 1-p-menthene, 3-p-menthene and p-cymene as substrates [75]. Limonene was degraded to perillyl alcohol, perillaldehyde and perillic acid. 

Kleno, J.G., Wolkoff, P., Clausen, P.A., Wilkins, C.K. and Pedersen, T. (2002) Degradation of the adsorbent Tenax TA by nitrogen oxides, ozone, hydrogen peroxide, OH radical and limonene oxidation products. Environmental Science and Technology, 36, 4121-6. 

Poncet-Vincent S. Desodorisation de fair par photocatalyse au contact de Ti02 degradation de l acide pentanoi que, du limonene et du sulfure d hydrogene. Thesis. France University of Lyon, 1999 309-399. 

Earlier workers established the presence of a-pinene, (3-pinene, 1-a-phellandrene, dl-limonene, piperonal, dihydrocarveol, a compound melting at 161°C, P-caryophyllene and a piperidine complex from the essential oil obtained by steam distillation of ground Malabar pepper. The above compounds were identified by the classical methods of derivatization and degradation. They also reported the presence of epoxy dihydrocary-... 

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