P-Caryophyllene, oxidation

SYNS CARYOPHYLLENE EPOXIDE CARYOPHYLLENE OXIDE (-)-CARYOPHYLLENE OXIDE P-CARYOPHYLLENE OXIDE EPOXY-CARYOPHYLLENE (-)-EPOXYDIHYDROCARY-OPHYLLENE 5-OXATRICYCLO(8.2.0.0 > DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R,4R,6R,10S)- 4.11.11-TRIMETHYL-8-METHYLENE-50XATRI-CYCL0-(8.2.0.0(4,6))DODECANE... 

Croton sylvaticus Hochst. The essential oil of semi-dried C. sylvaticus leaves (0.14%) contained mainly the sesquiterpenes p-caryophyllene oxide (35%) and a-humulen-1,2-epoxide (12%) (56). The aqueous extract of the stem bark of C. sylvaticus reduced exploratory activity, prolonged ether anesthesia, relaxed the muscles and had analgesic effects on mice (5 7). The plant is used for treatment of swellings caused by kwashiorkor, for tuberculosis and as a purgative (35). 

Euphorbiaceae Croton sylvaticus Hoscht. Leaves SD 0.14 P-caryophyllene oxide, a-humulen-1,2-epoxide 56... 

FI and F2 contain P-caryophyllene-oxide (9) at a 0.025% yield, 0-selinene (10) (0.09%), selin-1 l-en-4a-ol (11) (0.004%), and squalene (12) (0.017%). Compounds 9 and 10 potentially increased the time of hypnosis in the animals treated with pentobarbital. The administration of the compounds enhanced sleeping time up to 100% compared to the control group. 

P-Caryophyllene alcohol acetate. See Caryophyllene alcohol acetate Caryophyllene epoxide p-Caryophyllene epoxide. See P-Caryophyllene oxide P-Caryophyllene oxide CAS 1139-30-6 EINECS/ELINCS 214-519-7 Synonyms Caryophyllene epoxide p-Caryophyllene epoxide Epoxycaryophyllene (-... 

Trimethyl-9-methylene-5-oxatricyclo [8.2.2.0.0.4.6] dodecane. See P-Caryophyllene oxide... 

Sampling time 60 min extraction temperature 80°C. Monoterpenes a-pinene, p-myrcene, a-phellandreneand limonene sesquiterpenes a-cubebene, a-copaene, p-elemene, p-caryophyllene, a-humulene, y-muurolene, p-eudesmene and caryophyllene oxide diterpenes cembrene A and isoincensole acetate. 

The first observation is the similarity between the chemical compositions of both the Boswellia carteri and Boswellia sacra. For these three olibanum samples, a-pinene (2), (3-myrcene (8) and limonene (14) are the predominant monoterpenes. p-Caryophyllene (73) is the major sesquiterpene besides a-copaene (65), a-humulene (also called a-caryophyllene) (78) and caryophyllene oxide (95). The characteristic olibanum compounds isoincensole and isoincensole acetate (128) together with cembrene A (120) are the main diterpenes. 

Boswellia serrata olibanum has a chemical composition close to that of both the B. carteri and of B. sacra, but contains compounds that are absent in those from other Boswellia and could be used as markers methylchavicol (38), p-anisaldehyde (47), methyleugenol (70), isocaryophyllene (82), sesquiterpene 91, elemicin (92) and an unidentified diterpene (124) eluting between cembrene C (123) and verticilla-4(20),7,ll-triene (125). It is devoid of (5-caryophyllene (73), a-humulene (78), caryophyllene oxide (95) and bornyl acetate (50). 

Finally, p-caryophyllene was also subjected to the MTO-catalyzed oxidation. Here, the biphasic system with CH2C12 as the solvent is very effective, with full conversion and selectivity for the internal epoxide after only 1 h of reaction time and a very low catalyst amount of 0.1 mol%, using a 10 1 mixture of 3-methylpyrazole and 1-methylimidazole as nitrogen base [55],... 

Thevanmundi, Poonjaranmunda, Valiakaniak-kadan and Subhakara. Some of the newly developed cultivars are Panniyur-1, Panniyur-2, Panniyur-3 and Panniyur-4. By adopting GC and GC-MS techniques, researchers have identified over 55 compounds from the volatile oil of these pepper cultivars. The major compounds identified were a- and (3-pinene, sabinene, limonene, P-caryophyllene, myrcene, p-cymene and caryophellene oxide (Gopalakrishnan et al., 1993 Menon et al., 2000, 2002, 2003 Menon and Padmakumari, 2005). Table 2.7 illustrates this variability among different popular cultivars. 

Variety/ compound Limonene P-Pinene P-Caryophyllene Sabinene Caryophyllene oxide 8-3-Carene a-Pinene Myrcene p-Cymene Elemol... 

Floral volatiles could play many roles instead of or in addition to pollinator attraction. For example, many terpenes, including P-myrcene, ( )-P-ocimene, linalool, and ( )-P-caryophyllene, react readily with ozone and other reactive oxygen species (27). Thus, floral volatiles could function to protect the reproductive organs from oxidative damage. A variety of monoterpenes and sesquiterpenes is reported to have antimicrobial activity (28). Hence, floral terpenes could help defend floral organs, like the moist stigma, from bacterial or fungal infection. 

Figure 6. Change of main component content (%) in the composition of clove essential oil during 5 months of storage in light 1 - eugenol, 2 - P-caryophyllene, 3 - famezene, 4 - eugenyl acetate, 5 - 8-cadinene, 6 - caryophyllene oxide.

Alcohol 2.1 is the only example of this class, and was isolated from Lactarius camphoratus (79) which belongs to Section Olentes (2). The compound is presumably the product of 1-9 cyclization of a humulene precursor. The structure and absolute configuration of this new caryophyllene oxide (2.1) was determined by a combination of spectral data and a single-crystal X-ray analysis of the p-bromobenzoate derivative 2.3. The NMR spectrum of 2.1 exhibited only two methyl signals, one of them at 51.20, together with one-proton doublet of doublets centred at 52.93, strongly suggesting the presence of the 4,5-epoxide. The C-12 methylene protons were shifted downfield (5 3.84) in the 220 MHz NMR spectrum of the acetyl derivative (2.2). Moreover,... 

CarvyI acetate CarvyI propionate p-Caryophyllene Caryophyllene alcohol Caryophyllene alcohol acetate 3-Caryophyllene oxide Cedarwood oil alcohols Cedarwood oil terpenes 1,4-Cineole Cinnamal... 

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