Sesquiterpenes properties

The sesquiterpenes found in essential oils have low volatilities compared with monoterpenes and so are isolated mainly by steam distillation or extraction, but some are also isolated by distillation or crystallization. Most of the sesquiterpene alcohols are heavy viscous Hquids and many crystallize when they are of high enough purity. Sesquiterpene alcohols are important in perfume bases for their odor value and their fixative properties as well. They are valuable as carriers of woody, balsamic, or heavy oriental perfume notes. 

They have also carried out the oxidation of selinene by means of ozone and potassium permanganate and have thus been able to establish that the regenerated selinene is not absolutely identical with the natural selinene. They are the first to record the existence of a hemi-cyclic-sesquiterpene this compound is termed pseudo-()3)-selinene. By passing a current of ozone into a solution of natural selinene (pseudo-( 8)-selinene). in acetic acid, there is obtained a diketone, CjjHogOj, which is purified by treatment with permanganate in acetone solution. Its properties are as. follows —... 

Properties of panal (Nakamura etal., 1988a). Purified panal is a colorless, amorphous solid, soluble in alcohols, water, ethyl acetate, and chloroform. The absorption spectrum (Fig. 9.3) shows a single peak (A.max 217nm, e 15,300). Optical rotation [a]D —17° (c 0.9, methanol). Mass spectrometry and NMR analysis showed that panal is a sesquiterpene aldehyde, C15H18O5 (Mr 278.30), with the structure shown below. 

Effects of Sesquiterpene Lactones on Seed Germination. Sesquiterpene lactones are common constituents of the Asteraceae but are also found in other angiosperm families and in certain liverworts (31,32). These highly bitter substances exhibit a wide spectrum of biological activities (J 3) which include cytotoxicity, anti-tumor, anti-microbial, insecticidal (34) and molluscicidal (35) properties. Furthermore, they are known causes for livestock poisoning and contact dermatitis in humans (33). Structure-activity relationship studies on sesquiterpene lactones have demonstrated that biological activity frequently depend on the presence of the cr... 

Singh, M. M., A. Agnihotri, S. N. Garg, S. Agarwal, D. N. Gupta, G. Keshri, and V. P. Kamboj. Antifertility and hormonal properties of certain carotene sesquiterpenes of Ferula jaeschkeana. Planta Med 1988 54(6) 492-494. 

This was demonstrated by Fukumoto and co-workers in a synthesis of (+)-albicanol (251), a sesquiterpene with potent hsh antifeedant properties (272,273). Oxime 248 [prepared from the (+)-Wieland-Miescher ketone 247] was subjected to cycloaddition using sodium hypochlorite and gave isoxazoline 249 in very good yield (Scheme 6.95). Conversion of 249 into (3-hydroxyketone 250 was again accomplished by the reductive hydrolysis sequence using Raney Ni and trimethyl... 

The main constituents of the oil are the sesquiterpene alcohols guaiol [489-86-1] and bulnesol [22451-73-6] [542]. The oil may be used as a starting material for the synthesis of guaiazulene, which has anti-inflammatory properties. 

A wide variety of EOs are known to possess antimicrobial properties and in many cases this activity is due to the presence of active constituents, mainly attributable to isoprenes such as monoterpenes, sesquiterpenes and related alcohols, other hydrocarbons and phenols [8, 9]. 

Artemisia annua and (—)-o -bisabolol from Matricaria recutita (German chamomile). Addition of IPP to GPP produces 2 , 6 -famesylpyropho-sphate (FPP), the precursor for all sesquiterpenes. Farnesylpyrophosphate can cyclize by various cyclase enzymes in various ways, leading to the production of a variety of sesquiterpenes. Some of these sesquiterpenes are medicinally important hioactive compounds. For example, (—)-o -bisabolol and its derivatives have potent anti-inflammatory and spasmolytic properties, and artemisinin is an antimalarial drug. 

Curcuma longa L. C. domestica L. Yu Jin (Turmeric) (tuber) 1-curcamene, sesquiterpene, camphor, camphene, curmarin, curzernone, curzenene, curcumol, furanodienone, furanodiene, zederone, curcolone, diol, procurcumenol, curdione, curcumin. 33-398-460-510 Anti-inflammatory, antitumor, anti-infectious properties, antioxidative activity. Activate blood flow, remove blood stasis. 

Jasminum samba (L.) Aiton Mo Li Hua (Arabian jasmine) (flower, root) Formic acid, benzoic acid, acetic acid, anthranil acid, sesquiterpene, sesquijasmine.60 This herb (root) is toxic. Sedative, anesthetic, vulnerary properties. For congestive headache, lactifuge. 

Xanthoxylum piperitum DC Chuan Jian (fruit) Essential oils, phellandrene, limonene, citronellol, geraniol, and sanshol in fruit sesquiterpene lactones-xanthatin, limonene in seed saponin, citral, citronellol, geraniol in leaf berberine, xanthoxylinin root.49-430 Diaphoretic properties, prophylactic against hydrophobia, used as a diuretic, stomachic, carminative, stimulant, resolving inflammatory swellings, it is sedative. 

N.A. Saussurea lappa Clarke Terpenes, sesquiterpenes, aplotaxene, saussurine, resin.99 Depress the parasympathetic nervous system. It has tonic, stimulant, and antiseptic properties. 

Artemisinin 1, a naturally occurring sesquiterpene peroxy-lactone, has been isolated in up to 0.25% yield from the dry leaves of Artemisia annua L.1 Interest in artemisinin is based on its phytomedicinal properties. In 168 b.c. China, as described in a Treatment of 52 Sicknesses, the leaves of A. annua (Qinghao) were used for the treatment of chills and fever.2 It was not until 1972 that the active antimalarial agent qinghaosu was isolated in pure form. This allowed for the unequivocal elucidation of its structure through the use of x-ray crystallography. This complex tetracyclic peroxide is now referred to as artemisinin in various sources such as Chemical Abstracts or the Merck Index. 

Puupehenone (63) is a member of a distinctive family of sponge metabolites — a sesquiterpene joined to a C6-shikimate moiety — first exemplified by the quinol-quinone pair of avarol and avarone. Among the varied activities that have been reported for this diverse class of compounds is the property of ilimaquinone to inhibit replication of the HIV virus.78 Preliminary screening of puupehenone against Mycobacterium tuberculosis showed 99% inhibition of the organism. A series of chemical modifications have been conducted on puupehenone to study the effect on its biological activity. 

Furanoeudesma-1,3-diene, a sesquiterpene from myrrh with analgesic properties... 

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