Y-eudesmol

Epoxy-cis-eudesmane (300), the defence pheromone of the West African termite, has been synthesized from lO-epi-y-eudesmol (299) by means of an... 

Amyris Amyris balsamifera L. Cadinol (50), valerianol (22), ca-dinene (11), 7-epi-y-eudesmol (11), 10-epi-y-eudesmol (10)... 

About 20 oxygenated sesquiterpenes have been identified from pepper oil. They are 5,10(15)-cadinen-4-ol,caryophylla-3(12), 7(15)-dien-4-P-ol, caryophylla-2,7(15)-dien-4- 3-ol, caryophylla-2,7(15)-dien-4-ol, P-caryophellene alcohol, caryophyllene ketone, caryophellene oxide, epoxy-dihydrocaryophellene, cis-nero-lidol, 4,10,10-trimethyl-7-methylene bicycle-(6.2.0) decane-4-carboxaldehyde, cubenol, epi-cubenol, viridiflorol, a- and P-bisabolols, cubebol, elemol and y-eudesmol. 

The oil is sometimes incorrectly called West Indian sandalwood oil. However, its composition and odor are different from those of the oils obtained from sandalwood species. The major components of amyris oil are sesquiterpenoids such as elemol [639-99-6], / -eudesmol [473-15-4], and c/u -y-eudesmol [15051-81-7] [241-244],... 

The composition of the Bourbon oil differs quantitatively as well as qualitatively from that of North African oil. However, they both contain unusually high percentages of (-)-citronellol, isomenthone, formates, and tiglates, which are rarely found in essential oils. The two types of oil can be differentiated by two characteristic minor constituents the Bourbon type contains (-)-6,9-guaiadiene [36577-33-0] (5-9%) and the African type contains lO-c/u -y-eudesmol [15051-81-7] (3-6%) see p. 183 [521—53Id]. 

This class of compounds may be found in essential oils extracted with both polar solvents and non-polar solvents. The structure of a sesquiterpene alcohol, newly isolated from the oil extracted from the wood of Amyris balsamifera (Rutaceae), has been reported [76]. These investigators either identified by GC-MS or isolated a total of 23 sesquiterpenoids, including valerianol (23) (21.5% of oil), 1-epi-a-eudesmol (24) (10.7%), 10-e/ i -y-eudesmol (25) (9.7%), elemol (26) (9.1%), P-eudesmol (27) (7.9%), y-eudesmol (28) (6.6%), a-eudesmol (29) (4.8%) and P-sesquiphellandrene (30) (4.7%) as the major constituents. 7-... 

Three agaroflirans (85-87) and P-eudesmol (88) were isolated from the petroleum ether-soluble fraction of the methanolic extract of the fresh rhizomes of A. japonica [63]. It is biogenetically interesting that P-eudesmol was present in the same plant with agaroflirans which possess a 10-epieudesmol skeleton. From the rhizomes of A. japonica, three eudesmane-type sesquiterpenes, 10-ep/-5P-hydroperoxy-p-eudesmol (89), 10-e /-5a-hydroperoxy-P-eudesmol (90) and 4,10-e/ /-5P-hydroxydihydroeudesmol (91) were isolated and their structure were determined by spectroscopic methods and chemical conversions [64]. Compounds 89-91 are considered to be biosynthesized from lO-ep/ -y-eudesmol (92), which was a possible precursor of agarofuran-type... 

Well-known eudesmane derivatives in flavors and fragrances include a- and p-selinene from the oils of Cannabis saliva var. indica (Moraceae), celery (Apium graeveolens, Umbelliferae) and hops (Humulus lupulus, Moraceae), (+)-a- and (+)-P-eudesmol from some oils of eucalyptus (Eucalyplus macarlhuri), (-)-epi-y-eudesmol with its woody odor from the north African oil of geranium (Pelargonium odoralissimum and allied species), and the almost odorless diastereomeric (+)-y-eudesmol from various ethereal oils (+)-p-Costus acid and (+)-p-costol belong to the constituents of the essential oil obtained from the roots of Saussurea... 

The strikingly different odors of cis-trorw-isomers and diastereomers is demonstrated by various other pairs of terpenes. For example, the synthetie fragranee (E)-S-methyl-a-ionone has a lovely flowery smell like the blossoms of violets, whereas the (Z)-isomer emits a woody tobaceo-like odor. Likewise, the strongly woody smelling sesquiterpene (-)- /-y-eudesmol from Algerian oil of geranium eontrasts wifli the almost odorless diastereomer (-l-)-y-eudesmol whieh is wide-spread among ethereal oils. 

Malvaceae limonene, trans-carveol, and y-eudesmol A. retroflexus and L. multflorum, at hi er concentration effective against lettuce, bentgrass, and against one cyanobacterium ... 

ISO standard 10624 shows character and data for this oil. Elemol and elemicin are the lead compounds. As minor component lO-epi-y-eudesmol must be detected between 0.2% and 0.3% to ensure natur-ness. Adulteration is done by limonene, a-phellandrene, and sabinene. Detection is done by GC-MS. 

FIGURE 20.51 Biotransformation of p eudesmol (157) and y-eudesmol (157a) by Gibberella suabinetii. 

Maatooq, G.A., 2002a. Microbial transformation of a P- and y-eudesmols mixture. Z Naturforsch., 57C 654-659. 

Among the oxygenated sesquiterpenes (Fig. 96.12), the oxidation product from p-caryophyllene, caryophyllene oxide, is widespread in plants. Also spathulenol is a widespread sesquiterpene alcohol. For example, it occurs in German chamomile and together with y-eudesmol as major oil component in Eucalyptus oleosa [36]. Daucol and carotol are aroma components found in the fruit oils from carrots (Daucus carotd) [27]. 

Bates R B, Hendrickson E K 1962 y-Eudesmol from Callitropsis araucarioides. Chem Ind 1759-1760... 

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