East Indian Sandalwood Oil Research Articles

Diastereo and enantio-controlled synthesis of sandalwood constituents (-)-β-santalene and (+)-epi-β-santalene starting from the same (+)-norcamphor

(-)-β-Santalene and (+)-epi-β-santalene. both occurring in East Indian sandalwood oil and having an enamiomeric core bicyclo[2,2,1]heptane framework, have been synthesized in diastereo- and enantio-controlled manner staning from the same (+)-norcamphor.

Cyclosantalal and epicyclosantalal—new sesquiterpene aldehydes from east Indian sandalwood oil

AbstractTwo new minor components of East Indian sandalwood oil have been isolated by chromatography. Structure elucidation using spectroscopical methods resulted in formulae 1 and 2. The relative configurations of the epimeric sesquiterpene aldehydes 1, 2 were determined by two‐dimensional NMR‐analysis (HETCOR‐, INADEQUATE‐, and NOE‐experiments) of the corresponding acids, cyclosantalic acid (3) and epicyclosantalic acid (4). The proposed structures of the aldehydes were confirmed by oxidative degradation reactions. Both aldehydes could be oxidized under normal conditions resulting in the known products acetyldihydroalbene (7) and albene (12) but also some new products such as the acids 3,4 and the formates 8,9. Trace amounts of those oxidation products could also be detected as constituents of sandalwood oil. A possible biogenetic pathway leading from p‐santalane derivatives to the cyclosantalals is briefly discussed.

Total Syntheses, Optical Rotations and Fragrance Properties of Sandalwood Constituents: (−)‐(Z)‐ and (−)‐(E)‐β‐Santalol and Their Enantiomers, ent‐β‐Santalene

AbstractEnantiomerically pure 5‐norbornene‐2‐carboxylic acids 4, obtained by asymmetric Diels‐Alder additions, were oxidatively degraded to (+)‐ and (−)‐2‐norbornanone [(+)‐, (−)‐21] and (+)‐ and (−)‐3‐methyl‐2‐norbornanone [(+)‐, (‐)‐11] which were converted into the title compounds by stereoselective alkylations, subsequent cis‐ and trans‐selective Wittig reactions and reductions. Precise optical rotations were determined for (Z)‐ and (E)‐β‐santalol (1 and 2) and β‐santalene (3a) which were obtained by total synthesis and, in addition, by isolation from East Indian sandalwood oil. magnified image

Syntheses of epi-β-Santalene, β-Santalene and an Isomer of β-Santalene with 4-Methyl-4-pentenyl Side Chain

Abstract The olfactory characteristics of East Indian Sandalwood oil is mainly due to its major components α-santalol (1) and β-santalol (2), while many of the components like β-santalene (3) and epi-β-santalene (4) also contribute to the perfumery properties1. Since the pioneering work of Corey2, Brieger3 and Money4 a number of syntheses of these compounds have appeared5,6. Of late there has been great interest in the synthesis of certain minor components of the oil, like the isomer of β-santalene with 4-methyl-4-pentenyl side chain (5).

(+)‐ α‐santalol and ( − )‐ β‐santalol(Z) concentration, a new quality determinant of East Indian sandalwood oil

AbstractThe level of ( + )‐ α‐santalol (1) and ( − )‐ β‐santalol(Z) (2) measured by capillary gas chromatography (CGC) constitutes a better criterion than the currently accepted index, viz. ‘not less than 90% of alcohol calculated as santalol’ to judge East Indian sandalwood oil. The limits proposed are: 40% to 55% (1) and 17% to 27% (2). This novel approach deserves inclusion in all official specifications of the oil.

Über neue Säuren im ostindischen Sandelholzöl

New Acids in the East Indian Sandalwood OilThree new terpenoic acids, dihydro‐α‐norcurcumenic acid (2), α‐bergamotenic acid (3), and dihydro‐α‐santalic acid (4), could be identified by means of GC‐MS and GC‐FTIR techniques as genuine constituents of the East Indian sandalwood oil. The former postulated γ‐santalic acid (1) could not be detected. Also a series of pyrolytic experiments did not lead to its formation.

GC-FTIR and GC-MS in odour analysis of essential oils

The analysis of odour components in East Indian Sandalwood Oil (Santalum album L.) and in Patchouli Oil (Pogostemon cablin Benth.) based on GC-, GC-FTIR- and GC-MS-data resulted in the identification ofα-santalene,α-santalal,β-santalal, epi-β-santalal,α-santalol,β-santalol, (E)-β-santalol,α-bergamotol and spirosantalol in Sandalwood Oil and of (−)-patchoulol,α-guaiene,α-patchoulene, seychellene,α-bulnesene, norpatchoulenol and pogostol in Patchouli Oil as the most intense aroma compounds of these oils.

Enantiodivergent route to both enantiomers of β-santalene and epi-β-santalene from a single chiral template

An enantiodivergent route to both enantiomers of β-santalene and epi-β-santalene, constituents of East Indian sandalwood oil, has been developed using a single chiral template.

ChemInform Abstract: The Most Odor Intensive Constituents of East Indian Sandalwood Oil

Chemischer InformationsdienstVolume 17, Issue 49 Other Subjects ChemInform Abstract: The Most Odor Intensive Constituents of East Indian Sandalwood Oil A. NIKIFOROV, A. NIKIFOROVSearch for more papers by this authorL. JIROVETZ, L. JIROVETZSearch for more papers by this authorG. BUCHBAUER, G. BUCHBAUERSearch for more papers by this author A. NIKIFOROV, A. NIKIFOROVSearch for more papers by this authorL. JIROVETZ, L. JIROVETZSearch for more papers by this authorG. BUCHBAUER, G. BUCHBAUERSearch for more papers by this author First published: December 9, 1986 https://doi.org/10.1002/chin.198649364Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume17, Issue49December 9, 1986 RelatedInformation

Die geruchsintensivsten Inhaltsstoffe des ostindischen Sandelholz�les

The most odour intensive constituents of east indian sandal wood oil are β-santalol, β-santalal and α-santalene. This has been proved by a thorough GLC-investigation in combination with the sniffing technique of seven fractions of this highly priced essential oil, which have been obtained by TLC on silica-cellulose plates with simultaneous organoleptic evaluation. Using the headspace analysis these results could be confirmed and further the distribution of the main odour components was obtained in headspace at 37° and 80°.

ChemInform Abstract: STEREOSELECTIVE SYNTHESES OF (.+‐.)‐EPI‐β‐SANTALENE AND (.+‐.)‐EPI‐β‐SANTALOL

AbstractDas als Ausgangsmaterial für die Synthese sowohl von (iyepi‐β‐Santalen (VIII) als auch von (i)‐epi‐β‐Santalol (XIV) dienende cyclische Halbacetal (IV) ist durch eine stereospezifisch verlaufende Diels‐Alder‐Reaktion von Norbornen (I) mit Acrolein und eine säurekatalysierte Hydratisierung des Addukts (III) leicht zugänglich.

Stereoselective Syntheses of (±)‐epi‐β‐Santalene and (±)‐epi‐β‐Santalol

AbstractStereoselective syntheses of (±)‐epi‐β‐santalene (1) and (±)‐epi‐β‐santalol (2), minor constituents of East Indian sandalwood oil, are described. The starting material for both syntheses is the tricyclic hemiacetal 4, readily accessible in two steps from norbornene.

Identification of Trans-β-santalol and epi-cis-β-santalol in east indian sandalwood oil

An analysis of East Indian sandalwood oil (Santalum album) has resulted in the isolation and identification of trans-β-santalol and epi-cis-β- santalol.

A stereoselective synthesis of β,γ-disubstituted allylic alcohols of z-configuration

Reaction of alkyllithiums 1 with isoprene epoxide 2 gives β,γ-disubstituted allylic alcohols 3 of Z-configuration. The reaction of π-lithiotricyclene as alkyllithium gives α-santalol 5 , which is one of the main constituents in East Indian sandalwood oil.

(+)-epi-β-santalol isolierung aus sandelholzöl und partialsynthese aus (+)-α-santalol

Zusammenfassung The (+)-epi-β-santalol( 3a ) has been isolated for the first time from East Indian sandalwood oil. Structure elucidation was carried out by comparison with (−)-β-santalol( 2a ), using 1 H- and 13 C-NMR-, GLC/MS- and ORD-spectroscopy. Treatment of (+)-α-santalyl-acetate( 1b ) with 1. HCl/CHCl 3 (−40°C) and 2. basic alumina resulted in a mixture of 2b / 3b .

Synthesis with benzenesulfenyl chloride. On the structure of a C 12H 18 hydrocarbon from East Indian sandalwood oil

The tetracyclic hydrocarbon 1 was synthesized by means of the electrophilic addition of benzenesulfenyl chloride to an appropriately substituted methylenenorbornene 7 . The synthetic methodology used to prepare this letter compound includes a mild enol ether hydrolysis with acidic silica gel.

A Chemical Investigation of the Volatile Constituents of East Indian Sandalwood Oil (SantalumalbumL.)

AbstractDistillation foreruns from East Indian sandalwood oil (Santalum album L.), representing 5–8% of the oil, have been investigated using fractional distillation, preparative column chromatography, gas liquid chromatography (GLC.), and chemical treatments. This allowed the isolation and characterization by their spectral data of 46 compounds. 32 of them were newly identified sandalwood oil constituents including 4 novel substances: santalone (2), 4‐methylcyclohexa‐1,3‐dien‐1‐yl methyl ketone (4), 5,6‐dimethyl‐5‐norbornen‐exo‐2‐ol (7), and (E)‐5‐(2,3‐dimethyl‐3‐nortricyclyl)‐pent‐3‐en‐2‐one (20). The other constituents identified were 1‐furfuryl‐pyrrole (10) and 10 phenols accompanied by 17 terpene and sesquiterpene derivatives. Endo‐2,endo‐3‐dimethyl‐norbornan‐exo‐2‐ol (6), an α‐santenol (z), precursor, was present in the last group of constituents. The compounds 2, 4, 6, 7, 20 have been synthesized as well as another novel constituent, endo‐2‐mythyl‐3‐methylidene‐norbornan‐exo‐2‐ol (5).

Recent Development in Insect Pheromone Research, in Particular in the Netherlands

A review is given of recent pheromone work carried out in the Netherlands on Lepidoptera, cockroaches, pharaoh's ants and termites, special emphasis being given to isolation and identification aspects. The sex pheromones of three leaf roller moths (Tortricidae) have been isolated, identified and field tested, viz. those of Adoxophyes orana (cis-9-tetradecenyl acetate (tda) and cis-I1-tda in the ratio 9:1), Clepsis spectrana (cis-9-tda:cis-11-tda, 1:3) and Archipspodana (cis-11-tda:trans-l1-tda, about 1:1). For ?ponomeuta, data have been obtained indicating a correlation between taxonomic groups and pheromone structure. Two sex pheromones (periplanone A and B) of the American cockroach, Periplaneta americana, have been isolated and partially identified. Their elementary formulas, C. 15H. 20O. 2 and C. 15H. 20O. 3, respectively, suggest that they are sesquiterpenoids, spectral data of periplanone B indicating that it has the germacrane skeleton. The aggregation pheromone of the German cockroach, Blattella germanica appears to be a complex mixture in which certain free acids play an important role. Three heterocyclic compounds have been isolated from Pharaoh's ants, Monomorium pharaonis. Monomorine I, C. 13H. 25N, is the first indolizine derivative found in the animal kingdom. Monomorine II, C. 13H. 27N, and monomorine III, C. 15H. 29N, are pyrrolidine derivatives. The three compounds are constituents of the odour trail and are present in excretions collected from the insect's sting. These excretions have a function in trail-following as well as in defense. In choice tests monomorine I and III act as attractants. Cis-3, cis-6, trans-8-dodecatrienol, initially identified as a trail pheromone of the termite Reticulitermes virginicus, was found to be a trail pheromone also for Reticulitermes santonensis. Eight dodecatrienol isomers were tested for activity towards this termite. In their ability to evoke trail-following behaviour as well as their attractancy in choice tests, they resemble each other qualitatively, but quantitatively, they show considerable differences. From fungus-infected wood a compound was isolated which effectively induces trail-following behaviour, and moreover, is a potent attractant. Its elementary formula, C. 15H. 24O, and the presence of acorane among its hydrogenation products, show that it is a sesquiterpenoid. Two other potent attractants for R. santonensis were found in wood oils: tricycloekasantalal, C. 12H. 13O in East-Indian sandalwood oil and dihydroagarofuran, C. 15H. 20O in West-Indian sandalwood oil. © 1974 BRILL.

A Stereospecific Swihesis of 6-sanialene

Abstract We describe here a simple three step synthesis of B-santalene (1), one of the main hydrocarbons in East Indian Sandalwood oil,3 using the readily available camphene sultone (2) as a starting material. This synthesis, outlined in Figure 1, features the novel use of a sultone as a carbon activating group and involves a new desulfurization procechrre.

An approach to the synthesis of β-santalene sesquiterpenes. Isolation of [formula omitted]-norbicycloekasantalal from east indian sandalwood oil.

An approach to the synthesis of β-santalene sesquiterpenes. Isolation of [formula omitted]-norbicycloekasantalal from east indian sandalwood oil.