- An Efficient Synthesis of the Plant Growth Hormone 1-Triacontanol
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A high yield synthesis of 1-triacontanol was based on the cheap and easily available starting materials 1-octadecanol and 1,12-dodecanediol.The first one was converted to octadecanal using a phase transfer system, whereas the second one after phase transfer bromination and reaction with triphenylphosphine provided 1-hydroxy-12-triphenylphosphonium bromide.Wittig reaction of these two synthons and subsequent hydrogenation furnished the desired product. - Keywords: 1-Triacontanol: Wittig reaction; Phase transfer reaction; Plant growth hormone
- Tran-Thi, N. H.,Falk, H.
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- SYNTHESIS OF TRIACONTAN-1-OL FROM DODECANEDIOIC ACID
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A method has been developed for obtaining triacontan-1-ol - a natural plant growth stimulator.Synthesized triacontan-1-ol has an appreciable influence on the growth and crop yield of tomatoes and on the flowering of asters.
- Zakharkin, L. I.,Aksenova, N. P.,Guseva, V. V.,Bavrina, T. V.,Konstantinova, T. N.,Chailakhyan M. Kh.
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- A method for preparing high-purity triacontanol (by machine translation)
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A method for utilizing organic synthesis for preparing high-purity triacontanol method, which belongs to the field of organic synthesis. To provide a reliable source of raw materials, the process is simple, the yield is high purity, easy large-scale production of the method of preparing triacontanol. In order to 1, 12 - dodecanediol as raw material preparation 12 - tert butyl dimethyl siloxy lauryl alcohol, TEMPO oxidation for 12 - tert butyl dimethyl siloxy lauric aldehyde, preparation octadecyl triphenyl brominated [...], tertiary butyl dimethoxy melissane silane - 12 - ene, preparation triacontanol. The raw materials are all industrial chemistry, the process is simple, high chemical yield, high purity of the product, it is easy to industrialization and more environmentally friendly. (by machine translation)
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- New 19α-hydroxyursane-type triterpenes from the leaves of Meyna spinosa (= Vangueria spinosa), Rubiaceae
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Two new 19α-hydroxyursane-type triterpenes, 2α,3α, 19α,24,28-pentahydroxyurs-12-ene (1) and meyanthic acid, 3β-acetoxy-2β,19α,23-trihydroxyurs-12-en-28-oic acid (2) along with one new aliphatic ester, myricyl pentadecanoate (3) and five known compounds, 1
- Rudrapaul, Prasenjit,Das, Niranjan,De, Utpal Chandra,Dinda, Biswanath
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- METHOD FOR THE PRODUCTION OF PRIMARY LONG-CHAIN ALCOHOLS
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The invention relates to a method for the production of linear long-chain alcohols with 20 to 40 carbon atoms by means of a growth reaction with ethylene on aluminium compounds.
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Page/Page column 11-12
(2010/02/15)
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- PROCESS FOR THE PREPARATION OF ALIPHATIC PRIMARY ALCOHOLS AND RELATED INTERMEDIATES IN SUCH PROCESS
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The invention relates to protected alcohol with formula (R1 - O-)mPG, wherein R1 represents a linear, straight-chain alkyl group having 26-30 C-atoms, m is 1 or 2, and PG, forming an ether group in combination with the -O- of the former primary alcohol, represents a protecting group chosen from the group of substituted methyl, substituted ethyl, substituted benzyl and (substituted) silyl groups with at least one substituent on the Si-atom being not a methyl group, in case m = 1; and a diol protecting group in case m = 2, with the proviso that PG is no saccharide. The invention further relates to process for the preparation of such protected alcohols via an organometallic cross coupling reaction.
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Page/Page column 8
(2010/02/11)
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- A facile synthesis of long chain acyclic alkanols via Kolbe coupling: 1-Docosanol and 1-triacontanol
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A convenient synthesis of long chain acyclic alkanols viz., 1-docosanol and 1-triacontanol has been devised via Kolbe radical coupling of mono-methyl azelate 2, which has been synthesized from azelaic acid 1. The dimer viz. dimethyl thapsate 3, on Ba(OH)2 hydrolysis affords mono-methyl thapsate 4, which upon mixed Kolbe coupling with appropriate alkanoic acid [CH3(CH)2)nCOOH, n = 6 for 1-docosanol and n = 14 for 1-tri-acontanol] gives the cross coupled products methyl docosanoate 7 and methyl triacontanoate 8 along with the radical dimers dimethyl triacontanedioate 4′ and tetradecane 5′/triacontane 6′ as byproducts. Compounds 7 and 8 on LAH reduction in dry THF yield 1-docosanol 9 and 1- triacontanol 10, respectively in high yields. The mixed anodic coupling has been studied by varying parameters viz. degree of neutralization and molar ratio of compounds 4 and C8/C16 alkanoic acid, current density, anode material etc.
- Yadav, Ashok K.,Singh, Arpita
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p. 1724 - 1726
(2007/10/03)
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- Chemical constituents of Plumbago indica roots and reactions of plumbagin: Part II
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From Plumbago indica a new quinone derivative-plumbagic acid lactone, two flavonol methyl ethers-azaleatin (5-O-methylquercetin), ayanin (3,7,4', tri-O-methylquercetin), two aliphatics-palmitic acid, myricyl palmitate and one naphthoquinone-plumbagin have been isolated. The major constituent plumbagin has been subjected to Schmidt reaction, allylic bromination, oxymercuration and demercuration and Thiele-Winter addition. All the natural and reaction products have been characterized by spectroscopic studies.
- Dinda,Das,Hajra,Bhattacharya,De,Chel,Achari
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p. 577 - 582
(2007/10/03)
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- Organoboranes for synthesis. 13. Simple, efficient syntheses of long-chain alcohols and carboxylic acids
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General, convenient and simple syntheses of long straight chain alcohols and carboxylic acids were developed utilizing organoborane chemistry. One of the methods entails the thermal isomerization of long-chain alkyldicyclohexylboranes, followed by oxidation. An alternative procedure for the preparation of long-chain alcohols involves the KAPA isomerization of internal alkynes to the terminal derivative, followed by dihydroboration with 9-BBN and oxidation. Alternatively, the terminal alkyne can be oxidised directly to the carboxylic acid. In another strategy, the C30-alcohol triaxontanol was prepared by employing high pressure carbonylation of a borane intermediate.
- Brown, Herbert C.,Iyer, Ramakrishnan R.,Bhat, Narayan G.,Racherla, Uday S.,Brown, Charles A.
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p. 9187 - 9194
(2007/10/02)
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- FLAVONOIDS AND OTHER CONSTITUENTS FROM PEDALIUM MUREX
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Two new compounds isolated from the fruits of Pedalium murex were characterized as 2',4',5'-trihydroxy-5,7-dimethoxyflavone and triacontanyl dotriacontanoate by physico-chemical methods.Luteolin, rubusic acid, nonacosane, tritriacontane, triacontanoic acid, tritriacontanoic acid and sitosterol β-D-glucoside have also been isolated and identified. Key words: Pedalium murex; Pedaliaceae; fruits; 2',4',5'-trihydroxy-5,7-dimethoxyflavone; luteolin; rubusic acid; triacontanyl dotriacontanoate; lipids.
- Bhakuni, Rajendra S.,Shukla, Yogendra N.,Thakur, Raghunath S.
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p. 2917 - 2918
(2007/10/02)
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- OZONOLYSIS OF ALKENES AND REACTIONS OF POLYFUNCTIONAL COMPOUNDS XLI. SYNTHESIS OF OXYGEN-CONTAINING DERIVATIVES OF TRIACONTANE
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Triacontanoic acid, its ester, triacontan-1-ol, and also their 12-Z-unsaturated analogs were synthetized on the basis of methyl 12-oxododecenoate, which is the product from ozonolysis of cyclododecene.
- Odinokov, V. N.,Akhmetova, V. R.,Khasanov, Kh. D.,Abduvakhabov, A. A.,Tolstikov, G. A.
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p. 1209 - 1210
(2007/10/02)
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- DEFUSCIN, A NEW PHENOLIC ESTER FROM DENDROBIUM FUSCESCENS: CONFORMATION OF SHIKIMIC ACID
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Defuscin, a new phenolic ester shown to be n-triacontyl p-coumarate, and (-)-shikimic acid have been isolated from the whole plant of Dendrobium fuscescens Griff.The 1H NMR spectrum of shikimic acid is indicative of the weighted average of its two half-chair conformers, the one with 4-OH and 5-OH in equatorial orientations being the major contributor. - Keywords: Dendrobiu fuscescens; Orchidaceae; defuscin; n-triacontyl p-coumarate; (-)-shikimic acid; conformation.
- Talapatra, Bani,Das, Asoke K.,Talapatra, Sunil K.
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p. 290 - 292
(2007/10/02)
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- Synthesis of even C24-C30 primary normal aliphatic alcohols from cyclododecanone
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A simple method has been developed for the oxidation of cyclododecanone by sodium persulfate in an aqueous methanol solution of sulfuric acid to give 12-hydroxydodecanoic acid, which upon treatment with HBr in acetic acid gives 12-bromododecanoic acid with RMgX, where R=C12H25, C14H29, C16H33, and C18H37 in THF in the presence of Li2CuCl4 and subsequent reduction of the salts of the alkanecarboxylic acids by LiAlH4 give primary even normal C24-C30 alcohols.
- Zakharkin, L. I.,Churilova, I. M.,Anikina, E. V.
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- Synthesis of 1-Triacontanol via Stepwise Hydroboration
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A new efficient synthesis of 1-triacontanol through hydroboration-hydridation-hydroboration with dibromo-borane-dimethyl sulphide complex, LiAlH4, and iodine induced rearrangement of the resulting vinyl borane is described.
- Dhillon, Ranjit S.,Singh, Jasvinder,Gautam, Veena K.
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p. 689 - 690
(2007/10/02)
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- A New Synthesis of Long Chain Acid Esters and Carbinols
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A versatile synthesis of difficulty accessible long chain acid esters and carbinols is described.The synthesis involves acylations at 2- and 5-positions of thiophene.Thioketalation of the resulting ketoesters followed by Raney nickel desulfurization yield acid esters which on LAH reduction give the corresponding carbinols.
- Rao, S. Jagadishwar,Bhalerao, U. T.,Tilak, B. D.
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p. 208 - 211
(2007/10/02)
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- Plant Growth Regulators: Syntheses of n-Triacontynol, n-Triacontenol and n-Triacontanol
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Convenient syntheses of n-triacontynols (VII), n-triacontenols (VIII and IX) and n-triacontanol (X) are described.The alkynes (III) are coupled with bromo THP-ethers (VI) to yield the disubstituted n-triacontynols (VII).These on selective partial hydrogenation afford the disubstituted n-triacontenols (VIII and IX).Alkynols (VII) on complete hydrogenation give the n-triacontanol (X).Biological studies reveal that the acetylenes (VII) and olefins (VIII and IX) are better plant growth regulators than the n-triacontanol (X).
- Iyer, R. R.,Mamdapur, V. R.
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p. 1216 - 1219
(2007/10/02)
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- An Efficient Synthesis of 1-Triacontanol
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Reduction of 12-dodecanolide (1), readily accessible from cyclododecanone, with diisobutylaluminium hydride afforded a 98:2 mixture of 12-hydroxydodecanal (3) and 2-oxa-1-cyclotridecanol (2).Its reaction with triphenyloctadecylphosphorane yielded 12-triaconten-1-ol (4), the catalytic hydrogenation of which gave a total yield of 68percent of 1-triacontanol (5) starting from cyclododecanone.
- Kirchner, Gerald,Weidmann, Hans
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p. 214 - 216
(2007/10/02)
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- NEW SYNTHESIS OF 1-TRIACONTANOL
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Succinic anhydride and behenic acid have been used to attach C4 and C22 carbon chains on to 2 and 5 positions of thiophene through two alternate acylation sequences.Raney nickel desulphurization to the 2,5-disubstituted thiophene yielded triacontanoic acid esters which on LAH reduction gave 1-triacontanol.
- Bhalerao, U. T.,Rao, Jagadishwar S.,Tilak, B. D.
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p. 5439 - 5440
(2007/10/02)
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- A CONVENIEN SYNTHESIS OF 1-TRIACONTANOL, A PLANT CROWTH GORMONE
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A synthesis of 1-triacontanol, a plant growth regulator, starting from myristic acid and by two succesive additions of eight and nine carbon units from sebacic acid in Kolbe electro-organic process has been reported.
- Joshi, U. R.,Kapadi, A. H.
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p. 681 - 686
(2007/10/02)
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- A Simple Synthesis of 1-Triacontanol
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The new and efficient synthesis of 1-triacontanol (1) involves coupling between stearylmagnesium bromide (2) and 12-bromo-1-tetrahydropyranyloxydodecane (3) in the presence of Li2CuCl4, followed by acid hydrolysis of the coupled product.
- Kulkarni, S. M.,Mamdapur, V. R.,Chadha, M. S.
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- SYNTHESE DU TRIACONTANOL-1 PAR METATHESE FONCTIONALISEE
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The synthesis of triacontanol (4b) is described from the cross-metathesis of cyclododecene (2) and methyl oleate (1a) or oleyl acetate (1b).
- Villemin, Didier
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p. 2855 - 2856
(2007/10/02)
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- HYDROZIRKONATION/OXIDATION OF INTERNAL OLEFINS. A SIMPLE SYNTHESIS OF TRIACONTANOL
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Hydrozirkonation of internal olefins followed by oxidation with anhydrous t-butyl hydroperoxide generates primary alcohols in good yields and high purity.
- Gibson, Thomas
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p. 157 - 158
(2007/10/02)
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- UNSATURATED ANALOGUES OF 1-TRIACONTANOL
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A simple regio- and stereoselective synthesis of unsaturated analogues of the plant growth stimulator 1-triacontanol from ω-alkyn-1-ols is reported.Starting from the easily accessible 10-undecyn-1-ol, eight n-C30 alcohols containing , (E) -C=C- or (Z) -C=C- group in the position 21 and/or 10 have been prepared.Spectral and gas-chromatographic properties (Kovats retention indices) of the novel compounds are described.
- Kocian, Oldrich,Stransky, Karel,Zavada, Jiri
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p. 1346 - 1355
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 1-TRIACONTANOL
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1-Triacontanol, a new plant growth regulator, has been synthesised starting from stearic acid, and by two successive additions of six carbon units through enamine intermediates.
- Rama Rao, A. V.,Deshmukh, M. N.,Kamalam, M.
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p. 227 - 230
(2007/10/02)
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- Fluorescein esters and ethers and the preparation thereof
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Fluorescein esters and ethers including the dioleyl derivative of fluorescein are disclosed. These compounds have the useful property of being fluorescent under the influence of the proper frequency of electromagnetic irradiation. Further, dioleyl fluorescein is readily incorporated into low-density lipoproteins which can then become part of the cell matter; the compounds retain their fluorescent properties during this procedure. The fluorescence allows cells to be identified and separated. The fluorescein esters and ethers are prepared from fluorescein and the novel reagent O-alkenyl-N,N'-dialkylisourea.
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- Preparation of long-chain carboxylic acids and alcohols
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The process for the preparation of long-chain carboxylic acids which can be readily converted to alcohols. Shorter chain acids are converted to the acid chloride which may be further purified. The acid chloride is mixed with an enamine and a hindered tertiary amine in an organic solvent and then acidified to form the beta-diketone after washing the organic phase and removal of the solvent. The beta-diketone is reacted with an inorganic hydroxide or alkali metal alkoxide and acidified to produce the keto acid which can be readily converted to the respective aliphatic acid and alcohol.
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