70901-63-2

Usage

Uses

Used in the Plastics Industry:
(6E,10E)-7,11,15-Trimethyl-3-methylene-1,6,10,14-hexadecatetrene is used as a raw material for the production of various types of plastics. Its chemical properties contribute to the formation of durable and versatile plastic materials suitable for numerous applications.
Used in the Rubber Industry:
In the rubber industry, (6E,10E)-7,11,15-Trimethyl-3-methylene-1,6,10,14-hexadecatetrene is employed as a component in the manufacturing process of rubber products. It helps in creating rubber with specific characteristics, such as flexibility and resistance to wear.
Used in the Lubricants Industry:
(6E,10E)-7,11,15-Trimethyl-3-methylene-1,6,10,14-hexadecatetrene is used as an additive in the lubricants industry to enhance the performance of lubricating oils. It improves the lubricity and reduces friction in various mechanical applications.
Used in the Fragrance Industry:
(6E,10E)-7,11,15-Trimethyl-3-methylene-1,6,10,14-hexadecatetrene is also utilized in the fragrance industry as a component in perfumes and other scented products. Its strong odor makes it a valuable contributor to the overall scent profile of these products.

InChI:InChI=1/C20H32/c1-7-18(4)12-9-14-20(6)16-10-15-19(5)13-8-11-17(2)3/h7,11,14-15H,1,4,8-10,12-13,16H2,2-3,5-6H3/b19-15+,20-14+

Upstream product

• 6138-90-5 trans-geranyl bromide 
• 17909-72-7 (E)-8-bromo-7-methyl-3-methylene-1,6-octadiene 
• 24034-73-9 Geranylgeraniol 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 82462-90-6 7,11,15-Trimethylhexadeca-1,6(E),10(E),14-tetraen-3-one 
• 136853-13-9 (E,E)-2,6,10-trimethyl-14-methylene-1,6,10,15-hexadecatetraen-3-one 
• 110990-65-3 (2E,6E,10E)-1-Methoxy-3,7,11,15-tetramethyl-hexadeca-2,6,10,14-tetraene 
• 79577-50-7 2-((2E,6E,10E)-3,7,11,15-Tetramethyl-hexadeca-2,6,10,14-tetraenyloxy)-tetrahydro-pyran 
• 19493-09-5 Methylenetriphenylphosphorane 
• 106-24-1 Geraniol 
• 67858-77-9 (4E,8E)-5,9,13-trimethyl-4,8,12-tetradecatrien-1-ol 
• 67858-78-0 (4E, 8E)-5,9,13-trimethyl-4,8,12-tetradecatrienal 
• 1855-71-6 3,3-dimethoxy-2-methyl-1-butene 
• 106-28-5 Farnesol 

Relevant academic research and scientific papers

PROCESS FOR THE PRODUCTION OF SPRINGENE

The application relates to a process for the production of alpha-springene (formula (I)) and beta-springene (formula (II)) from geranyl geranyl acetate (formula (III)).

NEW PROCESS FOR THE PRODUCTION OF BETA-SPRINGENE

The present invention relates to a process for the production of β- springene of formula (I) wherein a compound of formula (II) is heated in the presence of a catalyst.

Synthesis of 9-geranylterpinolene as a mixture of isomers, and synthesis of α- and β-springene, possible kairomones of the beech leaf-mining weevil, Orchestes fagi (L.)

The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We have previously reported the synthesis of 9-geranyl-p-cymene and 9-geranyl-α-terpinene, as they are both found in eclosing beech buds, and have researched the synthesis of other diterpenes that are isomers of 9-geranyl-α-terpinene. We now wish to report a synthesis of the diterpene 9-geranylterpinolene as a mixture of isomers, as a novel diterpene, and as a possible kairomone of O. fagi. Also, all trans-α-springene, its 3Z-isomer, and β-springene were synthesized as a mixture, as well as pure β-springene, utilizing known methods.

Syntheses of All-trans Acyclic Isoprenoid Pheromone Components

All-trans acyclic isoprenoid skeletons were made through a two-step iterative sequence.The method involves the Claisen rearrangement of allyl vinyl ethers formed from allylic alcohols and the dimethyl acetal of methyl isopropenyl ketone, followed by LiAlH4 reduction of the α,β-unsaturated ketone formed by rearrangement.The α,β-unsaturated ketone was also transformed to the 2-methyl-1-propenyl group by using a one-pot deoxygenation reaction for the synthesis of (E)-β-farnesene, (E)-β-springene and dendrolasin.

Process for the preparation of terpenes

A terpene compound having the formula (III) is produced by reacting an allylic halide having the formula (I) with a Grignard reagent having the formula (II) in the presence of anhydrous zinc chloride and a copper compound or an organic zinc halide compound having the formula (IV) in the presence of a copper compound, provided that when A-A is C-C, R' is hydrogen and when A-A is C=C, X is chlorine. STR1

Selective Synthesis of 1,3-Dienic Terpenes in a β-Form through Regioselective 1,4-Elimination of Allylic Ethers

γ-Methyl-substituted allylic ethers proved to be converted into β-substituted dienes exclusively on treatment with t-BuOK in refluxing THF or cyclohexane.

A New Synthesis of β-Springene

A new synthesis of β-springene (I) is reported starting from 4-tetrahydropyranyloxybutan-1-al (III).Versatile reactions such as Claisen rearrangement and Wittig reaction have been successfully utilised for the introduction of double bonds in desired positions.

REGIO- AND STEREO-SPECIFIC SYNTHESES OF ACHIRAL TERPENOID ALLOMONES AND PHEROMONE COMPONENTS: DENDROLASIN, (E)-β-FARNESENE, AND β-SPRINGENE

Chemically and stereoisomerically pure dendrolasin (1c), an alarm and defence substance of Lasius fulginosus, has been prepared according to a simple reaction sequence in which the key step involves the reaction of the Grignard reagent derived from 3-(bromomethyl)furan (5) with geranyl acetate (9), in the presence of dilithium tetrachlorocuprate.An analogous reaction has been successfully used to prepare 99percent stereoisomerically pure (Z)-3-(4,8-dimethyl-3,7-nonadienyl)furan (1f) starting from neryl acetate (10).Compound 1c has been also obtained by coupling reaction of 5 with the ?-allylnickel(II) complex derived from geranyl bromide (3).However, in this case 1c was contamined by substantial amounts of 1f.Stereoisomerically pure (E)-β-farnesene (1d), the alarm pheromone of many aphids, has been analogously synthesized by coupling reaction either of the ?-allylnickel halide complex derived from (E)-1-bromo-2-methyl-6-methylene-2,7-octadiene (14) with 1-bromo-3-methyl-2-butene (16), or of ?-(1,1-dimethylallyl)nickel bromide (19) with 14.A similar coupling reaction involving the ?-allylnickel halide derived from 14 and 3 has been employed to prepare β-springene (1e), a diterpene isolated from the dorsal gland of the springbok, Antidorcas marsupialis.

Synthesis of β-Springene

Ethyl 2-carbethoxy-5,9,13-trimethyltetradeca-4(E),8(E),12-trienoate (IV) obtained by alkylation of 2(E),6(E)-farnesol (II), when refluxed in hexamethylphosphoramide after half-hydrolysis gives the ester (VI).VI on LAH reduction followed by oxidation affords the aldehyde (VIII).VIII on Grignard reaction with vinylmagnesium bromide affords the alcohol (IX), which upon oxidation followed by Wittig reaction with methylenetriphenylphosphorane furnishes the title compound (I).