3239-35-8

Basic information

• Product Name: (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate
• Synonyms: (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate;5,9-Undecadien-2-ol, 6,10-dimethyl-, acetate, (5E)-;(E)-5-Tangerinol;(E)-6,10-Dimethylundeca-5,9-dien-2-ylacetat;10-Dimethyl-5,9-undecadien-2-ol, acetate, (E)-6;9-Undecadien-2-ol, 6,10-dimethyl-, acetate, (E)-5;trans-5-Tangerinol;Acetic acid (E)-6,10-dimethyl-5,9-undecadien-2-yl ester
• CAS NO: 3239-35-8
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.36574
• EINECS: 221-803-4
• Mol File: 3239-35-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 294°Cat760mmHg
• Flash Point: 85.5°C
• Appearance: /
• Density: 0.893g/cm³
• Vapor Pressure: 0.00167mmHg at 25°C
• Refractive Index: 1.459
• CAS DataBase Reference: (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate(3239-35-8)
• EPA Substance Registry System: (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate(3239-35-8)

Safety Data

• Hazardous Substances Data: 3239-35-8(Hazardous Substances Data)

Usage

General Description

(E)-6,10-dimethylundeca-5,9-dien-2-yl acetate is a chemical compound commonly found in various natural sources, including fruits, flowers, and essential oils. It is known for its sweet, fruity aroma and is often used in the production of perfumes, cosmetics, and food flavorings. (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate is also used as a pheromone in insect communication, specifically in the attraction of moths. It is a volatile, colorless liquid with a molecular formula of C15H26O2 and is commonly used in the fragrance industry to enhance and create pleasant scents.

InChI:InChI=1/C15H26O2/c1-12(2)8-6-9-13(3)10-7-11-14(4)17-15(5)16/h8,10,14H,6-7,9,11H2,1-5H3/b13-10+

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 38228-51-2 2-acetoxy-6-methyl-6-heptene 
• 107697-27-8 1-acetoxy-6,10-dimethyl-9-undecen-6-ol 
• 7733-91-7 (E)-6,10-dimethyl-5,9-undecadien-2-ol 
• 75-36-5 acetyl chloride 
• 121424-59-7 6,10-dimethyl-9-undecene-2,6-diol 
• 107909-35-3 6-hydroxy-6-methylheptan-2-yl acetate 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 15146-94-8 5-chloro-2-pentanol 
• 2568-33-4 3-methyl-butane-1,3-diol 
• 3796-70-1 trans geranyl acetone 
• 108-24-7 acetic anhydride 

Downstream Products

• 17283-81-7 4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on 
• 24190-33-8 (+)-(S)-dihydro-γ-ionone 
• 24190-34-9 4-[(1S)-2,6,6-trimethylcyclohex-2-en-1-yl]butan-2-one 
• 1224875-99-3 (1S,2S)-(+)-1,3,3-trimethyl-2-(3-oxobutyl)cyclohexyl acetate 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 18454-69-8 Acetic acid 3-(5-methoxymethyl-2,6,6-trimethyl-cyclohex-1-enyl)-1-methyl-propyl ester 

Relevant articles and documents

Asymmetric Cation-Olefin Monocyclization by Engineered Squalene–Hopene Cyclases

Squalene–hopene cyclases (SHCs) have great potential for the industrial synthesis of enantiopure cyclic terpenoids. A limitation of SHC catalysis has been the enzymes’ strict (S)-enantioselectivity at the stereocenter formed after the first cyclization step. To gain enantio-complementary access to valuable monocyclic terpenoids, an SHC-wild-type library including 18 novel homologs was set up. A previously not described SHC (AciSHC) was found to synthesize small amounts of monocyclic (R)-γ-dihydroionone from (E/Z)-geranylacetone. Using enzyme and process optimization, the conversion to the desired product was increased to 79 %. Notably, analyzed AciSHC variants could finely differentiate between the geometric geranylacetone isomers: While the (Z)-isomer yielded the desired monocyclic (R)-γ-dihydroionone (>99 % ee), the (E)-isomer was converted to the (S,S)-bicyclic ether (>95 % ee). Applying the knowledge gained from the observed stereodivergent and enantioselective transformations to an additional SHC-substrate pair, access to the complementary (S)-γ-dihydroionone (>99.9 % ee) could be obtained.

Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae)

The male-produced sex pheromone of Hedypathes betulinus was identified as a mixture of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone) (1) and its respective alcohol (2) and acetate (3). Kinetic resolution of alcohol (2) promoted by CAL-B in organic media provided both, (R)-(-)-(E)-6,10-dimethyl-5,9- undecadien-2-yl acetate (3) and (S)-(+)-(E)-6,10-dimethyl-5,9-undecadien-2-ol (2) in high enantiomeric purity. Comparative GC analysis using a chiral column revealed the natural constituents as being (R)-(3) and a mixture of (R)- and (S)-(2) in a ratio of 82.3% and 17.6%, respectively.