108195-53-5

Basic information

• Product Name: 5,9-dimethylheptadecane
• Synonyms: 5,9-dimethylheptadecane
• CAS NO: 108195-53-5
• Molecular Formula: C₁₉H₄₀
• Molecular Weight: 268.5209
• Mol File: 108195-53-5.mol

Chemical Properties

• Boiling Point: 83 °C(Press: 0.8 Torr)
• Appearance: /
• Density: 0.783±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5,9-dimethylheptadecane(CAS DataBase Reference)
• NIST Chemistry Reference: 5,9-dimethylheptadecane(108195-53-5)
• EPA Substance Registry System: 5,9-dimethylheptadecane(108195-53-5)

Safety Data

• Hazardous Substances Data: 108195-53-5(Hazardous Substances Data)

Usage

Uses

Used in Biological Studies:
5,9-Dimethylheptadecane is used as a chemical marker in the biological study of age and time-related pheromone production in the coffee leafminer, Leucoptera coffeella. Its presence in the pheromones of this insect helps researchers understand the role of chemical communication in the insect's life cycle and behavior.
Used in Chemical Research:
As an alkane, 5,9-dimethylheptadecane can be utilized as a starting material or intermediate in the synthesis of various organic compounds for chemical research and development. Its unique structural features make it a valuable component in the creation of complex molecules with specific properties.
Used in Analytical Chemistry:
5,9-Dimethylheptadecane can serve as a reference compound in analytical chemistry, particularly in techniques such as gas chromatography and mass spectrometry. Its distinct properties allow for accurate identification and quantification of similar compounds in complex mixtures.
Used in Perfumery:
Due to its non-polar nature and relatively stable chemical structure, 5,9-dimethylheptadecane can be employed as a solvent or carrier in the perfumery industry. It can help dissolve and stabilize fragrant compounds, ensuring a consistent and long-lasting scent in perfumes and fragrances.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 5,9-dimethylheptadecane could potentially be used in the pharmaceutical industry as a solvent or excipient in the formulation of certain drugs. Its inert nature and compatibility with a range of substances make it a suitable candidate for various pharmaceutical applications.

Upstream product

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• 1393538-47-0 (S)-2-methyl-1-(4-methylphenylsulfonyl)decane 
• 130566-82-4 (R)-2-decanyl tosylate 
• 131906-80-4 (S)-1-(p-toluenesulfonyloxy)-3-methylundecane 
• 121404-71-5 (S)-(+)-1-phenylsulfonyl-3-methylundecane 
• 121404-70-4 (S)-1-phenylsulfide-3-methylundecane 

Relevant articles and documents

BAKER'S YEAST MEDIATED SYNTHESIS OF (5SR,9S)-5,9-DIMETHYL-HEPTADECANE AND (5SR,9S)-5,9-DIMETHYL-PENTADECANE; THE MAIN SEX-PHEROMONE COMPONENTS OF Leucoptera scitella AND Perileucoptera coffeella ENRICHED IN 9S-ISOMERS

A mixture of (5S,9S)-5,9-dimethyl-heptadecane (1a), the main sex-pheromone component of leucoptera scitella, and its (5R,9S)-isomer (2a) was synthesized conveniently from (R)-citronellal (4, obtained from racemic citronellal by enantiomer selective baker's yeast reduction) in four steps. (5SR,9S)-5,9-Dimethyl-pentadecane (mixture of 1b and 2b), a possible sex-attractant of Perileucoptera coffeella was prepared analogously.

Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones

All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis.

Catalytic asymmetric synthesis of enantiopure isoprenoid building blocks: Application in the synthesis of apple leafminer pheromones

The first catalytic asymmetric procedure capable of preparing all 4 diastereoisomers (ee > 99%, de > 98%) of a versatile saturated isoprenoid building block was developed and the value of this new method was demonstrated in its application to the concise total synthesis of two pheromones. The Royal Society of Chemistry 2005.

Pheromone synthesis, CCIS synthesis of the enantiomers of anti-2,6-dimethylheptane-1,7-diol monotetrahydropyranyl ether and their conversion into the enantiomers of the sex pheromone components of the apple leafminer, Lyonetia prunifoliella

Both (2R,6R)- and (2S,6S)-isomers of 2,6-dimethylheptane-1,7-diol monotetrahydropyranyl ether (4) were synthesized, and converted into the enantiomers of anti-10,14-dimethyl-1-octadecene (1), anti-5,9-dimethyloctadecane (2) and anti-5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella).

Pheromone synthesis, CXCII. - Synthesis of all the stereoisomers of 10,14-dimethyloctadec-1-ene, 5,9-dimethyloctadecane and 5,9- dimethylheptadecane, the sex pheromone components of the apple leafminer, Lyonetia prunifoliella

All of the stereoisomers of 10,14-dimethyloctadec-1-ene (1), 5,9- dimethyloctadecane (2) and 5,9-dimethylheptadecane (3), the sex pheromone components of the apple leafminer (Lyonetia prunifoliella), were synthesized by starting from the enantiomers of ci

Pheromone Synthesis, CXXIX - Synthesis of the (5S,9S)-Isomers of 5,9-Dimethylheptadecane and 5,9-Dimethyloctadecane, the Major and the Minor Components of the Sex Pheromone of Leucoptera malifoliella Costa

The synthesis of (5S,9S)-5,9-dimethylheptadecane (1) as well as that of (5S,9S)-5,9-dimethyloctadecane (2) has been achieved by starting from methyl (R)-3-hydroxy-2-methylpropanoate (3a) and (S)-citronellal (7). --- Key Words: Heptadecane, 5,9-dimethyl- /