62151-56-8

Usage

Uses

Used in the Chemical Industry:
3-Methylcyclopentadecan-1-ol is utilized as a raw material in the production of surfactants, which are essential for creating foams and emulsions in various cleaning and personal care products. Its hydrophobic and hydrophilic properties make it suitable for stabilizing formulations.
Used in the Lubricant Industry:
3-methylcyclopentadecan-1-ol serves as a component in lubricants due to its ability to reduce friction between surfaces, thereby enhancing the performance and longevity of mechanical parts.
Used in the Cosmetics and Personal Care Industry:
3-Methylcyclopentadecan-1-ol is employed as an ingredient in cosmetics and personal care products, where it contributes to the texture and consistency of formulations, as well as providing a pleasant scent.
Used as a Fragrance Ingredient:
In the perfumery and fragrance industry, 3-methylcyclopentadecan-1-ol is used to create complex and long-lasting scents for perfumes and other personal care products, capitalizing on its aromatic properties.
Used in Pharmaceutical Research:
Due to its unique chemical structure, 3-methylcyclopentadecan-1-ol has potential applications in pharmaceuticals, where it may be studied for its interactions with biological systems and possible therapeutic effects.
Used in Biochemistry Research:
In the field of biochemistry, 3-methylcyclopentadecan-1-ol may be used in research to understand its interactions with enzymes, proteins, and other biomolecules, potentially leading to new insights in biochemical processes and mechanisms.

InChI:InChI=1/C16H32O/c1-15-12-10-8-6-4-2-3-5-7-9-11-13-16(17)14-15/h15-17H,2-14H2,1H3

Upstream product

• 956-82-1 3-methylcyclopentadecanone 
• 22591-40-8 Essigsaeure-(3-methyl-cyclopentadecylester) 
• 102521-18-6 (1S, 15S)-bicyclo<13.1.0>hexadecan-2-one 
• 56345-01-8 (2E)-cyclopentadec-2-en-1-one 
• 10403-00-6 (R)-3-methyl-1-cyclopentadecanone 
• 102521-15-3 (E)-cyclopentadec-2-en-1-one 1,4-di-O-benzyl-D-threitol ketal 
• 102521-17-5 (1S,15S)-bicyclo<13.1.0>hexadecan-2-one 1,4-di-O-benzyl-D-threitol ketal 
• 102521-14-2 (E)-cyclopentadec-2-en-1-one 1,4-di-O-methyl-D-threitol ketal 
• 175275-95-3 bicyclo<13.1.0>hexadecan-2-one 
• 102535-18-2 2-bromocyclodecan-1-one 1,4-di-O-methyl-D-threitol ketal 
• 102521-16-4 (1S,15S)-bicyclo<13.1.0>hexadecan-2-one 1,4-di-O-methyl-D-threitol ketal 
• 60447-89-4 2-bromocyclopentadecan-1-one 
• 502-72-7 cyclopentadecanone 
• 108-05-4 vinyl acetate 

Downstream Products

• 10403-00-6 (R)-3-methyl-1-cyclopentadecanone 
• 63975-98-4 (S)-muscone 

Relevant academic research and scientific papers

Cp2ZrMeCl: A Reagent for Asymmetric Methyl Addition

The use of Cp2ZrMeCl is described as a source of nucleophilic methyl in asymmetric catalysis. This easily prepared reagent is bench stable, weighable in air, and generally useful in highly enantioselective copper-catalyzed addition reactions at room temperature. Methyl is successfully (generally >90% ee) added in 1,4-additions to cyclic and acyclic α,β-unsaturated ketones to provide tertiary and quaternary centers. Examples of catalyst controlled diastereoselective 1,6-addition and dynamic kinetic asymmetric allylic alkylation reactions are also reported. The reagent is used in the catalytic asymmetric synthesis of naturally occurring fragrance (R)-(-)-muscone (82% yield, 91% ee).

Stereoselective and enantioselective syntheses of the four stereoisomers of muscol from (3RS)-muscone

Two trans stereoisomers of 3-methylcyclopentadecanol (= muscol), (1R,3R)-2 and (1S,3S)-2, were efficiently synthesized from (3RS)-3- methylcyclopentadecanone (= muscone; (3RS)-1) by a highly stereoselective reduction (Scheme). L-Selectride (= lithium tri(sec-butyl)borohydride) was used, followed by the enantiomer resolution by lipase QLG (Alcaligenes sp.). The cis stereoisomers of muscol, (1S,3R)-2 and (1R,3S)-2, were obtained by the Mitsunobu inversion of (1R,3R)-2 and (1S,3S)-2, respectively (Scheme). The absolute configuration of (1R,3R)-2 was determined by X-ray crystal-structure analysis of its 3-nitrophthalic acid monoester, 2-[(1R,3R)-3- methylcyclopentadecyl hydrogen benzene-1,2-dicarboxylate ((1R,3R)-3b), and by oxidation of (1R,3R)-2 to (3R)-muscone.

Synthesis of (R)-(-)-muscone via enzymatic resolution of 3- methylcyclopentadecan-1-ol

(R)-(-)-Muscone was synthesized efficiently by oxidation of 3-(R)- methylcyclopentadecan-1-(RS)-ol, which was obtained by lipase-catalyzed resolution of its diastereomeric mixture.

Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone

An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described.Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid.The overall yield of (R)-muscone (>95percent R) from commercially available cyclopentadecanone is 60percent over seven steps.