55505-28-7

Usage

Uses

Used in Pharmaceutical Industry:
9-Methyldecan-1-ol is used as a synthetic intermediate for the production of apolipoprotein E secretion stimulator N 4909. Apolipoprotein E is a crucial protein involved in lipid metabolism and has been linked to various health conditions, including cardiovascular diseases and neurological disorders. The synthesis of N 4909, which stimulates the secretion of apolipoprotein E, can potentially contribute to the development of therapeutic agents for these conditions.
Used in Chemical Synthesis:
9-Methyldecan-1-ol can be utilized as a building block in the synthesis of various organic compounds, such as surfactants, detergents, and emulsifiers. Its unique structure allows it to form stable emulsions and improve the solubility of other compounds, making it a valuable component in the formulation of various products.
Used in Cosmetics Industry:
Due to its emollient and moisturizing properties, 9-Methyldecan-1-ol can be employed in the cosmetics industry as an ingredient in skincare and hair care products. It can help improve the texture and appearance of the skin and hair, providing a smooth and soft feel.
Used in Flavor and Fragrance Industry:
9-Methyldecan-1-ol may also find applications in the flavor and fragrance industry, where it can be used to create unique scents and flavors for various products. Its distinct chemical structure can contribute to the development of novel aromas and tastes.

InChI:InChI=1S/C11H24O/c1-11(2)9-7-5-3-4-6-8-10-12/h11-12H,3-10H2,1-2H3

Upstream product

• 905589-97-1 9-methyl-decanoic acid ethyl ester 
• 40345-86-6 O-(9-methyl-decyl)-hydroxylamine 
• 1119-63-7 9-methyl-1-decanoic acid 
• 50530-06-8 6-bromohexanoic acid sodium salt 
• 107-82-4 i-pentyl bromide 
• 4286-55-9 1-bromo-6-hexanol 
• 4548-78-1 (3-methylbutyl)magnesium bromide 
• 10160-24-4 7-bromoheptyl alcohol 
• 78-77-3 Isobutyl bromide 
• 143211-18-1 (E)-1-hydroxy-9-methyldec-7-ene 
• 179617-50-6 9-methyl-6-decen-1-ol 
• 861355-96-6 (7-methyl-octyl)-malonic acid diethyl ester 
• 10266-06-5 1-iodo-7-methyloctane 
• 108-12-3 isopentanoyl chloride 

Downstream Products

• 55504-93-3 (9-Methyl-decyloxysulfonyl)-phenyl-acetic acid 
• 1119-63-7 9-methyl-1-decanoic acid 
• 221696-10-2 (S)-benzyl 3-hydroxy-13-methyltetradecanoate 
• 137352-60-4 9-Methyldecanal 
• 677354-23-3 (Z)-11-methyldodec-2-enoic acid 

Relevant academic research and scientific papers

Synthesis of the quorum sensing molecule Diffusible Signal Factor using the alkyne zipper reaction

The development of a concise synthesis of the quorum sensing molecule Diffusible Signal Factor is described. This route exploits an alkyne zipper reaction to form a key terminal alkyne intermediate. The chemistry outlined here may also be applied to the preparation of cis-unsaturated analogues of Diffusible Signal Factor.

Volatile methyl esters of medium chain length from the bacterium Chitinophaga Fx7914

The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl- and dimethyl-branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C-chain length were identified, which belong to five main classes, methyl (S)-2-methylalkanoates (class A), methyl (S)-2,(ω-1)-dimethylalkanoates (class B), methyl 2,(ω-2)-dimethylalkanoates (class C), methyl (E)-2-methylalk-2-enoates (class D), and methyl (E)-2,(ω-1)-dimethylalk-2- enoates (class E). The structures of the compounds were verified by GC/MS analysis and synthesis of the target compounds as methyl (S)-2-methyloctanoate (28), methyl (S)-2,7-dimethyloctanoate ((S)-43), methyl 2,6-dimethyloctanoate (49), methyl (E)-2-methylnon-2-enoate (20a), and methyl (E)-2,7-dimethyloct-2- enoate (41a). Furthermore, the natural saturated 2-methyl-branched methyl esters showed (S)-configuration as confirmed by GC/MS experiments using chiral phases. Additionally, the biosynthetic pathway leading to the methyl esters was investigated by feeding experiments with labeled precursors. The Me group at C(2) is introduced by propanoate incorporation, while the methyl ester is formed from the respective carboxylic acid by a methyltransferase using S-adenosylmethionine (SAM).

Influence of terminal branching on the transdermal permeation-enhancing activity in fatty alcohols and acids

In order to investigate the effect of terminal chain branching in the skin permeation enhancers, seven alcohols and seven acids with the chain length of 8-12 carbons and terminal methyl or ethyl branching were prepared. Their transdermal permeation-enhancing activities were evaluated in vitro using theophylline as a model permeant and porcine skin, and compared to those of the linear standards. Terminal methyl branching increased the enhancing activity only in 12C acid, no effect was seen in the shorter ones. Terminal ethyl however produced a significant increase in activity. In the alcohols, the branching was likely to change the mode of action, due to a different relationship between the activity and the chain length.

First total synthesis of N-4909 and its diastereomer; A stimulant of apolipoprotein E secretion in human hepatoma Hep G2 cells

Both (R)- and (S)-3-hydroxy-13-methyltetradecanoic acids were prepared via a lipase-catalyzed enantioselective acylation. The total synthesis of N-4909 and its diastereomer were achieved by a coupling of either (R)- or (S)-3-hydroxy-13-methyltetradecanoic acid moiety with a hexapeptide moiety and by a cyclization with HATU (O-(7-azabenzotriazol-1-yl)- 1,1,3,3-tetramethyluronium hexafluorophosphate) and HOAt (1-hydroxy-7-azabenzotriazole) in a high dilution condition. The R configuration of 3-hydroxy-13-methyltetradecanoic acid was found to be important for stimulating the activity of apolipoprotein E secretion in human hepatoma Hep G2 cells.

Perfume composition

The present invention relates to a perfume composition comprising a methyl branched aliphatic compound and the methyl branched aliphatic compound useful as perfume material and a method for imparting a fragrance by using such compounds and compositions.

A perfume composition

The present invention relates to a perfume composition comprising a methyl branched aliphatic compound and the methyl branched aliphatic compound useful as perfume material and a method for imparting a fragrance by using such compounds and compositions.