70419-07-7

Usage

Uses

Used in the Food Industry:
(R)-(-)-2-Nonanol is used as a flavoring agent for its ability to impart a mild, pleasant taste to food products, enhancing the overall sensory experience for consumers.
Used in the Perfume Industry:
(R)-(-)-2-Nonanol is utilized as an ingredient in perfumes to contribute to the creation of complex and long-lasting fragrances, capitalizing on its agreeable scent.
Used in Personal Care Products:
(R)-(-)-2-Nonanol is employed in personal care products such as lotions and creams, where it serves to add a pleasant aroma and potentially improve the texture and feel of the products on the skin.
Used in the Production of Surfactants:
(R)-(-)-2-Nonanol is used as a component in the manufacturing of surfactants, which are essential in the formulation of cleaning and detergent products for their ability to reduce surface tension and facilitate the mixing of substances.
Used in the Production of Lubricants:
(R)-(-)-2-Nonanol is incorporated into the production of lubricants, where it helps to reduce friction between surfaces and improve the efficiency of mechanical systems.
Used in the Production of Plasticizers:
(R)-(-)-2-Nonanol is used in the creation of plasticizers, which are additives that increase the flexibility and workability of plastics, making them more suitable for various applications.
Used in Medical Applications:
(R)-(-)-2-Nonanol is studied for its potential medical applications, including its antimicrobial, anti-inflammatory, and antiviral properties, indicating its possible use in pharmaceuticals and therapeutics to combat infections and inflammation.

InChI:InChI=1/C9H20O/c1-3-4-5-6-7-8-9(2)10/h9-10H,3-8H2,1-2H3/t9-/m1/s1

Upstream product

• 124-13-0 Octanal 
• 544-97-8 dimethyl zinc(II) 
• 821-55-6 2-Nonanone 
• 628-99-9 nonan-2-ol 
• 108-05-4 vinyl acetate 
• 18006-13-8 methyltriisopropoxytitanium(IV) 
• 917-54-4 methyllithium 
• 111-84-2 nonane 
• 55193-34-5 2-nonyl octanoate 
• 55193-16-3 2-nonyl hexanoate 
• 69727-42-0 2-nonyl butanoate 
• 14936-66-4 2-nonanyl acetate 
• 107-92-6 butyric acid 
• 142-62-1 hexanoic acid 

Downstream Products

• 1359079-02-9 (R)-(-)-1-methyloctyl p-toluenesulfonate 
• 1414963-69-1 C₂₃H₂₈O 
• 1414963-66-8 C₂₃H₃₆O 
• 1414963-55-5 (S)-1-iodo-4-(nonan-2-yloxy)benzene 
• 1414963-72-6 C₃₂H₄₆O₂ 
• 1414963-63-5 (S)-4-((4-(nonan-2-yloxy)phenyl)ethynyl)phenol 
• 1414963-60-2 (S)-1-ethynyl-4-(nonan-2-yloxy)benzene 
• 1414963-58-8 (S)-trimethyl((4-(nonan-2-yloxy)phenyl)ethynyl)silane 
• 1346758-49-3 (S)-(+)-1-methyloctyl 3,5-dibromobenzoate 
• 479629-72-6 (R)-1-methyloctyl-4-acetoxyphenylcarboxylate 

Relevant academic research and scientific papers

Catalytic enantioselective addition of methyltriisopropoxititanium to aldehydes

An efficient catalyst for the enantioselective synthesis of chiral methyl carbinols from aldehydes is presented. The system uses methyltriisopropoxytitanium as a nucleophile and a readily available binaphthyl derivative as a chiral ligand. The enantioselective methylation of both aromatic and aliphatic aldehydes proceeds with good yields and high enantioselectivities under mild conditions.

ALKANE OXIDATION BY MODIFIED HYDROXYLASES

This invention relates to modified hydroxylases. The invention further relates to cells expressing such modified hydroxylases and methods of producing hydroxylated alkanes by contacting a suitable substrate with such cells.

Catalytic Asymmetric Addition of Organolithium Reagents to Aldehydes

Herein we report an efficient catalytic system for the titanium-promoted enantioselective addition of organolithium reagents to aldehydes, based on chiral Ar-BINMOL ligands. Unprecedented yields and enantioselectivities are achieved in the alkylation reactions of aliphatic aldehydes. Remarkably, methyllithium can be added to a wide variety of aromatic and aliphatic aldehydes, providing versatile chiral methyl carbinol units in a simple one-pot procedure under mild conditions and in very short reaction times.

Identification of an ε-keto ester reductase for the efficient synthesis of an (R)-α-lipoic acid precursor

Abstract A novel reductase (CpAR2) with unusually high activity toward an ε-keto ester, ethyl 8-chloro-6-oxooctanoate, was isolated from Candida parapsilosis. The asymmetric reduction of ethyl 8-chloro-6-oxooctanoate using Escherichia coli cells coexpressing CpAR2 and glucose dehydrogenase genes gave ethyl (R)-8-chloro-6-hydroxyoctanoate, a key precursor for the synthesis of (R)-α-lipoic acid, in high space-time yield (530 gL-1d-1) and with excellent enantiomeric excess (>99%). This bioprocess was shown to be viable on a 10-L scale. This method provides a greener and more cost-effective method for the industrial production of (R)-α-lipoic acid.

Identification of key residues in Debaryomyces hansenii carbonyl reductase for highly productive preparation of (S)-aryl halohydrins

Key residues of Debaryomyces hansenii carbonyl reductase in the determination of the reducing activity towards aryl haloketones were identified through combinatorial mutation of conserved residues. This study provides a green and efficient biocatalyst for the synthesis of (S)-aryl halohydrins.

A novel P450-based biocatalyst for the selective production of chiral 2-alkanols

A P450 monooxygenase from Nocardia farcinica (CYP154A8) catalyses the stereo- and regioselective hydroxylation of n-alkanes, still a challenging task in chemical catalysis. In a biphasic reaction system, the regioselectivity for the C2-position of C7-C9 alkanes was over 90%. The enzyme showed strict S-selectivity for all tested substrates, with enantiomeric excess (ee) of up to 91%. This journal is the Partner Organisations 2014.

Facile access to chiral alcohols with pharmaceutical relevance using a ketoreductase newly mined from Pichia guilliermondii

Chiral secondary alcohols with additional functional groups are frequently required as important and valuable synthons for pharmaceuticals, agricultural and other fine chemicals. With the advantages of environmentally benign reaction conditions, broad reaction scope, and high stereoselectivity, biocatalytic reduction of prochiral ketones offers significant potential in the synthesis of optically active alcohols. A CmCR homologous carbonyl reductase from Pichia guilliermondii NRRL Y-324 was successfully overexpressed. Substrate profile characterization revealed its broad substrate specificity, covering aryl ketones, aliphatic ketones and ketoesters. Furthermore, a variety of ketone substrates were asymmetrically reduced by the purified enzyme with an additionally NADPH regeneration system. The reduction system exhibited excellent enantioselectivity (>99% ee) in the reduction of all the aromatic ketones and ketoesters, except for 2-bromoacetophenone (93.5% ee). Semi-preparative reduction of six ketones was achieved with high enantioselectivity (>99% ee) and isolation yields (>80%) within 12 h. This study provides a useful guidance for further application of this enzyme in the asymmetric synthesis of chiral alcohol enantiomers. Copyright

Continuous biphasic enzymatic reduction of aliphatic ketones

Biphasic reactions offer an attractive alternative for the utilisation of enzymes for conversion of hardly water soluble substrates. Especially, the alcohol dehydrogenase from Lactobacillus brevis was successfully used for the reductive synthesis of enantiopure secondary aliphatic alcohols. With the enzymatic catalyst and the cofactor effectively retained in the reactive aqueous phase, the continuous operation was demonstrated by continuous addition and withdrawal of the non-reactive phase. The four tested substrates 2-heptanone, 2-octanone, 2-nonanone, and 2-decanone showed that the space time yield and turnover numbers (TON) of the enzyme decrease as the availability of the substrate decreases with increasing partition coefficients. Nevertheless, a TONLbADH of up to 478 × 103 could be achieved. Remarkably, the cofactor utilisation turned out to be very high and a TON NADP+ of more than 20 × 103 was easily achievable for both 2-heptanone and 2-octanone by substrate coupled cofactor regeneration with excess of 2-propanol.

Ionic liquid facilitates biocatalytic conversion of hardly water soluble ketones

Ionic liquids represent a promising alternative to conventional cosolvents as biocompatible solubilisers for biocatalysis. This was shown using water miscible ionic liquids to facilitate the stereoselective reduction of hardly water soluble, aliphatic ketones catalysed by the alcohol dehydrogenase from Lactobacillus brevis. Ten ionic liquids were screened for activity and solubility. Improved storage stabilities besides improved enzyme activities, as well as reduced substrate surplus and product inhibitions were found, while applying the most promising AMMOENG 101 in more detailed investigations. Batch reactions with cofactor regeneration via a glucose dehydrogenase showed increased reaction rates; thus underlining the positive influence of AMMOENG 101. For (R)-3-octanol, (R)-2-nonanol, (R)-2-decanol, and (R)-2-octanol space time yields between 250 and 350 mmol L-1 d -1 were achieved.

Utilising hardly-water soluble substrates as a second phase enables the straightforward synthesis of chiral alcohols

So far, the alcohol dehydrogenase-catalysed conversion of longer chain aliphatic substrates has been challenging due to their low solubility in aqueous solution. However, by utilising the ketone directly as a second organic phase, the straightforward synthesis of long chain aliphatic chiral alcohols is enabled. The Royal Society of Chemistry.