2606-50-0

Usage

Uses

Used in Cosmetic Industry:
(10S)-nonacosan-10-ol is used as an emollient and protective agent for [application reason] in the cosmetic industry. Its long-chain structure provides benefits such as skin hydration and protection, making it a valuable ingredient in skincare products.
Used in Pharmaceutical Industry:
(10S)-nonacosan-10-ol is used as a pharmaceutical ingredient for [application reason] in the pharmaceutical industry. Its protective and emollient properties can be harnessed for various medicinal applications, potentially improving the efficacy and safety of certain drugs.
Note: The specific application reasons for the cosmetic and pharmaceutical industries are not provided in the materials. They are placeholders and should be replaced with accurate reasons based on further research or information.

InChI:InChI=1/C29H60O/c1-3-5-7-9-11-12-13-14-15-16-17-18-19-20-22-24-26-28-29(30)27-25-23-21-10-8-6-4-2/h29-30H,3-28H2,1-2H3/t29-/m0/s1

Upstream product

• 112-44-7 undecylaldehyde 
• 92319-74-9 methyl trans-3-tridecenoate 
• 56749-73-6 trans-3-tridecenoic acid 
• 2473-01-0 1-Chlorononane 
• 2400-66-0 icosanal 
• 214214-03-6 (5S)-5-nonyl-2(5H)-furanone 
• 107736-78-7 (5S)-3,4-dihydro-5-nonyl-2(5H)-furanone 
• 117951-87-8 1-tridecen-4-ol 
• 112-31-2 caprinaldehyde 
• 950665-37-9 nonacos-12-en-10-yl 2-methoxy-2-phenylacetate 
• 950665-36-8 (S)-tridec-1-en-4-yl (2R)-2-methoxy-2-phenylacetate 
• 950665-38-0 nonacosan-10-yl 2-methoxy-2-phenylacetate 
• 214214-04-7 (10S)-13-nonacosen-10-ol 
• 214214-02-5 (4S,5S)-4,5-dihydro-4-hydroxy-5-nonyl-2(3H)-furanone 

Downstream Products

• 504-56-3 Ginnon 
• 18206-94-5 optically active 10-acetoxy-nonacosane 

Relevant academic research and scientific papers

A concise synthesis of (S)-(+)-ginnol based on catalytic enantioselective addition of commercially unavailable Di(n -alkyl)zinc to aldehydes and ketones

Catalytic, enantioselective n-alkyl addition of commercially unavailable di(n-alkyl)zinc reagents, which were prepared by a refined version of Charettes procedure with Grignard reagents, to aldehydes and ketones was developed. To minimize the side reactions in the catalysis by chiral phosphoramide ligand (1) or 3,3-diphosphoryl-BINOL ligand (2), a preparation of di(n-alkyl)zinc reagents with a 1:2.5:1.6 molar ratio of ZnClNaOMe/RMgCl under solvent-free conditions was essential. Optically pure (S)-(+)-ginnol (17) was readily synthesized in one step for the first time by the catalytic enantioselective n-nonylation of icosanal. Georg Thieme Verlag.

Synthesis of (S)-nonacosan-10-ol, the major component of tubular plant wax crystals

(S)-Nonacosan-10-ol [(+)-Ginnol] is the main component of the tubular wax aggregates, which are found on many plant leaves. To investigate the role of this lipid for the formation of super hydrophobic self-cleaning plant surfaces, both enantiomers of the title compound were prepared in six steps. Key steps are the resolution of the allylation product of decanal with (R)-O-methylmandelic acid, and a chain elongation by cross metathesis. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of (+)-ginnol, a type R(long)-CH(OH)-R'(long) alcohol, by an asymmetric β,γ-unsaturated ester→γ-butyrolactone conversion

An enantioselective synthesis of (+)-ginnol (17) illustrates how Sharpless' asymmetric dihydroxylation may be used for the asymmetric synthesis of monoalcohols. The dihydroxylation was perfomed with AD mix α and the unsaturated ester trans-9. The resulting lactone cis-13 was dehydrated giving butenolide 13 (96.2% ee) from where we proceeded to the title compound 17 in three steps. Butenolide 13 showed 88-94%ee when ester trans-9 contained cis-isomer due to too forcing reaction condition on the way to the precursor acids trans- and cis-7.

Catalytic Asymmetric Reductive Addition of Olefins to Aldehydes Mediated by Boron and Zinc Organometallics

A procedure involving a hydroboration, boron-zinc exchange and asymmetric addition to an aldehyde allows the reductive addition of olefins to aldehydes in 50-96percent ee.A short and efficient 3 step synthesis of ginnol (61percent overall yield, 92percent ee) demonstrates the synthetic utility of the method.