27925-02-6

Usage

Uses

Used in Manufacturing Industry:
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-, homopolymer is used as a raw material or additive for various manufacturing processes due to its polymeric characteristics. The specific applications and properties of this chemical compound can vary depending on the implementation technique, molecular weight, and the presence of other components in its structure.
Used in Chemical Production:
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-, homopolymer is employed as a key component in the production of certain chemicals, where its unique structural features and polymeric nature contribute to the desired properties of the final product.
Used in Material Science:
In the field of material science, 9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-, homopolymer is utilized for the development of new materials with specific properties, such as improved strength, flexibility, or thermal stability. Its polymeric nature and the presence of double bonds in its structure play a crucial role in determining the characteristics of these materials.
Used in Pharmaceutical Industry:
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-, homopolymer may be used as a component in the formulation of pharmaceutical products, where its unique chemical structure and properties can contribute to the effectiveness and stability of the final product. The specific applications in this industry can vary depending on the requirements of the particular drug or treatment.

Upstream product

• 111-71-7 heptanal 
• 112-38-9 10-undecenoic acid 
• 41015-43-4 methyl acetyl ricinoleate 
• 140-03-4 [R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester 
• 45317-49-5 12-ricinoloyloxy-octadec-9-enoic acid 
• 64-17-5 ethanol 
• 141-24-2 methyl ricinoleate 
• 141-22-0 Ricinoleic acid 
• 7706-01-6 methyl (12R)-hydroxyoctadec-(9E)-enoate 
• 5455-97-0 12-oxo-octadec-cis-9-enoic acid 
• 6629-55-6 (E)-12-Oxooctadec-9-enoic Acid 
• 2528-61-2 Heptanoic acid chloride 
• 84799-82-6 (Z)-(S)-12-hydroxyoctadec-9-enoic acid methyl ester 
• 57884-97-6 (Z)-(R)-12-methanesulfonyloksyoctadec-9-enoic acid methyl ester 

Downstream Products

• 1095618-59-9 12-hydroxy-9-octadecenoic acid ethyl ester 
• 2420-55-5 linoleic acid 
• 540-12-5 ricinelaidic acid 
• 5455-97-0 12-oxo-octadec-cis-9-enoic acid 
• 22418-62-8 3-hydroxy-nonanal 
• 124130-69-4 12-hydroxy-octadec-9-enoic acid-(N'-phenyl-hydrazide) 
• 15505-14-3 castor oil 
• 7378-88-3 12-octadecenoic acid 
• 28833-56-9 9,12-dioxooctadec-trans-10-enoic acid 
• 5416-59-1 threo-10,11-dihydroxy-9,12-dioxo-octadecanoic acid 
• 4179-48-0 9,12-Dioxo-octadecanoic acid 
• 5416-58-0 (+/-)-threo-10,11-epoxy-12-oxo-octadecanoic acid 
• 540-13-6 (R)-12-hydroxy-octadec-9-ynoic acid 
• 68396-17-8 12-oxo-octadec-9-ynoic acid 

Relevant academic research and scientific papers

Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists

The transient receptor potential vanilloid type-2 (TRPV2) protein is a nonselective Ca2+ permeable channel member of the TRPV subfamily, still considered an orphan TRP channel due to the scarcity of available selective and potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure-activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain fatty acid ethanolamides or primary amides acting as TRPV2 antagonists. Both synthetic and endogenous antagonists exhibited differential inhibition against known TRPV2 agonists characterized by distinct kinetic profiles. These findings represent the first example of both synthetic and naturally occurring TRPV2 modulators with efficacy in the submicromolar/low-micromolar range, which will be useful for clarifying the physiopathological roles of this receptor, its regulation, and its targeting in pathological conditions.

Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a

Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD+-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with α- or β-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 μM with a kcat of 7.6 × 10-3 s-1. The apparent Km value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 μM with a kcat of 5.7 × 10-1 s-1. In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group.

Newly synthesized bolaamphiphiles from castor oil and their aggregated morphologies for potential use in drug delivery

The present study focused on synthesizing bolaamphiphiles from the readily available and inexpensive castor oil, a vegetable oil, which contains about 90% of ricinoleic acid. Two classes of symmetric and asymmetric bolaamphiphiles with acetylcholine head groups were synthesized and characterized by spectroscopic analysis. These novel bolaamphiphilic compounds self-assemble in aqueous media to form stable cationic spherical nano-sized vesicles that are potential drug delivery systems.

Synthesis of β-ketoesters from renewable resources and Meldrum's acid

β-Ketoesters are valuable building blocks for the synthesis of compounds with different biological activities. In this study, a series of fatty β-ketoesters were obtained from fatty acids and Meldrum's acid using N,N-dicyclohexylcarbodiimide and dimethylaminopyridine. In addition, we demonstrate for the first time the synthesis of new fatty β-ketoesters from oleic (cis-C18:1), elaidic (trans-C18:1), ricinoleic (cis-C18:1, 12-OH), linoleic (cis,cis-C18:2), and linolenic (cis,cis,cis-C18:3) acids in good yields.

Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid

(R)-Ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products.

Tailored Oils Produced from Recombinant Oleaginous Microorganisms

Methods and compositions for the production of oil, fuels, oleochemicals, and other compounds in recombinant microorganisms are provided, including oil-bearing microorganisms and methods of low cost cultivation of such microorganisms. Microalgal cells containing exogenous genes encoding, for example, a lipase, a sucrose transporter, a sucrose invertase, a fructokinase, a polysaccharide-degrading enzyme, a keto acyl-ACP synthase enzyme, a fatty acyl-ACP thioesterase, a fatty acyl-CoA/aldehyde reductase, a fatty acyl-CoA reductase, a fatty aldehyde reductase, a fatty acid hydroxylase, a desaturase enzyme, a fatty aldehyde decarbonylase, and/or an acyl carrier protein are useful in manufacturing transportation fuels such as renewable diesel, biodiesel, and renewable jet fuel, as well as oleochemicals such as functional fluids, surfactants, soaps and lubricants.

Lactic acid and ricinoleic acid based copolyesters

Copolyesters based on purified ricinoleic (RA) and lactic (LA) acids with different RA:LA ratios were synthesized by thermal polycondensation and by transesterification of high molecular weight poly(lactic acid) (PLA) with ricinoleic acid and repolyesterification. Thermal polycondensation resulted in random P(LA-RA) copolyesters of molecular weights between 2000 and 8000 with the polymers containing 20% or more RA were liquid at room temperature. Transesterification of high molecular weight PLA with pure ricinoleic acid and repolymerization of those oligomers by condensation resulted in multiblock P(PLA-RA) copolyesters of molecular weights between 6000 and 14000. Polymers containing 50% RA were liq uid at room temperature. 1H NMR spectroscopy analysis coupled with information from DSC allowed de ;ermination of the polymer structure. Polymers prepared by thermal polycondensation are random cope lymers (h > 1), while the copolymers prepared by transesterification have a multiblock character (h LA) decreased from 12 to 4 for the LA-RA 9:1 and 5:5 copolymers prepared by thermal polycondensation and from 50 to 17 for the corresponding LA-RA copolymers prepared by transesterification. Thermal analysis by DSC revealed crystalline structure for polyester synthesized by transesterification. For polyesters synthesized by random condensation on y P(LA-RA) 90:10 w/w contained crystalline domains.

Cosmetic composition comprising at least one polyester resulting from esterification of at least one triglyceride of hydroxylated carboxylic acid(s) and also comprising at least one pasty compound

Disclosed herein is a cosmetic care or makeup composition comprising a) at least one polyester resulting from esterification of at least one triglyceride of at least one hydroxylated carboxylic acid with at least one aliphatic monocarboxylic acid and with at least one aliphatic dicarboxylic acid, and b) at least one pasty compound. This composition makes it possible to obtain a deposition on a keratin materials which can be lubricious, glossy, and comfortable, can have sharply defined outlines, does not migrate, and whose color intensity can be enhanced and/or whose color retention after challenge can be enhanced.

Cosmetic composition comprising at least one polyester resulting from esterification of at least one triglyceride of hydroxylated carboxylic acid(s) and at least one oil with a molar mass of 650 to 10 000 g/mol

Disclosed herein is a composition, for example, a cosmetic care and/or makeup composition for a keratin material, comprising, in a cosmetically acceptable medium, i) at least one polyester resulting from esterification of at least one triglyceride of at least one hydroxylated carboxylic acid with at least one aliphatic monocarboxylic acid and at least one aliphatic dicarboxylic acid, ii) at least one oil of a molar mass ranging from 650 to 10 000 g/mol, and iii) at least one colorant. The composition may possess cosmetic properties and can, for example, endow the makeup or care product with properties of gloss, smoothness of application and comfort. Further disclosed herein is the use of the at least one polyester and the at least one oil with a molar mass ranging from 650 to 10 000 g/mol in a physiologically acceptable composition as an agent for endowing the composition with properties of slip, gloss, comfort, definition, non-migration, enhanced color intensity and/or enhanced color retention after challenge.

Stereodivergent synthesis of (2R)-2,3-diricinolein by lipase-catalyzed hydrolysis of triricinolein

The preparation of 2,3-diricinolein by lipase-catalyzed hydrolysis of triricinolein has been developed. Lipase-catalyzed hydrolysis of triricinolein provided (2R)-2,3-diricinolein in high diastereoselectivity.