- 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.
- Ewonkem, Monique B.,Grinberg, Sarina,Lemcoff, Gabriel,Shaubi, Eleonora,Linder, Charles,Heldman, Eliahu
-
-
Read Online
- 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.
- Slivniak, Raia,Domb, Abraham J.
-
-
Read Online
- 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.
- Brinkerhoff, Rafael C.,Tarazona, Hernan F.,De Oliveira, Patrick M.,Flores, Darlene C.,Montes D'Oca, Caroline Da R.,Russowsky, Dennis,Montes D'Oca, Marcelo G.
-
-
Read Online
- 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.
- -
-
-
- 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.
- Hachiya, Iwao,Makino, Akihisa,Shimizu, Makoto,Akita, Masatsugu,Hamaguchi, Takashi
-
p. 2451 - 2454
(2007/10/03)
-
- 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.
- -
-
-
- Synthesis of phosphatidylcholines containing ricinoleic acid
-
1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields. The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only β-methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphocholine), respectively.
- Borsotti, Gianpietro,Guglielmetti, Gianfranco,Spera, Silvia,Battistel, Ezio
-
p. 10219 - 10227
(2007/10/03)
-
- Process for the synthesis of diricinoleyphosphatidylcholine
-
Diricinoleylphosphatidylcholine (I) in an optically active form is obtained with good yields and a high purity by means of a process which comprises: a) esterifying the terminal carboxylic group of ricinoleic acid (III) with an alcohol having from 1 to 4 carbon atoms to give the corresponding ester having formula (IV); b) protecting the hydroxylic group of the ester of ricinoleic acid (IV) with a protecting group removable under bland operating conditions and isolating the ester of ricinoleic acid of which the hydroxylic group (V) is protected; c) hydrolyzing the ester of ricinoleic acid of which the hydroxylic group (V) is protected and isolating the ricinoleic acid of which the hydroxylic group (VI) is protected; d) acylating L-α-glycerophosphatidylcholine (II) with an imidazolic or triazolic derivative of the compound having formula (VI) and isolating the diricinoleylphosphatidylcholine of which the hydroxylic group (VII) is protected; e) removing the protecting group from the hydroxylic group of the compound having formula (VII); and finally f) recovering and purifying the compound having formula (I) by means of chromatography.
- -
-
-
- Process for the synthesis of Diricinoleylphospatidylcholine
-
Diricinoleylphosphatidylcholine (I) in an optically active form is obtained with good yields and a high purity by means of a process which comprises: a) esterifying the terminal carboxylic group of ricinoleic acid (III) with an alcohol having from 1 to 4 carbon atoms to give the corresponding ester having formula (IV); b) protecting the hydroxylic group of the ester of ricinoleic acid (IV) with a protecting group removable under bland operating conditions and isolating the ester of ricinoleic acid of which the hydroxylic group (V) is protected; c) hydrolyzing the ester of ricinoleic acid of which the hydroxylic group (V) is protected and isolating the ricinoleic acid of which the hydroxylic group (VI) is protected; d) acylating L-α-glycerophosphatidylcholine (II) with an imidazolic or triazolic derivative of the compound having formula (VI) and isolating the diricinoleylphosphatidylcholine of which the hydroxylic group (VII) is protected; e) removing the protecting group from the hydroxylic group of the compound having formula (VII); and finally f) recovering and purifying the compound having formula (I) by means of chromatography.
- -
-
-
- Boc2O mediated macrolactonisation: Syntheses of R-(+)-ricinoleic acid lactone and (±)-12-OH-stearic acid lactone
-
An efficient chemoenzymatic synthesis of R-(+)-ricinoleic acid lactone and (±)-12-OH-stearic acid lactone using Boc2O mediated macrolactonisation is reported.
- Nagarajan
-
p. 2467 - 2475
(2007/10/03)
-
- Antioxidant, antiphospholipase derivatives of ricinoleic acid
-
Water or lipid soluble, pharmacologically active, antioxidant, anti-phospholipase compounds that are chemically defined. The compounds protect mammalian cells by inhibiting PLA2 and preventing oxidation. In particular, each compound has at least two fatty moieties and no active hydroxy group. The compound may also have at least one ionizable group, which may a carboxyl group, and each of the fatty moieties has from sixteen to twenty carbon atoms and at least one cis-unsaturated double bond.
- -
-
-
- Cleavage of Esters under Nearly Neutral Conditions at High Pressure. Chemo- and Regioselective Hydrolysis in Organic Solvents
-
Hydrolysis of esters proceeded at room temperature under high pressure in the presence of iPr2NEt or N-methylmorpholine using CH3CN-H2O (60:1) as the solvent.This very mild procedure enables the smooth hydrolysis of biologically important compounds such as amino esters, aliphatic unsaturated fatty esters, and β-hydroxy esters; no racemization, no isomerization, and no side reactions take place.
- Yamamoto, Yoshinori,Furuta, Toshiaki,Matsuo, Jiro,Kurata, Tetsuro
-
p. 5737 - 5738
(2007/10/02)
-
- Ethylaluminum Dichloride Catalyzed Ene Reactions of Aldehydes with Nonnucleophilic Alkenes
-
Ethylaluminum dichloride, which is a strong Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic aldehydes with nonnucleophilic alkenes.Higher aldehydes give good yields of ene adducts with terminal alkenes.Formaldehyde gives good yields of adducts with electron-deficient alkenes.This reaction has been used for the synthesis of recifeiolide, ricinelaidic acid, and the insect pheromones (E,E)-8,10-dodecadienyl acetate and (E)-9,11-dodecadienyl acetate.
- Snider, Barry B,Phillips, Gary B.
-
p. 464 - 469
(2007/10/02)
-
