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Isostearic acid Sale

(Synonyms: 异硬脂酸) 目录号 : GC63970

Isostearic acid 是一种独特的脂肪酸。Isostearic acid 可用于制药、个人护理和化妆品。

Isostearic acid Chemical Structure

Cas No.:2724-58-5

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产品描述

Isostearic acid is a unique fatty acid. Isostearic acid is useful in pharmaceutical, personal care, and cosmetic products[1].

[1]. Bahar Riazi, et al. Life Cycle Environmental and Cost Implications of Isostearic Acid Production for Pharmaceutical and Personal Care Products.

Chemical Properties

Cas No. 2724-58-5 SDF Download SDF
别名 异硬脂酸
分子式 C18H36O2 分子量 284.48
溶解度 DMSO : 100 mg/mL (351.52 mM; Need ultrasonic) 储存条件 Store at -20°C
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1 mM 3.5152 mL 17.5759 mL 35.1519 mL
5 mM 0.703 mL 3.5152 mL 7.0304 mL
10 mM 0.3515 mL 1.7576 mL 3.5152 mL
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Research Update

Isostearic acid is an active component of imiquimod formulations used to induce psoriaform disease models

Inflammopharmacology 2023 Mar 21.PMID:36943539DOI:10.1007/s10787-023-01175-3.

Topical imiquimod based creams are indicated as immune stimulants for papillomas and various skin neoplasms. Imiquimod is considered a TLR7 ligand. These creams are also used in research to induce skin inflammation in mice as a model for psoriasis. We observed that this inflammatory response was not strictly imiquimod dependent and we set out to establish which components drive the proinflammatory effects. To this end, we examined the induction response in a BALB/cJRj mouse model, in which 50 mg of cream is applied to 2 cm2 of skin (125 mg/kg imiquimod-5% W/V, and/or 625 mg/kg isostearic acid-25% W/V). Comparing cream formulations containing Isostearic acid, imiquimod and the combination, we observed that Isostearic acid causes skin inflammation within 2 days, whereas imiquimod requires up to 5 days for initial signs. Isostearic acid activated an inflammasome response, stimulated release of proinflammatory cytokines and upregulated the IL-23/17 axis. Animals treated with Isostearic acid had enlarged livers (+ 40% weight), which was not observed with imiquimod alone. Imiquimod was readily metabolized and cleared from plasma and liver, but was maintained at high levels in the skin throughout the body (200 mM at area of application; 200 µM in untreated skin). Imiquimod application was associated with splenomegaly, cytokine induction/release and initial body weight loss over 3 days. Despite high imiquimod skin levels throughout the animal, inflammation was only apparent in the treated areas and was less severe than in Isostearic acid groups. As the concentrations in these areas are well above the 10 µM required for TLR7 responses in vitro, there is an implication that skin inflammation following imiquimod is due to effects other than TLR7 agonism (e.g., adenosine receptor agonism). In brain, isostearic caused no major changes in cytokine expression while imiquimod alone sightly stimulated expression of IL-1β and CCL9. However, the combination of both caused brain induction of CCL3, -9, CXCL10, -13, IL-1β and TNFα. The implication of these data is that Isostearic acid facilitates the entry of imiquimod or peripherally secreted cytokines into the brain. Our data suggest that psoriaform skin responses in mice are more driven by Isostearic acid, than generally reported and that the dose and route used in the model, leads to profound systemic effects, which may complicate the interpretation of drug effects in this model.

Microemulsions based on TPGS and Isostearic acid for imiquimod formulation and skin delivery

Eur J Pharm Sci 2018 Dec 1;125:223-231.PMID:30316975DOI:10.1016/j.ejps.2018.10.007.

Imiquimod (IMQ) is an immunostimulant drug topically used for the treatment of actinic keratosis and basal cell carcinoma. IMQ formulation and skin delivery is difficult because of its very low solubility in the most of pharmaceutical excipients and very poor skin penetration properties. The purpose of this study was to develop a microemulsion to optimize imiquimod skin delivery using d‑α‑tocopherol polyethylene glycol-1000 succinate (TPGS) as surfactant (so as to take advantage of its thickening properties) and Isostearic acid as oil phase. This fatty acid was selected since it has demonstrated a good solubilizing power for imiquimod and it has also shown to contribute to its therapeutic activity. We have built pseudo-ternary diagrams using two different co-surfactants (Transcutol® and propylene glycol - PG) in a 1:1 ratio with TPGS and then selected microemulsions in the clear and viscous regions of the diagrams. The systems were characterized in terms of rheology and X-ray scattering; additionally, the capability to promote IMQ skin uptake was evaluated ex-vivo on a porcine skin model. All the formulations selected in the gel-microemulsion regions behaved as viscoelastic solids; X-rays scattering experiments revealed in all cases the presence of an ordered lamellar structure, but with differences in terms of interlamellar distance and flexibility between Transcutol® and PG-containing systems. A higher flexibility and a greater hydrophobic volume, possibly interconnected at some point, was associated to the use of Transcutol® and had an impact on the microemulsion capacity to solubilize IMQ as well as on the capability to enhance drug uptake into the skin. The best performing gel-like microemulsion was composed of ≈26% of water, ≈21% of Isostearic acid, ≈26% of TPGS and ≈27% of Transcutol® and accumulated, after 6 h of contact, 3.0 ± 1.1 μg/cm2 of IMQ. This value is higher than the one reported in the literature for the commercial cream (1.9 ± 0.8 μg/cm2), despite the 4-times lower concentration of the vehicle (13 mg/g for the microemulsion vs 50 mg/g for the commercial cream).

Methyl-branched poly(hydroxyalkanoate) biosynthesis from 13-methyltetradecanoic acid and mixed Isostearic acid isomer substrates

Appl Microbiol Biotechnol 2009 Nov;85(2):359-70.PMID:19644690DOI:10.1007/s00253-009-2134-1.

Pseudomonas resinovorans, a known medium-chain-length (mcl-) poly(hydroxyalkanoate) (PHA) producer, was grown on 13-methyltetradecanoic acid (13-MTDA) and a mixture of Isostearic acid (IA) isomers to produce methyl-branched mcl-PHA polymers. Shake-flask experiments revealed polymer productivities (the percent of the cell mass that is polymer) of 31 +/- 1% (n = 3) and 23 +/- 3% (n = 3) when grown in 13-MTDA and IA, respectively. Monomer content was determined by a combination of gas chromatography/mass spectrometry (GC/MS) of the acid hydrolyzed, silylated methyl esters, and nuclear magnetic resonance spectroscopy. Results showed that the mcl-PHA polymer derived from 13-MTDA was primarily composed of 3-hydroxy-7-methyloctanoic acid and 3-hydroxy-9-methyldecanoic acid (67 and 16 mol% by GC/MS, respectively). In contrast, the mcl-polymers synthesized from the IA isomeric mixture were more complex, containing both even and odd chain-length monomers as well as varying distributions of methyl-branched derivatives. The PHA distributions among the C8, C10, C12, and C14 carbon chain-length monomers included three isomers of C8, five isomers of C10, seven isomers of C12, and nine isomers of C14 each containing one linear-chain derivative and n-6 methyl-branched derivatives where n equals the total number of carbon atoms in each monomer unit (C8-C14).

Selective extraction equilibria of Sc(III), Y(III), Fe(III) and Al(III) from acidic media with toluene mixture of deep eutectic solvent (DES) composed of TOPO and Isostearic acid

Anal Sci 2023 Apr;39(4):473-481.PMID:36807888DOI:10.1007/s44211-022-00234-z.

A deep eutectic solvent (DES) composed of Isostearic acid and TOPO was newly found out and investigated for selective recovery of scandium. The four elements used in this study are scandium, iron, yttrium, and aluminum. It was difficult to separate the four elements owing to the overlap of extraction behavior when Isostearic acid or TOPO alone in toluene was used, respectively. However, scandium was able to be selectively extracted from other metals using DES prepared by 1:1 mol ratio of Isostearic acid and TOPO without toluene. In DES consisting of Isostearic acid and TOPO, synergistic and blocking effects with three extractants acted on the extraction selectivity for scandium. Both effects are proved also from the fact that scandium was easily stripped with diluted acidic solutions such as 2 M HCl and H2SO4. Thus, DES extracted selectively scandium and back-extraction was easily achieved. In order to elucidate these phenomena above, the extraction equilibria of Sc(III) using DES dissolved in toluene was investigated in detail. The extraction mechanism of scandium by DES in toluene indicates that the extracted chemical species vary with pH, and that trivalent scandium is extracted by forming stable metal complexes with DESs consisting of five molecules of Isostearic acid and five molecules of TOPO.

Viscosity of Nanoconfined Branched-Chain Fatty Acids Studied by Resonance Shear Measurements

Langmuir 2022 Oct 25;38(42):12944-12950.PMID:36240007DOI:10.1021/acs.langmuir.2c02090.

Lubricant performance can be improved using additives such as organic friction modifiers (OFMs) and is influenced by their conformation and properties in the space confined between the substrate surfaces, rendering the detailed property analysis of confined OFMs and lubricants a matter of high practical significance. To date, studies on fatty acids as confined OFMs have mainly focused on linear- and unsaturated-chain molecules, leaving branched-chain structures underexplored. To bridge this gap, we used resonance shear measurements in this study to probe the viscosity of two branched-chain C18 fatty acids (Isostearic acid T and Isostearic acid) confined between mica surfaces at different applied normal loads (L) and surface separation distances (D). The viscosity parameter (bs) of both acids significantly increased at D < ∼4 nm because of structuring and was lower for Isostearic acid than that for Isostearic acid T at L > ∼0.6 mN. This reversal of bulk viscosity order under nanoconfinement was ascribed to the ability of the bulky methyl-substituted side chain of Isostearic acid to prevent ordering in the nanospace between the mica surfaces and thus preserve fluidlike properties. The obtained results provide fundamental insights into the lubricity of branched-chain fatty acids and are expected to promote the development of novel high-performance OFMs.