33001-45-5

Basic information

• Product Name: (Z)-9-Octadecenoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester
• Synonyms: (Z)-9-Octadecenoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester;Oleic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester;9-Octadecenoic Acid (Z)-(2,2-DiMethyl-1,3-dioxolan-4-yl)Methyl Ester
• CAS NO: 33001-45-5
• Molecular Formula: C₂₄H₄₄O₄
• Molecular Weight: 396.6
• Product Categories: Fatty Acid Derivatives & Lipids;Glycerols;Glycerols, Fatty Acid Derivatives & Lipids
• Mol File: 33001-45-5.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Acetone, Chloroform, Dichloromethane, Ethanol, Ethyl Acetate, Hexane, Methanol
• CAS DataBase Reference: (Z)-9-Octadecenoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-9-Octadecenoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester(33001-45-5)
• EPA Substance Registry System: (Z)-9-Octadecenoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester(33001-45-5)

Safety Data

• Hazardous Substances Data: 33001-45-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

1,2-Isopropylidene-3-oleoyl-sn-glycerol (cas# 33001-45-5) is a compound useful in organic synthesis.

Upstream product

• 66291-51-8 cis-1-iodo-1-decene 
• 749266-09-9 oct-7-enoic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 764-93-2 1-decyne 
• 112-80-1 cis-Octadecenoic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 57-11-4 stearic acid 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 67826-81-7 iododecyne 
• 18719-24-9 oct-7-enoic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 112-62-9 Methyl oleate 
• 112-63-0 Methyl linoleate 
• 112-39-0 hexadecanoic acid methyl ester 

Downstream Products

• 111-03-5 1-monooleoyl glycerol 
• 3443-84-3 2-Oleoylglycerol 
• 121143-94-0 1-lauroyl-3-oleoyl-rac-glycerol 
• 3443-42-3 1,2-dilinoleoyl-3-oleoyl-rac-glycerol 
• 1867-91-0 1,2-dipalmitoyl-3-oleoyl-rac-glycerol 

Relevant articles and documents

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Amorphous SiO2-SO3H [1] with a small surface area and 1.32-mmol H+/g was used for the one-step preparation of solketal from glycerol and acetone; a 20%-w/w catalyst mixture (10% [1] and 10% (Bu4N)(BF4) was found to be very efficient for the synthesis of disolketal ether and of oxygenated biofuels fatty acids solketal esters (FASEs), by direct esterification of the caprylic, lauric, stearic, oleic and linoleic acids with solketal in a 4:1 acid:solketal ratio in refluxing toluene. Solketal acetate was also produced in quantitative yields.

Non-ionic self-assembling amphiphilic polyester dendrimers as new drug delivery excipients

Solubility enhancement of poorly soluble antibiotics via self-assembling nano systems could be a promising approach to effectively treat bacterial infections in the current scenario of evolving resistant species. The study in this paper reports the synthesis of novel biocompatible G2 and G3 polyester amphiphilic dendrimers (ADs) (GMOA-G2-OH, GMOA-G3-OH, GMS-G2-OH and GMS-G3-OH) and their application as: (i) solubility enhancers for fusidic acid (FSD) as a model antibiotic with poor aqueous solubility and (ii) as stearic stabilizers in the preparation of solid lipid nanoparticles (SLNs). Two different series of ADs from glycerol monostearate (GMS) and glycerol monooleate (GMOA) were synthesized and their structures were confirmed employing FT-IR, NMR (1H and 13C) and HR-MS. The MTT assay confirmed their non-toxicity to mammalian cells. The critical aggregation concentration value order for ADs was GMS-G3-OH (5 × 10?6 mol l?1) ?6 mol l?1) ?5 mol l?1). All ADs formed micelles in the size range of 6.48 ± 0.04 nm to 12.38 ± 0.36 nm. At 1% w/w concentration FSD solubility enhancement in GMOA-G2-OH, GMOA-G3-OH, GMS-G2-OH and GMS-G3-OH was 43, 11, 9.1 and 6.8-fold respectively compared to water. As GMOA-G2-OH enabled the highest solubility of FSD, it was further evaluated for its antibacterial activity against Staphylococcus aureus and methicillin-resistant S. aureus (MRSA). The minimum inhibitory concentration values for FSD with and without GMOA-G2-OH against S. aureus were 0.23 μg ml?1 and 0.53 μg ml?1 respectively whereas the values were 0.23 μg ml?1 and 0.39 μg ml?1 against MRSA respectively. These results suggested that GM-OA-G2 not only enhanced the solubility but also enhanced antibacterial potency of FSD. Furthermore, these ADs showed their potential as promising pharmaceutical excipients as they acted as stearic stabilizers in the preparation of SLNs. Using these ADs stable SLNs with zeta potential value in the range of ?15.30 ± 1.44 to ?38.46 ± 3.04 were formed.

Improved enzymatic synthesis route for highly purified diacid 1,3-diacylglycerols

The nutritional benefits and biological functions of diacylglycerols (DAGs) have attracted much attention regarding their synthesis. In this study, we improved the synthesis of diacid 1,3-DAGs by the enzymatic transesterification of 1-monoolein with a fatty acid vinyl ester as an acyl donor. First, 1-monoolein was prepared in 95% ethanol with Amberlyst resin as a catalyst by the cleavage of 1,2-acetonide-3-oleoylglycerol, which had been synthesized by enzymatic esterification of 1,2-acetonide glycerol with oleic acid. Second, purified 1-monoolein was reacted with vinyl palmitate in the presence of a lipase to obtain 1-oleoyl-3-palmitoylglycerol. Subsequently, the reaction conditions for the synthesis of diacid 1,3-DAGs were evaluated. Under the selected conditions, the crude mixture contained 90.6% pure 1-oleoyl-3-palmitoylglycerol. After purification by two-step crystallization, pure 1-oleoyl-3-palmitoylglycerol was obtained with a yield of 83.6%. The main innovations were the use of enzymatic transesterification to obtain highly purified diacid 1,3-DAGs instead of using chemical synthesis and the use of an irreversible reaction with a fatty acid vinyl ester as acyl donor rather than reversible reactions.