30836-40-9

Basic information

• Product Name: Glyceryl monooleate
• Synonyms: 1-Monooleoyl-rac-glycerol; 9-Octadecenoic acid, 2,3-dihydroxypropyl ester; 9-Octadecenoic acid, monoester with 1,2,3-propanetriol; Glyceryl oleate; Monoolein; 1-Glyceryl oleate; 1-Mono(cis-9-octacenoyl)glycerol; 1-Monoolein; 1-Monooleoylglycerol; 1-Oleoylglycerol; 1-Oleylglycerol; 2,3-Dihydroxypropyl oleate; Aldo HMO; Aldo MO; Danisco MO 90; FEMA No. 2526; Glycerin 1-monooleate; Glycerol 1-monooleate; Glycerol alpha-cis-9-octadecenate; Glycerol alpha-monooleate; Glycerol monooleate; Glyceryl Monooleate (VAN); Monoolein (VAN); NSC 406285; alpha-Monoolein; rac-1-Monoolein; rac-1-Monooleoylglycerol; 9-Octadecenoic acid (9Z)-, 2,3-dihydroxypropyl ester; 9-Octadecenoic acid (Z)-, 2,3-dihydroxypropyl ester (9CI); Olein, 1-mono- (8CI); 9-Octadecenenoic acid (Z)-, 2,3-dihydroxypropyl ester; 2,3-dihydroxypropyl octadec-9-enoate; 3-[(9Z)-octadec-9-en-1-yloxy]propane-1,2-diol; 2,3-dihydroxypropyl (9Z)-octadec-9-enoate
• CAS NO: 30836-40-9
• Molecular Formula: C₂₁H₄₀O₄
• Molecular Weight: 370.5234
• EINECS: 203-827-7
• Mol File: 30836-40-9.mol

Chemical Properties

• Refractive Index: 1.483
• CAS DataBase Reference: Glyceryl monooleate(CAS DataBase Reference)
• NIST Chemistry Reference: Glyceryl monooleate(30836-40-9)
• EPA Substance Registry System: Glyceryl monooleate(30836-40-9)

Safety Data

• Hazardous Substances Data: 30836-40-9(Hazardous Substances Data)

Upstream product

• 112-62-9 Methyl oleate 
• 112-80-1 cis-Octadecenoic acid 
• 56-81-5 glycerol 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 122-32-7 trioleoylglycerol 
• 111-62-6 oleic acid ethyl ester 
• 3896-58-0 vinyl oleate 
• 33001-45-5 (+/-)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl (Z)-9-octadecenoate 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 506-24-1 Stearolic acid 
• 1120-32-7 stearolic acid methyl ester 
• 50816-19-8 8-bromooctanol 
• 168136-39-8 2-(octadec-9-yn-1-yloxy)tetrahydro-2H-pyran 

Downstream Products

• 20299-66-5 1,2-bis-lauroyloxy-3-oleoyloxy-propane 
• 18985-53-0 silicic acid tetrakis-(2-hydroxy-3-oleoyloxy-propylester) 
• 120831-58-5 (+/-)-1,2-bis-octadeca-9c,11t,13t-trienoyloxy-3-oleoyloxy-propane 
• 2465-32-9 1,3-diolein 
• 3443-84-3 2-Oleoylglycerol 
• 101200-99-1 1-oleoyl-3-acetyl-rac-glycerol 
• 55401-64-4 (Z)-9-octadecenoic acid 2,3-bis(acetyloxy)propyl ester 
• 124109-45-1 (+/-)-O¹-butyryl-O³-oleoyl-glycerol 
• 121235-57-2 (+/-)-1,2-bis-butyryloxy-3-oleoyloxy-propane 
• 1867-91-0 1,2-dipalmitoyl-3-oleoyl-rac-glycerol 
• 2190-29-6 (+-)-1-oleoyloxy-2,3-bis-stearoyloxy-propane 
• 20299-65-4 1,2-bis-decanyloxy-3-oleoyloxy-propane 
• 74160-01-3 1,2-bis-myristoyloxy-3-oleoyloxy-propane 
• 2190-29-6 1-oleoyloxy-2,3-bis-stearoyloxy-propane 

Relevant articles and documents

High-selectivity synthesis method of long-chain fatty acid monoglyceride

The invention belongs to the field of fatty acid and synthetic fatty acid glycerides and relates to a high-selectivity synthesis method of long-chain fatty acid monoglyceride, in particular to a high-selectivity synthesis method of long-chain fatty acid and synthetic fatty acid glycerides. The method comprises the steps that tetraethyl silicate and glycerin are subjected to alcoholysis reaction, and part of glycerin is esterified to generate glyceryl silicate; then the glyceryl silicate is subjected to esterification reaction with fatty acid to generate fatty acid glyceride; finally the high activity (instability) of silicate ester is utilized to achieve hydrolysis under mild conditions to synthesize the synthetic fatty acid glyceride at high selectivity. A by-product is safe and harmlessSiO2. Accordingly, the product with high monoglyceride content is obtained by using a simple process under mild conditions.

Method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2

The invention belongs to the field of fatty acid glyceride synthesis and nano powder preparation, relates to a method for synthesizing high-content fatty acid monoglyceride and co-producing nano SiO2,and particularly relates to a method for synthesizing fatty acid monoglyceride and co-producing the nano SiO2 by long-chain fatty acid and glycerinum. The method comprises the following steps of: using silicon tetrachloride to react with the glycerinum, so as to enable the glycerinum to be partially esterified to generate silicic acid glyceride; and performing an esterification reaction with fatty acid to generate fatty acid silicic acid glyceride; finally using high-activity (instability) of silicate ester, hydrolyzing in a mild condition, synthesizing the high-content fatty acid monoglyceride, and by-producing SiO2 powder in a nano state. So that a fatty acid monoglyceride product is high-selectively obtained and nano SiO2 powder is co-produced by a simple technology in the mild condition.

Method for synthesizing high content of fatty acid monoglyceride production of nano TiO2 The method of (by machine translation)

The invention belongs to the fatty acid glyceride synthesis and nano powder preparation field. In particular to fatty acid and glycerin synthesis of fatty acid monoglyceride, and cogeneration nano TiO2 Method. Method of this invention is: for the reaction of titanium tetrachloride and glycerin, glycerol partial esterification, generating titanate glycerides. Then with the fatty acid esterification reaction, to generate fatty acid glyceride titanate. Finally the use of a titanate high activity (instability), hydrolysis under mild conditions, synthesizing high-content fatty acid monoglyceride, the pressure of the by-product TiO2 Powder. Thus a simple process, under mild conditions, a high content of fatty acid monoglyceride product, production of nano TiO2 Powder. (by machine translation)

Biochemical characterization of the PHARC-associated serine hydrolase ABHD12 reveals its preference for very-long-chain lipids

Polyneuropathy, hearing loss, ataxia, retinitis pigmentosa, and cataract (PHARC) is a rare genetic human neurological disorder caused by null mutations to the Abhd12 gene, which encodes the integral membrane serine hydrolase enzyme ABHD12. Although the role that ABHD12 plays in PHARC is understood, the thorough biochemical characterization of ABHD12 is lacking. Here, we report the facile synthesis of mono-1-(fatty)acyl-glycerol lipids of varying chain lengths and unsaturation and use this lipid substrate library to biochemically characterize recombinant mammalian ABHD12. The substrate profiling study for ABHD12 suggested that this enzyme requires glycosylation for optimal activity and that it has a strong preference for very-long-chain lipid substrates. We further validated this substrate profile against brain membrane lysates generated from WT and ABHD12 knockout mice. Finally, using cellular organelle fractionation and immunofluorescence assays, we show that mammalian ABHD12 is enriched on the endoplasmic reticulum membrane, where most of the very-long-chain fatty acids are biosynthesized in cells. Taken together, our findings provide a biochemical explanation for why very-long-chain lipids (such as lysophosphatidylserine lipids) accumulate in the brains of ABHD12 knockout mice, which is a murine model of PHARC.

Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids

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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.

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SYNTHESIS PROCESS FOR DIACETYL EPOXY GLYCERYL OLEATE

The present invention relates to a process for the synthesis of diacetyl epoxy glyceryl oleate, comprising the steps of: a). esterification of glycerol and oleic acid at 115-190° C. for 1.5-4.5 hours in the presence of an esterification catalyst to obtain glyceryl monooleate; b). acetylation of glyceryl monooleate and an acetylating reagent at 90-160° C. for 2-10 hours in the presence of an acetylation catalyst to obtain diacetyl glyceryl oleate; c). epoxidation of diacetyl glyceryl oleate and hydrogen peroxide at 60-80° C. for 2-4 hours in the presence of an epoxidation catalyst and a weak acid to obtain diacetyl epoxy glyceryl oleate. The prepared diacetyl epoxy glyceryl oleate can be used as plasticizer in plastics, with the advantages of improved stability, good flowability, and high compatibility with plastics.

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