GLYCEROL MONOOLEATE
GLYCEROL MONOOLEATE
GMO = GLYCERYL MONOOLEATE = GLYCERYL OLEATE = GLYCEROL OLEATE = GLYCEROL MONOOLEATE = GLYCERYL + OLEIC ACID ESTER = GYCEROL + OLEIC ACID ESTER = MONOOLEIN
GLYCERYL MONOOLEATE is the biodegradable esterification product of Glycerin and Oleic Acid.
GLYCERYL MONOOLEATE is an amber liquid to paste at room temperature, it can be used as a water-in-oil emulsifier, pigment dispersant, lubricant, and spreading agent in chemical formulations.
EC / List no.: 247-038-6
CAS no.: 25496-72-4
Glyceryl monooleate
Oleic acid, monoester with glycerol
IUPAC names: Olein, mono-; 9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol
CAS Numbers:
25496-72-4 (glycerol monooleate)
111-03-5 (glycerol oleate)
37220-82-9 (glycerol mono/dioleate)
Other Codes:
EINECS: 203-827-7; 253-407-2
Glycerol Monooleate is also known as 1-monoolein and 2, 3-Dihydroxypropyl oleate. Glycerol Monooleate is a classified member of 1-monoacylglycerols. It is white in color, odorless powder which is sweet in taste.
Glycerol Monooleate is the glycerol ester of esteric acid. Glycerol Monooleate is neutral in nature and insoluble in water. Glycerol Monooleate consists of 3 stereoisomers namely the enantiomeric pair of 1-glycerol Monooleate and 2-glycerol Monooleate.
Applications of Glycerol Monooleate:
Glycerol Monooleate is basically used as an emulsifier and thickening agent in food & beverage industry and cosmetic industry. It is also used as a stabilizer in the pharmaceutical industry. It is used as an emulsifying agent for oils and waxes. It acts as a protective coating for hygroscopic powders. It is also used as an anticaking agent and preservative agent in the baking industry. It used as an additive in fuels, paints & coatings, lubricants & greases.
Use: Emulsifiers for pharmaceuticals and cosmetics, Additives for lubricants
Glycerol Monooleate has a wide application as an Emulsifier, Fibre delustering agent, Manufacturing PVC bottles, films, foils.
Glycerol Monooleate can be used as Mould release agent, Pigment dispersant, Rust preventor, lubricant etc.
Glycerol Monooleate is used as a Water-in-oil emulsifier with a high degree of water absorbency, good resistance to temperature fluctuations for soft creams.
Glycerol Monooleate can be used in bath oil as emollient and spreading agent, in make-up as pigment dispersant and in vanishing and moisturizing cream to impart slip.
GMO is also used as a lubricant and antistatic aid in processing PVC films & frequently used as a rust preventive additive for compounded oils.
In textile industry, GMO finds applications in the preparations of neutral emulsions of Lubricating oils or finishing waxes. GMO is also used as a dispersing agent for pigments and as a fibre-delustering agent & as a lubricant component in synthetic fibre spin finishes.
Glycerol Monooleate is used as an Emulsifiers and diluents for the application in oleoresins and in lubrication application. Glycerol Monooleate gives the aid in preparation of the stable emulsion and improving the dispersibility for the coffee whiteners, liquids.
Glycerol Monooleate also acts as the antifoaming agents for the protein foams. Glycerol Monooleate can be used for the flavor stability in the sport drinks and Vitamin oil solubilizer for the Vitamins, Vitamin Mineral Supplements and Vitamin drops.
Use: Pharmaceutical and Veterinary, Flavours and Fragrances, Adhesives and Lubricants, Inks and Coatings, Industrial, Cosmetics and Personal Care, Cleaning and Detergents
Glycerol Monooleate is used as an antifoam in juice processing and as a lipophilic emulsifier for water-in-oil applications.
Glycerol Monooleate also serves as a moisturizer, emulsifier, and flavoring agent. Various forms of glycerol oleate are widely used in cosmetics.
Glycerol Monooleate is also widely used as an excipient in antibiotics and other drugs.
Glyceryl monooleate is prepared by esterification of commerical oleic acid that is derived either from edible sources or from tall oil fatty acids
Glyceryl Mono Oleate is a drug delivery system & encapsulating agent in pharmaceutical preparations.
Glyceryl Mono Oleate is an emulsifier, emollient in cosmetic formulations like sun care products, antiperspirants, hand and body lotions, shower gels/body washes, styling aids, color cosmetics etc.
Glyceryl Mono Oleate is an amber colored liquid, it can be used as a W/O emulsifier, pigment dispersant, lubricant & spreading agent.
Glyceryl Monooleate is an emulsifier and dispersing agent made using glycerin and oleic acid from vegetable oil sources
Glyceryl monooleate (GMO) is one of the most popular amphiphilic lipids, which, in the presence of different amounts of water and a proper amount of stabilizer, can promote the development of well defined, thermodynamically stable nanostructures, called lyotropic liquid crystal dispersions
Glyceryl monooleate (GMO) is a well-known molecule commonly used as an emulsifying agent, biocompatible controlled-release material, and a food additive.
Glyceryl monooleate is considered as a nontoxic, biodegradable, and biocompatible material classified as “generally recognized as safe” (GRAS).
Glyceryl monooleate is included in the FDA Inactive Ingredients Guide and present in nonparenteral medicines
Glyceryl monooleate (GMO) is often described as a special lipid that plays an important role in drug delivery systems, due to its ability to self-assemble in water and to form a variety of well-defined, thermodynamically stable liquid crystal structures.
Glyceryl monooleate also exhibits long-range order in one, two,or three dimensions.
Glyceryl monooleate is widely known as a non-toxic, biodegradable and biocompatible product.
Glyceryl monooleate received generally recognized as safe (GRAS) status from the Food and Drug Administration (FDA) and is included in the Inactive Ingredients Guide
GLYCEROL MONOOLEATE
Monooleoylglycerol, also known as glyceryl 1-oleate, glycerylmonooleate or 1-monoolein, is classified as a member of the 1-monoacylglycerols.
1-Monoacylglycerols are monoacylglycerols containing a glycerol acylated at the 1-position.
Glycerolmonooleate is considered to be practically insoluble (in water) and relatively neutral.
Glycerolmonooleate is an yellow to amber liquid at room temperature, biodegradable and can be used as a water-in-oil emulsifier, pigment dispersant, lubricant, and spreading agent.
Glyceryl Monooleate
Glycerol Esters
Synonym: Glycerine Oleate
Product Family: Glycerine Ester
Chain Length: C18:1 GLY Ester
CAS Number: 25496-72-4
Industries / Applications
Metal Working:
• Friction Modifier
Food Processing:
• Emulsifier
Lubricants and Greases:
• Friction Modifier in Hydraulics
• Friction Modifier in PCMO
Wax & Candles:
• Coupling Agent
Other special Applications: Glyceryl Monooleate can be used in extrusion; calendared film, profile extrusion, injection molding, color concentrate, mold release applications.
Glyceryl monooleate is derived from natural fats and oils and it is often used as internal lubricant in PVC, and can also be used as an antifogging agent, flow modifier and dispersing agent.
Glyceryl monooleate is an ester of Glyceryl and Oleic Acid. Glyceryl monooleate can be used is metalworking lubricants as friction modifier. Glyceryl monooleate is used as friction modifier in hydrolic fluids.
Glyceryl monooleate can be used as coupling agent in Wax and Candles.
Glycerol monooleate is a synthetic compound that is considered a monoglyceride.
One of the applications is for use as a defoamer, Glycerol monooleate has a number of food applications, as well as application as an excipient in pharmaceutical products.
Glyceryl Monooleate is a mixture of monoglycerides, mainly glyceryl monooleate, together with variable quantities of diglycerides and triglycerides. It is obtained by partial glycerolysis of vegetable oil that consists mainly of triglycerides of oleic acid, or by esterification of glycerol with oleic acid of vegetable or animal origin
Glyceryl monooleate also known as GMO is a multi-functional emulsifier useful in the production of cosmetics, pharmaceuticals, food and plastic products.
Glycerol monooleate (C21H40O4) is a clear amber or pale yellow liquid.
Glycerol monooleate is an oil soluble surfactant and is classified as a monoglyceride.
Glycerol monooleate is used as an antifoam in juice processing and as a lipophilic emulsifier for water-in-oil applications.
Glycerol monooleate is a moisturizer, emulsifier, and flavoring agent.
Various forms of glycerol oleate are widely used in cosmetics and Glycerol monooleate is also used as an excipient in antibiotics and other drugs.
Glycerin is classified by the U.S. Food and Drug Administration (FDA) as “generally recognized as safe” (GRAS).
Glyceryl Monooleate is a clear or light yellow oil that is used as an antifoam in juice processing. It has been used as an emulsifier, a moisturizer, and a flavoring agent
1-oleoylglycerol is a 1-monoglyceride where the acyl group is oleoyl. It has a role as a plant metabolite. It is a 1-acylglycerol 18:1 and a monooleoylglycerol. It derives from an oleic acid.
Melting Point: 35°C (literature)
Synonym: monoolein, glyceryl monooleate, 2,3-dihydroxypropyl oleate, 1-monoolein, 1-oleoylglycerol, 1-oleoyl-rac-glycerol, glyceryl oleate, 1-glyceryl oleate, 1-monooleoylglycerol, glycerol 1-monooleate
Formula Weight: 356.55
Molecular Formula: C21H40O4
Solubility Information: Soluble in chloroform (50mg/mL). Also soluble in hexane.
Physical Form: Cloudy waxy
Glyceryl Monooleate, commonly known as monoolein, is a glycerol monoester of oleic acid. Pharmaceutically, it is used as an emulsifier and permeation enhancer.[1]
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Application
Glyceryl Monooleate may be used as a pharmaceutical reference standard for the determination of the analyte in bulk drug and pharmaceutical formulations by high performance liquid chromatography.[2]
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
Chemical Name:Glyceryl Monooleate
Synonyms: Aldo MO;Aldo HMO;MONOLEIN;Mazol GMO;MONOOLEIN;Capmul GMO;Kessco GMO;Rylo MG 19;1-MONOLEIN;Ablunol GMO
Glyceryl Mono Oleate is a drug delivery system & encapsulating agent in pharmaceutical preparations.
Glyceryl Mono Oleate is an emulsifier, emollient in cosmetic formulations like sun care products, antiperspirants, hand and body lotions, shower gels/body washes, styling aids, color cosmetics etc.
Chemical Proporties: White Waxy Solid
Uses: Monoglycerides fatty acid esters 93% 1-Oleoyl, 7% 2-oleoyl.
Uses: glyceryl oleate is an emollient and stabilizer derived from olive oil. It is a water-in-oil emulsifier that allows for softer emulsions than glyceryl stearate.
Uses: Glyceryl Monooleate is a flavoring agent that is prepared by esterification of commercial oleic acid that is derived either from edible sources or from tall oil fatty acids. It contains and glyceryl esters of fatty acids present in commercial oleic acid. The ingredient is also used as an adjuvant and as a solvent and vehicle.
Definition: ChEBI: A 1-monoglyceride where the acyl group is oleoyl.
[Code of Federal Regulations]
[Title 21, Volume 3]
[Revised as of April 1, 2020]
[CITE: 21CFR184.1323]
Glycerol monooleate
Agent Name
Glycerol monooleate
CAS Number: 25496-72-4
Formula: C21-H40-O4
Major Category
Other Uses
Glycerol monooleate formula graphical representation
Synonyms: 1,2,3-Propanetriol mono((Z)-9-octadecenoate); 9-Octadecenoic acid (Z)-, monoester with 1,2,3-propanetriol; AJAX GMO; Adchem GMO; Aldo 40; Aldo MO-FG; Alkamuls GMO 45LG; Arlacel 129; Atmer 1007; Canamex Glicepol 182; Dimodan GMO 90; Dimodan LSQK; Dur-Em 114; Dur-Em 204; Edenor GMO; Emalsy MO; Emalsy OL; Emasol MO 50; Emcol O; Emerest 2400; Emerest 2421; Emery oleic acid ester 2221; Emrite 6009; Emuldan RYLO-MG 90; Excel O 95F; Excel O 95N; Excel O 95R; GMO 8903; Glycerin monooleate; Glycerine monooleate; Glycerol 1-monooleate; Glycerol oleate; Glycerol, 1-mono (9-octa-decenoate); Glyceryl monooleate; Glyceryl oleate; Glycolube 100; Harowax L 9; Kemester 2000; Kessco GMO; Loxiol G 10; Mazol GMO; Monoglyceryl oleate; Monomuls 90018; Monoolein; Monooleoylglycerol; Nikkol MGO; OL 100; Oleic acid glycerol monoester; Oleic acid monoglyceride; Oleic monoglyceride; Olein, mono-; Oleoylglycerol; Oleylmonoglyceride; Olicine; Peceol; Rikemal O 71D; Rikemal OL 100; S 1096; S 1096R; S 1097; Sinnoester OGC; Sunsoft O 30B; Supeol; [ChemIDplus]
Category: Emulsifiers/Surfactants
Description: Clear amber or pale yellow liquid; [Hawley] Yellow liquid or soft solid with a sweet odor; mp = 25 deg C (unstable); [HSDB] Solid; mp = 35.5 deg C; Opaque liquid; mp = 20 deg C; [MSDSonline]
Sources/Uses: Glycerol monooleate is used in foods, pharmaceuticals, cosmetics, rust-preventive oils, vinyl light stabilizers, odorless base paints, textile finishing, and flavoring;
Used as emulsifier for liquid and paste waxes, polishes, and cleaners; [Hawley]
TITLE 21–FOOD AND DRUGS
CHAPTER I–FOOD AND DRUG ADMINISTRATION
DEPARTMENT OF HEALTH AND HUMAN SERVICES
SUBCHAPTER B – FOOD FOR HUMAN CONSUMPTION (CONTINUED)
PART 184 — DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED AS SAFE
Subpart B – Listing of Specific Substances Affirmed as GRAS
Sec. 184.1323 Glyceryl monooleate.
(a) Glyceryl monooleate is prepared by esterification of commerical oleic acid that is derived either from edible sources or from tall oil fatty acids meeting the requirements of § 172.862 of this chapter. It contains glyceryl monooleate (C21H40O4, CAS Reg. No. 25496-72-4) and glyceryl esters of fatty acids present in commercial oleic acid.
(b) The ingredient must be of a purity suitable for its intended use.
(c) In accordance with § 184.1(b)(1), the ingredient is used in food with no limitation other than current good manufacturing practice. The affirmation of this ingredient as generally recognized as safe (GRAS) as a direct human food ingredient is based upon the following current good manufacturing practice conditions of use:
(1) The ingredient is used as a flavoring agent and adjuvant as defined in § 170.3(o)(12) of this chapter and as a solvent and vehicle as defined in § 170.3(o)(27) of this chapter.
(2) The ingredient is used in the following foods at levels not to exceed current good manufacturing practice: baked goods and baking mixes as defined in § 170.3(n)(1) of this chapter; nonalcoholic beverages and beverage bases as defined in § 170.3(n)(3) of this chapter; chewing gum as defined in § 170.3(n)(6) of this chapter; and meat products as defined in § 170.3(n)(29) of this chapter.
(d) Prior sanctions for this ingredient different from the use established in this section do not exist or have been waived.
[54 FR 7403 Feb. 21, 1989, as amended at 73 FR 8607, Feb. 14, 2008]
Glycerol monooleate (GMO), casein and whey proteins are surfactants that can stabilize emulsion systems.
This study investigates the impact of instantized GMO powders on creaming stability and oxidative stability in protein-stabilized emulsions.
Model emulsions with bulk Glyceryl monooleate, two instantized GMO powders, and two controls (without GMO) were produced by microfluidization.
The droplet size, ζ-potential, viscosity, and creaming index of the emulsions were measured, while oxidative stability was evaluated by analysis of volatile compounds during storage (28 days, 45 ◦C) using gas chromatography mass spectrometry.
Emulsions with GMO produced smaller average droplet sizes (180.0 nm) with a narrower distribution (polydispersity index of 0.161) compared to the controls (197.6 nm, 0.194).
The emulsion stability of instantized emulsions was as good as bulk GMO, which were both better than controls.
Based on the relative abundance of 3-octen-2-one, 2,4-heptadienal isomer 2, and 3,5-octadien-2-one isomer 1, the oxidative stability of the instantized emulsions was not significantly different from controls; however, bulk GMO emulsion showed significantly lower stability than controls.
Instantized Glyceryl monooleate powders can successfully produce physically stable protein-stabilized emulsions with good oxidative stability in a convenient powdered format.
Keywords: glycerol monooleate; sodium caseinate; whey protein concentrate; creaming stability; oxidative stability; volatile analysis
Protein-stabilized emulsions are examples of oil-in-water emulsions that have been used to deliver nutrients, bioactive compounds, and flavors.
The most common food emulsions are yogurt, cream, coffee creamer, milk, and plant-based beverages.
Proteins are the main group of emulsifiers that stabilize oil droplets in the aqueous phase.
Many proteins are amphiphilic molecules containing both hydrophilic and hydrophobic structures, which make them good emulsifiers.
The amphiphilic nature of protein allows them to adsorb at the oil-water interface and form a protective film surrounding the oil droplets.
The adsorbed proteins at the interface provide repulsive forces, such as steric and electrostatic forces, to stabilize the oil droplets in the aqueous phase.
However, oil droplets can simultaneously undergo multiple physical destabilization mechanisms such as creaming, flocculation, and coalescence that eventually lead to complete separation of oil and aqueous layers.
Casein and whey proteins are milk proteins primarily used in food formulations due to their outstanding emulsifying properties.
Milk proteins can also adsorb to the air-water interface under agitation leading to foam formation.
Foaming in milk beverages is undesirable as it can lead to inconsistent product quality, higher product loss, and lower productivity.
Low-molecular-weight Foods 2020, 9, 1237; doi:10.3390/foods9091237 www.mdpi.com/journal/foods Foods 2020, 9, 1237 2 of 16 emulsifiers, such as monoglycerides, can be added to the emulsion to increase emulsion stability and reduce foam formation during homogenization.
Creaming is the most common destabilization mechanism that occurs in oil-in-water emulsions such as milk beverages.
Creaming is an upward movement of dispersed oil droplets in the emulsion due to the density difference between oil and aqueous phases upon standing.
The cream layer is usually easy to re-suspend into the emulsion upon agitation, as the oil droplets retain their integrity due to the absence of physical and chemical interactions.
Previous work investigated various monoglyceride compositions in model emulsions, and the results showed that glycerol monooleate (GMO) produced smaller oil droplets with narrow size distribution and greater stability towards creaming during storage when compared to the control (no GMO).
Glyceryl monooleate is an unsaturated monoglyceride with only one of the hydroxyl groups of glycerol esterified with an unsaturated fatty acid, i.e., oleic acid.
The oil-soluble nature of Glyceryl monooleate means that it has high solubility in oil and poor dispersibility in water and is thus not suitable for many food formulations.
However, if Glyceryl monooleate could be transformed into an instantized powder with good dispersibility in water using spray-drying it could produce a suitable food ingredient.
Spray-drying is the most commonly available technique in the food industry to transform hydrophobic materials, such as oil and bioactive compounds, into instantized powders with good water dispersibility and protection against lipid oxidation.
The unsaturated fatty acids in GMO are prone to oxidation, which is the root cause of rancidity and off-flavor in these ingredients.
Measurement of volatile secondary oxidation products by headspace solid-phase microextraction (HS-SPME) with gas chromatography-mass spectrometry (GC-MS) has been used extensively to study the progression of lipid oxidation [10].
In our previous work, we reported on the feasibility of using spray-drying to prepare a novel instantized emulsifier based on Glyceryl monooleate that can be easily reconstituted in water and on the properties of the powders.
From this work, the two instantized GMO powders that exhibited the lowest surface oil (3%), good dispersibility in water (74–87%), and the smallest change in droplet size after reconstitution were selected for the current study.
The current study aims to evaluate the effect of instantized GMO powder on the physicochemical properties, creaming stability, and oxidative stability in protein-stabilized emulsions. The key comparisons were between emulsions with bulk GMO (bGMO) and instantized GMO powder, and between emulsions with GMO and control emulsions without GMO.
Applications
Emulsifiers for pharmaceuticals and cosmetics, Additives for lubricants
• Ablunol GMO
• Aldo HMO
• Aldo MO
• alpha-Monoolein
• Capmul GMO
• Glycerin 1-monooleate
• Glycerol alpha-cis-9-octadecenate
• Glycerol oleate
• Glycerol-1-oleate
• Glyceryl oleate
• Kemester 2000
• Kessco GMO
• Mazol 300 K
• Mazol GMO
• Monomuls 90-O18
• Olein, 1-mono-
• Radiasurf 7150
• Witconol 2421
• ARLACEL(TM) 186
• DL-ALPHA-MONOOLEIN
• DELTA 9 CIS MONOOLEIN
• GLYCEROL-1-MONOOLEATE
• GLYCEROL ALPHA-MONOOLEATE
• GLYCEROL MONOOLEATE
• GLYCERYL MONOOLEATE
• 9-Octadecenoicacid(Z)-,2,3-dihydroxypropylester
• rac-1-Monoolein
• rac-1-Monooleoylglycerol
• Rylo MG 19
• 1-Oleoyl-rac-glycerol technical, ~40% (TLC)
• 1-MONOOLEOYL-RAC-GLYCEROL*(C18:1,-CI
• GLYCERYL MONOOLEATE
• glycerine oleate
• Glyceryl MonoOleates
• Glycerol mono-oleate GMO
• Glyceryl Monooleate in stock GMP Factory
• ASTM D6584 Monoolein solution
• GLYCERYL CIS-9-OCTADECENOATE
• 1-O-OLEYL-RAC-GLYCEROL
• 1-OLEOYL-RAC-GLYCEROL
• 1-MONO[CIS-9-OCTADECENOYL]-RAC-GLYCEROL
• 1-MONOLEIN
• 1-MONOOLEIN
• 1-MONOOLEOYL-RAC-GLYCEROL
• 1-(CIS-9-OCTADECENOYL)-RAC-GLYCEROL
• RAC-GLYCEROL 1-MONOOLEATE
• MONOOLEIN
• 1-Glyceryl oleate
• 1-Monooleoylglycerol
• 1-Oleoylglycerol
• 1-Oleylglycerol
• 2,3-dihydroxypropyl
• 2,3-Dihydroxypropyl (9Z)-9-octadecenoate
• 2,3-dihydroxypropyloleate
• 3-oleoyloxy-propane-1,2-diol
• 9-Octadecenoic acid (Z)-, 2,3-dihydroxypropyl ester
• rac.-1-Oleoyl-glycerol
• 9-Octadecenoic acid (9Z)-, 2,3-dihydroxypropyl ester
Glycerol monooleate
Agent Name: Glycerol monooleate
CAS Number: 25496-72-4
Formula: C21-H40-O4
Major Category
Other Uses
Glycerol monooleate formula graphical representation
Synonyms: 1,2,3-Propanetriol mono((Z)-9-octadecenoate); 9-Octadecenoic acid (Z)-, monoester with 1,2,3-propanetriol; AJAX GMO; Adchem GMO; Aldo 40; Aldo MO-FG; Alkamuls GMO 45LG; Arlacel 129; Atmer 1007; Canamex Glicepol 182; Dimodan GMO 90; Dimodan LSQK; Dur-Em 114; Dur-Em 204; Edenor GMO; Emalsy MO; Emalsy OL; Emasol MO 50; Emcol O; Emerest 2400; Emerest 2421; Emery oleic acid ester 2221; Emrite 6009; Emuldan RYLO-MG 90; Excel O 95F; Excel O 95N; Excel O 95R; GMO 8903; Glycerin monooleate; Glycerine monooleate; Glycerol 1-monooleate; Glycerol oleate; Glycerol, 1-mono (9-octa-decenoate); Glyceryl monooleate; Glyceryl oleate; Glycolube 100; Harowax L 9; Kemester 2000; Kessco GMO; Loxiol G 10; Mazol GMO; Monoglyceryl oleate; Monomuls 90018; Monoolein; Monooleoylglycerol; Nikkol MGO; OL 100; Oleic acid glycerol monoester; Oleic acid monoglyceride; Oleic monoglyceride; Olein, mono-; Oleoylglycerol; Oleylmonoglyceride; Olicine; Peceol; Rikemal O 71D; Rikemal OL 100; S 1096; S 1096R; S 1097; Sinnoester OGC; Sunsoft O 30B; Supeol; [ChemIDplus]
Category: Emulsifiers/Surfactants
Description: Clear amber or pale yellow liquid; [Hawley] Yellow liquid or soft solid with a sweet odor; mp = 25 deg C (unstable); [HSDB] Solid; mp = 35.5 deg C; Opaque liquid; mp = 20 deg C; [MSDSonline]
Sources/Uses : Used in foods, pharmaceuticals, cosmetics, rust-preventive oils, vinyl light stabilizers, odorless base paints, textile finishing, and flavoring; Used as emulsifier for liquid and paste waxes, polishes, and cleaners; [Hawley]
Comments: May cause mild irritation; [MSDSonline]
Other names: Glyceryl Monooleate; Olein, 1-mono-; α-Monoolein; Aldo HMO; Aldo MO; Glycerin 1-monooleate; Glycerol α-cis-9-octadecenate; Glycerol α-monooleate; Glycerol 1-monooleate; Monoolein; 1-Glyceryl oleate; 1-Monoolein; 1-Monooleoylglycerol; 1-Oleoylglycerol; 1-Oleylglycerol; dl-α-Monoolein; 1-Monooleoyl-rac-glycerol; Ablunol GMO; Glycerol-1-oleate; Glycerol oleate; Glyceryl oleate; Witconol 2421; 9-Octadecenoic acid (9Z)-, 2,3-dihydroxypropyl ester; 1-Mono(cis-9-octacenoyl)glycerol; 2,3-Dihydroxypropyl oleate; Danisco MO 90; rac-1-Monoolein; rac-1-Monooleoylglycerol; 2,3-Dihydroxypropyl (9z)-9-octadecenoate
Synonyms:
aldo HMO
aldo HMO KFG
aldo MO
aldo MO FG
aldo MO KFG
capmul GMO-50
capmul GMO-50 EP/NF
cithrol GMO 90
cithrol GMO HP
2,3- dihydroxypropyl (Z)-octadec-9-enoate
2,3- dihydroxypropyl oleate
drewmulse GMO
drewmulse GMO kosher
dub green OD4
edenor GMO
excel O-95N
glycerin 1-monooleate
glycerol 1-monooleate
glycerol a-cis-9-octadecenate
glycerol a-monooleate
glycerol monoleate
glycerol monooleate
1- glycerol oleate
glyceryl mono / dioleate
1- glyceryl monooleate
glyceryl monooleate FCC grade
glyceryl monooleate food grade
glyceryl monooleate NF grade
glyceryl oleate
hallstar GMO
kemester 2000
lipo GMO
lonzest GMO
lubricit GMO-C
monegyl – O100
monegyl – GO60
monomuls 90-O 18
nikkol MGO
1-mono(cis-9- octacenoyl) glycerol
9- octadecenoic acid (Z)-2,3-dihydroxypropyl ester
9- octadecenoic acid monoester with 1,2,3-propane triol
oleic acid monoester with glycerol
alpha-mono olein
mono olein
mono- olein
olein, 1-mono-
rac 1- oleoyl glycerol
1-mono oleoyl-rac-glycerol
1- oleoylglycerol
1-mono oleoylglycerol
1-O- oleyl-rac-glycerol
rheodol MO-60
glycerol monooleate
Other Names:
9-Octadecenoic acid (Z)-, monester with 1,2,3-propanetriol; glycerol monoleate; glyceryl monooleate;glyceryl oleate; glyceryl oleate; glycerol oleate; GM;GMO; 1-Oleoyl-sn-glycerol; monoolein.
Trade Names:
Aldo MO FG; Atsurf 594; Atsurf 595, Atsurf 595K,Atsurf 596, Atsurf 596K, Lumulse GMO FGK; Capmul GMO, Cithrol GMO N/E; Drewmulse 200; Dur-Em GMO; Emrite 6008; GMO 0041; Hodag GMO; Hodag GMO-D; Mazol 300 K; Mazol GMO; Mazol GMO k; Monomuls 90-O18; Nikkol MGO; Pationic 1061, Pationic 1064; Pationic 1074 (Ash and Ash, 1995).
Characterization
Composition: Empirical: C21H40O4
Formula: CH3(CH2)7CH = CH(CH2)7COOCH2CCH2OHHOH
Properties: Glycerol monooleate is a clear amber or pale yellow liquid.
It is insoluble in water, very slightly soluble in cold alcohol, and soluble in hot alcohol, in chloroform, in ether, and in petroleum ether.
Glycerol monooleate is also oil soluble, giving it particularly desirable properties as a food emulsion.
Like other surfactants, its properties are distinct from those of the reactants.
Glycerol monooleate can form a micro-emulsion in water.
Glycerine is completely soluble in water, while oleic acid is insoluble in water.
The hydrophilic-lipophilic balance (HLB) of glycerol monooleate is 3.8 .
How Made: The processes described here are based on published literature.
Information on the manufacturing processes for the listed sources in the petition was not able to be obtained.
Glycerol monooleate is prepared by esterifying glycerin with food-grade oleic acid in the presence of a suitable catalyst to form a monoglyceride ester.
Glycerol Monooleate (GM) is a synthetic surface-active chemical widely used as a nonionic surfactant and emulsant.
It is produced by the reaction of glycerine and oleic acid over a catalyst to form a monoglyceride ester.
Both batch and continuous synthesis routes are used. Commercial production of monoglycerides is described in detail by Gupta (1996):
“Monoglycerides are made by reacting triglycerides with excess glycerol in presence of a catalyst” (glycerolysis reaction, which is a transesterification).
The finished product generally contains 35-50% monoglycerides, hence the Food Chemicals Codex requirement of “not less than 35% monoglycerides.”
“The rest consists of diglycerides, some unreacted triglycerides, residual glycerol, and free fatty acids.”
“It should be pointed out that the free fatty acid is not true fatty acid, but titratable acid.
Phosphoric acid, added in slight excess at the neutralization step, leaves some residue in the product along with the (fatty) acid salts.”
The basic ingredients for commercial production of monoglycerides are: partially or fully hydrogenated deodorized vegetable oils, glycerol, and sodium hydroxide as a catalyst.
Catalysts can also be Sn++, Zn++ 80 , sodium glyceroxide or other metal glyceroxides.
When NaOH is used as a catalyst, phosphoric acid is later added for neutralization.
Glycerin is obtained from fats or oils as a by-product of the production of soaps and fatty acids.
Glycerin can also be produced by fermentation of sugars and synthesized from propylene (Burdock 1997).
Saponification involves the reaction of a fat or oil with potassium hydroxide or another alkali solution (Streitweiser and Heathcock, 1985).
Recovery usually involves aluminum sulfate, sulfuric acid, or hydrochloric acid.
Glycerin can be purified by ion exchange.
Glycerin is on the National List of allowed synthetics at 7 CFR 205.605(b)(13): produced by hydrolysis of fats and oils.
Glycerin can also be prepared from a number of petrochemical sources by a variety of processes.
Early efforts to synthesize glycerin from fermentation sources involved acetaldehyde and sodium sulfite.
Other fermentation methods have been developed since that time.
The first entirely synthetic source of glycerin resulted from the large stream of products from the chlorination of propylene glycol to produce allyl chloride.
One method uses chlorohydrination of allyl chloride to produce a mixture of epichlorohydrin and dichlorohydrin.
Dichlorohydrin can be hydrolyzed to produce glycerin.
Oleic acid is usually obtained by hydrolysis of fats or oils.
Oleic acid is generally either extracted from natural fats or from tall oil, itself a pine sap derivative.
The source of fats can be vegetable or animal.
The primary vegetable oils used to manufacture oleic acid include soybean, cottonseed, corn, and canola.
Genetically modified varieties of each of these plants have been commercially released.
Oleic acid can also be synthesized and recovered from tall (pine) oil resulting from pulp and paper manufacture .
It is possible to enzymatically split fats using various lipolytic enzymes, although this is usually limited to sensitive fats and oils.
These are commercially available from a wide range of non-GMO sources.
For example, triacylglycerol lipase from fungal, bacterial, animal, or plant sources (White and White, 1997).
Solvents involved may be methanol, ethanol, isopropanol, or acetone.
Some glycerol esters are prepared by reaction with epoxides such as ethylene oxide and propylene oxide.
This review generally does not include the products of such a reaction, but some of the general references do not
distinguish glycerol esters based on the method of preparation.
Specific Uses: It is used as an antifoam in juice processing and as a lipophilic emulsifier for water-in-oil applications.
It also serves as a moisturizer, emulsifier, and flavoring agent. Various forms of glycerol oleate are widely used in cosmetics.
It is also widely used as an excipient in antibiotics and other drugs.
The petition addresses the specific use as a defoaming agent.
The petition states, “There is the potential for foam to be discharged up the exhaust line and to the roof”.
The petition states, “Flash boiling causes foaming and is one of the stages where anti-foam is critical.
If air (in the form of foaming) enters the system, it causes many problems.
One of the most difficult to deal with is the issue of under weight containers.
If there is air in the system it does not allow the fillers to put the legal weight of liquid into the container.
A second critical function of the anti-foam is the prevention of product loss from boil over in the vacuum chamber.
“After the vacuum chamber, the milk goes to final cooling, is transferred to a sterilized tank, and then sent to a filler.
These transfers, via pumps and valves, are further causes of air incorporating into the product.
The fillers do have anti125 foaming devices on them.
An example would be mesh screens that all products must pass through just before going into the milk carton.
Mechanical anti-foaming devices such as these do not provide sufficient anti-foam protection in productsnsusceptible to foaming.
Susceptible products include lowfat and nonfat milk products, which inherently have more severe foaming problems due to the reduced fat level.
Fat has anti-foam properties.
“In aseptic milk there is an additional step that causes foam.
As milk is going into the filler, the milk cartons are simultaneously being formed into shape and readied for the milk (in a sterile environment).
At that point, as the milk is filling the packages, nitrogen is injected in to displace oxygen.
Without this step, the milk would oxidize over time, and develop severe flavor defects.
This nitrogen addition causes foaming in no-fat and low fat milk products affecting the ability to fill to legal weight.
Additionally, excess foaming adversely affects the ability of the package to properly seal. . . .
“[Pineapple and carrot juices] tend to foam excessively during blending.
If anti-foam is not used, excess air from foaming will insulate the product and prevent adequate heat transfer for pasteurization.
By using anti-foam, air incorporated during blending is released, and therefore all particles are fully pasteurized, in keeping with Federal Regulations”.
The petition states, “During the harvest and processing, Spirulina and its media are pumped into the harvest building and concentrated by washing onto sequentially finer stainless steel screens.
The media is pumped at approximately 800 gallons per minute which results in a great deal of foaming due to the tremendous flow rates and turbulence caused by the screening.
An antifoam agent is necessary during this processing stage otherwise the algae foams, will not harvest properly, and most of the product is subsequently wasted” .
Containment and inhibition of foam is necessary in food processing for efficient operation of production equipment, to reduce product waste, to maintain a safe workplace, and to keep facilities clean and sanitary
Action: The surface tension and solubility in oil or water of the anti-foaming agent is based on the hydrophilic (‘water151 loving’) / lipophilic (‘oil-loving’) nature of a surface-active agent and is denoted by the HLB (hydrophilic-lipophilic
balance) number.
Surface-active agents with low HLB (2 – 8) are oil-soluble, while those with high HLB (14 – 18) are water-soluble.
Glycerol monooleate is lipophilic and binds to fatty parts of a liquid.
It is a surface-active agent (surfactant) that breaks the tension of a foam bubble.
Combinations: In juice production, glycerol monooleate is mixed with water.
Milk ultrapasteurization (UP) systems may also involve the use of ammonium hydroxide as a boiler water additive.
Commercial formulations may contain butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), citric acid, polymeric dyes, propyl gallate, propylene glycol, sorbitan monostearate, tertiary butylated hydroquinone (TBHQ), and various vegetable oils.
Status
Historic Use: The addition of fatty acid esters to improve the processing of dehydrated and reconstituted fruit and vegetable juices was patented in 1951 (Strashun).
OFPA, USDA Final Rule:
Glycerol monooleate is a monoglyceride. Mono- and di-glycerides are allowed for use in drum drying of food.
Otherwise, glycerol monooleate does not specifically appear on the National List of Allowed Non-organic ingredients .
Glycerol Monooleate and its precursors are not harmful to the environment.
All three materials occur in natural animal and plant fats.
Oleic acid is extracted from natural product.
Glycerine can be made from natural fats or petrochemicals.
Glycerine appears on the National List of allowed synthetic materials for processing with the annotation
“produced by hydrolysis of fats and oils” (7 CFR 205.605.b.12).
A similar annotation could be added to glycerol monooleate, if the material were to be added to the National List.
Glycerine produced from propane usually has the CAS # 115-07-1 instead of the more general # 56-81-5 (Jakobson et al., 1985).
Glycerol monooleate is a food processing aid that would only be used in large integrated plants.
It should not have any interactions with the agroecosystem.
An exception would be filtered juice solids, which are landfilled or later sold as a livestock food supplement.
The material is edible and does not appear to be harmful to humans at the concentrations used in food processing.
(9Z)-9-Octadécénoate de 1,3-dihydroxy-2-propanyle [French] [ACD/IUPAC Name]
1,3-Dihydroxy-2-propanyl (9Z)-9-octadecenoate [ACD/IUPAC Name]
1,3-Dihydroxy-2-propanyl-(9Z)-9-octadecenoat [German] [ACD/IUPAC Name]
1,3-Dihydroxypropan-2-yl (9Z)-octadec-9-enoate
247-038-6 [EINECS]
253-407-2 [EINECS]
25496-72-4 [RN]
2-hydroxy-1-(hydroxymethyl)ethyl (9Z)-octadec-9-enoate
2-Monoolein
2-oleoyl glycerol
2-Oleoylglycerol [Wiki]
37220-82-9 [RN]
9-Octadecenoic acid (9Z)-, ester with 1,2,3-propanetriol
9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol
9-Octadecenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (9Z)- [ACD/Index Name]
Glycerin monooleate
Glycerine monooleate
Glycerine oleate
glycerol monooleate
GLYCEROL OLEATE
MFCD00171536
MG(0:0/18:1(9Z)/0:0)
(Z)-octadec-9-enoic acid (2-hydroxy-1-methylol-ethyl) ester
(Z)-octadec-9-enoic acid [2-hydroxy-1-(hydroxymethyl)ethyl] ester
[2-hydroxy-1-(hydroxymethyl)ethyl] (Z)-octadec-9-enoate
1,3-dihydroxypropan-2-yl (Z)-octadec-9-enoate
1,3-dihydroxypropan-2-yl oleate
2-(9Z)-octadecenoylglycerol
2-(9Z-octadecenoyl)-glycerol
2-(9Z-Octadecenoyl)-rac-glycerol
2-glyceryl monooleate
2-Hydroxy-1-(hydroxymethyl)ethyl (9Z)-9-octadecenoate
2-hydroxy-1-(hydroxymethyl)ethyl ester-9Z-octadecenoic acid
2-mono-C18:1
2-mono-C18:1
2-monoolein|2-oleoyl-glycerol|2-oleoylglycerol (2OG)
2-Monooleoylglycerol
2-OG
2-Oleoyl Glycerol (80per cent)
2-Oleoyl glycerol ether
2-Oleoyl Glycerol???
2-oleoyl-glycerol
2-oleoylglycerol (2OG)
946524-37-4 [RN]
9-Octadecenoic acid (Z)-, 2-hydroxy-1-(hydroxymethyl)ethyl ester
9-Octadecenoic acid (Z)-, ester with 1,2,3-propanetriol
b-Monoacylglycerol
Glyceryl Monooleate
http://www.hmdb.ca/metabolites/HMDB0011537
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:73990
MAG(0:0/18:1)
MAG(0:0/18:1n9)
MAG(0:0/18:1w9)
MAG(18:1)
MG(0:0/18:1)
MG(0:0/18:1n9)
MG(0:0/18:1w9)
MG(18:1)
Oleic acid, monoester with glycerol
Olein, 2-mono-
β-Glyceryl monooloeate
β-Monoacylglycerol
β-Monoolein
β-Monoolein
Glycerol mono-oleate
Synonyms: XU 61518.10, Emerest 2400, Kemester 2000, Monomuls 90-018, Glycerine monooleate, A 300 (ester), GMO 8903, Esterol 272, Ajax GMO, Agnique GMO, Oleic acid glycerol monoester, Priolube 1407, Olein, mono- (6CI,8CI), Capmul GMO 50, Atmer 1007, Emasol MO 50, A 300, Emalsy OL 100H, Oleic monoglyceride, S 1096R, Emcol O, Dimodan LSQK, Glycerin monooleate, Oleic acid monoglyceride, Atsurf 595, Olicine, Glyceromonooleate, Glyceryl oleate, Aldo 40, Arlacel 129, Dur-Em 114, Excel O 95N, Rheodol MO 50, Rikemal OL 100, Glycerol monooleate, Emalsy OL 100, Sinnoester OGC, 9-Octadecenoic acid (Z)-, monoester with 1,2,3-propanetriol, Rheodol MO 60, Glycerol oleate, Harowax L 9, Poem OL 200V, Emrite 6009, OL 100, Emuldan RYLO-MG 90, S 1096, Aldo MO, GMOrphic 80, Monomuls 90O18, Sunsoft O 30B, Supeol, Loxiol G 10, Loxiol G 10V, Tegin OV, Edenor GMO, Kessco GMO, Monoolein, Synative ES-GMO, Rikemal OL 100E, Dur-Em 204, Aldo MO-FG, Crossential GMO, Emerest 2421, Dimodan GMO 90, Excel O 95R, Dremulse, Lumulse GMO, EAR 300, Polybatch AF 1085, Sunsoft 8070, Canamex Glicepol 182, Glyceryl monooleate, Emasol MO, Excel O 95F, Emalsy MO, Adchem GMO, Glycolube 100, Nikkol MGO, Oleylmonoglyceride, Radiasurf 7150, Rikemal XO 100, S 1097, Rylo MG 19 Pharma,Glyceryl Monooleate, 9-Octadecenoic acid (9Z)-, monoester with 1,2,3-propanetriol, Sunsoft 8070V, Monooleoylglycerol, Radiasurf 7149, Monoglyceryl oleate, Alkamuls GMO 45LG, Mazol GMO, Monegyl 0100, Emalsy OL