Glycerol
IUPAC name	Propane-1,2,3-triol
Other names	glycerin glycerine propane-1,2,3-triol 1,2,3-propanetriol 1,2,3-trihydroxypropane glyceritol glycyl alcohol
Identifiers
CAS number	[56-81-5]
SMILES	OCC(O)CO
Properties
Molecular formula	C3H5(OH)3
Molar mass	92. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 09382 g/mol
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 261 g/cm³
Melting point	18 °C (64. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 4°F)
Boiling point	290 °C (554°F)
Viscosity	1. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 5 Pa·s
Hazards
MSDS	External MSDS
NFPA 704	1 1 0
Flash point	160 °C (closed cup)
Supplementary data page
Structure and properties	n, εr, etc. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Glycerol Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air This page provides supplementary chemical data on Glycerol This page provides supplementary chemical data on Glycerol The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Glycerol is a chemical compound also commonly called glycerin or glycerine. This page provides supplementary chemical data on Glycerol This page provides supplementary chemical data on Glycerol Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. Glycerol is a sugar alcohol, and is sweet-tasting and of low toxicity. A sugar alcohol (also known as a Polyol, polyhydric alcohol, or polyalcohol) is a hydrogenated form of Carbohydrate, whose Glycerol has three hydrophilic alcoholic hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. Hydrophile, from the Greek (hydros "water" and φιλια (philia "friendship" refers to a physical property of a Molecule In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon Hydroxyl in Chemistry stands for a molecule consisting of an Oxygen atom and a Hydrogen atom connected by a Covalent bond. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Hygroscopy is the ability of a substance to attract Water Molecules from the surrounding environment through either absorption or Adsorption Its surface tension is 64. 00 mN/m at 20 °C , and it has a temperature coefficient of -0. 0598 mN/(m K). The glycerol substructure is a central component of many lipids. Lipids are broadly defined as any fat- Soluble ( lipophilic) naturally-occurring Molecule, such as fats oils waxes cholesterol sterols fat-soluble

Synthesis and production

Glycerol (3D model), showing the atoms and the lone electron pairs associated with the oxygen atoms (in pink)

Until recently, synthetic glycerol was mainly manufactured at an industrial scale from epichlorohydrin. Epichlorohydrin is a reactive Organic compound. It is an Epoxide and an Organochloride. Since glycerol forms the backbone of triglycerides, it is produced on saponification or transesterification. (more properly known as, TAG or triacylglyceride) is Glyceride in which the Glycerol is Esterified with three Fatty acids It is the Saponification is the Hydrolysis of an Ester under basic conditions to form an Alcohol and the Salt of a Carboxylic acid In Organic chemistry, transesterification is the process of exchanging the Alcohol group of an Ester compound with another Alcohol. Soap-making and biodiesel production are respective examples. SOAP (see below for name and origins is a protocol for exchanging XML -based messages over Computer networks normally using Biodiesel refers to a non-petroleum-based Diesel fuel consisting of short chain Alkyl ( Methyl or ethyl) Esters made by

Glycerol is a 10% by-product of biodiesel production (via the transesterification of vegetable oils). Biodiesel production is the act of producing the Biofuel, Biodiesel, through either Transesterification or Alcoholysis. This has led to a glut of crude glycerol in the market, making the epichlorohydrin process no longer economical. Current levels of glycerol production are running at about 350,000 tons per annum in the USA, and 600,000 tpa in Europe. This will increase as it implements EU directive 2003/30/EC which requires replacement of 5. The Directive on the Promotion of the use of biofuels and other renewable fuels for transport, officially 2003/30/EC and popularly better known as the biofuels directive 75% of petroleum fuels with biofuel, across all Member States by 2010^[1].

Applications

In foods and beverages, glycerol serves as humectant, solvent and sweetener, and may help preserve foods. A humectant is a Hygroscopic substance. It is often a molecule with several Hydrophilic groups most often Hydroxyl groups but Amines It is also used as filler in commercially prepared low-fat foods (e. g. , cookies), and as a thickening agent in liqueurs. In the United States and Canada, a cookie is a small flat-baked treat usually round containing milk flour eggs and sugar etc Thickening agents, or thickeners, are substances which when added to an aqueous mixture increase its Viscosity without substantially modifying its other properties A liqueur is a sweet Alcoholic beverage, often flavored with Fruits, Herbs Spices Flowers Seeds Roots Plants Glycerol also serves as a way, along with water, to preserve certain types of leaves. Glycerol is also used as a sugar substitute. In this regard, it has approximately 27 calories per teaspoon and is 60% as sweet as sucrose. Solubility of Pure SucroseTemperature(Cg Although it has about the same food energy as table sugar, it does not raise blood sugar levels, nor does it feed the bacteria that form plaques and cause dental cavities. Food energy is the amount of Energy in food that is available through Digestion. Blood sugar, used in a physiological context is a misnomer and misleading As a food additive, glycerol is also known as E number E422. E numbers are number codes for Food additives and are usually found on Food labels throughout the European Union.

In organic synthesis, glycerol is used as a readily available prochiral building block. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic In Chemistry, prochiral molecules can be converted from achiral to chiral in a single step

Feedstock

It is one of the major raw materials for the manufacture of polyols for flexible foams, and to a lesser extent rigid polyurethane foams. The name polyols refers to Alcohols containing multiple Hydroxyl groups A polyurethane, commonly abbreviated PU, is any Polymer consisting of a chain of organic units joined by urethane links

Glycerol is used to produce nitroglycerin, which is an essential ingredient of smokeless gunpowder and various munitions. Nitroglycerin ( NG) ( US spelling also known as nitroglycerine, ( UK Spelling trinitroglycerin, trinitroglycerine Reliance on soap-making to supply co-product glycerine made it difficult to increase production to meet wartime demand. Hence, synthetic glycerin processes were national defense priorities in the days leading up to World War II.

Glycerol is also used to manufacture mono- and di-glycerides for use as emulsifiers, as well as polyglycerol esters going into shortenings and margarine. An emulsion ( IPA: /ɪˈmʌlʃən/ is a mixture of two Immiscible (unblendable liquids Esters are a class of Chemical compounds and Functional groups Esters consist of an inorganic or organic Acid in which at least Shortening is a semisolid Fat used in food preparation especially baked goods and is so called because it promotes a "short" or crumbly texture (as in Shortbread Margarine (ˈmɑrdʒərɨn /ˈmɑrdʒəriːn/ or /ˈmɑrgəriːn/ as a generic term can indicate any of a wide range of Butter substitutes

Research laboratory usage

Glycerol is a common component of solvents for enzymatic reagents stored at temperatures below zero degrees Celsius due to the depression of the freezing temperature of solutions with high concentrations of glycerol. It is also dissolved in water to reduce damage by ice crystals to laboratory organisms that are stored in frozen solutions, such as bacteria, nematodes, and fruit flies. Samples are loaded into agarose gel electrophoresis mixed in loading buffers that mainly consist of glycerol; when the sample is injected into wells, the glycerol causes the solution to sink through the running buffer to the bottom of the well.

Pharmaceutical and personal care applications

Glycerol is used in medical and pharmaceutical and personal care preparations, mainly as a means of improving smoothness, providing lubrication and as a humectant. Medicine is the art and science of healing It encompasses a range of Health care practices evolved to maintain and restore Human Health by the Personal care or toiletries is the Industry which Manufactures Consumer Products used for Beautification and in Personal Lubrication is the process or technique employed to reduce wear of one or both surfaces in close proximity and moving relative to each another by interposing a substance called A humectant is a Hygroscopic substance. It is often a molecule with several Hydrophilic groups most often Hydroxyl groups but Amines It is found in cough syrups, elixirs and expectorants, toothpaste, mouthwashes, skin care products, shaving cream, hair care products, and soaps. A cough medicine is a medicinal drug used to treat Coughing and related conditions A mucolytic agent is any agent which dissolves thick Mucus usually used to help relieve respiratory difficulties Toothpaste is a Paste or Gel Dentifrice used to clean and maintain the aesthetics and health of Teeth. Mouthwash or mouth rinse is a product used for Oral hygiene. Antiseptic and anti-plaque mouth rinse claims to kill the bacterial plaque The skin is the outer covering of living tissue of an animal (or plant Hair care is an overall term for parts of Hygiene and Cosmetology involving the Hair on the human head SOAP (see below for name and origins is a protocol for exchanging XML -based messages over Computer networks normally using

As a 10% solution, glycerol prevents tannins from precipitating in ethanol extracts of plants (tinctures). In Medicine, a tincture is an Alcoholic Extract (eg of leaves or other plant material or Solution of a non- volatile substance It is also used as a substitute for ethanol as a solvent in preparing herbal extractions. It is less extractive and is approximately 30% less able to be absorbed by the body. Fluid extract manufacturers often extract herbs in hot water before adding glycerin to make glycerites. A glycerite is a Fluid extract of an herb or other medicinal substance made with Glycerin. ^[2][3][4]

Used as a laxative when introduced into the rectum in suppository or liquid (enema) form; irritates the bowel and induces a hyperosmotic effect. Laxatives (or purgatives) are foods compounds or drugs taken to induce bowel movements or to loosen the stool most often taken to treat Constipation. A suppository is a drug delivery system that is inserted either into the Rectum (rectal suppository Vagina (vaginal suppository or Urethra (urethral An enema (plural enemata or enemas) is the procedure of introducing liquids into the Rectum and colon via the Anus. Laxatives (or purgatives) are foods compounds or drugs taken to induce bowel movements or to loosen the stool most often taken to treat Constipation.

Glycerol is a component of glycerol soap, which is made from denatured alcohol, glycerol, sodium castorate (from castor), sodium cocoate, sodium tallowate, sucrose, water, and parfum (fragrance). SOAP (see below for name and origins is a protocol for exchanging XML -based messages over Computer networks normally using Denatured alcohol is Ethanol which has been rendered toxic or otherwise undrinkable and in some cases dyed The castor oil plant, Ricinus communis, is a Plant Species of the Euphorbiaceae (the evolution of this plant family is relatively unexplored Sodium cocoate is a generic name for the mixture of Fatty acid Salts ( Acid salts of Coconut oil that is used in Soap making Sodium tallowate is made from Sodium hydroxide (better known as caustic soda or lye steam and animal fat ( Tallow) Solubility of Pure SucroseTemperature(Cg Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living Perfume is a mixture of fragrant Essential oils and Aroma compounds Fixatives and Solvents used to give the human body animals objects and living Sometimes one adds sodium laureth sulfate. Sodium laureth sulfate, or sodium lauryl ether sulfate ( SLES) is a Detergent and Surfactant found in many personal care products ( This kind of soap is used by people with sensitive, easily-irritated skin because it prevents skin dryness with its moisturizing properties. The skin is the outer covering of living tissue of an animal (or plant It is possible to make glycerol soap at home.

It is also used in de-/anti-icing fluids, as in vitrification of blood cells for storage in liquid nitrogen

Potential uses

A great deal of research is being conducted to try to make value-added molecules from crude glycerol (typically containing 20 % water and residual esterification catalyst) obtained from biodiesel production, as an alternative to disposal by incineration. Vitrification is a process of converting a material into a Glass -like Amorphous solid that is free from any Crystalline structure either by the quick removal Liquid nitrogen (liquid density at the Triple point is 0707 g/mL is the liquid produced industrially in large quantities by Fractional distillation of Incineration is a waste treatment technology that involves the Combustion of organic materials and/or substances One such program to add value to this glut of glycerol is the UK-based initiative The Glycerol Challenge. Some potential uses for glycerol include the following:

• Hydrogen gas production unit
• Glycerine acetate (as a potential fuel additive)^[5]
• Compost additive
• Citric acid production
• Cosmetic bonding agent for makeup, including: eye shadow, lipstick, lipgloss, and lotions and also including eyedrops as well
• Conversion to propylene glycol^[6]. Glycerine acetate is the Ester produced from the Esterification of Glycerol with Acetic acid. Propylene glycol, known also by the systematic name propane-12-diol is an Organic compound (a Diol Alcohol) usually a faintly sweet odorless and
• Conversion to acrolein^[7][8]
• Conversion to ethanol^[9]
• Conversion to epichlorhydrin^[10], a raw material for epoxy resins. Acrolein (systematic name 2-propenal) is the simplest unsaturated Aldehyde. Epichlorohydrin is a reactive Organic compound. It is an Epoxide and an Organochloride. In Chemistry, epoxy or polyepoxide is a Thermosetting Epoxide Polymer that cures (polymerizes and crosslinks when mixed with a
• Glycerol may be used as antifreeze for plants, if mixed with water in a 10% solution. It is believed to be effective at temperaturs near -18oC

Metabolism

Glycerol is a precursor for synthesis of triacylglycerols and of phospholipids in the liver and adipose tissue. (more properly known as, TAG or triacylglyceride) is Glyceride in which the Glycerol is Esterified with three Fatty acids It is the Phospholipids are a class of Lipids and are a major component of all Biological membranes All phospholipids contain a Diglyceride, a Phosphate "Adipose" redirects here For the Doctor Who monster see " Partners in Crime " When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. In Chemistry, especially Biochemistry, a fatty acid is a Carboxylic acid often with a long unbranched Aliphatic tail ( chain) which The glycerol component can be converted to glucose by the liver and provides energy for cellular metabolism. Glucose (Glc a Monosaccharide (or simple Sugar) also known as grape sugar, is an important Carbohydrate in Biology. The liver is a vital organ in the human body and is present in Vertebrates and some other animals

Before glycerol can enter the pathway of glycolysis or gluconeogenesis (depending on physiological conditions), it must be converted to their intermediate glyceraldehyde 3-phosphate in the following steps:

Glycerol	Glycerol kinase		Glycerol-3-phosphate	Glycerol-3-phosphate dehydrogenase		Dihydroxyacetone phosphate	Triosephosphate isomerase		Glyceraldehyde 3-phosphate
	ATP	ADP		NAD+	NADH
				NAD+	NADH

The enzyme glycerol kinase is present only in the liver. See also Gluconeogenesis, which carries out a process wherein glucose is synthesized rather than catabolized Gluconeogenesis (abreviated GNG) is a Metabolic pathway that results in the generation of Glucose from non- Carbohydrate carbon substrates such Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GADP, GAP or PGAL Glycerol 3-phosphate is a chemical intermediate in the Glycolysis metabolic pathway Glycerol-3-phosphate dehydrogenase (GPDH is an enzyme that catalyzes the oxidation of sn- Glycerol 3-phosphate to Dihydroxyacetone phosphate (aka glycerone phosphate Dihydroxyacetone phosphate (DHAP is a biochemical compound involved in many reactions from the Calvin cycle in plants to the ether-lipid biosynthesis process in Leishmania Triose-phosphate isomerase (TPI or TIM is an Enzyme ( that catalyzes the reversible interconversion of the Triose phosphate Isomers Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GADP, GAP or PGAL Glycerol kinase is a Phosphotransferase Enzyme involved in Lipolysis. In adipose tissue, glycerol 3-phosphate is obtained from dihydroxyacetone phosphate (DHAP) with the enzyme glycerol-3-phosphate dehydrogenase. Dihydroxyacetone phosphate (DHAP is a biochemical compound involved in many reactions from the Calvin cycle in plants to the ether-lipid biosynthesis process in Leishmania Glycerol-3-phosphate dehydrogenase (GPDH is an enzyme that catalyzes the oxidation of sn- Glycerol 3-phosphate to Dihydroxyacetone phosphate (aka glycerone phosphate

Danger of contamination with diethylene glycol

On May 4, 2007, the US Food and Drug Administration advised all US makers of medicines to test all batches of glycerine for the toxic diethylene glycol. Diethylene glycol (DEG is an Organic compound described by the structural formula HO-CH2-CH2-O-CH2-CH2-OH ^[11] This follows an occurrence of 100 fatal poisonings in Panama resulting from a Chinese factory deliberately falsifying records in order to export the cheaper diethylene glycol as the more expensive glycerol. Panama, officially the Republic of Panama (República de Panamá) is the southernmost country of Central America. ^[12] Glycerine and diethylene glycol are similar in appearance, smell, and taste. The US Federal Food, Drug, and Cosmetic Act was passed following the 1937 "Elixir Sulfanilamide" incident of poisoning caused by diethylene glycol contamination of medicine. The United States Federal Food Drug and Cosmetic Act (abbreviated as FFDCA FDCA or FD&C is a set of laws passed by Congress in 1938 giving authority to the The Elixir Sulfanilamide disaster was a mass Poisoning in the United States in 1937

See also

• Oleochemicals
• Nitroglycerin

References

• U.S. Health.gov dietary guidelines

1. ^ The Glycerol Challenge
2. ^ Walter S. Oleochemicals are Chemicals derived from biological oils or Fats They are analogous to Petrochemicals which are chemicals derived from Petroleum Nitroglycerin ( NG) ( US spelling also known as nitroglycerine, ( UK Spelling trinitroglycerin, trinitroglycerine Long. The Composition of Commercial Fruit Extracts Transactions of the Kansas Academy of Science (1903-), Vol. 28, Jan. 14, 1916 - Jan. 13, 1917 (Jan. 14, 1916 - Jan. 13, 1917), pp. 157-161 doi:10. 2307/3624347
3. ^ David Winston www. David Winston RH(AHG (born 1956 is an American herbalist and ethnobotanist who since 1977 has practiced and taught herbal medicine in United States herbaltherapeutics. com
4. ^ Does Alcohol Belong In Herbal Tinctures?
5. ^ J. A. Melero, R. vanGrieken, G. Morales and M. Paniagua (2007). "Acidic Mesoporous Silica for the Acetylation of Glycerol: Synthesis of Bioadditives to Petrol Fuel". Energy Fuels 21 (3): 1782-1791. doi:10.1021/ef060647q. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
6. ^ Dow Chemical Company (15 Mar 2007). The Dow Chemical Company () is an American Multinational corporation headquartered in Midland Michigan. "Dow Achieves Another Major Milestone in its Quest for Sustainable Chemistries". Press release. A news release, media release, press release or press statement is a written or recorded Communication directed at members of the News
7. ^ L. Ott, M. Bicker and H. Vogel (2006). "The catalytic dehydration of glycerol in sub- and supercritical water: a new chemical process for acrolein production". Green Chemistry 8 (2): 214-220. doi:10.1039/b506285c. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.  
8. ^ Watanabe, M. et al (2007). "Acrolein synthesis from glycerol in hot-compressed water". Bioresource Technology 98: 1285-1290.  
9. ^ S. S. Yazdani and R. Gonzalez (2007). "Anaerobic fermentation of glycerol: a path to economic viability for the biofuels industry". Current Opinion in Biotechnology 18 (3): 213-219. Current Opinion is a series of review journals published by Elsevier on various subjects of biology doi:10.1016/j.copbio.2007.05.002. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. Lay summary – ScienceDaily (27 Jun 2007).  
10. ^ Dow Chemical Company (26 March 2007). The Dow Chemical Company () is an American Multinational corporation headquartered in Midland Michigan. "Dow Epoxy Advances Glycerine-To-Epichlorohydrin and Liquid Epoxy Resins Projects by Choosing Shanghai Site". Press release. A news release, media release, press release or press statement is a written or recorded Communication directed at members of the News
11. ^ U. S. Food and Drug Administration. "FDA Advises Manufacturers to Test Glycerin for Possible Contamination." Released May 4, 2007. Last retrieved May 8, 2007.
12. ^ WALT BOGDANICH and JAKE HOOKER. "From China to Panama, a Trail of Poisoned Medicine." New York Times. Published: May 6, 2007. Last retrieved May 8, 2007.

External links

• Glycerol on BioChemInfo.org
• Absolute alcohol using glycerol
• Computational Chemistry Wiki
• Physical Propetry of glycerol