Glycerol (), also called glycerine in
British English
British English (BrE, en-GB, or BE) is, according to Lexico, Oxford Dictionaries, "English language, English as used in Great Britain, as distinct from that used elsewhere". More narrowly, it can refer specifically to the English language in ...
and glycerin in
American English
American English, sometimes called United States English or U.S. English, is the set of variety (linguistics), varieties of the English language native to the United States. English is the Languages of the United States, most widely spoken lan ...
, is a simple
triol
In chemistry, a triol is a chemical compound containing three hydroxyl groups ( functional groups),viscous
The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water.
Viscosity quantifies the inter ...
liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in
lipid
Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include ...
s known as
glyceride
Glycerides, more correctly known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic.
Glycerol has three hydroxyl functional groups, which can be esterified with one, two, or three fatty acids ...
s. Because it has
antimicrobial
An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...
and
antiviral
Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Unlike most antibiotics, antiviral drugs do no ...
properties, it is widely used in wound and burn treatments approved by the U.S.
Food and Drug Administration
The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
. Conversely, it is also used as a bacterial culture medium. It can be used as an effective marker to measure liver disease. It is also widely used as a sweetener in the food industry and as a
humectant
A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture ...
in
pharmaceutical formulation
Pharmaceutical formulation, in pharmaceutics, is the process in which different chemical substances, including the active drug, are combined to produce a final medicinal product. The word ''formulation'' is often used in a way that includes dosage ...
s. Because of its three
hydroxyl group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...
s, glycerol is
miscible
Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). The term is most often applied to liquids but also applies ...
with
water
Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...
and is
hygroscopic
Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance ...
in nature.
Structure
Although
achiral
Chirality is a property of asymmetry important in several branches of science. The word ''chirality'' is derived from the Greek (''kheir''), "hand", a familiar chiral object.
An object or a system is ''chiral'' if it is distinguishable from i ...
, glycerol is
prochiral
In stereochemistry, prochiral molecules are those that can be converted from achiral to chiral in a single step. An achiral species which can be converted to a chiral in two steps is called proprochiral.
If two identical substituents are attach ...
with respect to reactions of one of the two primary alcohols. Thus, in substituted derivatives, the
stereospecific numbering labels the molecule with a "sn-" prefix before the stem name of the molecule.
Production
Glycerol is generally obtained from plant and animal sources where it occurs in
triglyceride
A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids (from ''tri-'' and ''glyceride'').
Triglycerides are the main constituents of body fat in humans and other vertebrates, as w ...
s,
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
s of glycerol with long-chain
carboxylic acids
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
. The
hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
,
saponification
Saponification is a process of converting esters into soaps and alcohols by the action of aqueous alkali (for example, aqueous sodium hydroxide solutions). Soaps are salts of fatty acids, which in turn are carboxylic acids with long carbon chains. ...
, or
transesterification
In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction can ...
of these triglycerides produces glycerol as well as the fatty acid derivative:
Triglycerides can be saponified with
sodium hydroxide
Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions .
Sodium hydroxide is a highly caustic base and alkali ...
to give glycerol and fatty sodium salt or
soap
Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are use ...
.
Typical plant sources include
soybeans
The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses.
Traditional unfermented food uses of soybeans include soy milk, from which tofu and ...
or
palm
Palm most commonly refers to:
* Palm of the hand, the central region of the front of the hand
* Palm plants, of family Arecaceae
**List of Arecaceae genera
* Several other plants known as "palm"
Palm or Palms may also refer to:
Music
* Palm (ba ...
. Animal-derived
tallow
Tallow is a rendering (industrial), rendered form of beef or mutton fat, primarily made up of triglycerides.
In industry, tallow is not strictly defined as beef or mutton fat. In this context, tallow is animal fat that conforms to certain techn ...
is another source. Approximately 950,000 tons per year are produced in the United States and Europe; 350,000 tons of glycerol were produced per year in the U.S. alone from 2000 to 2004. The
EU directive 2003/30/EC set a requirement that 5.75% of petroleum fuels were to be replaced with
biofuel
Biofuel is a fuel that is produced over a short time span from biomass, rather than by the very slow natural processes involved in the formation of fossil fuels, such as oil. According to the United States Energy Information Administration (E ...
sources across all
member states
A member state is a state that is a member of an international organization or of a federation or confederation.
Since the World Trade Organization (WTO) and the International Monetary Fund (IMF) include some members that are not sovereign states ...
by 2010. It was projected in 2006 that by 2020, production would be six times more than demand, creating an excess of glycerol as a byproduct of biofuel production.
Glycerol from triglycerides is produced on a large scale, but the crude product is of variable quality, with a low selling price of as low as 2–5 U.S. cents per kilogram in 2011. It can be purified, but the process is expensive. Some glycerol is burned for energy, but its heat value is low.
Crude glycerol from the hydrolysis of triglycerides can be purified by treatment with
activated carbon
Activated carbon, also called activated charcoal, is a form of carbon commonly used to filter contaminants from water and air, among many other uses. It is processed (activated) to have small, low-volume pores that increase the surface area avail ...
to remove organic impurities, alkali to remove unreacted glycerol esters, and
ion exchange
Ion exchange is a reversible interchange of one kind of ion present in an insoluble solid with another of like charge present in a solution surrounding the solid with the reaction being used especially for softening or making water demineralised, ...
to remove salts. High purity glycerol (> 99.5%) is obtained by multi-step distillation; a
vacuum chamber
A vacuum chamber is a rigid enclosure from which air and other gases are removed by a vacuum pump. This results in a low-pressure environment within the chamber, commonly referred to as a vacuum. A vacuum environment allows researchers to condu ...
is necessary due to its high boiling point (290 °C).
[
]
Synthetic glycerol
Although usually not cost-effective, glycerol can be produced by various routes from propene
Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petrole ...
. The epichlorohydrin process is the most important: it involves the chlorination Chlorination may refer to:
* Chlorination reaction
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transform ...
of propylene to give allyl chloride
Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a ch ...
, which is oxidized with hypochlorite
In chemistry, hypochlorite is an anion with the chemical formula ClO−. It combines with a number of cations to form hypochlorite salts. Common examples include sodium hypochlorite (household bleach) and calcium hypochlorite (a component of ble ...
to dichlorohydrins, which reacts with a strong base to give epichlorohydrin
Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organi ...
. This epichlorohydrin is then hydrolyzed to give glycerol. Chlorine
Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
-free processes from propylene include the synthesis of glycerol from acrolein
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...
and propylene oxide
Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its us ...
.
:
Because of the large-scale production of biodiesel
Biodiesel is a form of diesel fuel derived from plants or animals and consisting of long-chain fatty acid esters. It is typically made by chemically reacting lipids such as animal fat (tallow), soybean oil, or some other vegetable oil with ...
from fats, where glycerol is a waste product, the market for glycerol is depressed. Thus, synthetic processes are not economical
An economic system, or economic order, is a system of production, resource allocation and distribution of goods and services within a society or a given geographic area. It includes the combination of the various institutions, agencies, entities ...
. Owing to oversupply, efforts are being made to convert glycerol to synthetic precursors, such as acrolein
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...
and epichlorohydrin.
Applications
Food industry
In food and beverages, glycerol serves as a humectant
A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture ...
, solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
, and sweetener
{{Wiktionary, sweetener
A sweetener is a substance added to food or drink to impart the flavor of sweetness, either because it contains a type of sugar, or because it contains a sweet-tasting sugar substitute. Many artificial sweeteners have been ...
, and may help preserve foods. It is also used as filler in commercially prepared low-fat
Diet food (or dietetic food) refers to any food or beverage whose recipe is altered to reduce fat, carbohydrates, and/or sugar in order to make it part of a weight loss program or diet. Such foods are usually intended to assist in weight loss or ...
foods (e.g., cookie
A cookie is a baked or cooked snack or dessert that is typically small, flat and sweet. It usually contains flour, sugar, egg, and some type of oil, fat, or butter. It may include other ingredients such as raisins, oats, chocolate chips, n ...
s), and as a thickening agent
A thickening agent or thickener is a substance which can increase the viscosity of a liquid without substantially changing its other properties. Edible thickeners are commonly used to thicken sauces, soups, and puddings without altering their t ...
in liqueur
A liqueur (; ; ) is an alcoholic drink composed of spirits (often rectified spirit) and additional flavorings such as sugar, fruits, herbs, and spices. Often served with or after dessert, they are typically heavily sweetened and un-aged beyond ...
s. Glycerol and water are used to preserve certain types of plant leaves. As a sugar substitute
A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie () or low-calorie sweetener. Artificial sweeteners may be d ...
, it has approximately 27 kilocalories
The calorie is a unit of energy. For historical reasons, two main definitions of "calorie" are in wide use. The large calorie, food calorie, or kilogram calorie was originally defined as the amount of heat needed to raise the temperature of on ...
per teaspoon
A teaspoon (tsp.) is an item of cutlery. It is a small spoon that can be used to stir a cup of tea or coffee, or as a tool for Cooking measures, measuring volume. The size of teaspoons ranges from about . For cooking purposes and dosing of med ...
(sugar has 20) and is 60% as sweet
Sweetness is a basic taste most commonly perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasurable. In addition to sugars like sucrose, many other chemical compounds are sweet, including aldehydes, ketones ...
as sucrose
Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula .
For human consumption, sucrose is extracted and refined ...
. It does not feed the bacteria
Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...
that form a dental plaque
Dental plaque is a biofilm of microorganisms (mostly bacteria, but also fungi) that grows on surfaces within the mouth. It is a sticky colorless deposit at first, but when it forms tartar, it is often brown or pale yellow. It is commonly found bet ...
and cause dental cavities
Dental may refer to:
* Dental consonant, in phonetics
* Dental Records, an independent UK record label
* Dentistry, oral medicine
* Teeth
See also
*
* Dental care (disambiguation)
* Dentist (disambiguation)
* Tooth (disambiguation)
A tooth (plu ...
. As a food additive
Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salt ...
, glycerol is labeled as E number
E numbers ("E" stands for "Europe") are codes for substances used as food additives, including those found naturally in many foods such as vitamin C, for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly ...
E422. It is added to icing (frosting) to prevent it from setting too hard.
As used in foods, glycerol is categorized by the U.S. Academy of Nutrition and Dietetics
The Academy of Nutrition and Dietetics is a 501(c)(6) trade association in the United States. With over 112,000 members, the association claims to be the largest organization of food and nutrition professionals. It has registered dietitian nutr ...
as a carbohydrate
In organic chemistry, a carbohydrate () is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 (as in water) and thus with the empirical formula (where ''m'' may or ma ...
. The U.S. Food and Drug Administration
The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
(FDA) carbohydrate designation includes all caloric macronutrient
A nutrient is a substance used by an organism to survive, grow, and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi, and protists. Nutrients can be incorporated into cells for metabolic purposes or excret ...
s excluding protein and fat. Glycerol has a caloric density similar to table sugar, but a lower glycemic index
The glycemic (glycaemic) index (GI; ) is a number from 0 to 100 assigned to a food, with pure glucose arbitrarily given the value of 100, which represents the relative rise in the blood glucose level two hours after consuming that food. The GI of ...
and different metabolic pathway
In biochemistry, a metabolic pathway is a linked series of chemical reactions occurring within a cell. The reactants, products, and intermediates of an enzymatic reaction are known as metabolites, which are modified by a sequence of chemical reac ...
within the body, so some dietary advocates accept glycerol as a sweetener compatible with low-carbohydrate diet
Low-carbohydrate diets restrict carbohydrate consumption relative to the average diet. Foods high in carbohydrates (e.g., sugar, bread, pasta) are limited, and replaced with foods containing a higher percentage of fat and protein (e.g., meat, p ...
s.
It is also recommended as an additive when using polyol sweeteners such as erythritol
Erythritol is an organic compound, a four-carbon sugar alcohol (or polyol) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula i ...
and xylitol
Xylitol is a chemical compound with the formula , or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classifie ...
which have a cooling effect, due to its heating effect in the mouth, if the cooling effect is not wanted.
Medical, pharmaceutical and personal care applications
Glycerin is mildly antimicrobial and antiviral and is an FDA-approved treatment for wounds. The Red Cross reports that an 85% solution of glycerin shows bactericidal and antiviral effects, and wounds treated with glycerin show reduced inflammation after roughly 2 hours. Due to this it is used widely in wound care products, including glycerin based hydrogel
A hydrogel is a crosslinked hydrophilic polymer that does not dissolve in water. They are highly absorbent yet maintain well defined structures. These properties underpin several applications, especially in the biomedical area. Many hydrogels ar ...
sheets for burns and other wound care. It is approved for all types of wound care except third degree burns, and is used to package donor skin used in skin grafts.
Glycerol is used in medical
Medicine is the science and practice of caring for a patient, managing the diagnosis, prognosis, prevention, treatment, palliation of their injury or disease, and promoting their health. Medicine encompasses a variety of health care practic ...
, pharmaceutical
A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy (pharmacotherapy) is an important part of the medical field and re ...
and personal care
Personal care or toiletries are consumer products used in personal hygiene, personal grooming or for beautification.
Products
Personal care includes products as diverse as cleansing pads, colognes, cotton swabs, cotton pads, deodorant, eye lin ...
preparations, often as a means of improving smoothness, providing lubrication
Lubrication is the process or technique of using a lubricant to reduce friction and wear and tear in a contact between two surfaces. The study of lubrication is a discipline in the field of tribology.
Lubrication mechanisms such as fluid-lubric ...
, and as a humectant
A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture ...
.
Ichthyosis
Ichthyosis is a family of genetic skin disorders characterized by dry, thickened, scaly skin. The more than 20 types of ichthyosis range in severity of symptoms, outward appearance, underlying genetic cause and mode of inheritance (e.g., dominan ...
and xerosis
Xeroderma, xerosis or xerosis cutis, or simply dry skin, is a skin condition characterized by excessively dry skin.
The medical term ''xeroderma'', meaning "dry skin", derives from modern Latin, ''xero-'' 'dry' + Greek ''derma'' 'skin'.
In most ...
have been relieved by the topical use of glycerin. It is found in allergen immunotherapies
Immunotherapy or biological therapy is the treatment of disease by activating or suppressing the immune system. Immunotherapies designed to elicit or amplify an immune response are classified as ''activation immunotherapies,'' while immunotherap ...
, cough syrup
Cold medicines are a group of medications taken individually or in combination as a treatment for the symptoms of the common cold and similar conditions of the upper respiratory tract. The term encompasses a broad array of drugs, including a ...
s, elixir
ELIXIR (the European life-sciences Infrastructure for biological Information) is an initiative that will allow life science laboratories across Europe to share and store their research data as part of an organised network. Its goal is to bring t ...
s and expectorant
Mucoactive agents are a class of chemical agents that aid in the clearance of mucus or sputum from the upper and lower airways, including the lungs, bronchi, and trachea. Mucoactive drugs include expectorants, mucolytics, mucoregulators, and muco ...
s, toothpaste
Toothpaste is a paste or gel dentifrice used with a toothbrush to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it is an abrasive that aids in removing dental plaque and food from the teeth, a ...
, mouthwash
Mouthwash, mouth rinse, oral rinse, or mouth bath is a liquid which is held in the mouth passively or swilled around the mouth by contraction of the perioral muscles and/or movement of the head, and may be gargling, gargled, where the head is ti ...
es, skin care
Skin care is a range of practices that support skin integrity, enhance its appearance, and relieve skin conditions. They can include nutrition, avoidance of excessive sun exposure, and appropriate use of emollients. Practices that enhance appea ...
products, shaving cream, hair care
Hair care is an overall term for hygiene and cosmetology involving the hair which grows from the human scalp, and to a lesser extent facial, pubic and other body hair. Hair care routines differ according to an individual's culture and the physic ...
products, soap
Soap is a salt of a fatty acid used in a variety of cleansing and lubricating products. In a domestic setting, soaps are surfactants usually used for washing, bathing, and other types of housekeeping. In industrial settings, soaps are use ...
s, and water-based personal lubricant
Personal lubricants (colloquially termed lube) are specialized lubricants used during sexual acts, such as intercourse and masturbation, to reduce friction to or between the penis and vagina, anus or other body parts or applied to sex toys to red ...
s. In solid dosage forms like tablets, glycerol is used as a tablet holding agent. For human consumption, glycerol is classified by the FDA among the sugar alcohol
Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble solids ...
s as a caloric macronutrient. Glycerol is also used in blood banking
A blood bank is a center where blood gathered as a result of blood donation is stored and preserved for later use in blood transfusion. The term "blood bank" typically refers to a department of a hospital usually within a Clinical Pathology labora ...
to preserve red blood cell
Red blood cells (RBCs), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "holl ...
s prior to freezing.
Glycerol is a component of glycerin soap
Glycerin soaps are soaps that contain glycerol, a component of fat or oil. They are recognizably different from other soaps because they are translucent. The clarity is due to the alignment of the soap molecules, which can be induced through the a ...
. Essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...
s are added for fragrance
An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently vol ...
. This kind of soap is used by people with sensitive, easily irritated skin
Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation.
Other cuticle, animal coverings, such as the arthropod exoskeleton, have diffe ...
because it prevents skin dryness with its moisturizing properties. It draws moisture up through skin layers and slows or prevents excessive drying and evaporation.
Taken rectally, glycerol functions as a laxative
Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation.
Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...
by irritating the anal mucosa and inducing a hyperosmotic effect, expanding the colon by drawing water into it to induce peristalsis
Peristalsis ( , ) is a radially symmetrical contraction and relaxation of muscles that propagate in a wave down a tube, in an anterograde direction. Peristalsis is progression of coordinated contraction of involuntary circular muscles, which ...
resulting in evacuation. It may be administered undiluted either as a suppository
A suppository is a dosage form used to deliver medications by insertion into a body orifice where it dissolves or melts to exert local or systemic effects. There are three types of suppositories, each to insert into a different sections: rectal su ...
or as a small-volume (2–10 ml) enema
An enema, also known as a clyster, is an injection of fluid into the lower bowel by way of the rectum.Cullingworth, ''A Manual of Nursing, Medical and Surgical'':155 The word enema can also refer to the liquid injected, as well as to a device ...
. Alternatively, it may be administered in a dilute solution, e.g., 5%, as a high volume enema.
Taken orally (often mixed with fruit juice to reduce its sweet taste), glycerol can cause a rapid, temporary decrease in the internal pressure of the eye. This can be useful for the initial emergency treatment of severely elevated eye pressure.
In 2017 researchers showed that the probiotic '' Limosilactobacillus reuteri'' bacteria can be supplemented with glycerol to enhance its production of antimicrobial substances in the human gut. This was confirmed to be as effective as the antibiotic Vancomycin
Vancomycin is a glycopeptide antibiotic medication used to treat a number of bacterial infections. It is recommended intravenously as a treatment for complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, ...
at inhibiting ''Clostridioides difficile
''Clostridioides difficile'' ( syn. ''Clostridium difficile'') is a bacterium that is well known for causing serious diarrheal infections, and may also cause colon cancer. Also known as ''C. difficile'', or ''C. diff'' (), is Gram-positive spe ...
'' infection without having a significant effect on the overall microbial composition of the gut.
Glycerol has also been incorporated as a component of bio-ink
Bio-inks are materials used to produce engineered/artificial live tissue using 3D printing. These inks are mostly composed of the cells that are being used, but are often used in tandem with additional materials that envelope the cells. The combi ...
formulations in the field of bioprinting
Three dimensional (3D) bioprinting is the utilization of 3D printing–like techniques to combine cells, growth factors, and/or biomaterials to fabricate biomedical parts, often with the aim of imitating natural tissue characteristics. Generally, 3 ...
. The glycerol content acts to add viscosity to the bio-ink without adding large protein, carbohydrate, or glycoprotein molecules.
Botanical extracts
When utilized in "tincture" method extractions, specifically as a 10% solution, glycerol prevents tannins from precipitating in ethanol extracts of plants (tincture
A tincture is typically an extract of plant or animal material dissolved in ethanol (ethyl alcohol). Solvent concentrations of 25–60% are common, but may run as high as 90%.Groot Handboek Geneeskrachtige Planten by Geert Verhelst In chemistr ...
s). It is also used as an "alcohol-free" alternative to ethanol as a solvent in preparing herbal extractions. It is less extractive when utilized in a standard tincture methodology. Alcohol-based tinctures can also have the alcohol removed and replaced with glycerol for its preserving properties. Such products are not "alcohol-free" in a scientific or FDA regulatory sense, as glycerol contains three hydroxyl groups. Fluid extract
An extract is a substance made by extracting a part of a raw material, often by using a solvent such as ethanol, oil or water. Extracts may be sold as tinctures, absolutes or in powder form.
The aromatic principles of many spices, nuts, h ...
manufacturers often extract herbs in hot water before adding glycerol to make glycerite A traditional glycerite is a fluid extract of an herb or other medicinal substance made using glycerin as the majority of the fluid extraction medium.
Definition
According to ''King's American Dispensatory'' (1898), glycerite is:Glycerita.—Gl ...
s.
When used as a primary "true" alcohol-free botanical extraction solvent in non-tincture based methodologies, glycerol has been shown to possess a high degree of extractive versatility for botanicals including removal of numerous constituents and complex compounds, with an extractive power that can rival that of alcohol and water–alcohol solutions. That glycerol possesses such high extractive power assumes it is utilized with dynamic (i.e. critical) methodologies as opposed to standard passive "tincturing" methodologies that are better suited to alcohol. Glycerol possesses the intrinsic property of not denaturing or rendering a botanical's constituents inert like alcohols (i.e. ethyl (grain) alcohol, methyl (wood) alcohol, etc.) do. Glycerol is a stable preserving agent for botanical extracts that, when utilized in proper concentrations in an extraction solvent base, does not allow inverting or mitigates reduction-oxidation
Redox (reduction–oxidation, , ) is a type of chemical reaction in which the oxidation states of substrate change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a d ...
of a finished extract's constituents, even over several years. Both glycerol and ethanol are viable preserving agents. Glycerol is bacteriostatic
A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfect ...
in its action, and ethanol is bactericidal in its action.
Electronic cigarette liquid
Glycerin, along with propylene glycol
Propylene glycol (IUPAC nomenclature, IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH.
Containing two Alcohol (chemistry), alcoho ...
, is a common component of e-liquid
An electronic cigarette is a handheld battery-powered vaporizer that simulates smoking, but without tobacco combustion. E-cigarette components include a mouthpiece (drip tip), a cartridge (liquid storage area), a heating element/ atomizer, a mic ...
, a solution used with electronic vaporizers (electronic cigarettes
An electronic cigarette is an electronic device that simulates tobacco smoking. It consists of an atomizer, a power source such as a battery, and a container such as a cartridge or tank. Instead of smoke, the user inhales vapor. As such ...
). This glycerol is heated with an atomizer (a heating coil often made of Kanthal wire), producing the aerosol
An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be natural or Human impact on the environment, anthropogenic. Examples of natural aerosols are fog o ...
that delivers nicotine
Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
to the user.
Antifreeze
Like ethylene glycol
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odo ...
and propylene glycol, glycerol is a non-ionic kosmotrope that forms strong hydrogen bonds with water molecules, competing with water-water hydrogen bonds
In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a ...
. This interaction disrupts the formation of ice. The minimum freezing point temperature is about corresponding to 70% glycerol in water.
Glycerol was historically used as an anti-freeze for automotive applications before being replaced by ethylene glycol, which has a lower freezing point. While the minimum freezing point of a glycerol-water mixture is higher than an ethylene glycol-water mixture, glycerol is not toxic and is being re-examined for use in automotive applications.
In the laboratory, glycerol is a common component of solvents for enzymatic
Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
reagents
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
stored at temperatures below 0 °C due to the depression of the freezing temperature. It is also used as a cryoprotectant
A cryoprotectant is a substance used to protect biological tissue from freezing damage (i.e. that due to ice formation). Arctic and Antarctic insects, fish and amphibians create cryoprotectants (antifreeze, antifreeze compounds and antifreeze prot ...
where the glycerol is dissolved in water to reduce damage by ice crystals to laboratory organisms that are stored in frozen solutions, such as fungi
A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from ...
, bacteria
Bacteria (; singular: bacterium) are ubiquitous, mostly free-living organisms often consisting of one biological cell. They constitute a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria were among ...
, nematode
The nematodes ( or grc-gre, Νηματώδη; la, Nematoda) or roundworms constitute the phylum Nematoda (also called Nemathelminthes), with plant-Parasitism, parasitic nematodes also known as eelworms. They are a diverse animal phylum inhab ...
s, and mammalian embryos. Some organisms like the moor frog
The moor frog (''Rana arvalis'') is a slim, reddish-brown, semiaquatic amphibian native to Europe and Asia. Moor frogs are known for their ability to freeze solid and survive thawing. The frog makes use of various cryoprotectants i.e. antifreeze ...
produce glycerol to survive freezing temperatures during hibernation.
Chemical intermediate
Glycerol is used to produce nitroglycerin
Nitroglycerin (NG), (alternative spelling of nitroglycerine) also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating g ...
, which is an essential ingredient of various explosives such as dynamite
Dynamite is an explosive made of nitroglycerin, sorbents (such as powdered shells or clay), and Stabilizer (chemistry), stabilizers. It was invented by the Swedish people, Swedish chemist and engineer Alfred Nobel in Geesthacht, Northern Germa ...
, gelignite
Gelignite (), also known as blasting gelatin or simply "jelly", is an explosive material consisting of collodion-cotton (a type of nitrocellulose or guncotton) dissolved in either nitroglycerine or nitroglycol and mixed with wood pulp and saltpe ...
, and propellants like cordite
Cordite is a family of smokeless propellants developed and produced in the United Kingdom since 1889 to replace black powder as a military propellant. Like modern gunpowder, cordite is classified as a low explosive because of its slow burni ...
. Reliance on soap-making to supply co-product glycerol made it difficult to increase production to meet wartime demand. Hence, synthetic glycerol processes were national defense priorities in the days leading up to World War II. Nitroglycerin, also known as glyceryl trinitrate (GTN) is commonly used to relieve ''angina pectoris
Angina, also known as angina pectoris, is chest pain or pressure, usually caused by insufficient blood flow to the heart muscle (myocardium). It is most commonly a symptom of coronary artery disease.
Angina is typically the result of obstru ...
'', taken in the form of sub-lingual tablets, patches, or as an aerosol
An aerosol is a suspension (chemistry), suspension of fine solid particles or liquid Drop (liquid), droplets in air or another gas. Aerosols can be natural or Human impact on the environment, anthropogenic. Examples of natural aerosols are fog o ...
spray.
Trifunctional polyether polyols are produced from glycerol and propylene oxide
Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its us ...
. An oxidation of glycerol affords mesoxalic acid. Dehydrating glycerol affords hydroxyacetone.
Vibration damping
Glycerol is used as fill for pressure gauges to damp vibration. External vibrations, from compressors, engines, pumps, etc., produce harmonic oscillation, harmonic vibrations within Bourdon gauges that can cause the needle to move excessively, giving inaccurate readings. The excessive swinging of the needle can also damage internal gears or other components, causing premature wear. Glycerol, when poured into a gauge to replace the air space, reduces the harmonic vibrations that are transmitted to the needle, increasing the lifetime and reliability of the gauge.
Niche uses
Entertainment industry
Glycerol is used by set decorators when filming scenes involving water to prevent an area meant to look wet from drying out too quickly.
Glycerine is also used in the generation of theatrical smoke and fog as a component of the fluid used in fog machines as a replacement for glycol, which has been shown to be an irritant if exposure is prolonged.
Ultrasonic couplant
Glycerol can be sometimes used as replacement for water in ultrasonic testing, as it has favourably higher acoustic impedance (2.42MRayl vs 1.483MRayl for water) while being relatively safe, non-toxic, non-corrosive and relatively low cost.
Internal combustion fuel
Glycerol is also used to power diesel generators supplying electricity for the FIA Formula E series of electric race cars.
Research on uses
Research has been conducted to produce value-added products from glycerol obtained from biodiesel production. Examples (aside from combustion of waste glycerol):
* Hydrogen gas production
* Glycerine acetate is a potential fuel additive.
* Glycerol is one of the most used additive for starch thermoplastic.
* Conversion to propylene glycol
Propylene glycol (IUPAC nomenclature, IUPAC name: propane-1,2-diol) is a viscous, colorless liquid, which is nearly odorless but possesses a faintly sweet taste. Its chemical formula is CH3CH(OH)CH2OH.
Containing two Alcohol (chemistry), alcoho ...
* Conversion to acrolein
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a piercing, acrid smell. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fa ...
* Conversion to ethanol
* Conversion to epichlorohydrin
Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscible with most polar organi ...
, a raw material for epoxy resins
Metabolism
Glycerol is a precursor for synthesis of triacylglycerols and of phospholipids in the liver and adipose tissue. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream.
Glycerol is mainly metabolized in the liver. Glycerol injections can be used as a simple test for liver damage, as its rate of absorption by the liver is considered an accurate measure of liver health. Glycerol metabolism is reduced in both cirrhosis and fatty liver disease.
Blood glycerol levels are highly elevated during diabetes, and is believed to be the cause of reduced fertility in patients who suffer from diabetes and metabolic syndrome. Blood glycerol levels in diabetic patients average three times higher than healthy controls. Direct glycerol treatment of testes has been found to cause significant long-term reduction in sperm count. Further testing on this subject was abandoned due to the unexpected results, as this was not the goal of the experiment.
Circulating glycerol does not glycate proteins as do glucose or fructose, and does not lead to the formation of advanced glycation endproducts (AGEs). In some organisms, the glycerol component can enter the glycolysis pathway directly and, thus, provide energy for cellular metabolism (or, potentially, be converted to glucose through gluconeogenesis).
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:
The enzyme glycerol kinase is present mainly in the liver and kidneys, but also in other body tissues, including muscle and brain. In adipose tissue, glycerol 3-phosphate is obtained from dihydroxyacetone phosphate with the enzyme glycerol-3-phosphate dehydrogenase.
Glycerol has very low toxicity when ingested; its LD50, LD50 oral dose for rats is 12600 mg/kg and 8700 mg/kg for mice. It does not appear to cause toxicity when inhaled, although changes in cell maturity occurred in small sections of lung in animals under the highest dose measured. A sub-chronic 90-day nose-only inhalation study in Sprague-Dawley (SD) rats exposed to 0.03, 0.16 and 0.66 mg/L glycerin (Per liter of air) for 6-hour continuous sessions revealed no treatment-related toxicity other than minimal metaplasia of the epithelium lining at the base of the epiglottis in rats exposed to 0.66 mg/L glycerin.
Historical cases of contamination with diethylene glycol
On 4 May 2007, the FDA advised all U.S. makers of medicines to test all batches of glycerol for the toxic diethylene glycol. This followed an occurrence of Toxic cough syrup, hundreds of fatal poisonings in Panama resulting from a falsified import customs declaration by Panamanian import/export firm Aduanas Javier de Gracia Express, S. A. The cheaper diethylene glycol was relabeled as the more expensive glycerol. Between 1990 and 1998, incidents of DEG poisoning reportedly occurred in Argentina, Bangladesh, India, and Nigeria, and resulted in hundreds of deaths. In 1937, more than one hundred people died in the United States after ingesting DEG-contaminated elixir sulfanilamide, a drug used to treat infections.
Etymology
The origin of the gly- and glu- prefixes for glycols and sugars is from Ancient Greek, Greek γλυκύς ''glukus'' which means sweet.
Properties
Table of thermal and physical properties of saturated liquid glycerin:
See also
* Dioxalin
* Epichlorohydrin
* Nitroglycerin
* Oleochemicals
* Saponification/Soapmaking
* Solketal
* Transesterification
References
External links
Mass spectrum of glycerol
{{Authority control
Alcohol solvents
Biofuels
Commodity chemicals
Cosmetics chemicals
Demulcents
E-number additives
Food additives
Glassforming liquids and melts
Glycerols
Household chemicals
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Sugar alcohols
Triols