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Wikipedia

Glycerol

Glycerol (/ˈɡlɪsərɒl/),[6] also called glycerine in British English and glycerin in American English, is a simple triol compound. It is a colorless, odorless, viscous liquid that is sweet-tasting and non-toxic. The glycerol backbone is found in lipids known as glycerides. Because it has antimicrobial and antiviral properties, it is widely used in wound and burn treatments approved by the U.S. Food and Drug Administration. Conversely, it is also used as a bacterial culture medium.[7] 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 in pharmaceutical formulations. Because of its three hydroxyl groups, glycerol is miscible with water and is hygroscopic in nature.[8]

Glycerol
Names
Preferred IUPAC name
Propane-1,2,3-triol[1]
Other names
Glycerin
Glycerine
1,2,3-Trioxypropane
1,2,3-Trihydroxypropane
1,2,3-Propanetriol
Identifiers
  • 56-81-5 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17522 Y
ChEMBL
  • ChEMBL692 Y
ChemSpider
  • 733 Y
DrugBank
  • DB04077 Y
ECHA InfoCard 100.000.263
E number E422 (thickeners, ...)
  • 5195
KEGG
  • D00028 Y
  • 753
UNII
  • PDC6A3C0OX Y
  • DTXSID9020663
  • InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2 Y
    Key: PEDCQBHIVMGVHV-UHFFFAOYSA-N Y
  • InChI=1/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2
    Key: PEDCQBHIVMGVHV-UHFFFAOYAF
  • OCC(O)CO
Properties
C3H8O3
Molar mass 92.094 g·mol−1
Appearance Colorless hygroscopic liquid
Odor Odorless
Density 1.261 g/cm3
Melting point 17.8 °C (64.0 °F; 290.9 K)
Boiling point 290 °C (554 °F; 563 K)[5]
miscible[2]
log P -2.32[3]
Vapor pressure 0.003 mmHg (50 °C)[2]
-57.06·10−6 cm3/mol
1.4746
Viscosity 1.412 Pa·s (20 °C)[4]
Pharmacology
A06AG04 (WHO) A06AX01 (WHO), QA16QA03 (WHO)
Hazards
NFPA 704 (fire diamond)
1
1
0
Flash point 160 °C (320 °F; 433 K) (closed cup)
176 °C (349 °F; 449 K) (open cup)
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 15 mg/m3 (total) TWA 5 mg/m3 (resp)[2]
REL (Recommended)
None established[2]
IDLH (Immediate danger)
N.D.[2]
Safety data sheet (SDS) JT Baker
Supplementary data page
Glycerol (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Structure

Although achiral, glycerol is prochiral 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.[9][10][11]

Production

Glycerol is generally obtained from plant and animal sources where it occurs in triglycerides, esters of glycerol with long-chain carboxylic acids. The hydrolysis, saponification, or transesterification of these triglycerides produces glycerol as well as the fatty acid derivative:

3 NaOH / H2O

 

Δ

3 × soap

3 ×   

Triglycerides can be saponified with sodium hydroxide to give glycerol and fatty sodium salt or soap.

Typical plant sources include soybeans or palm. Animal-derived tallow 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.[12] The EU directive 2003/30/EC set a requirement that 5.75% of petroleum fuels were to be replaced with biofuel sources across all member 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.[8]

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.[13] It can be purified, but the process is expensive. Some glycerol is burned for energy, but its heat value is low.[14]

Crude glycerol from the hydrolysis of triglycerides can be purified by treatment with activated carbon to remove organic impurities, alkali to remove unreacted glycerol esters, and ion exchange to remove salts. High purity glycerol (> 99.5%) is obtained by multi-step distillation; a vacuum chamber is necessary due to its high boiling point (290 °C).[8]

Synthetic glycerol

Although usually not cost-effective, glycerol can be produced by various routes from propene. The epichlorohydrin process is the most important: it involves the chlorination of propylene to give allyl chloride, which is oxidized with hypochlorite to dichlorohydrins, which reacts with a strong base to give epichlorohydrin. This epichlorohydrin is then hydrolyzed to give glycerol. Chlorine-free processes from propylene include the synthesis of glycerol from acrolein and propylene oxide.[8]

 

Because of the large-scale production of biodiesel from fats, where glycerol is a waste product, the market for glycerol is depressed. Thus, synthetic processes are not economical. Owing to oversupply, efforts are being made to convert glycerol to synthetic precursors, such as acrolein and epichlorohydrin.[15]

Applications

Food industry

In food and beverages, glycerol serves as a humectant, solvent, and sweetener, and may help preserve foods. It is also used as filler in commercially prepared low-fat foods (e.g., cookies), and as a thickening agent in liqueurs. Glycerol and water are used to preserve certain types of plant leaves.[16] As a sugar substitute, it has approximately 27 kilocalories per teaspoon (sugar has 20) and is 60% as sweet as sucrose. It does not feed the bacteria that form a dental plaque and cause dental cavities.[citation needed] As a food additive, glycerol is labeled as E number 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 as a carbohydrate. The U.S. Food and Drug Administration (FDA) carbohydrate designation includes all caloric macronutrients excluding protein and fat. Glycerol has a caloric density similar to table sugar, but a lower glycemic index and different metabolic pathway within the body, so some dietary advocates[who?] accept glycerol as a sweetener compatible with low-carbohydrate diets.

It is also recommended as an additive when using polyol sweeteners such as erythritol and xylitol which have a cooling effect, due to its heating effect in the mouth, if the cooling effect is not wanted.[17]

Medical, pharmaceutical and personal care applications

 
A bottle of glycerin purchased at a pharmacy
 
Personal lubricants commonly contain glycerol
 
Glycerol is an ingredient in products such as hair gel
 
Glycerol suppositories used as laxatives

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 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. [18]

Glycerol is used in medical, pharmaceutical and personal care preparations, often as a means of improving smoothness, providing lubrication, and as a humectant.

Ichthyosis and xerosis have been relieved by the topical use of glycerin.[19][20] It is found in allergen immunotherapies, cough syrups, elixirs and expectorants, toothpaste, mouthwashes, skin care products, shaving cream, hair care products, soaps, and water-based personal lubricants. 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 alcohols as a caloric macronutrient. Glycerol is also used in blood banking to preserve red blood cells prior to freezing.

Glycerol is a component of glycerin soap. Essential oils are added for fragrance. This kind of soap is used by people with sensitive, easily irritated skin because it prevents skin dryness with its moisturizing properties. It draws moisture up through skin layers and slows or prevents excessive drying and evaporation.[citation needed]

Taken rectally, glycerol functions as a laxative by irritating the anal mucosa and inducing a hyperosmotic effect,[21] expanding the colon by drawing water into it to induce peristalsis resulting in evacuation.[22] It may be administered undiluted either as a suppository or as a small-volume (2–10 ml) enema. Alternatively, it may be administered in a dilute solution, e.g., 5%, as a high volume enema.[23]

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.[24]

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 at inhibiting Clostridioides difficile infection without having a significant effect on the overall microbial composition of the gut.[25]

Glycerol has also been incorporated as a component of bio-ink formulations in the field of bioprinting.[26] 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 (tinctures). 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 manufacturers often extract herbs in hot water before adding glycerol to make glycerites.[27][28]

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.[29] 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 of a finished extract's constituents, even over several years.[citation needed] Both glycerol and ethanol are viable preserving agents. Glycerol is bacteriostatic in its action, and ethanol is bactericidal in its action.[30][31][32]

Electronic cigarette liquid

 
Glycerin is often used in electronic cigarettes to create the vapor

Glycerin, along with propylene glycol, is a common component of e-liquid, a solution used with electronic vaporizers (electronic cigarettes). This glycerol is heated with an atomizer (a heating coil often made of Kanthal wire), producing the aerosol that delivers nicotine to the user.[33]

Antifreeze

Like ethylene glycol and propylene glycol, glycerol is a non-ionic kosmotrope that forms strong hydrogen bonds with water molecules, competing with water-water hydrogen bonds. This interaction disrupts the formation of ice. The minimum freezing point temperature is about −36 °F (−38 °C) 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.[34][35]

In the laboratory, glycerol is a common component of solvents for enzymatic reagents stored at temperatures below 0 °C due to the depression of the freezing temperature. It is also used as a cryoprotectant 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, bacteria, nematodes, and mammalian embryos. Some organisms like the moor frog produce glycerol to survive freezing temperatures during hibernation.[36]

Chemical intermediate

Glycerol is used to produce nitroglycerin, which is an essential ingredient of various explosives such as dynamite, gelignite, and propellants like cordite. 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, taken in the form of sub-lingual tablets, patches, or as an aerosol spray. Trifunctional polyether polyols are produced from glycerol and propylene oxide. An oxidation of glycerol affords mesoxalic acid.[37] 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 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.[38]

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.[39]

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.[40]

Internal combustion fuel

Glycerol is also used to power diesel generators supplying electricity for the FIA Formula E series of electric race cars.[41]

Research on uses

Research has been conducted to produce value-added products from glycerol obtained from biodiesel production.[42] Examples (aside from combustion of waste glycerol):

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.[54][55]

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.[56]

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.[57][58][59] 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 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.[60][61]

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.[62] This followed an occurrence of 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.[63][64] 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.[65]

Etymology

The origin of the gly- and glu- prefixes for glycols and sugars is from Greek γλυκύς glukus which means sweet.[66]

Properties

Table of thermal and physical properties of saturated liquid glycerin:[67][68]

Temperature (°C) Density (kg/m^3) Specific heat (kJ/kg K) Kinematic viscosity (m^2/s) Conductivity (W/m K) Thermal diffusivity (m^2/s) Prandtl Number Bulk modulus (K^-1)
0 1276.03 2.261 8.31E-03 0.282 9.83E-08 8.47E+04 0.00047
10 1270.11 2.319 3.00E-03 0.284 9.65E-08 3.10E+04 0.00047
20 1264.02 2.386 1.18E-03 0.286 9.47E-08 1.25E+04 4.80E-04
30 1258.09 2.445 5.00E-04 0.286 9.29E-08 5.38E+03 0.00048
40 1252.01 2.512 2.20E-04 0.286 9.14E-08 2.45E+03 0.00049
50 1244.96 2.583 1.50E-04 0.287 8.93E-08 1.63E+03 0.0005

See also

References

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External links

  • Mass spectrum of glycerol 13 February 2022 at the Wayback Machine
  • CDC – NIOSH Pocket Guide to Chemical Hazards – Glycerin (mist)

glycerol, this, article, about, chemical, compound, song, band, bush, glycerine, song, also, called, glycerine, british, english, glycerin, american, english, simple, triol, compound, colorless, odorless, viscous, liquid, that, sweet, tasting, toxic, glycerol,. This article is about the chemical compound For a song by the band Bush see Glycerine song Glycerol ˈ ɡ l ɪ s e r ɒ l 6 also called glycerine in British English and glycerin in American English is a simple triol compound It is a colorless odorless viscous liquid that is sweet tasting and non toxic The glycerol backbone is found in lipids known as glycerides Because it has antimicrobial and antiviral properties it is widely used in wound and burn treatments approved by the U S Food and Drug Administration Conversely it is also used as a bacterial culture medium 7 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 in pharmaceutical formulations Because of its three hydroxyl groups glycerol is miscible with water and is hygroscopic in nature 8 Glycerol NamesPreferred IUPAC name Propane 1 2 3 triol 1 Other names GlycerinGlycerine1 2 3 Trioxypropane1 2 3 Trihydroxypropane1 2 3 PropanetriolIdentifiersCAS Number 56 81 5 Y3D model JSmol Interactive imageChEBI CHEBI 17522 YChEMBL ChEMBL692 YChemSpider 733 YDrugBank DB04077 YECHA InfoCard 100 000 263E number E422 thickeners IUPHAR BPS 5195KEGG D00028 YPubChem CID 753UNII PDC6A3C0OX YCompTox Dashboard EPA DTXSID9020663InChI InChI 1S C3H8O3 c4 1 3 6 2 5 h3 6H 1 2H2 YKey PEDCQBHIVMGVHV UHFFFAOYSA N YInChI 1 C3H8O3 c4 1 3 6 2 5 h3 6H 1 2H2Key PEDCQBHIVMGVHV UHFFFAOYAFSMILES OCC O COPropertiesChemical formula C 3H 8O 3Molar mass 92 094 g mol 1Appearance Colorless hygroscopic liquidOdor OdorlessDensity 1 261 g cm3Melting point 17 8 C 64 0 F 290 9 K Boiling point 290 C 554 F 563 K 5 Solubility in water miscible 2 log P 2 32 3 Vapor pressure 0 003 mmHg 50 C 2 Magnetic susceptibility x 57 06 10 6 cm3 molRefractive index nD 1 4746Viscosity 1 412 Pa s 20 C 4 PharmacologyATC code A06AG04 WHO A06AX01 WHO QA16QA03 WHO HazardsNFPA 704 fire diamond 110Flash point 160 C 320 F 433 K closed cup 176 C 349 F 449 K open cup NIOSH US health exposure limits PEL Permissible TWA 15 mg m3 total TWA 5 mg m3 resp 2 REL Recommended None established 2 IDLH Immediate danger N D 2 Safety data sheet SDS JT BakerSupplementary data pageGlycerol data page Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Structure 2 Production 2 1 Synthetic glycerol 3 Applications 3 1 Food industry 3 2 Medical pharmaceutical and personal care applications 3 3 Botanical extracts 3 4 Electronic cigarette liquid 3 5 Antifreeze 3 6 Chemical intermediate 3 7 Vibration damping 3 8 Niche uses 3 8 1 Entertainment industry 3 8 2 Ultrasonic couplant 3 9 Internal combustion fuel 3 10 Research on uses 4 Metabolism 5 Historical cases of contamination with diethylene glycol 6 Etymology 7 Properties 8 See also 9 References 10 External linksStructure EditAlthough achiral glycerol is prochiral 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 9 10 11 Production EditGlycerol is generally obtained from plant and animal sources where it occurs in triglycerides esters of glycerol with long chain carboxylic acids The hydrolysis saponification or transesterification of these triglycerides produces glycerol as well as the fatty acid derivative Triglyceride 3 NaOH H2O D 3 soap3 glycerol Triglycerides can be saponified with sodium hydroxide to give glycerol and fatty sodium salt or soap Typical plant sources include soybeans or palm Animal derived tallow 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 12 The EU directive 2003 30 EC set a requirement that 5 75 of petroleum fuels were to be replaced with biofuel sources across all member 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 8 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 13 It can be purified but the process is expensive Some glycerol is burned for energy but its heat value is low 14 Crude glycerol from the hydrolysis of triglycerides can be purified by treatment with activated carbon to remove organic impurities alkali to remove unreacted glycerol esters and ion exchange to remove salts High purity glycerol gt 99 5 is obtained by multi step distillation a vacuum chamber is necessary due to its high boiling point 290 C 8 Synthetic glycerol Edit See also Chemical intermediate Although usually not cost effective glycerol can be produced by various routes from propene The epichlorohydrin process is the most important it involves the chlorination of propylene to give allyl chloride which is oxidized with hypochlorite to dichlorohydrins which reacts with a strong base to give epichlorohydrin This epichlorohydrin is then hydrolyzed to give glycerol Chlorine free processes from propylene include the synthesis of glycerol from acrolein and propylene oxide 8 Because of the large scale production of biodiesel from fats where glycerol is a waste product the market for glycerol is depressed Thus synthetic processes are not economical Owing to oversupply efforts are being made to convert glycerol to synthetic precursors such as acrolein and epichlorohydrin 15 Applications EditFood industry Edit In food and beverages glycerol serves as a humectant solvent and sweetener and may help preserve foods It is also used as filler in commercially prepared low fat foods e g cookies and as a thickening agent in liqueurs Glycerol and water are used to preserve certain types of plant leaves 16 As a sugar substitute it has approximately 27 kilocalories per teaspoon sugar has 20 and is 60 as sweet as sucrose It does not feed the bacteria that form a dental plaque and cause dental cavities citation needed As a food additive glycerol is labeled as E number 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 as a carbohydrate The U S Food and Drug Administration FDA carbohydrate designation includes all caloric macronutrients excluding protein and fat Glycerol has a caloric density similar to table sugar but a lower glycemic index and different metabolic pathway within the body so some dietary advocates who accept glycerol as a sweetener compatible with low carbohydrate diets It is also recommended as an additive when using polyol sweeteners such as erythritol and xylitol which have a cooling effect due to its heating effect in the mouth if the cooling effect is not wanted 17 Medical pharmaceutical and personal care applications Edit A bottle of glycerin purchased at a pharmacy Personal lubricants commonly contain glycerol Glycerol is an ingredient in products such as hair gel Glycerol suppositories used as laxatives 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 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 18 Glycerol is used in medical pharmaceutical and personal care preparations often as a means of improving smoothness providing lubrication and as a humectant Ichthyosis and xerosis have been relieved by the topical use of glycerin 19 20 It is found in allergen immunotherapies cough syrups elixirs and expectorants toothpaste mouthwashes skin care products shaving cream hair care products soaps and water based personal lubricants 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 alcohols as a caloric macronutrient Glycerol is also used in blood banking to preserve red blood cells prior to freezing Glycerol is a component of glycerin soap Essential oils are added for fragrance This kind of soap is used by people with sensitive easily irritated skin because it prevents skin dryness with its moisturizing properties It draws moisture up through skin layers and slows or prevents excessive drying and evaporation citation needed Taken rectally glycerol functions as a laxative by irritating the anal mucosa and inducing a hyperosmotic effect 21 expanding the colon by drawing water into it to induce peristalsis resulting in evacuation 22 It may be administered undiluted either as a suppository or as a small volume 2 10 ml enema Alternatively it may be administered in a dilute solution e g 5 as a high volume enema 23 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 24 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 at inhibiting Clostridioides difficile infection without having a significant effect on the overall microbial composition of the gut 25 Glycerol has also been incorporated as a component of bio ink formulations in the field of bioprinting 26 The glycerol content acts to add viscosity to the bio ink without adding large protein carbohydrate or glycoprotein molecules Botanical extracts Edit When utilized in tincture method extractions specifically as a 10 solution glycerol prevents tannins from precipitating in ethanol extracts of plants tinctures 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 manufacturers often extract herbs in hot water before adding glycerol to make glycerites 27 28 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 29 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 of a finished extract s constituents even over several years citation needed Both glycerol and ethanol are viable preserving agents Glycerol is bacteriostatic in its action and ethanol is bactericidal in its action 30 31 32 Electronic cigarette liquid Edit Glycerin is often used in electronic cigarettes to create the vapor Glycerin along with propylene glycol is a common component of e liquid a solution used with electronic vaporizers electronic cigarettes This glycerol is heated with an atomizer a heating coil often made of Kanthal wire producing the aerosol that delivers nicotine to the user 33 Antifreeze Edit Main article Antifreeze Like ethylene glycol and propylene glycol glycerol is a non ionic kosmotrope that forms strong hydrogen bonds with water molecules competing with water water hydrogen bonds This interaction disrupts the formation of ice The minimum freezing point temperature is about 36 F 38 C 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 34 35 In the laboratory glycerol is a common component of solvents for enzymatic reagents stored at temperatures below 0 C due to the depression of the freezing temperature It is also used as a cryoprotectant 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 bacteria nematodes and mammalian embryos Some organisms like the moor frog produce glycerol to survive freezing temperatures during hibernation 36 Chemical intermediate Edit Glycerol is used to produce nitroglycerin which is an essential ingredient of various explosives such as dynamite gelignite and propellants like cordite 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 taken in the form of sub lingual tablets patches or as an aerosol spray Trifunctional polyether polyols are produced from glycerol and propylene oxide An oxidation of glycerol affords mesoxalic acid 37 Dehydrating glycerol affords hydroxyacetone Vibration damping Edit Glycerol is used as fill for pressure gauges to damp vibration External vibrations from compressors engines pumps etc produce 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 38 Niche uses Edit Entertainment industry Edit Glycerol is used by set decorators when filming scenes involving water to prevent an area meant to look wet from drying out too quickly 39 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 Edit 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 40 Internal combustion fuel Edit Glycerol is also used to power diesel generators supplying electricity for the FIA Formula E series of electric race cars 41 Research on uses Edit Research has been conducted to produce value added products from glycerol obtained from biodiesel production 42 Examples aside from combustion of waste glycerol Hydrogen gas production 43 Glycerine acetate is a potential fuel additive 44 Glycerol is one of the most used additive for starch thermoplastic 45 46 Conversion to propylene glycol 47 Conversion to acrolein 48 49 50 Conversion to ethanol 51 52 Conversion to epichlorohydrin 53 a raw material for epoxy resinsMetabolism EditGlycerol 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 54 55 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 56 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 Glycerol Glycerol kinaseATP ADP Glycerol 3 phosphate Glycerol 3 phosphate dehydrogenaseNAD NADH NAD NADH Dihydroxyacetone phosphate Triosephosphate isomerase Glyceraldehyde 3 phosphate The enzyme glycerol kinase is present mainly in the liver and kidneys but also in other body tissues including muscle and brain 57 58 59 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 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 60 61 Historical cases of contamination with diethylene glycol EditOn 4 May 2007 the FDA advised all U S makers of medicines to test all batches of glycerol for the toxic diethylene glycol 62 This followed an occurrence of 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 63 64 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 65 Etymology EditThe origin of the gly and glu prefixes for glycols and sugars is from Greek glykys glukus which means sweet 66 Properties EditTable of thermal and physical properties of saturated liquid glycerin 67 68 Temperature C Density kg m 3 Specific heat kJ kg K Kinematic viscosity m 2 s Conductivity W m K Thermal diffusivity m 2 s Prandtl Number Bulk modulus K 1 0 1276 03 2 261 8 31E 03 0 282 9 83E 08 8 47E 04 0 0004710 1270 11 2 319 3 00E 03 0 284 9 65E 08 3 10E 04 0 0004720 1264 02 2 386 1 18E 03 0 286 9 47E 08 1 25E 04 4 80E 0430 1258 09 2 445 5 00E 04 0 286 9 29E 08 5 38E 03 0 0004840 1252 01 2 512 2 20E 04 0 286 9 14E 08 2 45E 03 0 0004950 1244 96 2 583 1 50E 04 0 287 8 93E 08 1 63E 03 0 0005See also EditDioxalin Epichlorohydrin Nitroglycerin Oleochemicals Saponification Soapmaking Solketal TransesterificationReferences Edit International Union of Pure and Applied Chemistry 2014 Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 The Royal Society of Chemistry p 690 doi 10 1039 9781849733069 ISBN 978 0 85404 182 4 a b c d e NIOSH Pocket Guide to Chemical Hazards 0302 National Institute for Occupational Safety and Health NIOSH glycerin msds Archived from the original on 8 March 2020 Retrieved 7 May 2018 Segur J B Oberstar H E 1951 Viscosity of Glycerol and Its Aqueous Solutions Industrial amp Engineering Chemistry 43 9 2117 2120 doi 10 1021 ie50501a040 Lide D R ed 1994 CRC Handbook of Data on Organic Compounds 3rd ed Boca Raton FL CRC Press p 4386 glycerol Definition of glycerol in English 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