Stearyl alcohol

Last updated
Stearyl alcohol [1]
1-Octadecanol.svg
Stearyl-alcohol-3D-vdW.png
Names
Preferred IUPAC name
Octadecan-1-ol
Other names
1-octadecanol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.652 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3 Yes check.svgY
    Key: GLDOVTGHNKAZLK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3
    Key: GLDOVTGHNKAZLK-UHFFFAOYAZ
  • OCCCCCCCCCCCCCCCCCC
Properties
C18H38O
Molar mass 270.49 g/mol
AppearanceWhite solid
Density 0.812 g/cm3
Melting point 59.4 to 59.8 °C (138.9 to 139.6 °F; 332.5 to 332.9 K)
Boiling point 210 °C (410 °F; 483 K)at 15 mmHg (~2.0 kPa)
1.1 x 10−3 mg/L
Hazards
Flash point 185 °C (365 °F; 458 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It takes the form of white granules or flakes, which are insoluble in water. It has a wide range of uses as an ingredient in lubricants, resins, perfumes, and cosmetics. It is used as an emollient, emulsifier, and thickener in ointments, and is widely used as a hair coating in shampoos and hair conditioners. Stearyl heptanoate, the ester of stearyl alcohol and heptanoic acid (enanthic acid), is found in most cosmetic eyeliners. Stearyl alcohol has also found application as an evaporation suppressing monolayer when applied to the surface of water. [2]

Stearyl alcohol is prepared from stearic acid or some fats by the process of catalytic hydrogenation. It has low toxicity. [3]

Related Research Articles

Alcohol Type of organic compound

In chemistry, alcohol is an organic compound that carries at least one hydroxyl functional group (−OH) bound to a saturated carbon atom. The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. An important class of alcohols, of which methanol and ethanol are the simplest members, includes all compounds for which the general formula is CnH2n+1OH. Simple monoalcohols that are the subject of this article include primary (RCH2OH), secondary (R2CHOH) and tertiary (R3COH) alcohols.

Fatty acid Carboxylic acid

In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with a long aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually not found in organisms in their standalone form, but instead exist as three main classes of esters: triglycerides, phospholipids, and cholesteryl esters. In any of these forms, fatty acids are both important dietary sources of fuel for animals and they are important structural components for cells.

Beeswax Natural wax produced by honey bees of the genus Apis

Beeswax is a natural wax produced by honey bees of the genus Apis. The wax is formed into scales by eight wax-producing glands in the abdominal segments of worker bees, which discard it in or at the hive. The hive workers collect and use it to form cells for honey storage and larval and pupal protection within the beehive. Chemically, beeswax consists mainly of esters of fatty acids and various long-chain alcohols.

Wax

Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to give low viscosity liquids. Waxes are insoluble in water but soluble in organic, nonpolar solvents. Natural waxes of different types are produced by plants and animals and occur in petroleum.

Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and other dairy products. Palmitates are the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4).

Hair conditioner Hair care product

Hair conditioner is a hair care product used to improve the feel, appearance and manageability of hair. Its main purpose is to reduce friction between strands of hair to allow smoother brushing or combing, which might otherwise cause damage to the scalp. Various other benefits are often advertised, such as hair repair, strengthening, or a reduction in split ends.

Polydimethylsiloxane Chemical compound

Polydimethylsiloxane (PDMS), also known as dimethylpolysiloxane or dimethicone, belongs to a group of polymeric organosilicon compounds that are commonly referred to as silicones. PDMS is the most widely used silicon-based organic polymer due to its versatility and properties leading to many applications.

Moisturizer Type of cosmetics

Moisturizer or emollient is a cosmetic preparation used for protecting, moisturizing, and lubricating the skin. These functions are normally performed by sebum produced by healthy skin. The word "emollient" is derived from the Latin verb mollire, to soften.

Oleyl alcohol Chemical compound

Oleyl alcohol, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7-CH=CH-(CH2)8OH. It is a colorless oil, mainly used in cosmetics.

Fatty alcohols (or long-chain alcohols) are usually high-molecular-weight, straight-chain primary alcohols, but can also range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils. The precise chain length varies with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleyl alcohols. They are colourless oily liquids (for smaller carbon numbers) or waxy solids, although impure samples may appear yellow. Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (–OH) attached to the terminal carbon. Some are unsaturated and some are branched. They are widely used in industry. As with fatty acids, they are often referred to generically by the number of carbon atoms in the molecule, such as "a C12 alcohol", that is an alcohol having 12 carbons, for example dodecanol.

Cetyl alcohol, also known as hexadecan-1-ol and palmityl alcohol, is a C-16 fatty alcohol with the formula CH3(CH2)15OH. At room temperature, cetyl alcohol takes the form of a waxy white solid or flakes. The name cetyl derives from the whale oil (cetacea oil, from Latin: cetus, lit. 'whale', from Ancient Greek: κῆτος, romanized: kētos, lit. 'huge fish') from which it was first isolated.

Panthenol Pair / mixture of stereoisomers

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used as a moisturizer and to improve wound healing in pharmaceutical and cosmetic products.

Diethanolamine Chemical compound

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool mean it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

Hydrolyzed jojoba esters are the hydrolysate of jojoba esters derived by acid, enzyme or other method of hydrolysis. Hydrolyzed jojoba esters are commonly used in cosmetic formulations.

Cetrimonium chloride, or cetyltrimethylammonium chloride (CTAC), is a topical antiseptic and surfactant. Long-chain quaternary ammonium surfactants, such as cetyltrimethylammonium chloride (CTAC), are generally combined with long-chain fatty alcohols, such as stearyl alcohols, in formulations of hair conditioners and shampoos. The cationic surfactant concentration in conditioners is generally of the order of 1–2% and the alcohol concentrations are usually equal to or greater than those of the cationic surfactants. The ternary system, surfactant/fatty alcohol/water, leads to a lamellar structure forming a percolated network giving rise to a gel.

Organosulfate Any ester derived from sulfuric acid

Organosulfates are a class of organic compounds sharing a common functional group commonly with the structure R-O-SO3. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols and sulfuric acid, although many are not prepared in this way. Many sulfate esters are used in detergents, and some are useful reagents. Alkyl sulfates consist of a hydrophobic hydrocarbon chain, a polar sulfate group (containing an anion) and either a cation or amine to neutralize the sulfate group. Examples include: sodium lauryl sulfate (also known as sulfuric acid mono dodecyl ester sodium salt) and related potassium and ammonium salts.

Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.

Oleochemistry is the study of vegetable oils and animal oils and fats, and oleochemicals derived from these fats and oils. The resulting product can be called oleochemicals (from Latin: oleum “olive oil”). The major product of this industry is soap, approximately 8.9×106 tons of which were produced in 1990. Other major oleochemicals include fatty acids, fatty acid methyl esters, fatty alcohols and fatty amines. Glycerol is a side product of all of these processes. Intermediate chemical substances produced from these basic oleochemical substances include alcohol ethoxylates, alcohol sulfates, alcohol ether sulfates, quaternary ammonium salts, monoacylglycerols (MAG), diacylglycerols (DAG), structured triacylglycerols (TAG), sugar esters, and other oleochemical products.

Decomposition in animals is a process that begins immediately after death and involves the destruction of soft tissue, leaving behind skeletonized remains. The chemical process of decomposition is complex and involves the breakdown of soft tissue, as the body passes through the sequential stages of decomposition. Autolysis and putrefaction also play major roles in the disintegration of cells and tissues.

Evaporation suppressing monolayers

Evaporation suppressing monolayers are materials that when applied to the air/water interface, will spread and form a thin film across the surface of the water. The purpose of these materials is to reduce evaporative water loss from dams and reservoirs.

References

  1. Merck Index , 11th Edition, 8762.
  2. Prime, E. L., Tran, D. N., Plazzer, M., Sunartio, D., Leung, A. H., Yiapanis, G., ... & Solomon, D. H. (2012). Rational design of monolayers for improved water evaporation mitigation. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 415, 47-58.
  3. Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2.