Fatty alcohols are aliphatic alcohols derived from natural fats and oils, originating in plants, but also synthesized in animals and algae. Their significance in nutrition and health has historically been overlooked, and is only now being realized, as they are closely related to fatty acids, including the well-documented omega 3 fatty acids. The other counterparts are fatty aldehydes. Fatty alcohols usually have even number of carbon atoms. Production from fatty acids yields normal-chain alcohols—the alcohol group (-OH) attaches to the terminal carbon. Other processing can yield iso-alcohols—where the alcohol attaches to a carbon in the interior of the carbon chain. In chemistry, non-aromatic and non-cyclic (acyclic) organic compounds are called aliphatic. ... This article does not cite any references or sources. ... For other uses, see FAT. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. ... Synthetic motor oil For other uses, see Oil (disambiguation). ... Osborne (talk) 20:17, 5 December 2007 (UTC):For the programming language, see algae (programming language) Laurencia, a marine red alga from Hawaii. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... To meet Wikipedias quality standards, this article or section may require cleanup. ...

Current and future uses

The smaller molecules are used in cosmetics and food, and as industrial solvents. Some of the larger molecules are simply seen as biofuels, but little research has been done until 2006 regarding many of these, and they have been shown to be have anticancer, antiviral, antifungal, anti-HIV properties, for potential use in medicine and health supplements. Make-up redirects here. ... For other uses, see Solvent (disambiguation). ... Bio-energy redirects here. ... Species Human immunodeficiency virus 1 Human immunodeficiency virus 2 Human immunodeficiency virus (HIV) is a retrovirus that causes acquired immunodeficiency syndrome (AIDS, a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections). ...

Due to their amphipathic nature, fatty alcohols behave as nonionic surfactants. They find use as emulsifiers, emollients and thickeners in cosmetics and food industry. It has been suggested that this article or section be merged with Amphiphiles. ... Surfactants, also known as tensides, are wetting agents that lower the surface tension of a liquid, allowing easier spreading, and lower the interfacial tension between two liquids. ... An emulsion is a mixture of two immiscible substances. ... Emollients soften skin (and moisturisers add moisture). ... Thickening agents, or thickeners, are substances which, when added to the mixture, increase its viscosity without substantially modifying its other properties, like eg. ... Make-up redirects here. ... The food industry is the complex, global collective of diverse businesses that together supply much of the food energy consumed by the world population. ...

Fatty alcohols are a common component of waxes, mostly as esters with fatty acids but also as alcohols themselves. candle wax This page is about the substance. ... For other uses, see Ester (disambiguation). ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ...

History

Search for polyisoprenoid alcohols was initiated with the accidental discovery of solanesol in tobacco leaves (Rowland RL et al., J Am Chem Soc 1956, 78, 4680) and isolation of several polyprenols (C30-C45) in cellulose pulp extracts (Lindgren BO, Acta Chem Scan 1965, 19, 1317).

Octacosanol, present in carrots and ginseng, was found to lower cholesterol levels in 1994. Following this, a major paper was released in 2006 and another in 2007 studying hundreds of previously unstudied fatty alcohols. More than 120 cytotoxic anticancer compounds have shown confirmed activity in vitro tumor cell lines bioassay and are of current interest to Natural Cancer Institute (of Poland) for further in vivo evaluation.^[1] Cytotoxicity is the quality of being poisonous to cells. ... In vitro (Latin: within the glass) refers to the technique of performing a given experiment in a test tube, or, generally, in a controlled environment outside a living organism. ... Also known as a biological assay, a bioassay is a measurement of the effects of a substance on living organisms. ...

Types

• Normal-chain alcohols
  • Saturated alcohols
  • Unsaturated alcohols
  • Acetylenic alcohols
  • Sulfated alcohols
• Branched-chain alcohols
  • Mono-methylated alcohols
  • Polyisoprenoid alcohols
    • Saturated polyisoprenoids (Isopranols)
    • Unsaturated polyisoprenoids (prenols or polyprenols) incl turpenols.
• Phenolic alcohols (aka phenolphthiocerol)

Common names

Those with common names include:

• capryl alcohol (1-octanol) -- 8 carbon atoms
• 2-ethyl hexanol -- 8 carbon atoms, branched
• pelargonic alcohol (1-nonanol) -- 9 carbon atoms
• capric alcohol (1-decanol, decyl alcohol) -- 10 carbon atoms
• 1-dodecanol (lauryl alcohol) -- 12 carbon atoms
• myristyl alcohol (1-tetradecanol) -- 14 carbon atoms
• cetyl alcohol (1-hexadecanol) -- 16 carbon atoms
• palmitoleyl alcohol (cis-9-hexadecen-1-ol) -- 16 carbon atoms, unsaturated, CH₃(CH₂)₅CH=CH(CH₂)₈OH
• stearyl alcohol (1-octadecanol) -- 18 carbon atoms
• isostearyl alcohol (16-methylheptadecan-1-ol) -- 18 carbon atoms, branched, (CH₃)₂CH-(CH₂)₁₅OH
• elaidyl alcohol (9E-octadecen-1-ol) -- 18 carbon atoms, unsaturated, CH₃(CH₂)₇CH=CH(CH₂)₈OH
• oleyl alcohol (cis-9-octadecen-1-ol) -- 18 carbon atoms, unsaturated
• linoleyl alcohol (9Z, 12Z-octadecadien-1-ol) -- 18 carbon atoms, polyunsaturated, a hydrolyzation of linolinic acid, an omega 6 fatty acid.
• elaidolinoleyl alcohol (9E, 12E-octadecadien-1-ol) -- 18 carbon atoms, polyunsaturated
• linolenyl alcohol (9Z, 12Z, 15Z-octadecatrien-1-ol) -- 18 carbon atoms, polyunsaturated
• elaidolinolenyl alcohol (9E, 12E, 15-E-octadecatrien-1-ol) -- 18 carbon atoms, polyunsaturated
• ricinoleyl alcohol (12-hydroxy-9-octadecen-1-ol) -- 18 carbon atoms, unsaturated, diol, CH₃(CH₂)₅CH(OH)CH₂CH=CH(CH₂)₈OH
• arachidyl alcohol (1-eicosanol) -- 20 carbon atoms
• behenyl alcohol (1-docosanol) -- 22 carbon atoms
• erucyl alcohol (cis-13-docosen-1-ol) -- 22 carbon atoms, unsaturated, CH₃(CH₂)₇CH=CH(CH₂)₁₂OH
• lignoceryl alcohol (1-tetracosanol) -- 24 carbon atoms
• ceryl alcohol (1-hexacosanol) -- 26 carbon atoms
• montanyl alcohol, cluytyl alcohol (1-octacosanol) -- 28 carbon atoms
• myricyl alcohol, melissyl alcohol (1-triacontanol) -- 30 carbon atoms
• geddyl alcohol (1-tetratriacontanol) -- 34 carbon atoms

Behenyl alcohol, lignoceryl alcohol, ceryl alcohol, 1-heptacosanol, montanyl alcohol, 1-nonacosanol, myricyl alcohol, 1-dotriacontanol, and geddyl alcohol are together classified as policosanol, with montanyl alcohol and myricyl alcohol being the most abundant. Octanol is a straight chain fatty alcohol with eight carbon atoms and the molecular formula CH3(CH2)7OH. Although the term octanol usually refers exclusively to the primary alcohol 1-octanol, there are other less common isomers of octanol such as the secondary alcohols 2-octanol, 3-octanol and 4... 2-Ethylhexanol, or isooctanol, is an organic compound used in the manufacture of a variety of products. ... 1-Nonanol is a straight chain fatty alcohol with nine carbon atoms and the molecular formula CH3(CH2)8OH. It is a colorless to slightly yellow liquid with a citrus odor similar to citronella oil. ... 1-Decanol is a straight chain fatty alcohol with ten carbon atoms and the molecular formula CH3(CH2)9OH. It is a colorless viscous liquid that is insoluble in water. ... Dodecanol, also known by its IUPAC name 1-dodecanol or dodecan-1-ol, and by its trivial name dodecyl alcohol and lauryl alcohol, is a fatty alcohol. ... 1-Tetradecanol, or commonly myristyl alcohol, is a straight-chain saturated fatty alcohol, with the molecular formula C14H30O. It is a white crystalline solid that is practically insoluble in water, soluble in diethyl ether, and slightly soluble in ethanol. ... Cetyl alcohol, also known as 1-hexadecanol, is a solid organic compound and a member of the alcohol class of compounds. ... Stearyl alcohol (also known as octadecyl alcohol or 1-octadecanol) is a substance prepared from stearic acid by the process of catalytic hydrogenation. ... Oleyl alcohol is an alcohol coming from inedible beef fat, chemical formula C18H36O. It is an non-ionic, unsaturated fatty alcohol. ... Arachidyl alcohol, also 1-eicosanol, is a straight-chain fatty alcohol, with formula C20H41OH. Categories: | ... This page is a candidate for speedy deletion. ... Octanosol, 1-octacosanol, montanyl alcohol, or cluytyl alcohol is a fatty alcohol with 28 carbon atoms and chemical formula C28H57OH. It is the main ingredient of Policosanol. ... Octanosol, 1-octacosanol, montanyl alcohol, or cluytyl alcohol is a fatty alcohol with 28 carbon atoms and chemical formula C28H57OH. It is the main ingredient of Policosanol. ... This page is a candidate to be moved to Wiktionary. ... Triacontanols are fatty alcohols of the general formula C30H62O, also known as Melissyl alcohol or Myricyl alcohol. ... This page is a candidate for speedy deletion. ... Octanosol, 1-octacosanol, montanyl alcohol, or cluytyl alcohol is a fatty alcohol with 28 carbon atoms and chemical formula C28H57OH. It is the main ingredient of Policosanol. ... This page is a candidate to be moved to Wiktionary. ... Policosanol (or polycosanol) is the generic term for a natural extract of plant waxes. ...

Nutrition

Very long chain fatty alcohols (VLCFA), obtained from plant waxes and beeswax have been reported to lower plasma cholesterol in humans. They can be found in unrefined cereal grains, beeswax, and many plant-derived foods. Reports suggest that 5–20 mg per day of mixed C24–C34 alcohols, including octacosanol and triacontanol, lower low-density lipoprotein (LDL) cholesterol by 21%–29% and raise high-density lipoprotein cholesterol by 8%–15%. Wax esters are hydrolyzed by a bile salt–dependent pancreatic carboxyl esterase, releasing long chain alcohols and fatty acids that are absorbed in the gastrointestinal tract. Studies of fatty alcohol metabolism in fibroblasts suggest that very long chain fatty alcohols, fatty aldehydes, and fatty acids are reversibly inter-converted in a fatty alcohol cycle. The metabolism of these compounds is impaired in several inherited human peroxisomal disorders, including adrenoleukodystrophy and Sjögren-Larsson syndrome. ^[2] Concentrations of VLCFA in blood plasma increase during fasting and when children are placed on ketogenic diets to suppress seizures. For the rock song by Nirvana, see Beeswax (song). ... Cholesterol is a sterol (a combination steroid and alcohol). ... This page is a candidate to be moved to Wiktionary. ... Low-density lipoprotein (LDL) refers to a class and range of lipoprotein particles, varying somewhat in their size and contents, which carry cholesterol in the blood and around the body, for use by various cells. ... High density lipoproteins (HDL) form a class of lipoproteins, varying somewhat in their size and contents, that carry cholesterol from the bodys tissues to the liver. ... Hydrolysis is a chemical process in which a molecule is cleaved into two parts by the addition of a molecule of water. ... Bile (or gall) is a bitter, yellow or green alkaline fluid secreted by hepatocytes from the liver of most vertebrates. ... The pancreas is a retroperitoneal organ that serves two functions: exocrine - it produces pancreatic juice containing digestive enzymes endocrine - it produces several important hormones Anatomy The pancreas is a retroperitoneal organ located posterior to the stomach on the posterior abdominal wall. ... Gut redirects here. ... A fibroblast is a cell that makes the structural fibers and ground substance of connective tissue. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid (or organic acid), often with a long aliphatic tail (long chains), either saturated or unsaturated. ... Basic structure of a peroxisome Peroxisomes are ubiquitous organelles in eukaryotes that function to rid the cell of toxic substances. ... Adrenoleukodystrophy (ALD) (also known as Schilders Disease and Sudanophilic Leukodystrophy) is a rare inherited disorder that leads to progressive brain damage, failure of the adrenal gland and eventually death. ... Sjogren-Larsson syndrome (or Ruds syndrome) is a form of ichthyosis associated with a deficiency of the enzyme fatty aldehyde dehydrogenase. It was characterized by Karl Sjögren and Tage Larsson It should not be confused with Sjögrens syndrome, which is a distinct condition named after a... Fasting is primarily the act of willingly abstaining from some or all food, drink, or both, for a period of time. ... The ketogenic diet is a treatment for epilepsy that relies on inducing a state of ketosis. ... This article is about the medical condition. ...

Article Sources

• Cyberlipid. Fatty Alcohols and Aldehydes. Retrieved on 2007-02-06. General overview of fatty alcohols, with references.
• CONDEA. Dr. Z Presents All about fatty alcohols. Retrieved on 2007-02-06.

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 37th day of the year in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 37th day of the year in the Gregorian calendar. ...

See also

• Fatty acids
• Fatty aldehydes

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ...

References