# Remedy/Alcohols

International Union of Pure and Applied Chemistry (IUPAC) nomenclature in naming simple alcohols, the name of the alkane chain loses the terminal e and adds the suffix -ol, e.g., as in "ethanol" from the alkane chain name "ethane". When necessary, the position of the hydroxyl group is indicated by a number between the alkane name and the -ol: propan-1-ol for CH $_3$CH $_2$CH $_2$OH, isopropyl alcohol (propan-2-ol) for CH $_3$CH(OH)CH $_3$. If a higher priority group is present (such as an aldehyde, ketone, or carboxylic acid), then the prefix hydroxy-is used, e.g., as in 1-hydroxy-2-propanone (CH $_3$C(O)CH $_2$OH).

## Simple alcohols

Some examples of simple alcohols and how to name them :
| CH $_3$–CH $_2$–CH $_2$–OH | | | | |
| n-propyl alcohol, propan-1-ol, or 1-propanol | isopropyl alcohol, propan-2-ol, or 2-propanol | cyclohexanol | isobutyl alcohol, 2-methylpropan-1-ol, or 2-methyl-1-propanol | tert-amyl alcohol, 2-methylbutan-2-ol, or 2-methyl-2-butanol |
| A primary alcohol | A secondary alcohol | A secondary alcohol | A primary alcohol | A tertiary alcohol |
In cases where the OH functional group is bonded to an sp$^2$ carbon on an aromatic compound (aromatic ring) the molecule is known as a phenol, and is named using the IUPAC rules for naming phenols.
| Type | Formula | IUPAC Name | Common name |
| Monohydric alcohols | CH $_3$OH | Methanol | Wood alcohol |
| Monohydric alcohols | C $_2$H $_5$OH | Ethanol | Alcohol |
| Monohydric alcohols | C $_3$H $_7$OH | Propan-2-ol | Isopropyl alcohol, Rubbing alcohol |
| Monohydric alcohols | C $_4$H $_9$OH | Butan-1-ol | Butanol, Butyl alcohol |
| Monohydric alcohols | C $_5$H $_{11}$OH | Pentan-1-ol | Pentanol, Amyl alcohol |
| Monohydric alcohols | C $_{16}$H $_{33}$OH | Hexadecan-1-ol | Cetyl alcohol |
| Polyhydric alcohols | C $_2$H $_4$(OH) $_2$ | Ethane-1,2-diol | Ethylene glycol |
| Polyhydric alcohols | C $_3$H $_6$(OH) $_2$ | Propane-1,2-diol | Propylene glycol |
| Polyhydric alcohols | C $_3$H $_5$(OH) $_3$ | Propane-1,2,3-triol | Glycerol |
| Polyhydric alcohols | C $_4$H $_6$(OH) $_4$ | Butane-1,2,3,4-tetraol | Erythritol, Threitol |
| Polyhydric alcohols | C $_5$H $_7$(OH) $_5$ | Pentane-1,2,3,4,5-pentol | Xylitol |
| Polyhydric alcohols | C $_6$H $_8$(OH) $_6$ | hexane-1,2,3,4,5,6-hexol | Mannitol, Sorbitol |
| Polyhydric alcohols | C $_7$H $_9$(OH) $_7$ | Heptane-1,2,3,4,5,6,7-heptol | Volemitol |
| Unsaturated aliphatic alcohols | C $_3$H $_5$OH | Prop-2-ene-1-ol | Allyl alcohol |
| Unsaturated aliphatic alcohols | C $_{10}$H $_{17}$OH | 3,7-Dimethylocta-2,6-dien-1-ol | Geraniol |
| Unsaturated aliphatic alcohols | C $_3$H $_3$OH | Prop-2-yn-1-ol | Propargyl alcohol |
| Alicyclic alcohols | C $_6$H $_6$(OH) $_6$ | Cyclohexane-1,2,3,4,5,6-hexol | Inositol |
| Alicyclic alcohols | C $_{10}$H $_{19}$OH | 5-Methyl-2-(propan-2-yl)cyclohexan-1-ol | Menthol |

## Polycosanols

Def. an "extract of plant waxes, rich in long-chain aliphatic alcohols" is called a polycosanol, or policosanol.
Policosanol was originally derived from sugar cane but the chemicals can also be isolated from beeswax, cereal grains, grasses, leaves, fruits, nuts, and seeds of many foods. Policosanols are very long chain alcohols with carbon backbones ranging from 24 to 34 carbons.
The first policosanol supplements were produced by Dalmer Laboratories in Cuba; studies conducted and published by that group have found that policosanol is safe and effective as a lipid-lowering agent; however these studies were small, and efforts by groups outside of Cuba have failed to replicate these results.
A meta-analysis in 2005 concluded that human policosanol consumption is safe and well tolerated and is effective at lowering the blood cholesterol. As of 2010, they were marketed as lipid-lowering agents in the Caribbean, Central and South America, and Canada. Furthermore, another meta-analysis was published in 2018 with 22 studies and 1886 subjects showed policosanol could improve dyslipidemia with raising HDL. The blood pressure lowering effect of Cuban policosanol has been shown in an animal model using spontaneously hypertensive rats (SHR) and a human trial.
"Weighted estimates of percent change in LDL were -11.0% for plant sterol and stanol esters 3.4 g/day (range 2-9 g/day [893 patients]) versus -2.3% for placebo (769 patients) in 23 eligible studies, compared with -23.7% for policosanol 12 mg/day (range 5-40 mg/day [1528 patients]) versus -0.11% for placebo (1406 patients) in 29 eligible studies."
A "nutraceutical combination (NC), consisting of 500 mg berberine, 200 mg red yeast rice and 10 mg policosanols, on cholesterol levels and endothelial function in patients with hypercholesterolemia [produced] a main outcome measure was decrease total cholesterol (C) levels in the NC arm. Secondary outcome measures were decreased low-density lipoprotein cholesterol (LDL-C) and triglyceride levels, and improved endothelial-dependent flow-mediated dilation (FMD) and insulin sensitivity in relation to NC. Evaluation of absolute changes from baseline showed significant reductions in NC versus placebo for C and LDL-C (C: −1.14 ± 0.88 and −0.03 ± 0.78 mmol/l, p < 0.001; LDL-C: −1.06 ± 0.75 and −00.4 ± 0.54 mmol/l, p < 0.001), and a significant improvement of FMD (3 ± 4% and 0 ± 3% respectively, p < 0.05). After the extension phase, triglyceride levels decreased significantly from 1.57 ± 0.77 to 1.26 ± 0.63 mmol/l, p < 0.05 and insulin sensitivity improved in a patient subgroup with insulin resistance at baseline (HOMA: from 3.3 ± 0.4 to 2.5 ± 1.3, p < 0.05)."
"Policosanol (10 mg/day) significantly reduced total cholesterol by 17.5% and LDL cholesterol by 21.8% compared with baseline and placebo. Furthermore, high-density lipoprotein (HDL) cholesterol was raised by 11.3% (not significant), and triglycerides showed a statistically nonsignificant decrease of 6.6%. These changes in lipid profile were similar to those induced by policosanol in nondiabetic patients with type II hyperlipoproteinemia."
"At 4 (p < 0.0001) and 8 (p < 0.00001) weeks, policosanol 10 mg/day significantly lowered serum LDL-C levels by 17.5 and 23.1%, respectively compared with baseline; corresponding values for atorvastatin were 28.4 and 29.8%. At study completion, policosanol significantly (p < 0.0001) reduced serum TC (16.4%), LDL-C/HDL-C ratio (25.5%) and TC/HDL-C ratio (19.3%), as well as (p < 0.001) triglyceride levels (15.4%). Atorvastatin significantly (p < 0.0001) decreased serum TC (22.6%), LDL-C/HDL-C (26.2%) and TC/HDL-C (19.8%) ratios, as well as (p < 0.001) triglyceride levels (15.5%). Atorvastatin was significantly more effective than policosanol in reducing LDL-C and TC, but similar in reducing both atherogenic ratios and triglyceride levels. Policosanol, but not atorvastatin, significantly (p < 0.05) increased serum HDL-C levels by 5.3%. Both treatments were well tolerated. At study completion, atorvastatin mildly, but significantly (p < 0.05) increased creatine phosphokinase (CPK) and creati-nine, whereas policosanol significantly reduced AST and glucose (p < 0.01) and CPK (p < 0.05) levels. All individual values, however, remained within normal limits. Three atorvastatin but no policosanol patients withdrew from the study because of adverse events: muscle cramps (1 patient), gastritis (1 patient) and uncontrolled hypertension, abdominal pain and myalgia (1 patient). Overall, no policosanol and seven atorvastatin patients (18.9%) reported a total of nine mild or moderate adverse events during the study (p < 0.01)."
"Fifty-three elderly patients (60 to 77 years of age) with primary hypercholesterolemia (total serum cholesterol ⩾240 mg/dL) were enrolled in a randomized, double-masked, parallel-group, comparative study of policosanol—a new cholesterol-lowering agent obtained from sugarcane wax—and simvastatin. Before randomization, all patients were advised to follow a standard cholesterol-lowering diet for 6 weeks. Patients were randomized to receive either policosanol or simvastatin, both at doses of 10 mg/d for 8 weeks. With policosanol, total cholesterol, low-density lipoprotein cholesterol (LDL-C), and triglycerides were significantly reduced 14.7%, 17.9%, and 13.8%, respectively. Simvastatin significantly lowered total cholesterol 15.2%, LDL-C 19.8%, and triglycerides 8.7%. Neither policosanol nor simvastatin significantly changed high-density lipoprotein cholesterol (HDL-C) levels. Total cholesterol:HDL-C and LDL-C:HDL-C ratios were significantly lowered by both therapies. The effects of both drugs on lipid profile variables were statistically similar. Both drugs were well tolerated."
"After 5 weeks of a standard step-1 lipid-lowering diet, 437 patients were randomized to receive, under double-blind conditions, 5 mg policosanol or placebo once a day with the evening meal for 12 weeks and 10 mg policosanol or placebo for the next 12 weeks."
"Both groups were similar at randomization. Policosanol (5 and 10 mg/day) significantly reduced (P < .001) serum low-density lipoprotein cholesterol (18.2% and 25.6%, respectively) and cholesterol (13.0% and 17.4%), and it significantly raised (P < .01) high-density lipoprotein cholesterol (15.5% and 28.4%). Triglycerides remained unchanged after the first 12 weeks and lowered significantly (5.2%; P < .01) at study completion. Policosanol was safe and well tolerated, and no drug-related disturbances were observed. Two male patients who received placebo died during the study—one because of a myocardial infarction and the other because of a cardiac arrest that occurred during a surgical intervention. There were 11 serious adverse events (5.1%) in 10 patients who received placebo (4.6%), 7 of which were vascular, compared with no serious adverse events reported in patients receiving policosanol (P < .01)."
Fatty alcohols (or long-chain alcohols), usually high-molecular-weight, straight-chain primary alcohols, can range from as few as 4–6 carbons to as many as 22–26, derived from natural fats and oils, where the precise chain length varies with the source.
"Policosanol is a mixture of alcohols isolated and purified from sugar cane (Saccharum officinarum L). It consists mainly of 66-percent octacosanol (C $_{28}$H $_{58}$O), 12-percent triacontanol, and 7-percent hexacosanol. Other alcohols (15%), namely tetracosanol, heptacosanol, nonacosanol, dotriacontanol and tetratriacontanol, are minor components.(1)"
Dodecanol, or lauryl alcohol, an organic compound (C$_{12}$H$_{26}$O) produced industrially from palm kernel oil or coconut oil, a fatty alcohol is tasteless and colorless with a floral odor.
Oleyl alcohol, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C $_{18}$H $_{36}$O or the condensed structural formula CH$_3$(CH$_2$)$_7$-CH=CH-(CH$_2$)$_8$OH. It is a colorless oil, mainly used in cosmetics.
Stearyl alcohol, or 1-octadecanol, an organic compound classified as a saturated fatty alcohol with the formula CH$_3$(CH$_2$)$_{16}$CH$_2$OH (C$_{18}$H$_{38}$O), application as an evaporation suppressing monolayer when applied to the surface of water.
1-Tetracosanol (lignoceryl alcohol) is a fatty alcohol containing 24 carbon atoms C $_{24}$H $_{50}$O, usually derived from the fatty acid lignoceric acid.
1-Hexacosanol a saturated primary fatty alcohol with a carbon chain length of 26 (C $_{26}$H $_{54}$O) that is a white waxy solid at room temperature, occurs naturally in the epicuticular wax and plant cuticle of many plant species.
1-Heptacosanol is a fatty alcohol with the formula C $_{27}$H $_{56}$O.
1-Octacosanol (also known as n-octacosanol, octacosyl alcohol, cluytyl alcohol, montanyl alcohol) is a straight-chain aliphatic 28-carbon primary fatty alcohol (C $_{28}$H $_{58}$O) that is common in the epicuticular waxes of plants, including the leaves of many species of Eucalyptus, of most forage and cereal grasses, of Acacia, Trifolium, Pisum and many other legume genera among many others, sometimes as the major wax constituent. Octacosanol also occurs in wheat germ.
Octacosanol is the main component in the mixture policosanol. Octacosanol has been subject to preliminary study for its potential benefit for patients with Parkinson's disease. Studies have also found that octacosanol may inhibit the production of cholesterol. In mice, octacosanol reduces stress and restores stress-affected sleep back to normal.
"Daily doses of 10 mg of policosanol have been shown to be equally effective in lowering total or LDL cholesterol as the same dose of simvastatin or pravastatin. Triglyceride levels are not influenced by policosanol."
1-Nonacosanol is a straight-chain aliphatic 29-carbon primary fatty alcohol with the formula C $_{29}$H $_{60}$O.
1-Triacontanol (n-triacontanol) is a fatty alcohol of the general formula C $_{30}$H $_{62}$O, also known as melissyl alcohol or myricyl alcohol, found in plant cuticle waxes and in beeswax, a growth stimulant for many plants, most notably roses, in which it rapidly increases the number of basal breaks, a natural plant growth regulator, widely used to enhance the yield of various crops around the world, mainly in Asia.
Triacontanol was first isolated in 1933 from alfalfa, identified as a saturated straight chain primary alcohol. Triacontanol is found in various plant species as a minor component of the epicuticular wax, in wheat, triacontanol is about 3-4% of the leaf wax. A substantial increase in yield and growth has been seen in different plants, such as cucumber, tomatoes, wheat, maize, lettuce, and rice.
1-Dotriacontanol is a fatty alcohol with 32 carbon atoms for a chemical formula C $_{32}$H $_{66}$O.
Geddic acid, or tetratriacontanoic acid, is a 34-carbon-long carboxylic acid and saturated fatty acid that occurs in cotton, carnauba, candelilla wax and in ghedda wax (wild beeswax), from which its common name is derived with the formula C $_{34}$H $_{68}$O $_2$. Tetratriacontanol has the chemical formula C $_{34}$H $_{70}$O.
"The total [polycosanol] PC contents of wheat straw (164 mg/kg) and sugar cane peel (270 mg/kg) were of the same order of magnitude. The total PC contents of brown beeswax were about 20 and 45 times higher than those of the [wheat germ oil] WGO-solids and sugar cane peel, respectively. Commercial dietary supplements contained less total PC than were claimed on the product labels."