1-Octacosanol

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1-Octacosanol
1-Octacosanol-folded.svg
Names
Preferred IUPAC name
Octacosan-1-ol
Other names
n-Octacosanol; Octacosyl alcohol; Octanosol; Montanyl alcohol; Cluytyl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.348 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH 1-octacosanol
PubChem CID
UNII
  • InChI=1S/C28H58O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29/h29H,2-28H2,1H3 Yes check.svgY
    Key: CNNRPFQICPFDPO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C28H58O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-29/h29H,2-28H2,1H3
    Key: CNNRPFQICPFDPO-UHFFFAOYAC
  • OCCCCCCCCCCCCCCCCCCCCCCCCCCCC
Properties
C28H58O
Molar mass 410.771 g·mol−1
Melting point 83 °C (181 °F; 356 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

1-Octacosanol[ pronunciation? ] (also known as n-octacosanol, octacosyl alcohol, cluytyl[ pronunciation? ] alcohol, montanyl[ pronunciation? ] alcohol) is a straight-chain aliphatic 28-carbon primary fatty alcohol 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. [1] Octacosanol also occurs in wheat germ. [2]

Contents

Chemistry

Octacosanol is insoluble in water but freely soluble in low molecular-weight alkanes and in chloroform.

Biological effects

Octacosanol is the main component in the mixture policosanol. [3] Octacosanol has been subject to preliminary study for its potential benefit for patients with Parkinson's disease. [4] [5] Studies have also found that octacosanol may inhibit the production of cholesterol. [3] In mice, octacosanol reduces stress and restores stress-affected sleep back to normal. [6]

Related Research Articles

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Germline

In biology and genetics, the germline is the population of a multicellular organism's cells that pass on their genetic material to the progeny (offspring). In other words, they are the cells that form the egg, sperm and the fertilised egg. They are usually differentiated to perform this function and segregated in a specific place away from other bodily cells.

Neurotrophin

Neurotrophins are a family of proteins that induce the survival, development, and function of neurons.

1-Triacontanol (n-triacontanol) is a fatty alcohol of the general formula C30H62O, also known as melissyl alcohol or myricyl alcohol. It is found in plant cuticle waxes and in beeswax. Triacontanol is a growth stimulant for many plants, most notably roses, in which it rapidly increases the number of basal breaks. 1-Triacontanol is a natural plant growth regulator. It has been widely used to enhance the yield of various crops around the world, mainly in Asia. Triacontanol has been reported to increase the growth of plants by enhancing the rates of photosynthesis, protein biosynthesis, the transport of nutrients in a plant and enzyme activity, reducing complex carbohydrates among many other purposes. The fatty alcohol appears to increase the physiological efficiency of plant cells and boost the potential of the cells responsible for the growth and maturity of a plant.

Germline mutation Inherited genetic variation

A germline mutation, or germinal mutation, is any detectable variation within germ cells. Mutations in these cells are the only mutations that can be passed on to offspring, when either a mutated sperm or oocyte come together to form a zygote. After this fertilization event occurs, germ cells divide rapidly to produce all of the cells in the body, causing this mutation to be present in every somatic and germline cell in the offspring; this is also known as a constitutional mutation. Germline mutation is distinct from somatic mutation.

Nerve growth factor

Nerve growth factor (NGF) is a neurotrophic factor and neuropeptide primarily involved in the regulation of growth, maintenance, proliferation, and survival of certain target neurons. It is perhaps the prototypical growth factor, in that it was one of the first to be described. Since it was first isolated by Nobel Laureates Rita Levi-Montalcini and Stanley Cohen in 1956, numerous biological processes involving NGF have been identified, two of them being the survival of pancreatic beta cells and the regulation of the immune system.

Appressorium

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Aldehyde dehydrogenase

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Wheat germ oil

Wheat germ oil is extracted from the germ of the wheat kernel, which makes up only 2.5% by weight of the kernel Wheat germ oil is particularly high in octacosanol - a 28-carbon long-chain saturated primary alcohol found in a number of different vegetable waxes. Octacosanol has been studied as an exercise- and physical performance-enhancing agent. Very long chain fatty alcohols obtained from plant waxes and beeswax have been reported to lower plasma cholesterol in humans. Wheat germ oil is also very high in vitamin E (255 mg/100g), and has the highest content of vitamin E of any food that has not undergone prior preparation or vitamin fortification. As a cooking oil, wheat germ oil is strongly flavored, expensive and easily perishable. Wheat germ oil contains the following fatty acids:

Plant cuticle waterproof covering of aerial plant organs

A plant cuticle is a protecting film covering the epidermis of leaves, young shoots and other aerial plant organs without periderm. It consists of lipid and hydrocarbon polymers impregnated with wax, and is synthesized exclusively by the epidermal cells.

Germ-free animal Multi-cellular organisms that have no microorganisms living in or on them

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Ursolic acid Pentacyclic chemical compound found in fruits

Ursolic acid, is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

cAMP responsive element modulator

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Gut–brain axis

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References

  1. EA Baker (1982) Chemistry and morphology of plant epicuticular waxes. pp. 139–165. In "The Plant Cuticle". edited by DF Cutler, KL Alvin and CE Price. Academic Press, London. ISBN   0-12-199920-3
  2. "Octacosanol". Natural Products (Professional). drugs.com. Archived from the original on 3 June 2009. Retrieved 9 July 2009. isolated from wheat germ oil or other plants
  3. 1 2 Taylor, Johanna C; Rapport, Lisa; Lockwood, G.Brian (2003). "Octacosanol in human health". Nutrition. 19 (2): 192–5. doi:10.1016/S0899-9007(02)00869-9. PMID   12591561.
  4. Snider, SR (1984). "Octacosanol in parkinsonism". Annals of Neurology. 16 (6): 723. doi:10.1002/ana.410160615. PMID   6395790. S2CID   43313071.
  5. Wang, T; Liu, YY; Wang, X; Yang, N; Zhu, HB; Zuo, PP (2010). "Protective effects of octacosanol on 6-hydroxydopamine-induced Parkinsonism in rats via regulation of ProNGF and NGF signaling". Acta Pharmacologica Sinica. 31 (7): 765–74. doi:10.1038/aps.2010.69. PMC   4007727 . PMID   20581854.
  6. Kaushik, MK; Aritake, K; Takeuchi, A; Yanagisawa, M; Urade, Y (21 August 2017). "Octacosanol restores stress-affected sleep in mice by alleviating stress". Scientific Reports. 7 (1): 8892. Bibcode:2017NatSR...7.8892K. doi:10.1038/s41598-017-08874-2. PMC   5566941 . PMID   28827687.