1-Triacontanol
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| Names | |
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| IUPAC name
Triacontan-1-ol
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| Other names
1-Triacontanol
n-Triacontanol Melissyl alcohol Myricyl alcohol | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.905 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C30H62O | |
| Molar mass | 438.81 g/mol |
| Density | 0.777 g/ml at 95 °C |
| Melting point | 87 °C (189 °F; 360 K) |
| Insoluble | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-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 or n-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. [2]. A number of researchers has published the results of using triacontanol for increasing the growth of the plant species as well as enhancing the rate of photosynthesis, protein biosynthesis, the transport of nutrients in a plant, increasing enzyme activity, reducing complex carbohydrates among many other purposes. Theoretically, the fatty-alcohol increases the physiological efficiency of the cells of a plant and boost up the potential of the cells responsible for the growth and maturity of a plant.
History
Triacontanol was first isolated in 1933 from a flowering plant Lucrene Alfalfa in the legume family Fabaceae. It was then identified as a saturated straight chain primary alcohol.[3]. Triacontanol is found in various plant species as a minor wax component including the wheat plants, which holds around 3-4 % of triacontanol as a component of the leaf wax.[4]. The effects of tricontanol also be seen when a chopped Alfafa plant is placed in the close proximity of the seedlings and various crop seeds. A substantiate increase in yield and growth has been seen in different plants like cucumber, tomatoes, wheat, corn, lettuce, rice and many more.[5]. The synthetic triacontanol has also shown similar results of enhanced growth in different plant species.
Characteristics
Triacontanol does not react the same way in all plant species. The effects of triacontanol various in terms of photosynthesis and the yield manipulation in plant species. The effects on C-3 plants and C-4 plants. In Tomato plant (C-3 plant), the treatment of triacontanol increases the dry leaf weight and inhibited the photosynthesis by 27% in dry leaves, whereas in the maize plants no change in photosynthesis occurs whether treated by triacontanol or not. [6]. Although, the basic effects of treating the seedlings of various plant species results in the increase in the plant growth, photosynthesis and the yield of the crops, but the effects of triacontanol are not the same in every plant species. Some exhibit these symptoms while some shows no response to the treatment to triacontanol. Different studies reveal that the effects of triacontanol differs with the amounts of the triacontanol used to treat the plant. A much higher dose of triacontanol could also have adverse effects on the growth of a plant.
Synthesis of Triacontanol
There are several chemical pathways through which the natural plant growth hormone can be artificially synthesized. One method includes an organic compound Succinic anhydride and a carboxylic acid docosanoic acid that have been used to attach the different carbon chains (C4 and C22) on 2 and 5 positions of thiophene, via two acylation sequences. Later, 2-5 substituted thiophene is reacted for desulphurization using Raney Nickel. It produces triacontanoic acid which can be reduced with Lithium Aluminum Hydride (LAH) to produce 1-triacontanol.[7].
Another method of synthesizing triacontanol focuses on the high yield with the easily available and feasible compounds that can form triacontanol through some chemical reactions in laboratory settings. 1-octadecanol and 1,12-dodecanediol. Using the phase transfer system the 1-octadecanol is converted to octadecanal. On the other hand, 1,12-dodecanediol goes through the phase transfer bromination and further reacted with 1-hydroxy-12-triphenylphosphonium bromide. Both the end products of the two compounds undergo Witting reaction to give us the product. The resulted mixture is hydrogenated to give us triacontanol.[8].
References
- ^ Merck Index, 11th Edition, 9506.
- ^ Naeem, M. & Khan, M. Masroor & Moinuddin, Anis Shaikh. (2012). Triacontanol: A potent plant growth regulator in agriculture. Journal of Plant Interactions. 7. 129-142. 10.1080/17429145.2011.619281
- ^ Chibnall, A.C., E.F. Williams, A.L, Latner, and S.H. Piper. 1933. The isolation of n-triacontanol from Lucrene wax. Biochem. J. 27:1885-1888
- ^ Tulloch, A.P., and L.L., Hoffman. 1974. Epicuticular wax of secale cereale and Trilicale Hexaploide leaves. Phytochemistry 13: 2535-2540.
- ^ Ries, S.K., H. Bittenbinder, R. Hangarter, L.Kolker, G. Morris, and V. Wert. 1976. Improved Growth and Yield of crops from organic supplements. Pages 377-384 in W. Lokeretz, ed. Energy and Agriculture. Academic Press, New York.
- ^ Eriksen, A.B., Selldén, G., Skogen, D. et al. Comparative analyses of the effect of triacontanol on photosynthesis, photorespiration and growth of tomato (C3-plant) and maize (C4-plant). Planta 152, 44–49 (1981). https://doi.org/10.1007/BF00384983
- ^ U.T. Bhalerao, S. Jagdishwar Rao, B.D. Tilak. 1984. New synthesis of 1-triacontanol. https://doi.org/10.1016/S0040-4039(01)91306-1
- ^ Tran-Thi, N.H., Falk, H. An efficient synthesis of the plant growth hormone 1-triacontanol. Monatsh Chem 126, 565–568 (1995). https://doi.org/10.1007/BF00807430
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