Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 1-Triacontanol: Difference between pages

{{short description|Straight-chain primary alcohol with formula C30H62O}}

| Watchedfields = changed

| verifiedrevid =

|Reference=<ref>''[[Merck Index]]'', 11th Edition, '''9506'''.</ref>

|ImageFile=Triacontanol.png

|ImageSize=250px

|=Triacontan-1-ol

|OtherNames=1-Triacontanol<br>''n''-Triacontanol<br>Melissyl alcohol<br>Myricyl alcohol

| = {{|correct|}}

| CASNo=593-50-0

| Beilstein = 1711965

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 28409

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1079147

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 209-794-5

| KEGG = C08392

| PubChem =68972

| Formula=C₃₀H₆₂O

| MolarMass=438.81 g/mol

| Appearance=

| Density=0.777 g/ at 95 °C

| MeltingPtC = 87

| BoilingPt=

| Solubility=Insoluble

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

'''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 wax]]es and in [[beeswax]]. Triacontanol is a [[growth factor|growth stimulant]] for many plants, most notably [[rose]]s, 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.<ref>{{cite journal | doi = 10.1080/17429145.2011.619281 | title = Triacontanol: A potent plant growth regulator in agriculture | year = 2012 | last1 = Naeem | first1 = M. | last2 = Khan | first2 = M. Masroor A. | last3 = Moinuddin | journal = Journal of Plant Interactions | volume = 7 | issue = 2 | pages = 129–142 | bibcode = 2012JPlaI...7..129N | s2cid = 84691493 | doi-access = free }}</ref> 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.

==History==

Triacontanol was first isolated in 1933 from [[alfalfa]] wax. It was identified as a saturated straight chain [[primary alcohol]].<ref name=Chibnall>{{cite journal |author=Chibnall, A.C. |author2=E.F. Williams |author3=A.L, Latner |author4=S.H. Piper|date=1933 |title=The isolation of n-triacontanol from lucerne wax |journal=Biochemical Journal |volume=27 |issue=6 |pages=1885–1888 |doi=10.1042/bj0271885 |pmid=16745314 |pmc=1253114 }}</ref> 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.{{citation needed|reason=given citation does not refer to wheat|date=May 2020}}.<ref>Tulloch, A.P., and L.L., Hoffman. 1974. [[Epicuticular wax]] of ''Secale cereale'' and ''Triticale hexaploide'' leaves. Phytochemistry 13: 2535-2540.</ref>

The effects of triacontanol may also be seen when a chopped{{clarify|date=May 2020}} alfafa plant is placed in close proximity to the [[seedlings]] and various crop seeds.{{which|date=May 2020}} A substantial increase in yield and growth has been seen in different plants, such as [[cucumber]], [[tomatoes]], [[wheat]], [[maize]], [[lettuce]], and [[rice]].<ref>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.</ref>

==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.{{clarify|date=May 2020}} 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,{{Eriksen AB, Selldén G, Skogen D, Nilsen S. Comparative analyses of the effect of triacontanol on photosynthesis, photorespiration and growth of tomato (C3-plant) and maize (C 4-plant). Planta. 1981 May;152(1):44-9. doi: 10.1007/BF00384983. PMID: 24302317.|reason=photosynthesis does not occur in dry leaves|date=May 2020}} whereas in the maize plants no change in photosynthesis occurs whether treated by triacontanol or not.<ref>{{cite journal | doi = 10.1007/BF00384983 | title = Comparative analyses of the effect of triacontanol on photosynthesis, photorespiration and growth of tomato (C3-plant) and maize (C4-plant) | year = 1981 | last1 = Eriksen | first1 = A. B. | last2 = Selldén | first2 = G. | last3 = Skogen | first3 = D. | last4 = Nilsen | first4 = S. | journal = Planta | volume = 152 | issue = 1 | pages = 44–49 | pmid = 24302317 | bibcode = 1981Plant.152...44E | s2cid = 9567091}}</ref>

Although, the basic effect of treating seedlings of various plant species is an increase in plant growth, photosynthesis and the yield of the crops, the effects of triacontanol are not the same in every plant species. Some exhibit these symptoms while some show 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.

Triacontanol has been reported to increase productivity of some plants that have some therapeutic properties.<ref>{{cite journal | doi = 10.1093/chromsci/47.10.936 | title = Chromatographic Estimation of p-Coumaric Acid and Triacontanol in an Ayurvedic Root Drug Patala (Stereospermum suaveolens Roxb.) | year = 2009 | last1 = Srivastava | first1 = N. | last2 = Khatoon | first2 = S. | last3 = Rawat | first3 = A. K. S. | last4 = Rai | first4 = V. | last5 = Mehrotra | first5 = S. | journal = Journal of Chromatographic Science | volume = 47 | issue = 10 | pages = 936–939 | pmid = 19930809 | doi-access = free }}</ref> In addition, the effects of triacontanol are observed in opium and morphine production.<ref name=Khan>{{Cite journal |author=M.M.A. Khan |author2=R. Khan |author3=M. Singh |author4=S. Nasir |author5=M. Naeem |author6=M.H. Siddiqui |author7=F. Mohammad |title=Gibberellic acid and triacontanol can ameliorate the opium yield and morphine production in opium poppy (''Papaver somniferum'') |journal=Acta Horticulturae |year=2007 |volume=756 |issue=756 |pages=289–298 |doi=10.17660/ActaHortic.2007.756.30}}</ref>

==Functionality==

There are numerous corporations{{example needed|date=May 2020}} making synthetic triacontanol for enhancing the crop yield and pest resistance in the crops.{{citation needed|date=May 2020}}

Triacontanol improves the rate of cell division in a plant that produces larger roots and shoots. It has been shown that if triacontanol is applied during the maximized growth period of a plant in an appropriate amount, it enhances the enzymatic activity in the roots and [[hormone]] functionality increasing the overall performance of the plant.<ref>Ries, S. and Houtz, R. 1983. Triacontanol as a plant growth regulator. Horticultural Science, 18: 654-662.</ref> Triacontanol basically operates by enhancing the basic functionality of the plant like increasing the rate of photosynthesis and producing more [[sugar]] such as [[glucose]].{{citation needed|date=May 2020}} When photosynthesis operates efficiently, the plant produce more sugars and absorb more [[sunlight]]. The plant then send more sugars to the rhizosphere via the root system where the growth, respiration and nutrient exchange take place in the vicinity of the soil.<ref>Nelson, N. ( 1944 ). A photometric adaptation of the Somogyi's method for the determination of glucose. J. Bioi. Chem. 153:375-380.</ref> Availability of more sugars lead to more respiration and nutrient exchange between the plants and the microorganisms in the soil.

when the microbes receive more sugars from the plant, it increases the microbial activity in the root zone and they perform more efficiently in mining the [[nutrients]] like in the case of [[nitrogen fixation]]. These microorganisms particularly trace the nutrients essential for the soil. These nutrients are further used by the plants to build more complex nutrients and compounds essential for rapid growth and defence from certain other microbes. These complex compounds{{which|date=May 2020}} maximize the yield of the crop. Overall, despite other benefits from adequate amounts of triacontanol, the effect of enhanced photosynthesis may increase the plant outcomes.{{Citation needed|date=May 2020}}

==Synthesis of triacontanol==

There are several chemical pathways via which triacontanol 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 [[desulfurization]] using [[Raney Nickel]]. It produces triacontanoic acid which can be reduced with [[lithium aluminium hydride]] (LAH) to produce 1-triacontanol.<ref>{{cite journal | doi = 10.1016/S0040-4039(01)91306-1 | title = New synthesis of 1-triacontanol | year = 1984 | last1 = Bhalerao | first1 = U.T. | last2 = Rao | first2 = S.Jagadishwar | last3 = Tilak | first3 = B.D. | journal = Tetrahedron Letters | volume = 25 | issue = 47 | pages = 5439–5440}}</ref>

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 or [[stearyl alcohol]] 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 the product. The resulted mixture is hydrogenated to give triacontanol.<ref>{{cite journal | doi = 10.1007/BF00807430 | title = An efficient synthesis of the plant growth hormone 1-triacontanol | year = 1995 | last1 = Tran-Thi | first1 = N. H. | last2 = Falk | first2 = H. | journal = Monatshefte für Chemie Chemical Monthly | volume = 126 | issue = 5 | pages = 565–568 | s2cid = 94909176 }}</ref>

==Physiological effects on some plant species==

===Cacao seedlings===

Cocoa seedlings (''Theobroma cacao'' L.) shows a positive growth in terms of plant length and the leaf size when treated with triacontanol. In a study, the cocoa seedlings when receive an appropriate amount of triacontanol, led to increase in the leaf size, plant length, leaf number as well as the stem diameter of the cocoa plant.<ref>{{cite journal | doi = 10.17503/Agrivita-2014-36-3-260-267 | year = 2014 | last1 = Sitinjak | first1 = Rama Riana | last2 = Pandiangan | first2 = Dingse | title = THE EFFECT OF PLANT GROWTH REGULATOR TRIACONTANOL TO THE GROWTH OF CACAO SEEDLINGS (Theobroma cacao L.) | journal = Agrivita Journal of Agricultural Science | volume = 36 | issue = 3 | doi-access = free }}</ref> which is due to [[biosynthesis]] of secondary metabolites which alters the physiology and the [[biochemistry]] of the plants. Treating the cocoa plant with excess amount of triacontanol led to inhibition of plant growth and bearing of adverse effects on the plant [[physiology]].<ref>Jaybhay, S., P. Chate and A. Ade. 2010. Isolation and identification of crude triacontanol from rice bran wax. Journal of Experimental sciences. 1 (2): 26.</ref>

The provision of triacontanol rapidly increase the morphogenetic response in the plant during the [[embryogenesis]] process. The enhanced response lead to increase in the [[cell division]] and cell growth by the growth regulators. Moreover, it also leads to increased shoots and roots of the plant. The whole process results from the formation of new growth and development proteins and new [[mRNA]].

===''Rhizophora apiculata'' (Mangrove)===

In the hypocotyl treatment of triacontanol in the mangrove plant resulted in increased root and shoot growth. The rise in the number of primary and secondary roots, the length of roots, height and the [[biomass]] resulted from triacontanol treatment. Moreover, the reduction of nitrate reductase as well as increase amount of chlorophylls in the photosystem 1 and 2 observed.<ref>{{cite journal | doi = 10.1007/BF02928035 | title = Physiological responses of mangrove seedling to triacontanol | year = 1993 | last1 = Moorthy | first1 = P. | last2 = Kathiresan | first2 = K. | journal = Biologia Plantarum | volume = 35 | issue = 4 | s2cid = 36478378 }}</ref> However, the increase in the concentration of triacontanol resulted in the decrease of the plant growth. hence, the amount of the alcohol treatment is the driving force for the enhanced results.

===Cell cultures in vitro===

Triacontanol also increases the growth of a cell ''in vitro'' by increasing the cell number in the culture. It can be attributed to the increase protein formation and rapid cell division induced by triacontanol.<ref>{{cite journal | doi = 10.1104/pp.61.5.855 | title = Effect of Triacontanol on Plant Cell Cultures in Vitro | year = 1978 | last1 = Hangarter | first1 = Roger | last2 = Ries | first2 = Stanley K. | last3 = Carlson | first3 = Peter | journal = Plant Physiology | volume = 61 | issue = 5 | pages = 855–857 | pmid = 16660401 | pmc = 1091993 }}</ref>

The growth of cell culture ''in vitro'' has been done with various plant species to observe the effects of triacontanol. Similar effects of triacontanol can be seen with a variety of plants like rice, wheat, corn, maize, cucumber, and many more.

== References ==

{{reflist}}

{{alcohols}}

{{DEFAULTSORT:Triacontanol, 1-}}

[[Category:Fatty alcohols]]

[[Category:Plant hormones]]

[[Category:Primary alcohols]]

[[Category:Alkanols]]

Eriksen AB, Selldén G, Skogen D, Nilsen S. Comparative analyses of the effect of triacontanol on photosynthesis, photorespiration and growth of tomato (C3-plant) and maize (C 4-plant). Planta. 1981 May;152(1):44-9. doi: 10.1007/BF00384983. PMID: 24302317.