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6-benzylaminopurine, also known as 6-benzyl adenine, etc., chemical substance, molecular formula C12H11N5, white crystalline powder, insoluble in water and general organic solvents, soluble in hot ethanol, slightly soluble in hot water , Soluble in dilute acid and dilute alkaline aqueous solution. Stable, does not react with strong oxidants, is flammable, and burns to produce toxic nitrogen oxide fumes. The main function is to promote the formation of buds, and can also induce callus. It can be used to improve the quality and output of tea and tobacco; to keep vegetables and fruits fresh and to cultivate rootless bean sprouts, and to obviously improve the quality of fruits and leaves.
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Chemical Formula |
C12H11N5 |
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Exact Mass |
225 |
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Molecular Weight |
225 |
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m/z |
225 (100.0%), 226 (13.0%), 226 (1.8%) |
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Elemental Analysis |
C, 63.99; H, 4.92; N, 31.09 |
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6-Benzylaminopurine (6-BA), as the first artificially synthesized cytokinin plant growth regulator, has been widely used in agriculture, horticulture, food preservation, and industry since its first synthesis by the Wilcombe Laboratory in 1952 due to its properties of promoting cell division, delaying aging, and preserving greenery and preventing aging.
Chemical properties: 6-BA is a white crystalline powder with the molecular formula C 12H11N5, melting point 234-235 ℃, insoluble in water but easily soluble in organic solvents. Its chemical structure is stable and not easily decomposed in acidic or alkaline environments, making it suitable for storage and application in various environments.
Mechanism of action: As a cytokinin, 6-BA regulates plant growth through the following pathways:
Promote cell division and differentiation: Activate the expression of cyclin genes, accelerate the cell cycle process, and induce non differentiated tissues (such as callus) to differentiate into organs such as roots and shoots.
Delaying aging: Inhibiting the degradation of chlorophyll, nucleic acids, and proteins, maintaining cell membrane integrity, reducing the accumulation of reactive oxygen species (ROS), thereby delaying leaf yellowing and fruit softening.
Regulating substance transport: promoting the targeted transport of amino acids, auxin, and inorganic salts to the treatment site, enhancing local nutrient supply.
Breaking the apical advantage: By inhibiting the polar transport of auxin, weakening the inhibitory effect of apical meristem on lateral buds, and promoting lateral branch germination.
1. Increase and improve the quality of grain crops
Rice: Spraying stems and leaves with 10mg/L 6-BA solution during the 1-1.5 leaf stage can inhibit premature senescence of lower leaves, maintain root vitality, and increase the survival rate of rice seedlings by 15% -20%.
Wheat: Soaking treatment (20-30mg/L, 24 hours) can increase germination rate by 10% -15%, shorten emergence time by 2-3 days, and significantly enhance stress resistance during seedling stage.
Corn: Spraying 20mg/L 6-BA solution during the female flower development period can increase the number of female ear branches, improve the seed setting rate by 8% -12%, and increase the yield per plant by 0.2-0.3kg.
2. Improvement of economic crop benefits
Citrus flower and fruit preservation: Spraying 33.3-50mg/L 6-BA solution at 2/3 of flower senescence and during the second physiological fruit drop period can reduce the fruit drop rate by 30% -40% and increase the soluble solids content of the fruit by 1.5% -2.0%.
Seedless cultivation of grapes: Dip the inflorescence in 100mg/L 6-BA before flowering, and treat with gibberellin to induce seedless fruit formation, resulting in a 20% -30% increase in fruit weight.
Tea quality improvement: Spraying 5-10mg/L 6-BA solution during the growth period of tea tree shoots can increase the tenderness of buds and leaves, increase amino acid content by 15% -20%, reduce tea polyphenol content by 8% -10%, and significantly improve tea flavor.
3. Optimization of vegetable production
Induction of female flowers in cucumber: Soaking roots in 15mg/L 6-BA solution for 24 hours before transplanting can increase the proportion of female flowers by 25% -30% and increase early yield by 18% -22%.
Tomato fruit setting enhancement: Spraying 100mg/L 6-BA solution during flowering can reduce the incidence of hollow fruits, increase single fruit weight by 10% -15%, and increase the commercial fruit rate by 20%.
Rootless cultivation of bean sprouts: Adding 0.01g/kg 6-BA in bean sprout production can inhibit root and shoot growth, make bean sprouts thick, crispy, and tender, and extend their shelf life by 2-3 days.
Innovation in Horticulture and Flower Management
1. Cut flower preservation technology
Rose cut flowers: Soaking the base in a 50mg/L 6-BA solution for 10 minutes after harvesting can delay petal wilting, extend vase life by 4-5 days, and increase flower diameter by 10% -15%.
Chrysanthemum preservation: Adding 30mg/L 6-BA to the preservation solution can inhibit ethylene synthesis, reduce petal shedding, and extend the ornamental period of cut flowers by 7-10 days.
2. Shape control of ornamental plants
Rhododendron lateral bud promotion: Spraying the whole plant with a 250-500mg/L 6-BA solution twice during the growth period (with an interval of 1 day) can break the top dominance, increase the number of lateral buds by 3-5 times, and make the plant more compact and plump.
Crab claw orchid bud promotion: Spraying 100mg/L 6-BA solution during short day treatment can advance flower bud differentiation time by 10-15 days and increase the number of buds by 40% -50%.
3. Improvement of stress resistance in potted plants
Drought resistance training for green ivy: Spraying 20mg/L 6-BA solution before drought stress can prolong the relative water content maintenance time of leaves by 3-5 days, reduce stomatal conductance by 40%, and significantly improve drought resistance.
Succulent plant tissue culture: Adding 0.5mg/L 6-BA to MS medium can induce rapid proliferation of callus tissue, increase differentiation rate to over 90%, and shorten the propagation cycle by 50%.
Breakthrough in Food Preservation Technology
1. Preservation of leafy vegetables
Preservation of water spinach: Soaking in 30mg/L 6-BA solution for 15 minutes at 10 ℃ and 90% -95% humidity can prolong the maintenance time of chlorophyll content by 8-10 days, increase the activity of superoxide dismutase (SOD) by 30%, and reduce the accumulation of malondialdehyde (MDA) by 50%.
Spinach preservation: Spraying 20mg/L 6-BA solution after harvesting, combined with 1-MCP treatment, can extend the shelf life by 12-15 days and increase vitamin C retention rate by 25%.
2. Maintenance of post harvest quality of fruits and vegetables
Litchi preservation: After harvesting, soaking in 100mg/L 6-BA solution for 1 minute (combined with gibberellin treatment) can reduce the browning index of the fruit peel by 60%, increase the yield of good fruit to over 90%, and extend the storage period to 30 days.
Mango preservation: Fumigation treatment with 50mg/L 6-BA solution at 13 ℃ for 4 hours can reduce respiratory intensity by 40%, ethylene release by 65%, and extend hardness and color maintenance time by 10-15 days.
Innovative applications in the industrial sector
1. Synthesis of polymer materials
Special rubber modification: As a monomer involved in the synthesis of nitrile rubber, it can improve the oil resistance of rubber by 30% -40% and increase the tensile strength by 15% -20%. It is widely used in the manufacturing of automotive seals.
Engineering plastic reinforcement: Adding 0.5% -1.0% 6-BA derivatives to polycarbonate (PC) can increase the heat deformation temperature by 20-30 ℃ and the impact strength by 40% -50%, meeting the high temperature environment requirements in the electronic and electrical field.
2. Optimization of adhesive performance
Epoxy resin curing agent: As a modifier added to the epoxy resin system, it can shorten the curing time by 30% -50% and increase the adhesive strength by 25% -30%. It is widely used in the manufacturing of aerospace composite materials.
Thickening of water-based adhesive: adding 0.2% -0.5% 6-BA sodium salt to acrylic lotion can increase the viscosity by 50% -80%, improve the sizing uniformity, and reduce the amount of paint by 10% -15%.
The existing synthesis process is: hypoxanthine is used as a raw material, reacts with phosphorus oxychloride in the presence of N,N-dimethylaniline to obtain 6-chloropurine, and 6-chloropurine is then reacted with benzylamine in the presence of triethylamine The following reaction is carried out to synthesize 6-benzylaminopurin. The main problem of existing technology is: the first step reaction, use greatly excess phosphorus oxychloride (both as chlorination reagent and do solvent), side reaction is many, and productive rate is low, and excessive phosphorus oxychloride can not be obtained by distillation. Recycling can only be decomposed with water, and a large amount of phosphorus-containing wastewater is discharged. N,N-dimethylaniline needs to be recycled, and the discharged wastewater also contains N,N-dimethylaniline, which seriously pollutes the environment; the second step Reaction, in order to improve reaction conversion rate and reaction speed, need to use excessive benzylamine, cause separation and purification process to be complicated.
specific method:
In 5g hypoxanthine, add 20mLSOCl2, 0.25gDMAP, 10gBTC is dissolved in 20mLSOCl2. Heat and add BTC/SOCl2 dropwise. Reflux (refrigerant cooling) to complete dissolution, distill off SOCl2 (containing phosgene, recover and use mechanically), evaporate completely (drain), cool to room temperature, and obtain milky yellow solid (6-chloropurine and DMAP hydrochloride). Add 4g of benzylamine and 25g of triethylamine directly to it, heat to 70-80°C, or microwave heating, until the reaction of 6-chloropurine is complete (TLC monitoring), add ethanol, wash the filtered solid with ethanol, and dry it to get 7 g of the product 6-benzylaminopurine with a brown color.
6-Benzylaminopurine (abbreviated as 6-BA) is the first artificially synthesized cytokinin in the world. Its discovery and application represent a milestone in the field of plant growth regulators.
Research Background and Synthetic Breakthrough
In the late 1940s, the team led by plant physiologist Folke K. Skoog found that adenine exhibited weak cell division-promoting activity, laying the foundation for the artificial synthesis of highly effective analogs.In 1952, based on Skoog's research, the Wellcome Research Laboratories in the United States successfully synthesized 6-BA for the first time. By introducing a benzyl group at the 6-position of the purine ring, its cytokinin activity was significantly enhanced, making it the first synthetic cytokinin with a clear structure and stable activity.
Verification and Early Application
After synthesis, 6-BA was validated in plant tissue culture to efficiently induce callus differentiation, promote bud formation and cell division, with activity superior to that of natural kinetin.In the 1960s, Japan commercialized 6-BA for the first time. It was widely used in plant tissue culture media (such as MS and N6 media) and became a core reagent in plant biotechnology. During the same period, its agricultural applications were gradually expanded to flower and fruit retention in fruit trees, vegetable preservation, and crop yield increase.
Domestic Development and Industrialization in China
In 1971, Shanghai Dongfeng Reagent Factory and Shenyang Research Institute of Chemical Industry jointly developed and realized the industrial production of 6‑BA, making it the first commercially produced cytokinin regulator in China.Since then, its application has extended from tissue culture to the entire agricultural sector. After the 1990s, mature compounding technologies with gibberellic acid and other regulators were developed, forming broad-spectrum and high-efficiency plant growth regulation schemes.To this day, 6-BA remains one of the most widely used cytokinins worldwide.
FAQ
What is 6-benzylaminopurine used for?
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6-Benzylaminopurine, benzyl adenine (BAP) is a synthetic cytokinin which together with auxins elicits plant growth and development responses. BAP is a widely use cytokinin supplement to plant growth media such as Murashige and Skoog medium, Gamborg′s medium, and Chu′s N6 medium.
Is 6-benzylaminopurine toxic?
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Harmful if swallowed. Irritating to eyes, respiratory system and skin. Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
What is 6-benzylaminopurine solution?
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Benzylaminopurine (BAP) solution is a plant growth regulator commonly used in plant tissue culture applications to promote cell division and shoot proliferation.
What is 6 BA used for?
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6-Benzylaminopurine (6-BA) Pure Grade is designed to enhance agricultural productivity by promoting robust cell division and healthy shoot formation. Its application is straightforward, supporting a range of crops including vegetables, fruits, cereals, and ornamentals.
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