trans-Zeatin
[CAS# 1637-39-4]

Identification

• Classification: Chemical pesticide >> Plant growth regulator
• Name: trans-Zeatin
• Synonyms: (E)-2-Methyl-4-(1H-purin-6-ylamino)-2-buten-1-ol; trans-6-(4-Hydroxy-3-methylbut-2-enylamino)purine
• Molecular Formula: C₁₀H₁₃N₅O
• Molecular Weight: 219.25
• CAS Registry Number: 1637-39-4
• EC Number: 605-343-5
• SMILES: C/C(=C\CNC1=NC=NC2=C1NC=N2)/CO

Properties

• Solubility: soluble (water) (Expl.)
• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 207 ºC (Expl.)
• Index of Refraction: 1.684, Calc.^*
• Boiling Point: 395.0±52.0 ºC (760 mmHg), Calc.^*
• Flash Point: 192.7±30.7 ºC, Calc.^*

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319
• Precautionary Statements: P264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Trans-zeatin is a naturally occurring cytokinin, a type of plant hormone that plays a crucial role in regulating cell division, growth, and differentiation. It is one of the most studied and biologically active forms of zeatin, which belongs to a group of compounds known as adenine derivatives. Trans-zeatin is primarily found in plants, where it helps modulate a variety of physiological processes, including the formation of lateral buds, chloroplast development, and the delay of leaf senescence. The discovery of trans-zeatin can be traced back to the study of plant growth regulators in the 1950s, when scientists were first exploring the chemical signals that control plant development.

The discovery of trans-zeatin came about during research into plant hormones that control cell division. It was first identified in the late 1950s by scientists studying the effects of kinetin, a synthetic cytokinin, on plant growth. Kinetin was found to stimulate cell division, and through subsequent studies, natural cytokinins, including zeatin, were isolated from plant tissues, with trans-zeatin being one of the most prominent forms. The structure of zeatin was determined to be a derivative of adenine, with a hydroxy group at the 9-position of the purine ring and an isopentenyl side chain at the 6-position. This structural feature distinguishes it from other types of adenine derivatives and contributes to its biological activity.

The synthesis of trans-zeatin is primarily achieved through the isolation from plant tissues or by chemical synthesis. One common approach for obtaining trans-zeatin is by extracting it from plant tissues such as maize kernels or coconut milk, where it is found in relatively high concentrations. Another method is chemical synthesis, where zeatin can be synthesized through reactions involving adenine and isopentenyl pyrophosphate. The chemical synthesis of trans-zeatin often involves protecting groups to prevent unwanted reactions, and purification techniques such as chromatography are used to isolate the pure compound.

Trans-zeatin has significant applications in both plant biology and agriculture. In plants, it is involved in the regulation of numerous growth processes, such as promoting cell division in the shoot and root meristems, and delaying senescence in leaves. These properties make it a valuable tool in agricultural practices, particularly in crop production and plant tissue culture. In agriculture, trans-zeatin has been used to improve the growth of certain crops by promoting branching and increasing yield. In tissue culture, it is often used in combination with other plant hormones to induce callus formation and shoot regeneration, making it essential for plant propagation. Additionally, trans-zeatin is being investigated for its potential applications in agriculture to help crops cope with environmental stresses such as drought or salinity.

In conclusion, trans-zeatin is a pivotal plant hormone with significant roles in regulating plant growth and development. Its discovery has expanded the understanding of plant biology and has led to its application in agriculture, where it is used to improve crop yields and facilitate plant tissue culture. Further research continues to explore its potential in improving agricultural practices and developing crops that are more resilient to environmental stresses.