trans-Zeatin

Base Information

• Chemical Name: trans-Zeatin
• CAS No.: 1637-39-4
• Molecular Formula: C10H13N5O
• Molecular Weight: 219.246
• Hs Code.: 29335990
• UNII: 7I6OOJ9GR6
• DSSTox Substance ID: DTXSID9040631
• Nikkaji Number: J7.540J,J3.243.127E
• Wikipedia: Zeatin
• Wikidata: Q22807318
• Metabolomics Workbench ID: 41910
• ChEMBL ID: CHEMBL525239
• Mol file: 1637-39-4.mol

Synonyms:Zeatin

Chemical Property of trans-Zeatin

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 1.78E-14mmHg at 25°C
• Melting Point: 207 °C
• Refractive Index: 1.719
• Boiling Point: 583.885 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 306.923 °C
• PSA: 86.72000
• Density: 1.388 g/cm³
• LogP: 0.77640
• Storage Temp.: −20°C
• Solubility.: H2O: soluble
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 219.11201006
• Heavy Atom Count: 16
• Complexity: 258

Purity/Quality:

99% ^*data from raw suppliers

Trans-Zeatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCNC1=NC=NC2=C1NC=N2)CO
• Isomeric SMILES: C/C(=C\CNC1=NC=NC2=C1NC=N2)/CO
• Description: trans-Zeatin is a cytokinin plant growth regulator with antioxidant and neuroprotective activities. It binds to the cytokinin receptor Arabidopsis histidine kinase 3 (AHK3) with a KD value of 1.3 nM. trans-Zeatin increases chlorophyll levels in etiolated Cucumus sativus cotyledons in a concentration-dependent manner. It increases callus growth and shoot formation in N. tabacum calluses when used at concentrations of 5 and 50 μM. trans-Zeatin (25-100 μM) reduces production of reactive oxygen species (ROS) induced by amyloid β (25-35) (Aβ25-35) in PC12 cells. It reduces scopolamine-induced spontaneous alternations in the Y-maze, indicating enhanced spatial memory, in mice when administered at doses of 1.5, 3, and 4.5 mg/kg per day.
• Uses: Labelled Zeatin. It is purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form -induced matrix metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging. Zeatin, purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging. Zeatin, purified from Zea mays, is a member of the cytokinin group of plant growth factors, the activity of which is attributed to its more stable trans form. Trans-Zeatin inhibits UVB-induced matrix metalloproteinase-1 expression via MAP kinase signaling in human skin fibroblasts. Trans-Zeatin is a potential agent for the management of skin photoaging.

Technology Process of trans-Zeatin

There total 25 articles about trans-Zeatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4-hydroxy-3-methyl-trans-but-2-enylamine (1795-76-2,26806-03-1,35042-70-7) + 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (5399-92-8) → trans-zeatin (1637-39-4)

Guidance literature:

With triethylamine; In ethanol; for 3h; Reflux;

Reference yield: 96.8%

4-hydroxy-3-methyl-trans-but-2-enylamine (1795-76-2,26806-03-1,35042-70-7) + 6-chloropurine (87-42-3) → trans-zeatin (1637-39-4)

Guidance literature:

With triethylamine; In ethanol; for 5h; Reflux;

Reference yield: 71.0%

4-hydroxy-3-methyl-trans-but-2-enylamine (1795-76-2,26806-03-1,35042-70-7) + 6-chloro-7H-purine (87-42-3,111055-92-6) → trans-zeatin (1637-39-4)

Guidance literature:

With triethylamine; In butan-1-ol; for 4h; Reflux;

DOI:10.14233/ajchem.2014.17644

upstream raw materials:

4-hydroxy-3-methyl-trans-but-2-enylamine

6-chloropurine

(2E)-4-hydroxy-3-methylbut-2-enenitrile

(E)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enylamine

Downstream raw materials:

trans-zeatin 9-β-D-ribofuranoside

4-hydroxy-3-methyl-trans-but-2-enylamine

hypoxanthine

(Z)-4-amino-2-methyl-2-buten-1-ol

Refernces

• 1、 Pei, Jianyun,Li, Jie,Xie, Yan,Weng, Jiangsen,Ge, Chengsheng,Wang, Shuhua. "Large-scale synthesis of (E)-4-amino-2-methylbut-2-en-1-ol: Key building block for the synthesis of trans-zeatin". . p. 8155 - 8157. Retrieved 2014.
• 2、 Corse,Kuhnle. "-". . p. 618,619. Retrieved 1972.
• 3、 Mornet,Gouin. "-". . p. 167. Retrieved 1977.
• 4、 -. "Preparation method of zeatin". Paragraph 0073-0076. . Retrieved 2020/09/23.
• 5、 -. "Method for synthesizing adenine and derivatives thereof". Paragraph 0047; 0048. . Retrieved 2017/07/19.