1637-39-4 Usage
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.
Chemical Properties
white to light yellow crystal powder
Uses
Different sources of media describe the Uses of 1637-39-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
Definition
ChEBI: The trans-isomer of zeatin.
General Description
trans-Zeatin contains a hydroxylated isoprenoid side chain.
Biochem/physiol Actions
Zeatin upon reduction forms zeatin O-glucoside, which is widely present in plants. It possesses transportation and storage functions, along with defence against zeatin oxidases.
Purification Methods
Purify zeatin by recrystallisation from EtOH or H2O. The UV has max at 207 and 275nm ( 1,400 and 14,650) in 0.1N aqueous HCl; 212 and 270nm ( 17,050 and 16,150) in aqueous buffer pH 7.2; 220 and 276nm ( 15,900 and 14,650) in 0.1N aqueous NaOH. The picrate has m 192-194o (from H2O) from which zeatin can be recovered by treatment with Dowex-1 x 8 (200-400 mesh, OH-form). [Letham et al. Aust J Chem 22 205 1969, Proc Chem Soc (London) 230 1964, Shaw & Wilson Proc Chem Soc (London) 231 1964.] It is a cell division factor (plant growth regulator) [Letham & Palni Ann Rev Plant Physiol 34 163 1983] and inhibits mitochondrial function [Miller Plant Physiol 69 1274 1982]. The commercially available trans -9-riboside derivative, [6025-53-2], M 351.4,is a cytokine which separates from aqueous AcOH with m 177-179o. It solubility in AcOH is ~5%. [McDonald & Morris Methods Enzymol 100 347 1985].
Check Digit Verification of cas no
The CAS Registry Mumber 1637-39-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,3 and 7 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1637-39:
(6*1)+(5*6)+(4*3)+(3*7)+(2*3)+(1*9)=84
84 % 10 = 4
So 1637-39-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H13N5O/c1-7(4-16)2-3-11-9-8-10(13-5-12-8)15-6-14-9/h2,5-6,16H,3-4H2,1H3,(H2,11,12,13,14,15)/b7-2+
1637-39-4Relevant articles and documents
-
Shaw,G. et al.
, p. 921 - 924 (1966)
-
A purine nucleoside phosphorylase in Solanum tuberosum L. (potato) with specificity for cytokinins contributes to the duration of tuber endodormancy
Bromley, Jennifer R.,Warnes, Barbara J.,Newell, Christine A.,Thomson, Jamie C.P.,James, Celia M.,Turnbull, Colin G.N.,Hanke, David E.
, p. 225 - 237 (2014)
StCKP1 (Solanum tuberosum cytokinin riboside phosphorylase) catalyses the interconversion of the N9-riboside form of the plant hormone CK (cytokinin), a subset of purines, with its most active free base form. StCKP1 prefers CK to unsubstituted aminopurines. The protein was discovered as a CK-binding activity in extracts of tuberizing potato stolon tips, from which it was isolated by affinity chromatography. The N-terminal amino acid sequence matched the translation product of a set of ESTs, enabling a complete mRNA sequence to be obtained by RACE-PCR. The predicted polypeptide includes a cleavable signal peptide and motifs for purine nucleoside phosphorylase activity. The expressed protein was assayed for purine nucleoside phosphorylase activity against CKs and adenine/adenosine. Isopentenyladenine, trans-zeatin, dihydrozeatin and adenine were converted into ribosides in the presence of ribose 1-phosphate. In the opposite direction, isopentenyladenosine, trans-zeatin riboside, dihydrozeatin riboside and adenosine were converted into their free bases in the presence of Pi. StCKP1 had no detectable ribohydrolase activity. Evidence is presented that StCKP1 is active in tubers as a negative regulator of CKs, prolonging endodormancy by a chill-reversible mechanism.
-
Letham et al.
, p. 479 (1967)
-
Synthesis method of (E)-4-hydroxy-3-methyl-2-butenylamine and zeatin
-
, (2020/11/10)
The invention relates to a synthetic method of (E)-4-hydroxyl-3-methyl-2-butenylamine and zeatin. The synthesis method of (E)-4-hydroxy-3-methyl-2-butenylamine comprises the following steps: synthesizing a compound I from (E)-1,4-dibromo-2-methylbutyl-2-ene, wherein the chemical formula of the compound I is as described in the specification; adding acetate and a solvent into the compound I, performing a reaction under an inert gas condition until the reaction is finished; then adding an alkaline solution, conducting a reaction until the reaction is finished; and finally, adding concentrated hydrochloric acid and a solvent, conducting a reaction under an inert gas condition until the reaction is finished, and carrying out purification. Compared with the prior art, the method has the advantages that reaction steps are simple, amino groups do not need to be protected, purification of (E)-4-hydroxy-3-methyl-2-butenylamine can be achieved through distillation after the reaction is finished,and production cost is reduced.
A Novel Method for Synthesis of cis-Zeatin and Its Valuable Precursor (Z)-4-Chloro-2-methyl-but-2-en-1-ol
Hanu?, Jan,Nisler, Jaroslav,Strnad, Miroslav
, p. 368 - 374 (2019/05/21)
-