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N-6-(Δ2-Isopentenyl)-adenine (CAS 2365-40-4)

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Alternate Names:
6-(γ,γ-Dimethylallylamino)purine; Triacanthine; 2iP; N6-(2-Isopentenyl)adenine
Application:
N-6-(Δ2-Isopentenyl)-adenine is a weakly active olomoucine
CAS Number:
2365-40-4
Purity:
≥99%
Molecular Weight:
203.24
Molecular Formula:
C10H13N5
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N-6-(Δ2-Isopentenyl)-adenine, an analog of olomoucine, possesses kinase inhibitory properties albeit weakly active. This compound proves valuable for conducting structure-activity analyses within the olomoucine series. As a small molecule, it has garnered extensive attention within the scientific research field. N-6-(Δ2-Isopentenyl)-adenine serves as a intermediate in the synthesis of various compounds, including pharmaceuticals, pesticides, and dyes. Its utility expands to multiple areas, such as serving as a reagent in organic synthesis, a catalyst in chemical reactions, and a chromogenic reagent in spectrophotometric assays. In organic synthesis, it acts as a nucleophile, partaking in reactions with electrophiles (e.g., alkyl halides) to form new C-C bonds. Moreover, it exhibits catalytic properties in reactions like Diels-Alder reactions and carbon-carbon bond formation. Furthermore, N-6-(Δ2-Isopentenyl)-adenine acts as a cytokinin, functioning as a plant-growth regulator. Studies have shown its support in propagating microshoot cultures of Genista plants in vitro. It has also demonstrated applicability in growing plant tissues such as tobacco and soybean callus.


N-6-(Δ2-Isopentenyl)-adenine (CAS 2365-40-4) References

  1. 3-Methyl-2-butenal: an enzymatic degradation product of the cytokinin, N-6-(delta-2 isopentenyl)adenine.  |  Brownlee, BG., et al. 1975. Can J Biochem. 53: 37-41. PMID: 1120289
  2. Zeatin biosynthesis from N-(Delta-isopentenyl)adenine in Actinidia and other woody plants.  |  Einset, JW. 1986. Proc Natl Acad Sci U S A. 83: 972-5. PMID: 16593660
  3. Biosynthesis of zeatin from N-(Delta-isopentenyl)adenine in Actinidia: Sites and seasonal changes in activity.  |  Einset, JW. 1986. Proc Natl Acad Sci U S A. 83: 7751-4. PMID: 16593769
  4. Isolation and Estimation of Cytokinins and Cytokinin-Containing Transfer RNAs from Cucumis sativus L. var. Guntur Seedlings.  |  Jayabaskaran, C. and Jacob, TM. 1982. Plant Physiol. 70: 1396-400. PMID: 16662686
  5. Hydroxylation of N-(Delta-Isopentenyl)adenine to Zeatin: Relative Activities of Organ Systems from Actinidia arguta.  |  Einset, JW. and Silverstone, A. 1987. Plant Physiol. 84: 208-9. PMID: 16665417
  6. An enzyme mediating the conversion of zeatin to dihydrozeatin in phaseolus embryos.  |  Martin, RC., et al. 1989. Plant Physiol. 90: 1630-5. PMID: 16666974
  7. Changes in Cytokinins before and during Early Flower Bud Differentiation in Lychee (Litchi chinensis Sonn.).  |  Chen, WS. 1991. Plant Physiol. 96: 1203-6. PMID: 16668321
  8. Subcellular localization and biochemical comparison of cytosolic and secreted cytokinin dehydrogenase enzymes from maize.  |  Smehilová, M., et al. 2009. J Exp Bot. 60: 2701-12. PMID: 19436049
  9. Cytokinins act synergistically with salicylic acid to activate defense gene expression in rice.  |  Jiang, CJ., et al. 2013. Mol Plant Microbe Interact. 26: 287-96. PMID: 23234404
  10. Amino acid transport in a water-mould: the possible regulatory roles of calcium and N6-(delta2-isopentenyl)adenine.  |  Singh, DP. and LéJohn, HB. 1975. Can J Biochem. 53: 975-88. PMID: 241477
  11. A highly selective biosensor with nanomolar sensitivity based on cytokinin dehydrogenase.  |  Tian, F., et al. 2014. PLoS One. 9: e90877. PMID: 24595403
  12. Evidence for the oxidation of N6-(delta 2-isopentenyl)adenine and N6-(3-hydroxy-3-methylbutyl)adenine by xanthine oxidase.  |  McLennan, BD. and Pater, A. 1973. Can J Biochem. 51: 1123-6. PMID: 4737636
  13. Inhibition of cyclin-dependent kinases by purine analogues.  |  Veselý, J., et al. 1994. Eur J Biochem. 224: 771-86. PMID: 7925396

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N-6-(δ2-Isopentenyl)-adenine, 1 g

sc-279669
1 g
$133.00

N-6-(δ2-Isopentenyl)-adenine, 5 g

sc-279669A
5 g
$467.00

N-6-(Δ2-Isopentenyl)-adenine, 10 g

sc-279669B
10 g
$923.00

N-6-(Δ2-Isopentenyl)-adenine, 50 g

sc-279669C
50 g
$4595.00

N-6-(Δ2-Isopentenyl)-adenine, 100 g

sc-279669D
100 g
$8165.00