6-(γ,γ-Dimethylallylamino)purine

Names

[ Name ]:
6-(γ,γ-Dimethylallylamino)purine

[Synonym ]:
6-(y,y-Dimethylallylamino)purine
6-isopentenyladenine
MFCD00132998
N-(3-Methyl-2-buten-1-yl)-7H-purin-6-amine
N-(3-Methylbut-2-en-1-yl)-1H-purin-6-amin
iPeAde
6-[(3-methylbut-2-en-1-yl)amino]-9H-purine
N-(3-methylbut-2-enyl)-7H-purin-6-amine
6-[(3-Methyl-2-butenyl)amino]purine
N(6)-dimethylallyladenine
N6-[(3-methylbut-2-en-1-yl)amino]purine
N6-ISOPENTENYLADENINE (iP)
3H-Purin-6-amine, N-(3-methyl-2-buten-1-yl)-
N6-(2-Isopentenyl)-adenosin
N-(3-methylbut-2-en-1-yl)-9H-purin-6-amine
N6-Isopentenyladenine
N6-(2-Isopentenyl)adenine
N6-(2-Isopentenyl)-adenine
N6-(δ 2-Isopentenyl)-adenine
Isopentenyl adenine
N6-iPeAde
adenine, isopentenyl-
N-(3-methylbut-2-en-1-yl)-1H-purin-6-amine
N6-(3-methylbut-2-enyl)adenine
isopentenyladenine
enadenine
TRIACANTHINE
N-Isopentenyladenine
7H-Purin-6-amine, N-(3-methyl-2-buten-1-yl)-
N6-2-isopentenyladenine
Adenine, N- (3-methyl-2-butenyl)-
N-(3-methylbut-2-en-1-yl)-7H-purin-6-amine
N-(3-methylbut-2-enyl)adenine
Isopentenyl-Adenine
2-iP N6-(2-Isopentenyl)adenine
1H-Purin-6-amine, N- (3-methyl-2-butenyl)-
2iP
N6-(delta 2-Isopentenyl)-adenine
N-(3-Methyl-2-buten-1-yl)-3H-purin-6-amine
N-(3-methyl-2-buten-1-yl)-1H-purin-6-amine
6-(γ,γ-Dimethylallylamino)purine

Biological Activity

[Description]:

6-(γ,γ-Dimethylallylamino)purine is a plant growth substance.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

[In Vitro]

Derivative UV spectroscopic data show that the plant growth substances 6-(γ,γ-Dimethylallylamino)purine (N6-(delta 2-isopentenyl) adenine, i6Ade)and indolylacetic acid (IAA) can bind to the yeast alcohol dehydrogenase (ADH) and affect coenzyme-enzyme binding. At fixed ethanol concentrations (27.8 and 111.1 mM) and varying NAD+ concentrations (0.033-2 mM), as well as at fixed levels of coenzyme (0.67 and 2 mM), and at varying concentrations of ethanol (1.4-111.1 mM), the rate of ethanol oxidation is significantly inhibited by i6Ade and IAA. The kinetics of the ADH reaction is affected by two inhibition constants (Ki and Ki') which correspond to the dissociation constants of complexes EI and ESI, respectively. For i6Ade the Ki=0.52±0.06 mM and Ki'=0.74±0.07 mM, and for IAA the Ki=0.88±0.03 mM and Ki'=0.99±0.02 mM[1].

[References]

[1]. Zikmanis P, et al. Indolylacetic acid and N6-(delta 2-isopentenyl) adenine affect NADH binding to yeast alcohol dehydrogenase and inhibit in vitro the enzymatic oxidation of ethanol. Biofactors. 1990 Oct;2(4):237-40.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
477.1±30.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₀H₁₃N₅

[ Molecular Weight ]:
203.244

[ Flash Point ]:
242.4±24.6 °C

[ Exact Mass ]:
203.117096

[ PSA ]:
66.49000

[ LogP ]:
2.31

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.683

[ Storage condition ]:
-20°C

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934993000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives

Bioorg. Med. Chem. 17 , 1938-47, (2009)

Synthesis of 9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-yl benzylaminopurines, their stability, cytokinin activity, perception by cytokinin receptors, degradation by cytokinin oxidase/dehydrogenas...

Thidiazuron influences the endogenous levels of cytokinins and IAA during the flowering of isolated shoots of Dendrobium.

J. Plant Physiol. 163(11) , 1126-34, (2006)

This study reports the effects of thidiazuron (TDZ) on the endogenous levels of indoleacetic acid (IAA), zeatin, zeatin riboside ([9R]Z), isopentenyladenine and isopentenyladenosine ([9R]iP) as well a...

Functional identification of OsHk6 as a homotypic cytokinin receptor in rice with preferential affinity for iP.

Plant Cell Physiol. 53(7) , 1334-43, (2012)

Cytokinins are involved in key developmental processes in rice (Oryza sativa), including the regulation of cell proliferation and grain yield. However, the in vivo action of histidine kinases (OsHks),...

Related Compounds

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