N6-(delta 2-Isopentenyl)-adenine Chemical Properties

Melting point:

218-220 °C

Boiling point:

318.1±52.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMF (Slightly), Methanol (Slightly)

form 

Solid

pka

9.36±0.20(Predicted)

color 

White to Off-White

InChIKey

HYVABZIGRDEKCD-UHFFFAOYSA-N

Safety Information

WGK Germany 

3

HS Code 

2933599590

MSDS

• Language:English Provider:SigmaAldrich

N6-(delta 2-Isopentenyl)-adenine Usage And Synthesis

Uses

N6-(2-Isopentenyl)adenine can be used in biological study for cytokinins stimulated expression of stress-related proteins and transcripts in Arabidopsis thaliana with isopentenyltransferase overexpression.

Description

A purine alkaloid, this base was first isolated from the leaves of Gleditsia triacanthus L., and subsequently discovered in Chidlowia sanguinea and Holar_x0002_rhena floribunda (G. Don.) Dur. et Schinz. The free alkaloid forms colourless crystals and yields crystalline salts and derivatives, e.g. the hydrochloride, m.p. 218-9°C; hydrobromide, m.p. 215-6°C; sulphate, two salts are formed with m.p. 175-6°C and 216-7°C respectively depending upon the amount of acid used in their preparation; picrate, m.p. 246-7°C (dec.); picrolonate, m.p. 229-231 0 C; methiodide, m.p. 227-9°C and the N-benzyl derivative, m.p. 150°C. Oxidation of the alkaloid with KMn04 gives 7-(2:3-dihydroxy-3-methylbutyl)-6-aminopurine which, on periodate oxidation, furnishes 7-(formylmethyl)- 6-aminopurine and Me2CO. Heating the base with Ba(OHh gives one mole each of NH3, C02 and 4-N-(r:r-dimethylallyl)-N-amino-imidazole-5-carboxamide.

Uses

N6-(2-Isopentenyl)adenine can be used in biological study for cytokinins stimulated expression of stress-related proteins and transcripts in Arabidopsis thaliana with isopentenyltransferase overexpression.

Uses

6-(γ,γ-Dimethylallylamino)purine (2iP) is a bacteria-derived riboside cytokinin used to grow plant tissues such as tobacco and soybean callus. 2iP is a precursor of the cytokinin Zeatin. 2iP has been used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.

Definition

ChEBI: A 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group.

Biochem/physiol Actions

6-(γ,γ-Dimethylallylamino)purine (2iP) is a bacteria-derived riboside cytokinin used to grow plant tissues such as tobacco and soybean callus. 2iP is a precursor of the cytokinin Zeatin. 2iP is used in Schenk and Hildebrandt medium to support in vitro propagation of microshoot cultures from shoot tips of Genista plants.

References

Belikov, Ban'kowsky, Tsarev.,J. Gen. Chern., USSR, 24,919 (1954)
Janot, Cave, Goutarel., Bull. Soc. Chirn. Fr., 896 (1959)
Monseur, Adriaens.,J. Pharrn. Belg., 279 (1960)
Leonard, Deyrup., J. Arner. Chern. Soc., 84, 2148 (1962)
Leonard, Laursen.,J. Org. Chern., 27, 1778 (1962)
Belikov., Ref. Zh. Khirn., 13Zh608 (1970)

N6-(delta 2-Isopentenyl)-adenine(2365-40-4)Related Product Information

• 3-Methyl-1-butene
• 3,3-Dimethylallyl bromide
• ZIP
• Adenine
• N6-ISOPENTENYLADENOSINE-D6
• ZEATIN
• ZEATIN
• TRANS-ZEATIN RIBOSIDE
• 6-[4-HYDROXY-3-METHYL-CIS-2-BUTENYLAMINO]PURINE
• Purine
• TRANS-ZEATIN GLUCOSIDE
• N6-(delta 2-Isopentenyl)-adenine
• TRANS-ZEATIN RIBOSIDE [ADENOSINE 8-3H]
• TIMTEC-BB SBB003513
• N-6-(DELTA-2-ISOPENTENYL)ADENOSINE HEMIHYDRATE
• 2-IP DIHYDROCHLORIDE
• ZEATIN-8-14C