Isopentenyladenine
Basic information
- CAS
2365-40-4- Standard SMILES
CC(C)=CCNc1ncnc2nc[nH]c12- InChIKey
HYVABZIGRDEKCD-UHFFFAOYSA-N- Molecular formula
- C10H13N5
- Average molar mass
- 203.24 g/mol
- Monoisotopic mass
- 203.11709544
Overview
N(6)-dimethylallyladenine is a 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group. It has a role as a cytokinin.
Names & identifiers
- Preferred name
- Isopentenyladenine
- IUPAC
- N-(3-methylbut-2-enyl)-7H-purin-6-amine
- English name
- N6-(delta 2-Isopentenyl)-adenine
- Molecular formula
- C10H13N5
- Molecular weight
- 203.24
Names & synonyms
2365-40-4Isopentenyladenine6-(gamma,gamma-Dimethylallylamino)purineIPADEIsopentenyl adenineDimethylallyladenine1H-Purin-6-amine, N-(3-methyl-2-butenyl)-N(6)-dimethylallyladenineN(6)-(delta(2)-Isopentenyl)adenineN-(3-Methyl-2-butenyl)-1H-purin-6-aminei6AdeN6-(3-Methylbut-2-enyl)adenine
Show more names
2IPTRIACANTHINE6-(3,3-DIMETHYLALLYLAMINO)PURINE6-(Y6-(γiPeAdeEnadenineN6-iPeAdeNSC 106958
V500BB256ZCHEBI:176606-(3-methyl-2-butenylamino)purineRefChem:821412N-(3-METHYLBUT-2-EN-1-YL)-9H-PURIN-6-AMINEN6-(2-Isopentenyl)adenineN6-IsopentenyladenineN6-Dimethylallyladenine
Database identifiers
- CAS
2365-40-4- PubChem CID
- 92180
- DTXSID
DTXSID10178325- ChEMBL
CHEMBL476189- ChEBI
CHEBI:17660- UNII
- V500BB256Z
- EC Number
- 812-988-8
- Nikkaji
- J120.788A
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 66.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 236
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid; [Sigma-Aldrich MSDS]
Collision Cross Section
145.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
150.8 Ų [M-H]-
Physicochemical properties
- Melting point
- 218 · 218-220 °C
- Boiling point
- 318.1 · 318.1±52.0 °C(Predicted)
- Density
- 1.28 · 1.28±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- DMF (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 9.36 · 9.36±0.20(Predicted)
- color
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information6-((3-Methyl-2-butenyl)amino)purine: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 2933599590
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Applications
UsesN6-(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.
DescriptionA 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.
UsesN6-(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.
Uses6-(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.
Additional notes
DefinitionChEBI: A 6-isopentenylaminopurine in which has the isopentenyl double bond is located between the 2 and 3 positions of the isopentenyl group.
Related reactions
2 records
Compound notes
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