1214-39-7 Usage
Chemical Properties
Colorless to off-white or yellow powder. Corrosive. Insoluble in water, slightly soluble in ethanol, stable in acid and alkali.
Uses
6-Benzylaminopurine is a plant growth regulator that belongs to the class of first generation synthetic cytokinin used in agriculture.6-Benzylaminopurine has been used:to induce sprouting in plant materials.in seed germination medium for culturing of seeds.to modify Murashige and Skoog (MS) media for shoot initiation.inhibitor of respiratory kinase in plants.6-Benzylaminopurine, benzyl adenine (BAP) is a synthetic cytokinin which together with auxins elicits plant growth and development responses. BAP is a widely use cytokinin supplement to plant growth media such as Murashige and Skoog medium, Gamborg’s medium, and Chu’s N6 medium.
Application
6-Benzylaminopurine solution has been used as a component in the Murashige & Skoog medium (MS) for culturing mandarin explants and plantlets of Dendrocalamus asper (Schultes f.). It has also been used as a supplement in Nitsch and Nitsch medium (NN) of grapevine explants.
Preparation
synthesis of 6-benzylaminopurine: To 5g hypoxanthine, add 20mL SOCl2, 0.25g DMAP, 10gBTC dissolved in 20mL SOCl2. Heat and add BTC/SOCl2 dropwise. Reflux (refrigerant cooling) to complete dissolution, steam out SOCl2 (containing phosgene, which is used for recovery), evaporated (drained), cooled to room temperature to obtain a milky yellow solid (6-chloropurine and DMAP.Hcl). Directly add 4g benzylamine and 25g triethylamine to it, heat to 70～80 ℃, or microwave heating, until the 6-chloropurine reaction is complete (TLC monitoring), add ethanol, the solid filtered out is washed with ethanol, and dried to obtain 7 g of product 6-benzylaminopurine with a brown color.Preparation and biological activity of 6-benzylaminopurine derivatives in plants and human cancer cells
Definition
ChEBI: 6-Benzylaminopurine is a member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group. It has a role as a plant metabolite and a cytokinin. It derives from an adenine.
General Description
6-Benzylaminopurine is a plant growth regulator that belongs to the class of first generation synthetic cytokinin used in agriculture commodities.
Health Hazard
6-benzylaminopurine (6-BA) is widely used in agriculture and horticulture as plant growth regulator. Its excessive use may pose a potential risk to both environment and human health, which is causing great concern. Vapor is irritating when breathed at high concentrations. Contact with liquid causes irritation of skin and burning of eyes; Vapors cause a slight smarting of the eyes or respiratory system if present in high concentrations; If spilled on clothing and allowed to remain, may cause smarting and reddening of the skin.
Agricultural Uses
6-Benzylaminopurine is a plant growth promoter, is the first applied synthetic cytokinin, mainlyused as a broad- spectrum plant growth regulator. It can be used inagriculture, horticulture, for plants at different stages, from germination to harvest. It enhance the shape of apples and to increase the fruit set in pears. It increases the yield of pistachios and tomatoes. Not listed for use in EU countries. Registered for use in the U.S.
Trade name
ABG? 3034; ACCEL?; AGTROL?;
6-BA?; BA? (growth stimulant); CHRYSAL BVB?;
EXILIS?; PERLAN?; PROMALIN?; SD? 4901; SQ?
4609
Safety Profile
Moderately toxic by ingestion andskin contact. Human mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.
Potential Exposure
A polyamine plant growth regulator
used to lengthen and enhance the shape of apples and to
increase the fruit set in pears. It increases the yield of pistachios
and tomatoes. Not listed for use in the EU countries.
Shipping
UN3259 Amines, solid, corrosive, n.o.s, or
Polyamines, solid, corrosive, n.o.s., Hazard class: 8;
Labels: 8—Corrosive material, Technical Name Required.
Purification Methods
It is purified by recrystallisation from aqueous EtOH. It has at 207 and 270nm (H2O), 268 nm max (pH 6), 274nm (0.1 N HCl) and 275nm (0.1 N NaOH). [Daly J Org Chem 21 1553 1956, Bullock et al. J Am Chem Soc 78 3693 1956, Beilstein 26 III/IV 3575.]
Incompatibilities
May react with strong oxidizers such as
chlorates, peroxides, nitrates, etc. May release heat on contact
with water. Solid and corrosive amines are chemical
bases. Neutralize acids to form salts plus water in exothermic
reactions. May be incompatible with isocyanates, halogenated
organics, peroxides, phenols (acidic), epoxides,
anhydrides, and acid halides. May generate flammable gaseous
hydrogen in combination with strong reducing agents,
such as hydrides.
Waste Disposal
Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator
equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be
observed.
Check Digit Verification of cas no
The CAS Registry Mumber 1214-39-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,1 and 4 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1214-39:
(6*1)+(5*2)+(4*1)+(3*4)+(2*3)+(1*9)=47
47 % 10 = 7
So 1214-39-7 is a valid CAS Registry Number.
InChI:InChI=1/C12H11N5/c1-2-4-9(5-3-1)6-13-11-10-12(15-7-14-10)17-8-16-11/h1-5,7-8,10H,6H2,(H,13,14,15,16,17)
1214-39-7Relevant articles and documents
Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter
Lougiakis, Nikolaos,Gavriil, Efthymios-Spyridon,Kairis, Markelos,Sioupouli, Georgia,Lambrinidis, George,Benaki, Dimitra,Krypotou, Emilia,Mikros, Emmanuel,Marakos, Panagiotis,Pouli, Nicole,Diallinas, George
, p. 5941 - 5952 (2016)
In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have been performed, suggesting that all active compounds interact with FcyB through the formation of hydrogen bonds with Asn163, while the insertion of hydrophobic fragments at position 9 and N6 of 3-deazaadenine enhanced the inhibition.
N6-isopentenyladenosine a new potential anti-angiogenic compound that targets human microvascular endothelial cells in vitro
Castiglioni, Sara,Romeo, Valentina,Casati, Silvana,Ottria, Roberta,Perrotta, Cristiana,Ciuffreda, Pierangela,Maier, Jeanette A. M.
, p. 533 - 545 (2018)
N6-isopentenyladenosine is an anti-proliferative and pro-apoptotic atypical nucleoside for normal and tumor cells. Considering the role of angiogenesis in various diseases, we investigated the cytotoxic effect of N6-isopentenyladenosine on human microvascular endothelial cells, protagonists in angiogenesis. Our results show that N6-isopentenyladenosine induced a significant reduction of cell viability, upregulated p21 and promoted caspase-3 cleavage in a dose dependent manner leading to apoptotic cell death as detected by FACS analysis. To understand structure-function relationship of N6-isopentenyladenosine, we investigated the effect of some N6-isopentenyladenosine analogs. Our results suggest that N6-isopentenyladenosine and some of its derivatives are potentially novel angiostatic agents and might be associated with other anti-angiogenic compounds for a better outcome.
Mechanism of formation of N2-benzylguanine in the reaction of 2-amino- 6-chloropurine with sodium benzyl oxide, and benzylation of nucleic acid bases
Koyama, Ken-Ichi,Hitomi, Kenichi,Terashima, Isamu,Kohda, Kohfuku
, p. 1395 - 1399 (1996)
The mechanism of formation of N2-benzylguanine in the reaction of 2- amino-6-chloropurine with a large excess (12-13 molar eq) of sodium benzyl oxide in benzyl alcohol at 130°C was studied. N2,O6-Dibenzylguanine, a reaction intermediate, was isolated and a possible mechanism for its formation is discussed. Furthermore, using this sodium benzyl oxide system, benzylation at the amino group of nucleic acid bases was facilitated.
Reactions of Adenine and Its N-Exo Substituted Analogues with Phenyl Glycidyl Ether
Neporozhneva,Studentzsov,Ramsh
, p. 2248 - 2254 (2021/02/12)
Abstract: The features of reactions of adenine with phenyl glycidyl ether depending on the solvent nature were studied. In DMF in the presence of K2CO3, an N9-alkyl derivative, an experimental antiviral drug 9-(2-hydroxy-3-phenoxypropyl)adenine, was formed predominantly. During alkylation in acetic acid, besides N9-, N3-, and N7-alkylation products were also isolated. Alkylation of 6-[alkyl(dialkyl)amino]purines with phenyl glycidyl ether in DMF produced N-exo substituted 9-(2-hydroxy-3-phenoxypropyl)adenine analogues.
Chemoenzymatic synthesis of cytokinins from nucleosides: Ribose as a blocking group
Oslovsky, Vladimir E.,Solyev, Pavel N.,Polyakov, Konstantin M.,Alexeev, Cyril S.,Mikhailov, Sergey N.
, p. 2156 - 2163 (2018/03/26)
Nucleoside phosphorylases are involved in the salvage pathways of nucleoside biosynthesis and catalyze the reversible reaction of a nucleobase with α-d-ribose-1-phosphate to yield a corresponding nucleoside and an inorganic phosphate. The equilibrium of these reactions is shifted towards nucleosides, especially in the case of purines. Purine nucleoside phosphorylase (PNP, EC 2.4.2.1) is widely used in labs and industry for the synthesis of nucleosides of practical importance. Bacterial PNPs have relatively broad substrate specificity utilizing a wide range of purines with different substituents to form the corresponding nucleosides. To shift the reaction in the opposite direction we have used arsenolysis instead of phosphorolysis. This reaction is irreversible due to the hydrolysis of the resulting α-d-ribose-1-arsenate. As a result, heterocyclic bases are formed in quantitative yields and can be easily isolated. We have developed a novel method for the preparation of cytokinins based on the enzymatic cleavage of the N-glycosidic bond of N6-substituted adenosines in the presence of PNP and Na2HAsO4. According to the HPLC analysis the conversion proceeds in quantitative yields. In the proposed strategy the ribose residue acts as a protective group. No contamination of the final products with AsO43- has been detected via HPLC-HRMS; simple analytical arsenate detection via ESI-MS has been proposed.
