6-Benzylaminopurine

Description

6-Benzyladenine, also called 6-benzylaminopurine, is a synthetic cytokinin that stimulates cell division in plants. Among other actions, it spurs plant growth, sets blossoms, and improves fruit quality.
Cytokinins are in the plant growth hormone family. As part of his pioneering research in plant growth regulators, plant physiologist Folke K. Skoog at the University of Wisconsin–Madison synthesized 6-benzyladenine and demonstrated its efficacy.
In a recent C&EN “Periodic Graphics” page, author Andy Brunning included 6-benzyladenine in a roundup of how “flower food” helps to?preserve cut flowers. He notes that the growth regulator’s contribution to preservation is maintaining petal colors. 6-Benzyladenine is similarly used to extend the shelf lives of broccoli florets and shredded cabbage to make them more attractive to customers.

Chemical properties

Colorless to off-white or yellow powder. Corrosive. Insoluble in water, slightly soluble in ethanol, stable in acid and alkali.

The Uses of 6-Benzylaminopurine

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.

What are the applications of Application

6-Benzylaminopurine is a purine reported to induce positive inotropic effects through activation of P2-purinergic receptors

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.

What are the applications of 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

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.