6-Benzylaminopurine

6-Benzylaminopurine
Names
	Systematic IUPAC name N-(Phenylmethyl)-7H-purin-6-amine
	Other names Benzyl adenine; 6-Benzyladenine
Identifiers
CAS Number	1214-39-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29022 ;
ChEMBL	ChEMBL228862 ;
ChemSpider	56177 ;
ECHA InfoCard	100.013.570
KEGG	C11263 ;
PubChem CID	62389;
UNII	KXG6A989PS ;
CompTox Dashboard (EPA)	DTXSID7032630 ;
	InChI InChI=1S/C12H11N5/c1-2-4-9(5-3-1)6-13-11-10-12(15-7-14-10)17-8-16-11/h1-5,7-8H,6H2,(H2,13,14,15,16,17) Key: NWBJYWHLCVSVIJ-UHFFFAOYSA-N ; InChI=1/C12H11N5/c1-2-4-9(5-3-1)6-13-11-10-12(15-7-14-10)17-8-16-11/h1-5,7-8H,6H2,(H2,13,14,15,16,17) Key: NWBJYWHLCVSVIJ-UHFFFAOYAZ;
	SMILES c3ccc(CNc1ncnc2[nH]cnc12)cc3;
Properties
Chemical formula	C12H11N5
Molar mass	225.255 g·mol−1
Appearance	White to off-white powder
Solubility in water	0.44 g/L (15°C)
Hazards
Safety data sheet (SDS)	External MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

6-Benzylaminopurine, benzyl adenine, BAP or BA^[2] is a first-generation synthetic cytokinin that elicits plant growth and development responses, setting blossoms and stimulating fruit richness by stimulating cell division. It is an inhibitor of respiratory kinase in plants, and increases post-harvest life of green vegetables. Influence of cytokinin as 6-benzylaminopurine (BAP) in combination with other methods on postharvest green color retention on broccoli heads and asparagus spears, showed positive results for quality retention. Treatment with 10 and 15 ppm BAP can be used to extend shelf life of fresh-cut broccoli florets and shredded cabbage during storage at 6±1°C at commercial level.^[3]^[4]

It can be used to extend the shelf life of flowers and cut greens in floristry. The shelf life of cut shoots of Polygonatum multiflorum 'Variegatum' kept in water is about 7 days. To extend their life after cutting, conditioning with gibberellic acid or BA is used. This doubles their possible use.^[5]

6-Benzylaminopurine was first synthesized and tested in the laboratories of plant physiologist Folke K. Skoog.^[6]

References

^ 6-Benzylaminopurine (6-BAP). (n.d.). Duchefa Biochemie. Retrieved December 10, 2022, from https://www.duchefa-biochemie.com/product/details/number/B0904
^ Teixeira da Silva, Jaime A. "Is BA (6-benzyladenine) BAP (6-benzylaminopurine)?". ResearchGate. Retrieved 2019-02-14.
^ Siddiqui, M. W.; Bhattacharjya, A.; Chakraborty, I. and Dhua, R. S. 2011. 6-benzylaminopurine improves shelf life, organoleptic quality, and health-promoting compounds of fresh-cut broccoli florets. Journal of Scientific and Industrial Research, 70 (6): 461–465.
^ Siddiqui, M.W.; Bhattacharjya, A. and Chakraborty, I. 2011. Maintaining organoleptic quality of minimally processed cabbage using 6-benzylaminopurine. International Symposium on System Intensification towards Food and Security, Feb. 24- 27, 2011, Kalyani, Nadia, West Bengal, India, p. 405.
^ Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P (December 2023). "The longevity of cut Polygonatum multiflorum (L.) All. shoots depending on postharvest handling". Acta Agrobotanica. 76. Polish Botanical Society: 1–11. doi:10.5586/aa/176280.
^ "Molecule of the Week Archive 6-Benzyladenine". 2016-04-18. Retrieved 2019-12-02.

[1] 6-Benzylaminopurine (6-BAP). (n.d.). Duchefa Biochemie. Retrieved December 10, 2022, from https://www.duchefa-biochemie.com/product/details/number/B0904

[2] Teixeira da Silva, Jaime A. "Is BA (6-benzyladenine) BAP (6-benzylaminopurine)?". ResearchGate. Retrieved 2019-02-14.

[3] Siddiqui, M. W.; Bhattacharjya, A.; Chakraborty, I. and Dhua, R. S. 2011. 6-benzylaminopurine improves shelf life, organoleptic quality, and health-promoting compounds of fresh-cut broccoli florets. Journal of Scientific and Industrial Research, 70 (6): 461–465.

[4] Siddiqui, M.W.; Bhattacharjya, A. and Chakraborty, I. 2011. Maintaining organoleptic quality of minimally processed cabbage using 6-benzylaminopurine. International Symposium on System Intensification towards Food and Security, Feb. 24- 27, 2011, Kalyani, Nadia, West Bengal, India, p. 405.

[AA-5] Krzymińska-Bródka A, Ulczycka-Walorska M, Łysiak GP, Czuchaj P (December 2023). "The longevity of cut Polygonatum multiflorum (L.) All. shoots depending on postharvest handling". Acta Agrobotanica. 76. Polish Botanical Society: 1–11. doi:10.5586/aa/176280.

[6] "Molecule of the Week Archive 6-Benzyladenine". 2016-04-18. Retrieved 2019-12-02.

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See also

References