Sains Malaysiana 50(4)(2021): 989-996

http://doi.org/10.17576/jsm-2021-5004-09

Colorimetric Amine Detection by Vanillin-Hydrazone Derivatives during Chicken Meat Spoilage

(Pengesanan Amina Colorimetrik oleh Terbitan Vanilin-Hidrozon semasa Kerosakan Daging Ayam)

BAMBANG PURWONO¹*, BETA ACHROMI NUROHMAH¹ & SUHARMAN²

¹Department of Chemistry, Faculty of Mathematics and Natural Science, Universitas Gadjah Mada, Jalan Kaliurang Sekip Utara Bulaksumur 21, Yogyakarta, 55281, Indonesia

²Department of Chemistry, Universitas Sumatera Utara, Jalan T. Dr. Mansyur No. 9, Padang Bulan, Medan Baru, Medan, Sumatera Utara, 201555, Indonesia

Received: 10 June 2020/Accepted: 2 September 2020

ABSTRACT

Two vanillin-hydrazone compounds as the colorimetric amine detection during chicken meat spoilage are described. Two hydrazone compounds (1 and 2) have been synthesized from the condensation reaction of vanillin with phenylhydrazine and 2,4-dinitrophenylhydrazine. Their properties for colorimetric recognition of amine were determined by the naked eye and UV-vis spectra. Their properties as amine indicators were investigated toward primary amine: butylamine (BA); secondary amine: dimethylamine (DMA), diethylamine (DEA); tertiary amine: triethylamine (TEA), and also ammonia (Amm). The hydrazone 1 in DMSO showed no significant color changes (colorless) after the addition of amines solution. Hydrazone 2 (5×10^-5 M in DMSO) showed color changes from yellow to violet in the presence of ammonia, DEA and BA, to reddish-violet for DMA, and light brown after addition of TEA solutions. The colorimetric amine detection by vanillin-hydrazone 2 could recognize the real amine during chicken meat spoilage from yellow to light brown after 24 h storage at room temperature.

Keywords: Colorimetric; food spoilage; hydrazone; indicator

ABSTRAK

Dua sebatian vanilin-hidrazon sebagai pengesanan am kolorimetrik semasa kerosakan daging ayam dijelaskan. Dua sebatian hidrazon (1 dan 2) telah disintesis daripada tindak balas pemeluwapan vanilin dengan fenilhidrazin dan 2,4-dinitrofenilhidrina. Sifat mereka untuk pengecaman amina kolorimetrik ditentukan oleh mata kasar dan spektrum UV-vis. Sifat mereka sebagai petunjuk amina dikaji terhadap amina primer: butilamina (BA); amina sekunder: dimetilamina (DMA), dietilamina (DEA); amina tertier: trietilamina (TEA) dan juga amonia (Amm). Hidrazon 1 dalam DMSO tidak menunjukkan perubahan warna yang ketara (tidak berwarna) setelah penambahan larutan amina. Hidrazon 2 (5 × 10-5 M dalam DMSO) menunjukkan perubahan warna daripada kuning ke ungu dengan adanya amonia, DEA dan BA, menjadi ungu kemerahan untuk DMA dan coklat muda setelah penambahan larutan TEA. Pengesanan amina kolorimetrik oleh vanillin-hidrazon2 dapat mengenali amina sebenar semasa kerosakan daging ayam daripada kuning ke coklat muda setelah penyimpanan 24 jam pada suhu bilik.

Kata kunci: Hidrazon; kerosakan makanan; kolorimetrik; penunjuk

REFERENCES

Arulkumar, A., Karthik, G., Paramasivam, S. & Rabie, M.A. 2017. Histamine levels in Indian fish via enzymatic, TLC and HPLC methods during storage. Journal of Food Measurement and Characterization 11(1): 281-289.

Basavaraja, D., Dibyendu, D., Varsha, T.L., Chettiyan, T.F., Manas, K.P. & Sasidhar, B.S. 2020. Rapid visual detection of amines by pyrylium salts for food spoilage taggant. ACS Applied Bio Materials 3: 772-778.

Bóka, B., Adányi, N., Virág, D., Sabela, M. & Kiss, A. 2012. Spoilage detection with biogenic amine biosensors, comparison of different enzyme electrodes. Electroanalysis 24(1): 181-186.

Boruah, B.S., Daimari, N.K. & Biswas, R. 2019. Functionalized silver nanoparticles as an effective medium towards trace determination of arsenic (III) in aqueous solution. Results in Physics 12: 2061-2065.

Brightwell, G. & Clemens, R. 2012. Development and validation of a real-time PCR assay specific for Clostridium estertheticum and C. estertheticum-like psychrotolerant bacteria. Meat Science 92(4): 697-703.

Chen, X., Zhou, Y., Peng, X. & Yoon, J. 2010. Fluorescent and colorimetric probes for detection of thiols. Chemical Society Review 391(6): 2120-2135.

Duong, H.D. & Rhee, J.I. 2014. A ratiometric fluorescence sensor for the detection of ammonia in water. Sensors and Actuators B: Chemical 190: 768-774.

Erande, Y., Chemate, S., More, A. & Sekar, N. 2015. PET governed fluorescence “Turn ON” BODIPY probe for selective detection of picric acid. RSC Advances 5(109): 89482-89487.

Fletcher, B., Mullane, K., Platts, P., Todd, E., Power, A., Roberts, J., Chapman, J., Cozzolino, D. & Chandra, S. 2018. Advances in meat spoilage detection: A short focus on rapid methods and technologies. CyTA - Journal of Food 16(1): 1037-1044. 

Gao, M., Li, S., Lin, Y., Geng, Y., Ling, X., Wang, L., Qin, A. & Tang, B.Z. 2016. Fluorescent light-up detection of amine vapors based on aggregation-induced emission. ACS Sensors 1(2): 179-184.

Gribble, A. & Brightwell, G. 2013. Spoilage characteristics of Brochothrix thermosphacta and campestris in chilled vacuum packaged lamb, and their detection and identification by real time PCR. Meat Science 94(3): 361-368.

Janzen, M.C., Ponder, J.B., Bailey, D.P., Ingison, C.K. & Suslick, K.S. 2006. Colorimetric sensor arrays for volatile organic compounds. Analytical Chemistry 78(11): 3591-3600.

Li, Y., Li, J., Lin, H., Shao, J., Cai, Z.S. & Lin, H. 2010. A novel colorimetric receptor responding AcO^‒ anions based on an azo derivative in DMSO and DMSO/water solution. Journal of Luminescence 130(3): 466-472.

Naila, A., Flint, S., Fletcher, G., Bremer, P. & Meerdink, G. 2010. Control of biogenic amines in food-existing and emerging approaches. Journal of Food and Science 75(7): 139-150.

Raudienė, E., Gailius, D., Vinauskienė, R., Eisinaitė, V., Balčiūnas, G., Dobilienė, J. & Tamkutė, L. 2018. Rapid evaluation of fresh chicken meat quality by electronic nose. Czech Journal of Food Science 36(5): 420-426.

Reid, R., Burgess, C.M., McCabe, E., Fanning, S., Whyte, P., Kerry, J. & Bolton, D. 2017. Real-time PCR methods for the detection of blown pack spoilage causing Clostridium species; C. estertheticum, C. gasigenes and C. ruminantium. Meat Science 133: 56-60. 

Rodriguez-Lazaro, D., Gonzalez-García, P., Delibato, E., De-Medici, D., García-Gimeno, R., Valero, A. & Hernandez, M. 2014. Next day Salmonella spp. detection method based on real-time PCR for meat, dairy and vegetable food products. International Journal of Food Microbiology 13(8): 113-120. 

Ruiz-Capillas, C. & Herrero, A.M. 2019. Impact of biogenic amines on food quality and safety. Foods 8(62): 1-16.

*Corresponding author; email:  purwono.bambang@ugm.ac.id