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Synthesis and characterization of a novel sweetener with high sweetness strength

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Abstract

A novel sweetener with extremely sweetness potency, N-[N-3-(2-hydroxy-4-methyl-phenyl) propyl-α-aspartyl]-l-phenylalanine-1-methylester, was synthesized through a new synthetic method. 7-methylcoumarin was used as the raw material to synthesize 2-hydroxy-7-methylchroman, an important intermediate, by reduction reaction catalyzed by palladium-carbon and dialuminum hydride. The prepared 2-hydroxy-7-methylchroman then reacted with aspartame through carbonyl-amino condensation reaction and reduction reaction. The yield was approximately 58 %; results of FTIR, EI-MS, and NMR confirmed that the product was N-[N-3-(2-hydroxy-4-methylphenyl) propyl-α-aspartyl]-l-phenylalanine-1-methylester. The synthesized sweetener was a B1, B2, AH1, XH2, G1, E1, G2, E2, G3, G4-type sweetener shown by constructed multipoint attachment model, which well explained why the synthesized sweetener presented so formidable sweetness potency.

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References

  1. Wu PQ, Zhao GX, Zhang YN, Cui JD (2010) Research progress of aspartame on application and synthesis. China Condiment 35:30–37

    CAS  Google Scholar 

  2. Nofre C, Tinti JM (1996) N-substituted derivatives of aspartame useful as sweetening agents. US, 5480668 (A)

  3. Nofre C, Tinti JM (2000) Neotame: discovery, properties, utility. Food Chem 69:245–257

    Article  CAS  Google Scholar 

  4. Prakash I, Wachholder K (2004) Method for the purification N-[N-(3, 3-dimethylbutyl)-L-a-aspartyl]-l-phenylalanine-1-methylester. US, 6784309 (B)

  5. Prakash I, Corliss G, Ponakala R, Ishikawa G (2002) Neotame: the next-generation sweetener. Food Technol 56:36–45

    CAS  Google Scholar 

  6. Yusuke A, Kazuko A, Tadashi T, Ryoichiro N (2001) Preparation of aspartyl dipeptide ester derivatives as sweeteners. CN, 1296493 (A)

  7. Kenichi M, Shinji F, Nao F, Tadashi T (2003) Process for producing cinnamyl aldehyde derivatives and use thereof as intermediate for aspartame derivative, CN, 1429193 (A)

  8. Shigeru K, Kazutaka N, Tadashi T (2003) Process for producing aspartyl dipeptide ester derivatives. CN, 1429234 (A)

  9. Kazutaka N, Shinji F, Yuuichi A, Shigeru K, Tadashi T, Eriko O (2002) Processes for producing and purifying aspartame derivatives and process for producing production intermediates, CN, 1378558 (A)

  10. Kazutaka N, Yuuichi A, Eriko O, Tadashi T (2003) Aspartame derivative crystals. CN, 1413218 (A)

  11. Gan SF, Yan RA, Li AJ (2011) Synthesis of N-[N-3-(3-Hydroxy-4-MethoxyPhenyl) Propyl-L-α-Aspartate]-l-Phenylalanine-l-Methylester. Chinese J Science Technol Food Industry 32:336–369

    CAS  Google Scholar 

  12. Jia CX, Rao ZJ, Zheng JX (2002) The multipoint attachment theory of sweet molecules. Food Ferment Ind 28:40–45

    CAS  Google Scholar 

  13. Shallenberger RS (1967) Acree T E. Nature 206:480–482

    Article  Google Scholar 

  14. Kier LB (1972) A molecular theory of sweet taste. J Pharm Sci 61:1394–1397

    Article  CAS  Google Scholar 

  15. Wu MH, Zheng JX (2009) Synthesis of high potency sweetener n-[3-(3-hydroxy-4-methoxyphenyl) propyl]-aspartyl-l-phenylalanine-l-methylester. Food Ferment Ind 35:1–5

    Google Scholar 

  16. Chen WJ (2009) Preparation of a new sweetener NC-Asp. Modern Food Science Technol 25:172–175

    CAS  Google Scholar 

  17. Tinti JM, Nofre C (1995) Sweetening agent derived from L-aspartic or l-glutamic acid. US, 5430182 (C)

  18. Zheng JX, Gao XF, Yuan ED (2001) Theory development on AH, B, X sweet molecular. China Food Addit 5:32–36

    Google Scholar 

  19. Wiet SG, Miller GA (1997) Does chemical modification of tastants merely enhances their intrinsic taste qualities? Food Chem 58:305–311

    Article  CAS  Google Scholar 

  20. Hoppe K (1991) Sweeteners: discovery, molecular design and chemoreception. ACS Symp Ser 450(35):68–87

    Google Scholar 

Download references

Acknowledgments

This work was supported by Guangdong Province Campus Total Achievement Conversion under Grant cgzhzh0805 and Guangdong Province Key Science & Technology Item under Grant 2010A08043001.

Conflict of interest

Rian Yan has received research grants from Guangdong Province Campus Total Achievement Conversion (cgzhzh0805) and Guangdong Province Key Science & Technology (2010A08043001). Shuifeng Gan and Yuyun Lu declare that they have no conflict of interest.

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This article does not contain any studies with human or animal subjects.

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Authors and Affiliations

  1. Department of Food Science and Engineering, College of Science and Engineering, **an University, No. 601 Huangpu Road West, Guangzhou, 510632, People’s Republic of China

    Shuifeng Gan, Rian Yan & Yuyun Lu

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  1. Shuifeng Gan
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  2. Rian Yan
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  3. Yuyun Lu
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Correspondence to Rian Yan.

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Gan, S., Yan, R. & Lu, Y. Synthesis and characterization of a novel sweetener with high sweetness strength. Eur Food Res Technol 238, 113–120 (2014). https://doi.org/10.1007/s00217-013-2084-9

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  • DOI: https://doi.org/10.1007/s00217-013-2084-9

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