Skip to main content

Summary

Vanilla extract is widely used in the food and the confectionery industry. Vanillin is the most abundant component of vanilla extract. An understanding of the biosynthetic pathway of vanillin may be important for regulating the production of the compound in plants. It is agreed that vanillin (C6-C1) is a product of phenylpropanoid (C6-C3) compounds. One school of thought suggests that vanillin is formed from ferulic acid that undergoes chain shortening. It was shown that inVanilla planifoliatissue cultures the benzoate derivative pathway operates using phenylpropanoid substrates, leading from trans-cinnamic acid to flavor compounds. The branch point between the C6-C3and C6-C1pathways most likely occurs at the level of p-coumaric acid. The tissue possesses constitutive 3-0-methyltransferase, capable of methylation of externally added 3,4-dihydroxybenzaldehyde. Aromatic C6-C1aldehydes are reduced to the corresponding alcohols by a specific alcohol dehydrogenase and stored.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Clark, G. S. Vanillin. A profile: An aroma chemical. Perfumers and flavorist 1990, 15, 45–54.

    CAS  Google Scholar 

  • Dixon, R. A.; Lamb, C. J.; Masoud, S.; Sewalt, V. J. H.; Paiva, N. L. Metabolic engineering: Prospects for crop improvement through genetic manipulation of phenylpropanoid biosynthesis and defense responses-a review. Gene 1996, 179, 61–71.

    Article  PubMed  CAS  Google Scholar 

  • French, C. J.; Vance, C. R; Towers, G. H. N. Conversion of p-coumaric to p-hydroxybenzoic acid by cell-free extract of potato tuber and Polyporus hispidus. Phytochem 1976, 15, 564–566

    Article  CAS  Google Scholar 

  • Funk, C.; Brodelius, P. E. Phenylpropanoid metabolism in suspension cultures of Vanilla planifolia Andr. III. Con-version of 4-methoxycinnamic acids into 4-hydroxybenzoic acids. Plant Physiol. 1990, 94, 102–108.

    Article  PubMed  CAS  Google Scholar 

  • Gasson, M. J.; Kitamura, Y.; McLauchlan, W. R.; Narbad, A.; Parr, A. J.; Lindsay, E.; Parsons, H.; Payne, J.; Rhodes, M. J. C.; Walton, N. J. Metabolism of ferulic acid to vanillin; J. B C. 1998, 273 (7), 4163–4170

    CAS  Google Scholar 

  • Hartman, T. G.; Karmas, K.; Chen, J.; Shevade, A.; Deagro, M.; Hwang, H. Determination of vanillin, other phenolic compounds, and flavors in vanilla bean. In Phenolic Compounds in Food and Their Effect on Health; Ho, C. T., Leland, C. Y., Huang, M. T., Eds.; American Chemical Society: Washington, DC, 1992; pp 66–70.

    Google Scholar 

  • Havkin-Frenkel, D.; Dorn, R. Vanilla. In Spices: Flavor Chemistry and Antioxidant Properties; Risch, S. J., Ho, C. T., Eds.; American Chemical Society: New Orleans, LA, 1996; pp 29–40

    Google Scholar 

  • Havkin-Frenkel, D.; Podstolski, A.; Knorr, D. Effect of light on vanillin precursors formation by in vitro cultures of vanilla planifolia. Plant Cell, Tissue and Organ Culture 1996, 46, 169–170.

    Article  Google Scholar 

  • Heide, L.; Floss, H. G.; Tabata, M. Incorporation of shikimic acid into p-hydroxybenzoic acid in Lithospermum erythrorhizon cell cultures. Phytochemistry 1989, 28, 2643–2645.

    Article  CAS  Google Scholar 

  • Kanisawa, T.; Tokoro, K.; Kawahara, S. Flavor development in the beans of Vanilla planifolia. In Olfaction and Taste; Kurihara, K., Suzuki, N., Ogawa, H., Eds.; Springer-Verlag: Tokyo 1994; Vol. Xl.

    Google Scholar 

  • Knorr, D.; Caster, C.; Dörnenburg, H; Dorn, R; Graf, S; Havkin-Frenkel, D; Podstolski, A; Werrman, U. Biosynthesis and yield improvement of food ingredients from plant cell and tissue cultures. Food Technology 1993, 47(12), 57–63.

    CAS  Google Scholar 

  • Loffelhardt, W.; Kindle, I. The conversion of L-phenylalanine into benzoic acid on the thylakoid membrane of higher plants. Z. Physiol. Chem. 1975, 356, 487–493.

    Article  CAS  Google Scholar 

  • Lopez-Malo, A.; Alzamora, S. M.; Argaiz, A. Effect of natural vanillin on germination and radial growth on moulds in fruit-based agar systems. Food Microbiology 1995, 12, 213–219.

    Article  CAS  Google Scholar 

  • Rithe, M. S.; Waller, G. R; Murray, D. S.; Sgaramello, R. P. Composition of essential oil from Proboscidea louisianica (Martyniaceae). Proc Oklahoma Acad. Sci 1991, 71, 35–42.

    Google Scholar 

  • Romagnoli, L. G.; Knorr, D. The effect of ferulic acid treatment on growth and flavor development of cultured Vanilla planifolia cells. Food Biotechnol. 1988, 2(1), 93–104.

    Article  CAS  Google Scholar 

  • Schnitzler, J. P.; Madlung, J.; Rose, A.; Stitz, H. O. Biosynthesis of p-hydroxybenzoic acid in elicitor treated carrot cell cultures. Planta 1992, 188, 594–600.

    Article  CAS  Google Scholar 

  • Swamy, B. G. L. On the life history of Vanilla planifolia. Bot. Gaz. 1967, 108, 449–456.

    Article  Google Scholar 

  • Yazaki, K.; Heide, I.; Tabata, M. Formation of p-hydroxybenzioc acid by cell-free extract of Lithospermum erythrorhizon cell cultures. Phytochem 1991, 30, 2233–2236.

    Article  CAS  Google Scholar 

  • Zenk, M. H. Biosynthese von vanillin in Vanilla planifolia Andr. Z. Plan Physiol.Bd. 1965, 53, 404–414.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer Science+Business Media New York

About this chapter

Cite this chapter

Havkin-Frenkel, D., Podstolski, A., Witkowska, E., Molecki, P., Mikolajczyk, M. (1999). Vanillin Biosynthetic Pathways. In: Fu, TJ., Singh, G., Curtis, W.R. (eds) Plant Cell and Tissue Culture for the Production of Food Ingredients. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4753-2_4

Download citation

  • DOI: https://doi.org/10.1007/978-1-4615-4753-2_4

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-7155-7

  • Online ISBN: 978-1-4615-4753-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics