A comprehensive review on vanilla flavor: Extraction, isolation and quantification of vanillin and others constituents

International Journal of Food Sciences and Nutrition

Volumn 59, Issue 4, 2008, Pages 299-326

  Sinha, Arun K ^a   Sharma, Upendra K ^a   Sharma, Nandini ^a  

^a CSIR INSTITUTE OF HIMALAYAN BIORESOURCE TECHNOLOGY   (India)

Author keywords

Comprehensive review; Gas chromatography; High performance liquid chromatography; Vanilla flavor; Vanilla planifolia; Vanillin

Indexed keywords

FLAVORING AGENT; PERFUME; VANILLIN; WATER;

ANTIINFLAMMATORY ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; BEVERAGE; CAPILLARY ELECTROPHORESIS; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; DENSITY; DISSOCIATION CONSTANT; DRUG INDUSTRY; EXTRACTION; FLAVOR; FOOD QUALITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION PROCEDURE; MELTING POINT; MICELLAR ELECTROKINETIC CHROMATOGRAPHY; MOLECULAR WEIGHT; PHYSICAL CHEMISTRY; QUALITY CONTROL; QUANTITATIVE ANALYSIS; REVIEW; SOLID PHASE EXTRACTION; SUPERCRITICAL FLUID EXTRACTION; THIN LAYER CHROMATOGRAPHY; VANILLA; VAPOR PRESSURE;

BENZALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVORING AGENTS; FOOD TECHNOLOGY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MICROWAVES; PLANT EXTRACTS; ULTRASONICS; VANILLA;

VANILLA PLANIFOLIA;

EID: 42649096954     PISSN: 09637486     EISSN: 14653478     Source Type: Journal    
DOI: 10.1080/09687630701539350     Document Type: Review

References (143)

1. Abraham, DJ, Mehanna, AS, Wireko, FC, Whitney, J., Thomas, RP and Orringer, EP (1991) Vanillin, a potential agent for the treatment of sickle cell anemia. Blood, 77, pp. 1334-1341.
2. Adedeji, J., Hartman, TG and Ho, C-T (1993) Flavor characterization of different varieties of vanilla beans. Perfumer Flavorist, 18, pp. 25-33.
3. Akagi, K., Hirose, M., Hoshiya, T., Mizoguchi, Y., Ito, N. and Shirai, T. (1995) Modulating effects of elagic acid, vanillin and quercetin in a rat medium term multi-organ carcinogenesis model. Cancer Lett, 94, pp. 113-121.
4. Anklam, E., Gaglione, S. and Müller, A. (1997) Oxidation behaviour of vanillin in dairy products. Food Chem, 60, pp. 43-51.
5. Anwar, MH (1963) Paper chromatography of monohydroxyphenols in vanilla extract. Anal Chem, 35, pp. 1974-1976.
6. Arditti, J. (1992) Fundamental of orchid biology, p. 624. John Wiley and Sons, New York USA
7. Arthur, CL and Pawliszyn, J. (1990) Solid phase microextraction with thermal desorption using fused silica optical fibers. Anal Chem, 62, pp. 2145-2148.
8. Aruoma, OI (1999) Antioxidant actions of plant foods: Use of oxidative DNA damage as a tool for studying antioxidant efficacy. Free Radic Res, 30, pp. 419-427.
9. Asche, S., Michand, AL and Brenna, JT (2003) Sourcing organic compounds based on natural isotopic variations measured by high precision isotope ratio mass spectrometry. Curr Org Chem, 7, pp. 1527-1543.
10. Association of Official Analytical Chemists (1990) Official methods of analysis, 2, pp. 890-896. AOAC, Arlington, VA
11. Banks, CE and Compton, RG (2003) Ultrasonically enhanced voltammetric analysis and applications: An overview. Electroanal, 15, pp. 329-346.
12. Bartnick, DD, Mohler, CM and Giel, TH. (2005) Method for the production of natural botanical extracts. US Patent
13. Bedoukian, PZ. (1986) Perfumery and flavoring synthesis, Allured Publishing Corp, Wheaton, IL, USA
14. Belay, MP and Poole, CF (1993) Determination of vanillin and related flavor compounds in natural vanilla extracts and vanilla flavored foods by thin layer chromatography and automated multiple development. Chromatographia, 37, pp. 365-373.
15. Bensaid, FF, Wietzerbin, K. and Martin, GJ (2002) Authentification of natural vanilla flavourings: Isotopic characterization using degradation of vanillin into guaiacol. J Agric Food Chem, 50, pp. 6271-6275.
16. Benz, I. and Muheim, A. (1996) Biotechnological production of vanilin. Flavor science recent development, pp. 111-117. Royal Society of Chemistry, Cambridge UK
17. Bettazzi, F., Palchetti, I., Sisalli, S. and Mascini, M. (2006) A disposable electrochemical sensor for vanillin detection. Anal Chim Acta, 555, pp. 134-138.
18. Bjørsvik, H-R (1999) Fine chemicals from ligunosulfonates. Synthesis of vanillin by oxidation of ligunosulfonates. Org Process Res Dev, 3, pp. 330-340.
19. Boonchird, C. and Flegel, TW (1982) In vitro antifungal activity of eugenol and vanillin against Candida albicans and Cryptococcus neoformans. Can J Microbiol, 28, pp. 1235-1241.
20. Boyce, MC, Haddad, PR and Sostaric, T. (2003) Determination of flavour components in natural vanilla extracts and synthetic flavourings by mixed micellar electrokinetic capillary chromatography. Anal Chim Acta, 485, pp. 179-186.
21. Breas, O., Fourel, F. and Martin, GJ (1994) 13C analysis of aromas and perfumes by a coupled GC-IRMS technique. The case of vanillin and leaf alcohol extracts. Analusis, 2, pp. 268-272.
22. Burri, J., Graf, M., Lambelet, P. and Löliger, J. (1989) Protection of a food product against oxidation.
23. Burri, J., Graf, M., Lambelet, P. and Löliger, J. (1989) Vanillin: more than a flavouring agent - a potent antioxidant. J Sci Food Agric, 48, pp. 49-56.
24. Burri, J., Graf, M., Lambelet, P. and Löliger, J. (1991) Protection of food against oxidation by the use of vanillin. US Patent
25. Bütehorn, U. and Pyell, U. (1996) Micellar electrokinetic chromatography as a screening method for the analysis of vanilla flavorings and vanilla extracts. J Chromatogr A, 736, pp. 321-332.
26. Caer, V., Trierweiler, M., Martin, GJ and Martin, ML (1991) Determination of site-specific carbon isotope ratios at natural abundance by carbon-13 nuclear magnetic resonance spectroscopy. Anal Chem, 63, pp. 2306-2313.
27. Cerrutti, P. and Alzamora, SM (1996) Inhibitory effects of vanillin on some food spoilage yeasts in laboratory media and fruit purees. Int J Food Microbiol, 29, pp. 379-386.
28. Cerruti, P., Alzamora, SM and Vidales, SL (1997) Vanillin as an antimicrobial for producing shelf-stable strawberry puree. J Food Sci, 62, pp. 608-610.
29. Cheetham, PSJ (1997) Combining the technical push and the business pull for natural flavours. Adv Biochem Eng/Biotechnol, 55, pp. 1-49.
30. de Jager, LS, Perfetti, GA and Diachenko, GW. (2007) Determination of coumarin, vanillin, and ethyl vanillin in vanilla extract products: Liquid chromatography mass spectrometry method development and validation studies. J Chromatogr A, 1145, pp. 83-88.
31. Dennis, M. (1998) Recent developments in food authentification. Analyst: R, 123, p. 151R.
32. Dennis, MJ, Wilson, P., Kelly, S. and Parker, I. (1998) The use of pyrolytic techniques to estimate site specific isotope data of vanillin. J Anal Appl Pyrolysis, 47, pp. 95-103.
33. Dignum, MJW, Kerler, J. and Verpoorte, R. (2001) Vanilla production: Technological, chemical, and biosynthetic aspects. Food Rev Int, 17, pp. 199-219.
34. Dignum, MJW, Kerler, J. and Verpoorte, R. (2002) Vanilla curing under laboratory conditions. Food Chem, 79, pp. 165-171.
35. Dignum, MJW, Heijden, RV-D, Kerler, J., Winkel, C. and Verpoorte, R. (2004) Identification of glucosides in green beans of Vanilla planifolia Andrews and kinetics of vanilla β-glucosidase. Food Chem, 85, pp. 199-205.
36. Duke, JA, Bogenschutz-Godwin, MJ, duCellier, J. and Duke, PK (2003) CRC handbook of medicinal spice, pp. 303-308. CRC Press, Boca Raton, FL
37. Durant, S. and Karran, P. (2003) Vanillins - a novel family of DNA-PK inhibitors. Nucleic Acids Res, 31, pp. 5501-5512.
38. Ehlers, D. (1999) HPLC-Untersuchung von handelsprodukten mit vanilla oder vanillearoma. Dtsch Lebensm Rundschau, 95, pp. 464-468.
39. Ehlers, D. and Bartholomae, S. (1993) Hochdruckflussigchromatographische Untersuchung von vanilla-CO2-hochdruckextraktenvergleich mit konventionell hergestellten alkoholischen vanilla. Extrakten Z Lebensm Unters Forsch, 197, pp. 550-557.
40. Ehlers, D. and Pfister, M. (1997) Compounds of Vanillons (Vanilla pompona Schiede). J Essent Oil Res, 9, pp. 427-431.
41. Ehlers, D., Pfister, M. and Bartholomae, S. (1994) Analysis of Tahiti vanilla by high-performance liquid chromatography. Z Lebensm Unters Forsch, 199, pp. 38-42.
42. Ehlers, D., Schafer, P., Doliva, H., Kirchhoff, J. and Fachbereich, V. (1999) Vanillin content and component ratios of vanilla beans: The influence of extraction conditions on the detection yields. Dtsch Lebensm Rundschau, 95, pp. 123-129.
43. Fang, Y., Shi, Z. and Zhang, K. (2002) Study on extraction of vanillin from Vanilla planifolia Andr. with supercritical CO2 fluid. Xianglio Xiangjing Huazhuangpin, 4, pp. 22-24.
44. Farthing, D., Sica, D., Abernathy, C., Fakhry, I., Roberts, JD, Abraham, DJ and Swerdlow, P. (1999) High-performance liquid chromatographic method for determination of vanillin and vanillic acid in human plasma, red blood cells and urine. J Chromatogr B, 726, pp. 303-307.
45. Ferguson, LR (1994) Antimutagens as cancer chemopreventive agents in the diet. Mutat Res, 307, pp. 395-410.
46. Fitzgerald, DJ, Stratford, M., Gasson, MJ and Narbad, A. (2004) The potential application of vanillin in preventing yeast spoilage of ready-to-drink beverages. J Food Prot, 67, pp. 391-395.
47. Fitzgerald, DJ, Stratford, M., Gasson, MJ, Ueckert, J., Bos, A. and Narbad, A. (2004) Mode of antimicrobial action of vanillin against Escherichia coli, Lactobacillus plantarum and Listeria innocua. J Appl Microbiol, 97, pp. 104-113.
48. Fitzgerald, DJ, Stratford, M., Gasson, MJ and Narbad, A. (2005) Structure-function analysis of the vanillin molecule and its antifungal properties. J Agric Food Chem, 53, pp. 1769-1775.
49. 18O) values of extracted and synthetic vanillin. Helv Chim Acta, 84, pp. 351-359.
50. Fu, S., Huang, M., Zhou, J. and Li, S. (2002) Determination of chemical constituents of vanilla by supercritical CO2 fluid extraction. Huaxue Yanjiu Yu Yingyong, 14, pp. 208-210.
51. Galetto, WG and Hoffman, PG (1978) Some benzyl ethers present in the extract of vanilla (Vanilla planifolia). J Agric Food Chem, 26, pp. 195-197.
52. Gerasimov, AV, Gornova, NV and Rudometova, NV (2003) Determination of vanillin and ethylvanillin in vanilla flavorings by planar (thin-layer) chromatography. J Anal Chem, 58, pp. 677-684.
53. Goodner, KL, Jella, P. and Rouseff, RL (2000) Determination of Vanillin in orange, grapefruit, tangerine, lemon, and lime juices using GC-Olfactometry and GC-MS/MS. J Agric Food Chem, 48, pp. 2882-2886.
54. Gustafson, DL, Franz, HR, Ueno, AM, Smith, CJ, Doolittle, DJ and Waldren, CA (2000) Vanillin (3-methoxy-4-hydroxybenzaldehyde) inhibits mutation induced by hydrogen peroxide, N-methyl-N-nitrosoguanidine and mitomycin C but not 137Cs ?-radiation at the CD59 locus in human-hamster hybrid AL cells. Mutagenesis, 15, pp. 207-213.
55. Hardcastle, JL, Paterson, CJ and Compton, RG (2001) Biphasic sonoelectroanalysis: Simultaneous extraction from, and determination of vanillin in food flavoring. Electroanalysis, 13, pp. 899-905.
56. Havkin-Frenkel, D. and Dorn, R. (1996) Vanilla. Spices flavor chemistry and antioxidant properties. ACS Symposium Series 660, p. 29. American Chemical Society., Washington, DC
57. Hearon, WM and Lo, CF. (1980) Method for preparing vanillin from old newsprint. US Patent, 4
58. Heck, G., Mileham, C. and Martin, GJ (1997) Hydrogen exchange in aromatic compounds subsituent effects studied by experimental design. Analysis, 25, pp. 202-206.
59. Hocking, MB (1997) Vanillin: Synthetic flavoring from spent sulfite liquor. J Chem Educ, 74, pp. 1055-1059.
60. Hoffman, PG and Salb, M. (1979) Isolation and stable isotope ratio analysis of vanillin. J Agric Food Chem, 27, pp. 352-355.
61. Hromádková, Z., Ebringerová, A. and Valachovic, P. (2002) Ultrasound-assisted extraction of water soluble polysaccharides from the roots of valerian (Valeriana officinalis L). Ultrason Sonochem, 9, pp. 37-44.
62. Hübner, H. (1983) Biologische Isotopieeffekte des Kohlenstoffs, pp. 87-88. Akademie der Wissenschaften der DDR, Leipzig, Germany
63. Imanishi, H., Sasaki, YF, Matsumoto, K., Watanabe, M., Ohta, T., Shirasu, Y. and Tutikawa, K. (1990) Suppression of 6-TG-resistant mutations in V79 cells and recessive spot formations in mice by vanillin. Mutat Res, 243, pp. 151-158.
64. Jagerdeo, E., Passetti, E. and Duger, SM (2000) Liquid chromatographic determination of vanillin and related aromatic compounds. J AOAC Int, 83, pp. 237-240.
65. John, TV and Jamin, E. (2004) Chemical investigation and authenticity of Indian vanilla beans. J Agric Food Chem, 52, pp. 7644-7650.
66. Kamat, JP, Ghosh, A. and Devasagayam, TPA (2000) Vanillin as an antioxidant in rat liver mitochondria: Inhibition of protein oxidation and lipid peroxidation induced by photosensitization. Mol Cell Biochem, 209, pp. 47-53.
67. Karas, AJ, Hall, RL and Stahl, WH (1972) Vanilla bean drying and curing. US Patent, 663, 3, p. 238.
68. Kauzinger, A., Juchelka, D. and Mosandl, A. (1997) Progress in the authenticity assessment of vanilla. Initiation of authenticity profiles. J Agric Food Chem, 45, pp. 1752-1757.
69. Keshava, C., Keshava, N., Ong, T. and Nath, J. (1998) Protective effect of vanillin on radiation-induced micronuclei and chromosomal aberrations in V79 cells. Mutat Res, 397, pp. 149-159.
70. Kiridena, W., Poole, SK and Poole, CF (1994) Identification of 5-(hydroxymethyl)-2-furfural in vanilla extracts. J Planar Chromatogr Mod TLC, 7, pp. 273-277.
71. Klimes, I. and Lamparsky, D. (1976) Vanilla volatiles - a comprehensive analysis. Int Flavours Food Additive, 7, pp. 272-291.
72. Kozlov, IA and Gogotov, AF (2001) Method for production of aromatic aldehydes from lignin containing material.
73. Krueger, DA and Krueger, HW (1983) Carbon isotopes in vanillin and the detection of falsified 'natural' vanillin. J Agric Food Chem, 31, pp. 1265-1268.
74. Krueger, DA and Krueger, HW (1985) Detection of fraudulent vanillin labeled with 13C in the carbonyl carbon. J Agric Food Chem, 33, pp. 323-325.
75. Kumar, SS, Priyadarsini, KI and Sainis, KB (2002) Free radical scavenging activity of vanillin and o-vanillin using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical. Redox Rep, 7, pp. 35-40.
76. Kumar, SS, Priyadarsini, KI and Sainis, KB (2004) Inhibition of peroxynitrite-mediated reactions by vanillin. J Agric Food Chem, 52, pp. 139-145.
77. Lamprecht, G., Pichlmayer, F. and Schmid, ER (1994) Determination of the authenticity of vanilla extracts by stable isotope ratio analysis and component analysis by HPLC. J Agric Food Chem, 42, pp. 1722-1727.
78. Lang, Q. and Wai, CM (2001) Supercritical fluid extraction in herbal and natural product studies - a practical review. Talanta, 53, pp. 771-782.
79. Lavoine, S., Arnaudo, JF and Coutiere, D. (1998) Applications of the HP-TLC to the study of vanilla extracts from Madagascar. Ann Falsif Expert Chim Toxicol, 91, pp. 41-51.
80. Li, Y-H, Sun, Z-H and Zheng, P. (2004) Determination of vanillin, eugenol and isoeugenol by RP-HPLC. Chromatographia, 60, pp. 709-713.
81. Longares-Patrón, A. and Canizares-Macías, MP (2006) Focused microwaves-assisted extraction and simultaneous spectrophotometric determination of vanillin and p-hydroxybenzaldehyde from Vanilla fragans. Talanta, 69, pp. 882-887.
82. López-Malo, A. and Alzamora, SM (1995) Effect of natural vanillin on germination time and radial growth of moulds in fruit based agar systems. Food Microbiol, 12, pp. 213-219.
83. López-Malo, A., Alzamora, SM and Angriz, A. (1998) Vanillin and pH synergistic effects on mould growth. J Food Sci, 63, pp. 143-146.
84. Mahal, HS, Badheka, LP and Mukherjee, T. (2001) Radical scavenging properties of a flavouring agent-vanillin. Res Chem Intermediat, 27, pp. 595-604.
85. Makkar, HPS and Beeker, K. (1994) Isolation of tannins from leaves of some trees and shrubs and their properties. J Agric Food Chem, 42, pp. 731-734.
86. Martin, GE, Guinand, GG and Figert, DM (1973) Comparison of gas-liquid, gas-solid, liquid-liquid, and liquid-solid chromatographic techniques in analysis of vanillin and ethyl vanillin in alcoholic solutions. J Agric Food Chem, 21, pp. 544-546.
87. Martin, GE, Figert, DM and Burggraff, JM (1981) Stable isotope ratio determination of the origin of vanillin in vanilla extracts and its relationship to vanillin/potassium ratios. J Assoc Off Anal Chem, 64, pp. 1149-1153.
88. Maubert, C., Guérin, C., Mabon, F. and Martin, GJ (1988) Determination of the origin of vanillin by multivariate analysis of the sitespecific natural isotope fractionation factors of hydrogen. Analusis, 16, pp. 434-439.
89. Mokshagundam, LRV and Mokshagundam, SL. (2003) Triglyceride reducing agent. US Patent, 6
90. Mykolaiivna, DT and Petrivna, ZL (2005) Method of inhibiting the autooxidation of milk fat.
91. Negishi, O. and Ozawa, T. (1996) Determination of hydroxycinnamic acids, hydroxybenzoic acids, hydroxybenzaldehydes, hydroxybenzyl alcohols and their glucosides by high-performance liquid chromatography. J Chromatogr A, 756, pp. 129-136.
92. Nguyen, K., Barton, P. and Spencer, JS (1991) Supercritical fluid extraction of vanillin. J Supercrit Fluids, 4, pp. 40-46.
93. Pan, X., Niu, G. and Liu, H. (2002) Comparison of microwave-assisted extraction and conventional extraction techniques for the extraction of tanshinones from Salvia miltiorrhiza bunge. Biochem Eng J, 12, pp. 71-77.
94. Panossian, A., Mamikonyan, G., Torosyan, M., Gabrielyan, E. and Mkhitaryan, S. (2001) Analysis of aromatic aldehydes in brandy and wine by high-performance capillary electrophoresis. Anal Chem, 73, pp. 4379-4383.
95. Pérez-Silva, A., Odoux, E., Brat, P., Ribeyre, F., Rodriguez-Jimenes, G., Robles-Olvera, V., García-Alvarado, MA and Günata, Z. (2006) GC-MS and GC-olfactometry analysis of aroma compounds in a representative organic aroma extract from cured vanilla (Vanilla planifolia G. Jackson) beans. Food Chem, 99, pp. 728-735.
96. Poole, SK, Kiridena, W., Miller, KG and Poole, CF (1995) Planar chromatographic methods for determination of the quality of spices and flavors as exemplified by cinnamon and vanilla. J Planar Chromatogr Mod TLC, 8, pp. 257-268.
97. Priefert, H., Rabenhorst, J. and Steinbüchel, A. (2001) Biotechnological production of vanillin. Appl Microbiol Biotechnol, 56, pp. 296-314.
98. Pyell, U., Pletsch-Viehmann, B. and Ramus, U. (2002) Component analysis of vanilla extracts and vanilla containing commercial preparations by micellar electrokinetic chromatography or high-performance liquid chromatography - a method comparison. J Sep Sci, 25, pp. 1035-1042.
99. Qiang, Z. and Zhonghao, C. (2001) Process for synthesizing vanillin from alkali lignin by green chemical method.
100. Ramaroson-Raonizafinimanana, B., Gaydou, ÉM and Bombarda, I. (1997) Hydrocarbons from three vanilla bean species: V. fragrans, V. madagascariensis and V. tahitensis. J Agric Food Chem, 45, pp. 2542-2545.
101. Ranadive, AS (1992) Vanillin and related flavour compounds in vanilla extracts made from beans of various global origins. J Agric Food Chem, 40, pp. 1922-1924.
102. Ranadive, AS (1994) Vanilla - cultivation, curing, chemistry, technology and commercial products. Spices, herbs and edible fungi, pp. 517-577. Elsevier, Amsterdam
103. Rao, SR and Ravishankar, GA (1999) Biotransformation of isoeugenol to vanilla flavour metabolites and capsaicin in suspended and immobilized cell cultures of Capsicum frutescens: Study of the influence of β-cyclodextrin and fungal elicitor. Process Biochem, 35, pp. 341-348.
104. Rao, SR and Ravishankar, GA (2000) Vanilla flavor: Production by conventional and biotechnological routes. J Sci Food Agric, 80, pp. 289-304.
105. Reineccius, G. (1997) Source book of flavours, pp. 351-360. CBS Publishers and Distributors, New Delhi
106. Remaud, GS, Martin, YL, Martin, GG and Martin, GJ (1997) Detection of sophisticated adulterations of natural vanilla flavors and extracts: Application of the SNIF-NMR method to vanillin and p-hydroxybenzaldehyde. J Agric Food Chem, 45, pp. 859-866.
107. Retnakaran, A. (1984) Repellent for black fly. US Patent, 4
108. Ruiz-Teran, F., Perez-Amador, I. and Lopez-Munguia, A. (2001) Enzymatic extraction and transformation of glucovanillin to vanillin from vanilla green pods. J Agric Food Chem, 49, pp. 5207-5209.
109. Sachan, A., Ghosh, S. and Mitra, A. (2004) An efficient isocratic separation of hydroxycinnamates and their corresponding benzoates from microbial and plant sources by HPLC. Biotechnol Appl Biochem, 40, pp. 197-200.
110. Sande, WE and Sears, KD (1996) Separating phenols from alkaline pulping spent liquors. US Patent, 5, pp. 589-30.
111. Sasaki, YF, Ohta, T., Imanishi, H., Watanabe, M., Matsumoto, K., Kato, T. and Shirasu, Y. (1990) Suppressing effects of vanillin, cinnamaldehyde and anisaldehyde on chromosome aberrations induced by X-rays in mice. Mutat Res, 243, pp. 299-302.
112. Sawa, T., Nakao, M., Akaike, T., Ono, K. and Maeda, H. (1999) Alkylperoxyl radical-scavenging activity of various flavonoids and other phenolic compounds: Implications for the anti-tumor-promoter effect of vegetables. J Agric Food Chem, 47, pp. 397-402.
113. Scharrer, A. and Mosandl, A. (2001) Reinvestigation of vanillin contents and component ratios of vanilla extracts using high-performance liquid chromatography and gas chromatography. Dtsch Lebensm Rundschau, 97, pp. 449-456.
114. Schmidt, H-L (1986) Food quality control and studies on human nutrition by mass spectrometric and nuclear magnetic resonance isotope ratio determination. Anal Bioanal Chem (Hist Arch), 324, pp. 760-766.
115. 2H patterns in natural compounds and its importance for the elucidation of biosynthetic pathways. Phytochem Rev, 2, pp. 61-85.
116. Sharma, A., Verma, SC, Saxena, N., Chadda, N., Singh, NP and Sinha, AK (2006) Microwave and ultrasound-assisted extraction of vanillin and its quantification by high-performance liquid chromatography in Vanilla planifolia. J Sep Sci, 29, pp. 613-619.
117. Sinha, AK, Verma, SC and Sharma, UK (2007) Development and validation of a RP-HPLC method for quantitative determination of vanillin and related phenolics in Vanilla planifolia. J Sep Sci, 30, pp. 15-20.
118. Sobolev, VS (2001) Vanillin content in boiled peanuts. J Agric Food Chem, 49, pp. 3725-3727.
119. Sophie, L. and Francois, MJ (2003) Use of a composition containing a vanilla extract to protect the skin against superoxide radicals or to limit the appearance of sunburn cells.
120. Sostaric, T., Boyce, MC and Spickett, EE (2000) Analysis of the volatile components in vanilla extracts and flavorings by solid-phase microextraction and gas chromatography. J Agric Food Chem, 48, pp. 5802-5807.
121. Stahl, E. (1969) Thin-layer chromatography: A laboratory handbook, Springer-Verlog, Berlin
122. Sun, R., Sacalis, JN, Chin, C-K and Still, CC (2001) Bioactive aromatic compounds from leaves and stems of Vanilla fragrans. J Agric Food Chem, 49, pp. 5161-5164.
123. Suresh, B., Ritu, T. and Ravishankar, GA (2003) Vanilla flavour production through biotransformation using Capsicum frutescens root cultures. Biocatal Biotransform, 21, pp. 333-340.
124. Tawatsin, A., Wratten, SD, Scott, RR, Thavara, U. and Techadamrongsin, Y. (2001) Repellency of volatile oils from plants against three mosquito vectors. J Vector Ecol, 26, pp. 76-82.
125. Teissedre, PL and Waterhouse, AL (2000) Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties. J Agric Food Chem, 48, pp. 3801-3805.
126. 13C NMR. J Agric Food Chem, 52, pp. 7782-7787.
127. 13C distribution in natural products: Vanillin. Anal Chem, 76, pp. 3818-3825.
128. Terabe, S., Markuszewskil, MJ, Inoue, N., Otsuka, K. and Nishioka, T. (2001) Capillary electrophoretic techniques toward the metabolome analysis. Pure Appl Chem, 73, pp. 1563-1572.
129. Toshio, U., Toshio, I. and Hideki, M. (2000) Antioxidant.
130. Toulemonde, B., Horman, I., Egli, H. and Derbesy, M. (1983) Differentiation between natural and synthetic vanillin samples using 2H NMR. Helv Chim Acta, 66, pp. 2342-2345.
131. Tripathi, U., Rao, SR and Ravishankar, GA (2002) Biotransformation of phenylpropanoid compounds to vanilla flavor metabolites in cultures of Haematococcus pluvialis. Process Biochem, 38, pp. 419-426.
132. Vaghasiya, YK, Nair, R., Soni, M., Baluja, S. and Chanda, S. (2004) Synthesis, structural determination and antibacterial activity of compounds derived from vanillin and 4-aminoantipyrine. J Serb Chem Soc, 69, pp. 991-998.
133. Velanker, MH and Heble, MR (2004) Biotransformation of externally added vanillin related compounds by multiple shoot culture of Vanilla planifolia L. J Plant Biochem Biotechnol, 13, pp. 153-156.
134. Voisine, R., Carmichael, L., Chalier, P., Cormier, F. and Morin, A. (1995) Determination of glucovanillin and vanillin in cured vanilla pods. J Agric Food Chem, 43, pp. 2658-2661.
135. Waliszewski, KN, Ovando, SL and Pardio, VT. (2007) Effect of hydration and enzymatic pretreatment of vanilla beans on the kinetics of vanillin extraction. J Food Eng, 78, pp. 1267-1273.
136. Waliszewski, KN, Pardio, VT and Ovando, SL. (2007) A simple and rapid HPLC technique for vanillin determination in alcohol extract. Food Chem, 101, pp. 1059-1062.
137. Walton, NJ, Mayer, MJ and Narbad, A. (2003) Molecules of interest - vanillin. Phytochemistry, 63, pp. 505-515.
138. Wekhhoff, P. and Guntert, M. (1997) Identification of some esters compounds in Bourbon vanilla beans. Lebensm Wiss Technol, 30, pp. 429-431.
139. Westcott, RJ, Cheetham, PSJ and Arraclough, AJB (1994) Use of organized viable vanilla plant aerial roots for the production of natural vanillin. Phytochemistry, 35, pp. 135-138.
140. Wu, G., Heitz, M. and Chornet, E. (1994) Improved alkaline oxidation process for the production of aldehydes (vanillin and syringaldehyde) from steam-explosion hardwood lignin. Ind Eng Chem Res, 33, pp. 718-723.
141. Zhang, C., Li, X., Lian, L., Chen, Q., Abdulmalik, O., Vassilev, V., Lai, C-S and Asakura, T. (2004) Anti-sickling effect of MX-1520, a prodrug of vanillin: An in vivo study using rodents. Br J Haematol, 125, pp. 788-795.
142. Zheng, L., Zheng, P., Sun, Z., Bai, Y., Wang, J. and Guo, X. (2007) Production of vanillin from waste residue of rice bran oil by Aspergillus niger and Pycnoporus cinnabarinus. Bioresource Technol, 98, pp. 1115-1119.
143. Zhu, FG and Zhou, SH (2002) A contactor for liquid-liquid and liquid-solid extraction of vanillin. Ind Eng Chem Res, 41, pp. 2316-2319.