Chemistry of the Main Component of Essential Oil of Litsea cubeba and Its Derivatives


The tree of Litsea cubeba is widely spread in China, Indonesia and other part of Southeast Asia. The essential oil of Litsea cubeba (EOLC) is obtained by steam distillation from the pepper-like fruits tree Litsea cubeba. The EOLC consists of about 29 active compounds. Among them, citral is the main component; the content of citral is nearly 80% of the EOLC. Due to the special function group, citral is easy to react with many chemicals. Thus, EOLC is usually applied as starting material to carry out aldol condensation, reduction, and six-member ring forming reaction. The EOLC is extensively employed to synthesis of geranal nitriles, pseudonoe, ionone, methyl ionone, Vitamin E and Vitamin A. These products are broadly applied in the fields of fragrance, perfume, medicine and so on. This paper presents comprehensive utilization of EOLC as raw materials to synthesize many active chemicals.

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Hu, L. , Du, M. , Zhang, J. and Wang, Y. (2014) Chemistry of the Main Component of Essential Oil of Litsea cubeba and Its Derivatives. Open Journal of Forestry, 4, 457-466. doi: 10.4236/ojf.2014.45050.

Conflicts of Interest

The authors declare no conflicts of interest.


[1] Ayrilmis, N., Buyuksari, U., Avci, E., & Koc, E. (2009). Utilization of Pine (Pinus pinea L.) Cone in Manufacture of Wood Based Composite. Forest Ecology and Management, 259, 65-70.
[2] Bakkali, F., Averbeck, S., Averbeck, D., & Idaomar, M. (2008). Biological Effects of Essential Oils—A Review. Food and Chemical Toxicology, 46, 446-475.
[3] Bonrath, W., Dittel, C., Giraudi, L., Netscher, T., & Pabst, T. (2007). Rare Earth Triflate Catalysts in the Synthesis of Vitamin E and Its Derivatives. Catalysis Today, 121, 65-70.
[4] Bowry, V. W., Mohr, D., Cleary, J., & Stocker, R. (1995). Prevention of Tocopherol-Mediated Peroxidation in Ubiquinol-10-Free Human Low Density Lipoprotein. Journal of Biological Chemistry, 270, 5756-5763.
[5] Bulychev, é. Y., & Kartsev, G. (1999). On the Mechanism of α-Tocopherol Synthesis. Effect of Amines on the Yield and Purity of α-Tocopherol. Pharmaceutical Chemistry Journal, 33, 267-268.
[6] Chen, Y., Wang, Y., Han, X., Si, L., Wu, Q., & Lin, L. (2013). Biology and Chemistry of Litsea cubeba, a Promising Industrial Tree in China. Journal of Essential Oil Research, 25, 103-111.
[7] Cheng, K. (1995). Raising Citral Content of Litsea cubeba Oil by Reduced-Pressure Distillation. Hunan Chemistry Industry, 25, 34-36.
[8] Cooper, C. M., Davies, N. W., & Menary, R. C. (2003). C-27 Apocarotenoids in the Flowers of Boronia megastigma (Nees). Journal of Agricultural and Food Chemistry, 51, 2384-2389.
[9] Damodaran, S., & Parkin, K. L. (2008). Fennema’s Food Chemistry. Boca Raton, FL: CRC Press.
[10] Djeridane, A., Yousfi, M., Nadjemi, B., Boutassouna, D., Stocker, P., & Vidal, N. (2006). Antioxidant Activity of Some Algerian Medicinal Plants Extracts Containing Phenolic Compounds. Food Chemistry, 97, 654-660.
[11] Guo, M., Wang, D., Jiang, M., & Xiao, Y. (1980). The Study of Modification of Iso-Methyl Ionone, Methyl Ionone Process. Flavor and Perfume, 5, 1-11.
[12] Hu, L., Yang, W., Du, M., & Zhang, J. (2011). Characterization of the Volatiles and Active Components in Ethanol Extracts of Fruits of Litsea cubeba (Lour.) by Gas Chromatography-Mass Spectrometry (GC-MS) and Gas Chromatography-Olfactometry (GC-O). Journal of Medicinal Plants Research, 5, 3298-3303.
[13] Isman, M. B. (2000). Plant Essential Oils for Pest and Disease Management. Crop Protection, 19, 603-608.
[14] Jin, X., Wang, J., & Bai, J. (2009). Synthesis and Antimicrobial Activity of the Schiff Base from Chitosan and Citral. Carbohydrate Research, 344, 825-829.
[15] Jordan, M. J., Margaria, C. A., Shaw, P. E., & Goodner, K. L. (2002). Aroma Active Components in Aqueous Kiwi Fruit Essence and Kiwi Fruit Puree by GC-MS and Multidimensional GC/GC-O. Journal of Agricultural and Food Chemistry, 50, 5386-5390.
[16] Kaiser, R., & Lamparsky, D. (1980). Volatile Constituents of Osmanthus Absolute. In B. D. Mookheijee, & C. J. Mussinan (Eds.), Essential Oils (pp. 159-192). Wheaton, IL: Allured Publishing.
[17] Kanei, N., Tamura, Y., & Kunieda, H. (1999). Effect of Types of Perfume Compounds on the Hydrophile-Lipophile Balance Temperature. Journal of Colloid and Interface Science, 218, 13-22.
[18] Lin, H. (2004). Synthesis of Pseudomethylionone Using Fluoride Ion Supported on Anion Exchange Resin as a Catalyst. Chinese Journal of Synthetic Chemistry, 12, 402-404.
[19] Lin, H., & Liang, C. (2002). Cyclization of Pseudomethylionone by Catalyzing of Macroreticular Resin. Liaoning Chemical Industry July, 31, 3.
[20] Liu, R., Liu, H., & Dong, A. (2000). Study on the Synthesis of Ionone Violet in the Presence of Phase Transfer Catalysis. Speciality Petrochemicals, 200, 31-33.
[21] Liu, X., Chen, M., & Chen, X. (2001). Extracting Citral from Litsea cubeba Fruits and Determination of Citral. Chemistry and Industry of Forest Products, 21, 87-90.
[22] Lu, J., & Yao, Y. (2007). Improvement on the Synthesis of Beta-Ionone. Guizhou Chemical Industry, 32, 12-14.
[23] Matsui, M., Karibe, N., Hayashi, K., & Yamamoto, H. (1995). Synthesis of Alpha-Tocopherol: Scandium (III) Trifluoromethanesulfonate as an Efficient Catalyst in the Reaction of Hydroquinone with Allylic Alcohol. Bulletin of the Chemical Society of Japan, 68, 3569-3571.
[24] Nong, K., Lu, D., Nong, R., Wei, Y., & Huang,W. (2001). Research on the Synthesis of Lemonile by Dehydrat Ion through Phase T Ransfer Base Catalysis. Chemistry Society, 10, 3.
[25] Packer, L., Rimbach, G., & Virgili, F. (1999). Antioxidant Activity and Biologic Properties of a Procyanidin-Rich Extract from Pine (Pinus maritima) Bark, Pycnogenol. Free Radical Biology and Medicine, 27, 704-724.
[26] Plotto, A., Barnes, K. W., & Goodner, K. L. (2006). Specific Anosmia Observed for β-Ionone, but not for α-Ionone: Significance for Flavor Research. Journal of Food Science, 71, 401-406.
[27] Qian, D., Yao, L., Tan, Y., & Cui, J. (1999). Catalyzed Synthesis of D-L-α-tocopherol by Phosphomolybdic Acid. Synthesis Chemistry, 7, 2-4.
[28] Zeng, L. H., Lian, H. M., Zhang, Q. (2012). Resources of Cinnamomum camphora and Its Utilization. Guangdong Forestry Science and Technology, 3, 014.
[29] Qin, F., Shen, W., Wang, C., & Xu, H. (2008). Selective Hydrogenation of Citral over a Novel Platinum/MWNTs Nanocomposites. Catalysis Communications, 9, 2095-2098.
[30] Raju, V., Radhakrishnan, R., Jaenicke, S., & Chuah, G. K. (2011). KF on γ-alumina: An Efficient Catalyst for the Aldol Condensation to Pseudoionones. Catalysis Today, 164, 139-142.
[31] Robeson, C. D., Blum, W. P., Dieterle, J. M., Cawley, J. D., & Baxter, J. G. (1955). Chemistry of Vitamin A. XXV. Geometrical Isomers of Vitamin A Aldehyde and an Isomer of Its α-Ionone Analog. Journal of the American Chemical Society, 77, 4120-4125.
[32] Saddiq, A. A., & Khayyat, S. A. (2010). Chemical and Antimicrobial Studies of Monoterpene: Citral. Pesticide Biochemistry and Physiology, 98, 89-93.
[33] Sato, K., Kurihara, Y., & Abe, S. (1963). Synthesis of Isophytol. The Journal of Organic Chemistry, 28, 45-47.
[34] Stubbs, B. J., Specht, A., & Brushett, D. (2004). The Essential Oil of Cinnamomum camphora (L.) Nees and Eberm. Variation in Oil Composition throughout the Tree in Two Chemotypes from Eastern Australia. Journal of Essential Oil Research, 16, 200-205.
[35] Tang, J. (2011). Synthesis of Methyl Ionone. Hebei Chemical Industry, 34, 56-58.
[36] Tanumihardjo, S. A. (2011). Vitamin A: Biomarkers of Nutrition for Development. The American Journal of Clinical Nutrition, 94, 658S-665S.
[37] Wang, F., Wang, S., Hu, H., Huang, Q., Yang, D., Zhu, B., & Liu, H. (2002). Raising Citral Content of Litsea cubeba Oil by Reduced-Pressure Distillation. Natural Products Research and Development, 14, 55-57.
[38] Wang, L. (1990). Review of Preparation of β-Ionone. Chinese Journal of Pharmaceuticals, 21, 230-232.
[39] Wang, Q., & Jiang, J. (1993). Preparation of Citral and Synthesis of Ionones. Speciality Petrochemicals, 4, 20-22.
[40] Ye, Q. (1992). Analysis of the Content of Aldehyde in the Esstenial Oil of the Litsea cubeba. Froestry Products and Processing Communication, 10, 18-20.
[41] Yu, S. G., Anderson, P. J., & Elson, C. E. (1995). Efficacy of β-Ionone in the Chemoprevention of Rat Mammary Carcinogenesis. Journal of Agricultural and Food Chemistry, 43, 2144-2147.
[42] Zhang, W., Lei, A., & Zhao, Z. (2010). Synthesis of Pseudoionones over Solid Base Catalyst. Guangzhou Chemical Industry, 38, 157-162.
[43] Zhou, X., Yu, Q., & Guo, W. (2009). Synthetic Conditions of Pseudoionone. Journal of University of Science and Technology Liaoning, 32, 4-7.

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