Skip to main content
Log in

Diacylglycerol Oil—Properties, Processes and Products: A Review

  • Review Paper
  • Published:
Food and Bioprocess Technology Aims and scope Submit manuscript

Abstract

Diacylglycerol (DAG) oil has beneficial effects on obesity and weight-related disorders. A survey of literature has shown the effects of DAG on the reduction in the accumulation of body fat in both animals and humans. The physiological effect of DAG is believed to be attributed to its metabolic pathway, which is different from triacylglycerol (TAG) metabolism. Physicochemical properties, such as melting and smoke points and polymorphic forms, of DAG are also distinct from TAG. Various patented processes for DAG oil production from several reaction routes are discussed. A review of patent literature of commercial products based on DAG oils and fats is also provided.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Bell, R. M., & Coleman, R. A. (1980). Enzymes of glycerolipid synthesis in eukaryotes. Annual Review of Biochemistry, 49, 459–487.

    Article  CAS  Google Scholar 

  • Benson, F. R. (1967). Polyol surfactants. In M. J. Shick (Ed.), Nonionic surfactants (pp. 247–299). New York, NY: Marcel Dekker.

    Google Scholar 

  • Bockish, M. (1998). Composition, structure, physical data, and chemical reactions of fats and oils, their derivatives, and their associates. In M. Bockish (Ed.), Fats and oils handbook (pp. 53–120). Illinois, USA: AOCS.

    Google Scholar 

  • Cain, F. W., Manson, H. G. A., Quinlan, P. T., & Moore, S. R. (1999). Ice-cream coating fats. US Patent no .US5891495 (in English).

  • Cases, S., Smith, S. J., Zheng, Y. W., Myers, H. M., Lear, S. R., Sande, E., et al. (1998). Identification of a gene encoding an acyl CoA:diacylglycerol acyltransferase, a key enzyme in triacylglycerol synthesis. Proceedings of the National Academy of Sciences of the United States of America, 95, 13017–13023.

    Google Scholar 

  • Cases, S., Stone, S. J., Zhou, P., Yen, E., Tow, B., Lardizabal, K. D., et al. (2001). Cloning of DGAT2, a second mammalian diacylglycerol acyltransferase, and related family members. Journal of Biological Chemistry, 276, 38870–38876.

    Article  CAS  Google Scholar 

  • Choo, Y. M., Puah, C. W., Ma, A. N., & Basiron, Y. (2007). Production of edible oil. US Patent Application no. US20070021625 (in English).

  • Doucet, J., & Olathe, K. (1999). Shortening system, products therewith, and methods for making and using the same. US Patent no. US5908655 (in English).

  • Doucet, J., Olathe, K., Rethwill, C. E., McHugh, K., & Willhelm, C. L. (1999). Shortening system. European Patent Application no. EP1057887 (in English).

  • Flatt, J. P. (1988). Importance of nutrient balance in body weight regulation. Diabetes/Metabolism Reviews, 4, 571–581.

    CAS  Google Scholar 

  • Formo, M. W. (1979). Physical properties of fats and fatty acids. In D. Swern (Ed.), Bailey’s industrial oil and fat products (vol. 1, 4th ed., pp. 53–120). Illinois, USA: AOCS.

    Google Scholar 

  • Friedman, H. I., & Nylund, B. (1980). Intestinal fat digestion, absorption and transport. American Journal of Clinical Nutrition, 33, 1108–1139.

    CAS  Google Scholar 

  • Goto, N., Nishide, T., Tanaka, Y., & Yasukawa, T. (2000a). Oil and fat composition containing phytosterol. US Patent no. US6025348 (in English).

  • Goto, N., Nishide, T., Tanaka, Y., Yasukawa, T., & Masui, K. (2000b). Phytosterol-containing fat composition. European Patent Application no. EP0990391 (in English).

  • Goto, N., Nishide, T., Tanaka, Y., Yasukawa, T., & Masui, K. (2001). Oil or fat composition containing phytosterol. US Patent no. US6326050 (in English).

  • Hara, K., Onizawa, K., Honda, H., Otsuji, K., Ide, T., & Murata, M. (1993). Dietary diacylglycerol-dependent reduction in serum triacylglycerol concentration in rats. Annals of Nutrition and Metabolism, 37, 185–191.

    CAS  Google Scholar 

  • Hendriks, H. F. J., Weststrate, J. A., van Vliet, A. T., & Meijer, G. W. (1999). Spread enriched with three different levels of vegetable oil sterols and the degree of cholesterol lowering in normocholesterolaemic and mildly hypercholesterolaemic subjects. European Journal of Clinical Nutrition, 53, 319–327.

    Article  CAS  Google Scholar 

  • Jacobs, L., Lee, I., & Poppe, G. (2003). Chemical process for the production of 1,3-diglyceride oils. PCT International Patent no. WO03029392 (in English).

  • Jones, P. J. H., MacDougall, D. E., Ntanious, F., & Vanstone, C. A. (1997). Dietary phytosterols as cholesterol-lowering agents in humans. Canadian Journal of Physiology and Pharmacology, 75, 217–227.

    Article  CAS  Google Scholar 

  • Kamphuis, M. M., Mela, D. J., & Westerterp-Plantenga, M. S. (2003). Diacylglycerol affects substrate oxidation and appetite in humans. American Journal of Clinical Nutrition, 77, 1133–1139.

    CAS  Google Scholar 

  • Kawai, S., & Konishi, Y. (2000). Acid oil-in-water emulsified composition. PCT International Patent Application no. WO0078162 (in English).

  • Koike, S., Hosaya, N., & Yasumasu, T. (2001). Oil composition and use thereof. European Patent Application no. EP1135991 (in English).

  • Koike, S., Hosoya, N., & Yasumasu, T. (2002a). Fat compositions. European Patent Application no. EP1211305 (in English).

  • Koike, S., Yasumasu, T., Hase, T., Murase, T., & Yasukawa, T. (2002b). Oil/fat composition. PCT International Application no. WO0211551 (in English).

  • Koike, S., Yasumasu, T., Hase, T., Murase, T., Yasukawa, T., Katsuragi, Y., et al. (2002c). Oil/fat composition. PCT International Application no. WO0211552 (in English).

  • Koike, S., Yasumasu, T., Hase, T., Murase, T., Yasukawa, T., Katsuragi, Y., & Takei, A. (2002d). Oil/fat composition. PCT International Patent Application no. WO0211550 (in English).

  • Koike, S., Murase, T., & Hase, T. (2003). Oil or fat composition. US Patent Application no. 2003/0054082 (in English).

  • Kondo, H., Hase, T., Murase, T., & Tokimitsu, I. (2003). Digestion and assimilation features of dietary DAG in the rat small intestine. Lipids, 38, 25–30.

    Article  CAS  Google Scholar 

  • Kudo, N., Kameo, Y., & Mizuno, W. (2002). Oil-cooked or baked potatoes. European Patent Application no. EP1203534 (in English).

  • Lai, O. M., Yusoff, M. S. A., Lo, S. K., Long, K., Tan, C. P., Lim, J. W., et al. (2006). Process for the production of diacylglycerol. PCT International Application no. PCT/MY2006/000034 (in English).

  • Lai, O. M., Yusoff, M. S. A., Lo, S. K., Long, K., Tan, C. P., Tahiruddin, S., et al. (2007). Production of acylglycerol esters. PCT International Application no. PCT/MY2007/000025 (in English).

  • Lean, M., Gruer, L., Alberti, G., & Sattar, N. (2006). Obesity—Can we turn the tide? British Medical Journal, 333, 1261–1264.

    Article  Google Scholar 

  • Lehner, R., & Kuksis, A. (1993). Triacylglycerol synthesis by sn-1,2(2,3)-diacylglycerol transacylase from rat intestinal microsomes. Journal of Biological Chemistry, 268, 8781–8786.

    CAS  Google Scholar 

  • Lehner, R., & Kuksis, A. (1996). Biosynthesis of triacylglycerols. Progress in Lipid Research, 35, 169–201.

    Article  CAS  Google Scholar 

  • Lehner, R., Kuksis, A., & Itabashi, Y. (1993). Stereospecificity of monoacylglycerol and diacylglycerol acyltransferases from rat intestineas determined by chiral phase high-performance liquid chromatography. Lipids, 28, 19–34.

    Article  Google Scholar 

  • Ling, W. H., & Jones, P. J. H. (1995). Dietary phytosterols: a review of metabolism, benefits and side effects. Life Science, 57, 195–206.

    Article  CAS  Google Scholar 

  • Lo, S. K., & Baharin, B. S. (2001). Process for producing phytonutrient-enriched diacylglycerols. Malaysian Patent Application no. PI20014817 (in English).

  • Maki, K. C., Davidson, M. H., Tsushima, R., Matsuo, N., Tokimitsu, I., Umporowicz, D., et al. (2002). Consumption of diacylglycerol oil as part of a reduced-energy diet enhances loss of body weight and fat in comparison with consumption of a triacylglycerol control oil. American Journal of Clinical Nutrition, 76, 1230–1236.

    CAS  Google Scholar 

  • Mansbach II, C. M., & Nevin, P. (1998). Intracelllular movement of triacylglycerols in the intestine. Journal of Lipid Research, 39, 963–968.

    CAS  Google Scholar 

  • Masui, K., Katsuragi, Y., Toi, T., & Yasukawa, T. (2001). Fat or oil composition. PCT International Application no. WO0113733 (in English).

  • Masui, K., & Konishi, Y. (2001). Water-in-oil type emulsified fat and/or oil composition. PCT International Patent Application no. WO0101787 (in English).

  • Masui, K., & Yasunaga, K. (2001). Water-in-oil type emulsified fat and/or oil composition. PCT International Patent Application no. WO0115542 (in English).

  • Mazur, A. W., & Hiler, G. D. (1992). Regioselective synthesis of 1,3-disubstituted glycerides. Canadian Patent no. CA2106316 (in English).

  • Meguro, S., Higashi, K., Hase, T., Honda, Y., Otsuka, A., Tokimitsu, Y., et al. (2001). Solubilization of phytosterols in diacylglycerol versus triacylglycerol improves the serum cholesterol lowering effect. European Journal of Clinical Nutrition, 55, 513–517.

    Article  CAS  Google Scholar 

  • Meng, X., Zou, D., Shi, Z., Duan, Z., & Mao, Z. (2004). Dietary diacylglycerol prevents high-fat diet-induced lipid accumulation in rat liver and abdominal adipose tissue. Lipids, 39, 37–41.

    Article  Google Scholar 

  • Mori, H., Masui, K., Tanaka, Y., & Yasukawa, T. (1999a). Water-in-oil emulsified fat composition. PCT International Patent Application no. WO9959422 (in English).

  • Mori, H., Sakai, H., Tanaka, Y., & Yasukawa, T. (1999b). Fried food and shortening. PCT International Patent Application no. WO9959424 (in English).

  • Mori, H., & Watanabe, T. (2000). Food containing fat or oil. European Patent no. EP0970615 (in English).

  • Murase, T., Aoki, M., Wakisaka, T., Hase, T., & Tokimitsu, I. (2002a). Anti-obesity effect of dietary diacylglycerol in C57BL/6J mice: dietary diacylglycerol stimulates intestinal lipid metabolism. Journal of Lipid Research, 43, 1312–1319.

    CAS  Google Scholar 

  • Murase, T., Mizuno, T., Omachi, T., Onizawa, K., Komine, Y., Kondo, H., et al. (2001). Dietary diacylglycerol suppresses high fat and high sucrose diet-induced body fat accumulation in C57BL/6J mice. Journal of Lipid Research, 42, 372–378.

    CAS  Google Scholar 

  • Murase, T., Nagasawa, A., Suzuki, J., Wakisaka, T., Hase, T., & Tokimitsu, I. (2002b). Dietary alpha-linolenic acid-rich diacylglycerols reduce body weight gain accompanying the stimulation of intestinal beta-oxidation and related gene expressions in C57BL//KsJ-db/db mice. Journal of Nutrition, 132, 3018–3022.

    CAS  Google Scholar 

  • Murata, M., Hara, K., & Ide, T. (1994). Alteration by diacylglycerol of the transport and fatty acid composition of lymph chylomicrons in rats. Bioscience, Biotechnology and Biochemistry, 58, 1416–1419.

    Article  Google Scholar 

  • Murata, M., Ide, T., & Hara, K. (1997). Reciprocal responses to dietary diacylglycerol of hepatic enzymes of fatty acid synthesis and oxidation in the rat. British Journal of Nutrition, 77, 107–121.

    Article  CAS  Google Scholar 

  • Nagao, T., Watanabe, H., Goto, N., Onizawa, K., Taguchi, H., Matsuo, N., et al. (2000). Dietary diacylglycerol suppresses accumulation of body fat compared to triacylglycerol in men in a double-blind controlled trial. Journal of Nutrition, 130, 792–797.

    CAS  Google Scholar 

  • Nakajima, Y., Fukasawa, J., & Shimada, A. (2004). Physicochemical properties of diacylglycerol. In Y. Katsuragi, T. Yasukawa, N. Matsuo, B. D. Flickinger, I. Tokimitsu, & M. G. Matlock (Eds.), Diacylglycerol oil (pp. 182–196). Illinois, USA: AOCS.

    Google Scholar 

  • Nakajima, Y., Nishide, T., & Sakuma, T. (2002). Edible oil and production process thereof. United States Patent Application no. US20020045000 (in English).

  • Nomura, M., Koike, S., Yamashita, K., Okisaka, K., Sano, Y., Omura, H., et al. (1992). Edible oil-in-water emulsion. US Patent no. US5160759 (in English).

  • Sakai, H., Ishibashi, M., & Kohori, J. (2002a). Fat compositions. European Patent Application no. EP1186648 (in English).

  • Sakai, H., Katada, M., & Ishibashi, M. (2002b). Oil or fat composition. European Patent Application no. EP1249173 (in English).

  • Schutz, Y. (1995). Macronutrients and energy balance in obesity. Metabolism, 44(3), 7–11.

    Article  CAS  Google Scholar 

  • Sedarevich, B. (1967). Glyceride isomerisation in lipid chemistry. Journal of the American Oil Chemists’ Society, 44, 381–393.

    Article  Google Scholar 

  • Shiiba, D., Asabu, Y., Kawai, S., & Nakajima, Y. (2002). Acidic oil-in-water type emulsion composition. United States Patent Application no. US20020119239 (in English).

  • Soni, M. G., Kimura, H., & Burdock, G. A. (2001). Chronic study of diacylglycerol oil in rats. Food Chemistry and Toxicology, 39, 317–329.

    Article  CAS  Google Scholar 

  • Sugimoto, T., Fukuda, H., Kimura, T., & Iritani, N. (2003a). Dietary diacylglycerol-rich oil stimulation of glucose intolerance in genetically obese rats. Journal of Nutritional Science and Vitaminology, 49, 139–144.

    CAS  Google Scholar 

  • Sugimoto, T., Kimura, T., Fukuda, H., & Iritani, N. (2003b). Comparisons of glucose and lipid metabolism in rats fed diacylglycerol and triacylglycerol oils. Journal of Nutritional Science and Vitaminology, 49, 47–55.

    CAS  Google Scholar 

  • Sugiura, M., Shimizu, M., Yamada, Y., Mine, K., Maruyama, E., & Yamada, N. (2002a). Process for producing partial glyceride. US Patent no. US 6337414 (in English).

  • Sugiura, M., Yamaguchi, H., & Yamada, N. (2002b). Preparation process of diglyceride. US Patent no. US6361980 (in English).

  • Tada, N., Watanabe, H., Matsuo, N., Tokimitsu, I., & Okazaki, M. (2001). Dynamics of postprandial remnant-like lipoproteins particles in serum after loading of diacylglycewrols. Clinica Chimica Acta, 311, 109–117.

    Article  CAS  Google Scholar 

  • Taguchi, H., Omachi, T., Nagao, T., Matsuo, N., Tokimitsu, I., & Itakura, H. (2002). Dietary diacylglycerol suppresses high fat diet-induced hepatic fat accumulation and microsomal triacylglycerol transfer protein activity in rats. Journal of Nutritional Biochemistry, 13, 678–683.

    Article  CAS  Google Scholar 

  • Taguchi, H., Watanabe, H., Onizawa, K., Nagao, T., Gotoh, N., Yasukawa, T., et al. (2000). Double-blind controlled study on the effects of dietary diacylglycerol on postprandial serum and chylomicron triacylglycerol responses in healthy humans. Journal of the American College of Nutrition, 19, 789–796.

    CAS  Google Scholar 

  • Takano, H., & Itabashi, Y. (2002). Molecular species analysis of 1,3-diacylglycerols in edible oils by HPLC/ESI-MS. Bunseki Kagaku, 51, 437–442.

    Article  CAS  Google Scholar 

  • Takase, H., Koike, S., Sakai, H., Nishide, T., Hase, T., & Murase, T. (2003). Oil composition. PCT International Patent Application no. WO03024237 (in English).

  • Teramoto, T., Watanabe, H., Ito, K., Omata, Y., Furukawa, T., Shimoda, K., et al. (2004). Significant effects of diacylglycerol on body fat and lipid metabolism in patients on hemodialysis. Clinical Nutrition, 23, 1122–1126.

    Article  CAS  Google Scholar 

  • Toshinori, I., Yasuharu, N., Shinichi, H., & Shoichi, K. (2000). Production of diglyceride-containing fat and oil composition and fat and oil composition using the same. Japanese Patent no. JP2000345189 (in Japanese).

  • Watanabe, H., Onizawa, K., Taguchi, H., Kobori, M., Chiba, H., & Naito, S. (1997). Nutritional characterization of diacylglycerols in rats. Journal of the Japanese Oil Chemists’ Society, 46, 301–307.

    CAS  Google Scholar 

  • William, C. L., Gulli, M. T., & Deckelbaum, R. J. (2001). Prevention and treatment of childhood obesity. Current Atherosclerosis Reports, 3, 486–497.

    Article  Google Scholar 

  • Yamada, Y., Shimizu, M., Sugiura, M., & Yamada, N. (1999). Process for producing diglycerides. PCT International Application no. WO9909119 (in English).

  • Yamamoto, K., Asakawa, H., Tokunaga, K., Meguro, S., Watanabe, H., Tokimitsu, I., et al. (2005). Effects of diacylglycerol administration on serum triacylglycerol in a patient homozygous for complete lipoprotein lipase detection. Metabolism, 54, 67–71.

    Article  CAS  Google Scholar 

  • Yamamoto, K., Asakawa, H., Tokunaga, K., Watanabe, H., Matsuo, N., Tokimitsu, I., et al. (2001). Long-term ingestion of dietary diacylglycerol lowers serum triacylglycerol in type II diabetic patients with hypertriglyceridemia. Journal of Nutrition, 131, 3204–3207.

    CAS  Google Scholar 

  • Yanagisawa, Y., Kawabata, T., & Hasegawa, K. (2003). Improvement in blood lipid levels by dietary sn-1,3-diacylglycerol in young women with variants of lipid transporters 54T-FABP2 and -493g-MTP. Biochemical and Biophysical Research Communications, 302, 743–750.

    Article  CAS  Google Scholar 

  • Yoon, D.-H., Han, G.-W., Hong, S.-G., & Lee, Y.-H. (2004). Preparation method of conjugated linoleic acid diglycerides. PCT International Application no. WO2004096748 (in English).

Download references

Acknowledgment

The authors thank Golden Hope Research Centre Sdn. Bhd. for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Oi-Ming Lai.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lo, SK., Tan, CP., Long, K. et al. Diacylglycerol Oil—Properties, Processes and Products: A Review. Food Bioprocess Technol 1, 223–233 (2008). https://doi.org/10.1007/s11947-007-0049-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11947-007-0049-3

Keywords

Navigation