| Literature DB >> 35761969 |
Harsh B Jadhav1, Uday S Annapure1.
Abstract
Medium-chain triglycerides contain medium-chain fatty acid esterified to the glycerol backbone. These MCFA have a shorter chain length and are quickly metabolized in the body serving as an immediate energy source. They are known to have good physiological as well as functional characteristics which help in treating various health disorders. Naturally, they are found in coconut oil, milk fat, and palm kernel oil, and they are synthetically produced by esterification and interesterification reactions. Due to their numerous health benefits, MCT is used as a functional or nutraceutical oil in various food and pharmaceutical formulations. To increase their nutraceutical benefits and food applications MCFA can be used along with polyunsaturated fatty acids in the synthesis of structured lipids. This review aims to provide information about triglycerides of MCFA, structure, metabolism, properties, synthetic routes, intensified synthesis approaches, health benefits, application, and safety of use of MCT in the diet. © Association of Food Scientists & Technologists (India) 2022.Entities:
Keywords: Coconut oil; Esterification; Interesterification; Medium-chain fatty acid; Medium-chain triglyceride; Nutraceutical
Year: 2022 PMID: 35761969 PMCID: PMC9217113 DOI: 10.1007/s13197-022-05499-w
Source DB: PubMed Journal: J Food Sci Technol ISSN: 0022-1155 Impact factor: 3.117
General information of medium chain fatty acids
| Medium chain fatty acid | Number of carbons | Molecular formula | Structural formula | Systematic name | Molecular weight (g/mol) |
|---|---|---|---|---|---|
| Caproic acid | C6:0 | C6H12O2 | CH3(CH2)4COOH | Hexanoic acid | 116.15 |
| Caprylic acid | C8:0 | C8H16O2 | CH3(CH2)6COOH | Octanoic acid | 144.21 |
| Capric acid | C10:0 | C10H20O2 | CH3(CH2)8COOH | Decanoic acid | 172.26 |
| Lauric acid | C12:0 | C12H24O2 | CH3(CH2)10COOH | Dodecanoic acid | 200.31 |
Fig. 1Chemical structure of medium chain fatty acids
Fig. 2General esterification reaction for synthesis of triglycerides
Points of comparison between chemical and enzymatic esterification reaction
| Characteristics | Chemical | Enzymatic |
|---|---|---|
| Type of catalyst | Chemical catalyst like sulphuric acid, hydrochloric acid, sodium methoxide, para-toluene sulphonic acid etc | Lipases from animal, plant and microorganisms |
| Temperature | Reaction is usually carried out at higher temperature (150–200 °C) | Reaction is carried out at moderate temperature below 50 °C |
| Bi-product formation | Many undesirable by-products are formed and hence product needs purification | Insignificant or no by-products are formed |
| Eco-friendly | No, since it produces many by-products which are toxic in nature | Yes, it is cleaner and eco-friendly |
| Challenges | It produces toxic products and final product is dark in color hence processes like bleaching, deodorization, purification is necessary | Little change in temperature, pH of reaction medium affects the activity of enzyme |
| Rate of reaction | Rate of reaction is faster; hence less time is required for completion of reaction | Rate of reaction is very slow; hence more time is required for completion of reaction |
| Economical aspect | Chemical catalyst are inexpensive, hence the process is economical as compared with enzymatic process | Enzymes are very expensive, which increases the cost of production |
Synthetic routes for synthesis of medium chain triglycerides
| Reaction | Substrate | Catalyst/enzyme | Reaction temp (°C) and time | Intensification approach | Yield (%) | References |
|---|---|---|---|---|---|---|
| Esterification | Caproic acid, caprylic acid, capric acid, lauric acid and glycerol | Tungsten oxide, calcium oxide, tungsten chloride | 160–180 °C in 22–24 h | Conventional reaction | 90–93% | Boulos ( |
| Caprylic acid and glycerol | Amberlyst-15 | 80 °C in 16 min | Microwave assisted synthesis | 99.7% | Jadhav and Annapure ( | |
| Lauric acid and glycerol | Sulphuric acid | 90 °C in 300 min | Ultrasound assisted synthesis | 77.8% | Mohod and Gogate ( | |
| Lauric acid and glycerol | Sulphuric acid | 90 °C in 1. 20 min 2. 120 min 3. 180 min | 1.Microwave assisted 2.Ultrasound assisted 3.Conventional synthesis | 1. 99.7% 2. 97.5% 3. 40% | Mohod and Gogate ( | |
| Caprylic acid (60.35%), Capric acid (38.11%), lauric acid (1.15%) and glycerol | Sulphuric acid | 90 °C in 300 min | Ultrasound assisted synthesis | 98.5% | Deshmane et al. ( | |
| Caprylic acid and glycerol | Sulphuric acid, hydrochloric acid, PTSA, Sodium methoxide | 170 °C in 9 h | Ultrasound assisted synthesis (More et al. | 96.6% | More et al. ( | |
| Capric acid, lauric acid, myristic acid and glycerol | Immobilized lipase (Lipozyme IM 20) | 60–90 °C in 26 h | Conventional synthesis | 50%-Tricaprin 70%- Trilaurin 70%-Trimyristin | Langone and Sant’Anna ( | |
| Caprylic acid and glycerol | Novozyme 435, Lipozyme IM RM | 50 °C in 6 h | Supercritical CO2 Technology | 97.3% | More et al. ( | |
| Caprylic acid and glycerol | Novozyme 435 and Lipozyme RM IM | 50 °C in 7 h | Ultrasound assisted synthesis | 94.8% | More et al. ( | |
| Interesterification | Medium chain triglycerides and soyabean oil | Lipozyme 435 | 90 °C in 300 min | Conventional synthesis | 74.9% | Lu et al. ( |
| Coconut oil | Potassium methoxide | 40–60 °C in 12 h | Conventional synthesis | 24% | Nugrahini and Soerawidjaja ( |
Fig. 3Figure representing comparison between microwave and conventional reaction
Commercially available MCT products in market
| MCT oil brand | Application | Producer |
|---|---|---|
| MCT oil | Act as a fuel to brain and body | Nature way, USA |
| Powdered MCT Oil | Ketogenic diet | Quest Nutrition USA |
| MCT Oil (mixture of C8 and C10) | Food applications like bakery and confectionary | AAK Kamani, India |
| Joymix MCT Oil | For weight management | Malaysia |
| Keto products | Source of energy | 360 Nutrition, USA |
| Keto organic MCT Oil | Used for weight loss | Ancient Nutrition, USA |
| MCT powder | Help to control cardiovascular diseases | Ogranika, Canada |
| Liquid MCT Oil | Supplement to be used in food formulation | Supplement manufacturer, UK |
| Spring valley oil | Management of weight and for athletes | Spring valley, USA |
| Soft gel (MCT Oil) | Improved fat metabolism | Carlson Lab, USA |
| Melrose MCT powder and MCT oil | Energy for brain and body | Melrose, Australia |
| MCT Oil | Source of energy | Bioglan, Australia |
| Max-C8 | Proper metabolism, digestion, energy, weight management | Zenwise health, Germany |
| Pure tricaprylin oil | Weight management | Weight world, UK |
| Diet MCT Oil | Nutraceutical fat and source of energy | Diet works, USA |