Partition coefficient calculation of selected terpenes and low molecular weight solvents between tall oil fatty acid and air and polydimethyl siloxane oil and air

Headspace gas chromatography-mass spectrometry (GC-MS) has been applied to the analysis of the temperature-dependent tall oil fatty acid (TOFA)/air partition coefficient (k ₁) and the polydimethyl siloxane oil/air partition coefficient (k ₂) of selected terpenes and low molecular weight solvents. As expected, both the TOFA and the silicone oil are effective trapping media for the nonpolar terpenes, but they are also efficient traps for acetone, methanol, n-propanol, and n-butanol. However, several species of low and moderate molecular weight (less than 150 amu) aldehydes, ketones, and organic acids that might adversely affect its trapping capacity were detected in the TOFA. This article will report the empirically gathered data and the subsequent calculation of the partition coefficients for the terpenes: α- and β-pinene, limonene, and α-terpineol and the solvents: acetone, methanol, n-propanol, and n-butanol between 50 and 130°C.     

The Effect of Operational Parameters of the Rancimat Method on the Determination of the Oxidative Stability Measures and Shelf-Life Prediction of Soybean Oil

Operational parameters of the Rancimat method, including oil sample size, airflow rate, and temperature, were evaluated to determine their effects on the oxidative stability index (OSI), temperature coefficient, Q ₁₀ number, and shelf-life prediction for soybean oil. Operational parameters of the Rancimat method had statistically significant effects (P < 0.05) on the OSI. Whenever the oil sample size and airflow rate at a given temperature were such that the air-saturated condition could be established, the OSIs showed no statistically significant differences. As temperature increased, OSIs decreased, while their average coefficient of variation (CV) increased. In general, the conditions where the sample was saturated with air and had a relatively lower CV were an oil sample size of 6 g at all temperatures and airflow rates, then 3-g oil sample size at low temperatures (100 and 110 °C) and low airflow rates (10 and 15 L h⁻¹). The temperature coefficient and Q ₁₀ number were found to be independent of the oil sample size and airflow rate, and their mean values for soybean oil were calculated to be −3.12 × 10⁻² °C⁻¹ and 2.05, respectively. Oil sample size and airflow rate showed a significant effect on shelf-life prediction for soybean oil. Therefore, choosing the right levels of these operational parameters in the Rancimat method may produce the least possible difference between predictions from long-term storage studies and the OSI test.     

The avrami index and the fractal dimension in vegetable oil crystallization

The behavior of the Avrami plot during TAG crystallization was studied by DSC and rheological measurements in oil blends of palm stearin (26 and 80%) in sesame oil, using different crystallization temperatures (T _Cr ^o) attained under several cooling rate conditions (1, 10, and 30°C/min). In the same way, the relationship between the growth mechanisms of TAG, measured by the Avrami index (n), and the mass fractal dimension (D) of the crystal network was investigated. This last parameter was measured as TAG crystallized in the oil blend under isothermal conditions. Results showed that TAG crystallization in a vegetable oil involves the process of TAG lamellar development, nucleation, and crystal growth. Each event occurred at a different rate and extent as affected by cooling rate and T _Cr ^o, and as a function of crystallization time under isothemal conditions at a given cooling rate. Within this framework, we proposed that n calculated from the second region of the Avrami plot is a parameter mainly associated with crystal growth, whereas n from the first region is associated more with nucleation. On the other hand, changes in D values followed the different polymorphic states developed by TAG as a function of T _Cr ^o. Additionally, it was shown that, independent of the concentration of palm stearin in the oil blend, at cooling rates of 1 and 10°C/min the increase in n from ∼3 to ∼4 produced a curvilinear increase in D from ∼1.75 to ∼3.0. The growth mechanism of the TAG crystals (i.e., n), also affected the magnitude of D. However different behavior was observed in the n-D relationship when n<2.7 and at 30°C/min.     

The effect of supercooling on crystallization of cocoa butter-vegetable oil blends

The solid fat content (SFC), Avrami index (n), crystallization rate (z), fractal dimension (D), and the pre-exponential term [log(γ)] were determined in blends of cocoa butter (CB) with canola oil or soybean oil crystallized at temperatures (T _Cr) between 9.5 and 13.5°C. The relationship of these parameters with the elasticity (G′) and yield stress (σ^*) values of the crystallized blends was investigated, considering the equilibrium melting temperature (T _M ^o) and the supercooling (i.e., T _Cr ^o−T _M ^o) present in the blends. In general, supercooling was higher in the CB/soybean oil blend [T _M ^o=65.8°C (±3.0°C)] than in the CB/canola oil blend [T _M ^o=33.7°C (±4.9°C)]. Therefore, under similar T _Cr values, higher SFC and z values (P<0.05) were obtained with the CB/soybean oil blend. However, independent of T _Cr TAG followed a spherulitic crystal growth mechanism in both blends. Supercooling calculated with melting temperatures from DSC thermograms explained the SFC and z behavior just within each blend. However, supercooling calculated with T _M ^o explained both the SFC and z behavior within each blend and between the blends. Thus, independent of the blend used, SFC described the behavior of G′_eq and σ^* and pointed out the presence of two supercooling regions. In the lower supercooling region, G′_eq and σ^* decreased as SFC increased between 20 and 23%. In this region, the crystal network structures were formed by a mixture of small β′ crystals and large β crystals. In contrast, in the higher supercooling region (24 to 27% SFC), G′_eq and σ^* had a direct relationship with SFC, and the crystal network structure was formed mainly by small β′ crystals. However, we could not find a particular relationship that described the overall behavior of G′_eq and σ^* as a function of D and independent of the system investigated.     

EPA,but not DHA,decreases mean platelet volume in normal subjects

The first indication of platelet activation is an increase in mean platelet volume (MPV). n−3 FA are known to inhibit platelet function and to reduce the risk for coronary heart disease. The purpose of this study was to determine the effects of FPA and DHA on MPV. Healthy subjects received olive oil placebo for 4 wk and then were randomly assigned to receive 4g of ethyl esters of either safflower oil (n=11), EPA (n=10), or DHA (n=12) for 4 wk. At the end of placebo run-in and treatment periods, MPV (fL; mean±SEM) and platelet count (PLT-CT; 10³/μL blood) were measured in the basal state and after ex vivo stimulation with collagen (10 μg/mL), cold (4°C), and heat (37°C). Unlike DHA, EPA lowered MPV as compared with safflower oil (7.2±0.1 vs. 7.5±0.1 fL; P<0.05) and raised PLT-CT (211±18 vs. 192±18 10³/μL; P<0.05) in the fasting state. Collagen and cold significantly increased MPV whereas heat lowered MPV regardless of treatment. All stimuli decreased PLT-CT. EPA significantly increased platelet EPA (0.2±0.1 vs. 3.3±0.4%) and docosapentaenoic acid (DPA; 2.2±0.3 vs. 2.9±0.3%) concentrations, but not DHA. DHA treatment significantly increased DHA (1.4±0.2 vs. 4.1±0.5%) and DPA (2.0±0.4 vs. 3.0±0.4%) concentrations, but not EPA. In conclusion, EPA, but not DHA, reduces platelet activation, an early step in platelet aggregation.     

Redox and transport behaviors of Cu(I) ions in TMHA-Tf<Subscript>2</Subscript>N ionic liquid solution

The redox and transport behavior of monovalent copper species in an ammonium imide-type ionic liquid, trimethyl-n-hexylammonium bis((trifluoromethyl)sulfonyl)amide (TMHA-Tf₂N) were examined with a micro-disc electrode to clarify its applicability to, for example, electroplating. It was found that the diffusion coefficient of Cu(I) ions in TMHA-Tf₂N containing 12 mmol dm⁻³ Cu(I) ions was 1.2 × 10⁻⁶ cm² s⁻¹ and the redox potential of Cu(I)/Cu was in the potential range 0.1–0.2 V vs. I ⁻/I ₃⁻ at 50 °C. The diffusion coefficient was one order smaller than that of Cu(II) ions in aqueous solution due to the high viscosity of the ionic liquid. The diffusion coefficient of Cu(I) ion increased with rising temperature and was 1.0 × 10⁻⁵ cm² s⁻¹ at 112 °C, which was comparable to that of Cu(II) ions in aqueous CuSO₄ solutions at ambient temperature. This is accounted for by the drastic decrease in the viscosity of the ionic liquid solution with increasing temperature. The activation energy of diffusion was estimated to be 39 kJ mol⁻¹ in the ionic liquid solution.     

Biodiesel production by the transesterification of cottonseed oil by solid acid catalysts

Methyl esters (biodiesel) were produced by the transesterification of cottonseed oil with methanol in the presence of solid acids as heterogeneous catalysts. The solid acids were prepared by mounting H₂SO₄ on TiO₂ · nH₂O and Zr(OH)₄, respectively, followed by calcining at 823K. TiO₂-SO₄ ²⁻ and ZrO₂-SO₄ ²⁻ showed high activity for the transesterification. The yield of methyl esters was over 90% under the conditions of 230°C, methanol/oil mole ratio of 12:1, reaction time 8 h and catalyst amount (catalyst/oil) of 2% (w). The solid acid catalysts showed more better adaptability than solid base catalysts when the oil has high acidity. IR spectral analysis of absorbed pyridine on the samples showed that there were Lewis and Br?nsted acid sites on the catalysts. Translated from The Chinese Journal of Process Engineering, 2006, 6(4): 571–575 [译自: 过程工程学报]     

Effect of temperature and chainlength on the densities and molal volumes ofn-alkyl chlorides

The densities ofn-alkyl chlorides from pentyl chloride to hexadecyl chloride were determined at temperatures between 15–80°C at 5°C intervals. The densities increase linearly with temperature and chainlength. A four-constant equation, V=n/(−3.6640 × 10⁻⁵ T+0.07151)+1/(−5.6526 × 10⁻⁵ T+0.04243), was formulated. This formula accurately predicted the molal volume and, hence, the density for all then-alkyl chlorides at any temperature within the range.     

Synthesis of mycolic acid biosurfactants and their physical and surface-active properties

Five mycolic acids [2-alkyl-3-hydroxy FA: R₁C^*(OH)C^*HR₂COOH] were synthesized using acyl chlorides with alkyl chains of different lengths (total carbon numbers of mycolic acids, 12, 16, 20, 24, 36). The relationship between the chemical structures of the mycolic acids and their surface-active properties was determined. The acids were synthesized in three steps: (i) dimerization of acyl chloride into alkyl ketene dimer, (ii) selective reduction of C=C to C-C by hydrogenation, and (iii) β-lactone ring cleavage under alkaline conditions. The yields of C₁₂-, C₁₆-, C₂₀-, C₂₄-, and C₃₆-mycolic acid were 72, 73, 73, 73, and 73%, respectively. The critical micelle concentrations (CMC) of C₁₂-, C₁₆-, and C₂₀-mycolic acid were 2.2×10⁻⁴, 1.36×10⁻⁴, and 7.4×10⁻⁵ M, respectively. As the carbon number increased, the surface tension at the CMC value was also lower; the values for C₁₂-, C₁₆- and C₂₀-mycolic acid were 46.54, 43.59, and 41.57 dyn/cm, respectively. The emulsifying activities of mycolic acids were determined for n-tetradecane, n-hexadecane, cyclohexane, and diesel oil. The results showed that C₁₂-mycolic acid was the best emulsifier for diesel oil, C₁₆-mycolic acid was the best emulsifier for n-tetradecane and n-hexadecane, and C₂₀-mycolic acid was the best emulsifier for cyclohexane. This study showed that mycolic acids having, surface-active properties can be chemically synthesized for potential applications in the detergent/cleaning material industries, for example, in oil spill cleanup, oil recovery, textiles, pharmaceuticals, and cosmetics.     

Impact of oxidized off-flavor of ice cream prepared from milk fat

The influence of light-induced oxidation on ice cream quality was investigated by monitoring hydroperoxide formation of the oil fraction, sensory evaluation for oxidized off-flavor, and gas GC-MS analysis of developed volatile aldehydes following steam distillation/extraction of ice cream. Two ice cream samples containing 14.3% milk fat prepared from different milk fat materials, and a sample with 1000 ppm tocopherol added were exposed to 650 lx fluorescent light at −20°C. Ice cream prepared from each milk material showed a different time dependence for peroxide formation, and the addition of tocopherol reduced hydroperoxide formation. The correlation coefficient (r ²) between the PV and the sensory score was 0.483 (n=9), and the r ² between the total concentration of 10 volatile aldehydes developed during light exposure and the sensory score was 0.365. Among the 10 aldehydes, however, the highest correlation observed was between the amount of trans-2-decenal and the sensory score (r ²=0.864, n=9), and lowest correlation was between the amount of hexanal and the sensory score (r ²=0.302, n=9). These results suggest that exposure of ice cream in the frozen state to fluorescent light produces a unique composition of volatile aldehydes related to flavor deterioration induced by photooxidation of the milk fat in ice cream.     

Biocatalytic Properties of Lipase from Walnut Seed (<Emphasis Type="Italic">Juglans regia</Emphasis> L.)

Lipase (E.C. 3.1.1.3) from walnut seed was purified 28.6-fold with 31% yield using Sephadex G-100 gel chromatography. Olive oil served as good substrate for the enzyme. The optimum pH and temperature were 9.0 and 70 °C, respectively. The lipase was stable between 30 and 80 °C for 5 min. K _m and V _max values were determined as 48 mM and 23.06 × 10⁻³ U/min mg for triolein as substrate. Lipase activity was slightly reduced by Cu²⁺, Ca²⁺, Hg²⁺, Mn²⁺, and Ni²⁺ ions, while Mg²⁺ and Zn²⁺ had no effects. Anionic surfactant sodium dodecyl sulfate stimulated lipase activity while non-ionic surfactants Tween-80 and Triton X-100 had negligible effects on enzymatic activity. The enzyme activity was not affected by 50 mM urea and thioacetamide. Potassium ferricyanide, n-bromosuccinamide and potassium cyanide reduced the enzyme activity. The enzyme showed a good stability in organic solvents, the best result being in n-hexane (113% residual activity). The activity of dialysate was maintained approximately 80% for 1 year at −20 °C.     

Kinetics of the formation of symmetrical wax esters from the corresponding alcohols with the use of hydrobromic acid and hydrogen peroxide

The primary aliphatic alcohols n-octanol, n-decanol, and n-dodecanol have been converted to their corresponding symmetrical esters by using HBr and H₂O₂ in the absence of a solvent. The reaction was carried out at 30, 40, and 50°C and at mole ratios of alcohol to HBr of 1∶0.1, 1∶0.2, 1∶0.3, and 1∶0.5. The rate of the reaction was found to increase with increase in the reaction temperature and concentration of HBr. The maximal conversion of n-octanol was 72% at 40°C and a mole ratio of n-octanol to HBr of 1∶0.5. The kinetics of the reaction have been established, and the reaction was found to be first-order with respect to alcohol and bromine concentration in the organic phase, and second-order with respect to both. The second-order rate constants for n-octanol, n-decanol, and n-dodecanol are 27.08, 32.58, and 37.42 mL mol⁻¹ min⁻¹, respectively, at 40°C. The activation energy for the esterification reaction of n-octanol was found to be 16.32 kcal mol⁻¹.     

Kinetics of halogen-exchange fluorination of 2,6-dichlorobenzaldehyde

Under the conditions of phase transfer catalysis and nitrobenzene as the solvent, the halogen-exchange fluorination of 2,6-dichlorobenzaldehyde using KF as fluorinating agent was studied. The kinetics was investigated and the reaction rate constants were obtained under the optimum conditions of n(KF):n(2,6-dichlorobenzaldehyde): n(Ph₄PBr):n(acetone-furan crown ether) = 4:1:0.1:0.05 and temperatures of 433 K, 443 K, 453 K and 463 K. The results illustrated the activation energy of the first and the second step is 4.57 × 10⁴ J·mol⁻¹ and 3.53 × 10⁴ J·mol⁻¹, respectively. The pre-exponential factor is 4.50 × 10⁵ h⁻¹ and 1.08 × 10⁴ h⁻¹, respectively. Thus a reliable kinetics data could be obtained for further research. __________ Translated from Chemical Engineering (China), 2007, 35(8): 33–36 [译自: 化学工程]     

Optimization of enzymatic methanolysis of soybean oil by response surface methodology

Enzymatic methanolysis of refined soybean oil with methanol was investigated using Rhizomucor miehei lipase, Lipozyme RM IM, in n-hexane for reaction times of 30 min. Response surface methodology (RSM) based on three-level, three-factor (variable) face-centered cube design was used for the optimization of methanolysis. The independent variables that affect the methanolysis reaction conducted in n-hexane are temperature (°C), enzyme/oil weight ratio, and oil/methanol molar ratio. A good quadratic model was obtained for the methyl ester production by multiple regression and backward elimination. A linear relationship was observed between the observed and predicted values (R²−0.9635). The effects of temperature and enzyme amount, which affected methyl ester content of the product (response) positively, were significant (P<0.01). The quadratic term of temperature and the interaction term of enzyme amount with temperature affected the response negatively (P<0.01). The interaction term of enzyme amount with substrate mole ratio had a positive effect on the response (P<0.05). Critical conditions for the response at which methyl ester content of the product was 76.9% were determined to be 50°C, 2.37 methanol/oil mole ratio, and 0.09 enzyme/oil weight ratio.     

Voltammetric behavior and the determination of quercetin at a flowerlike Co<Subscript>3</Subscript>O<Subscript>4</Subscript> nanoparticles modified glassy carbon electrode

Flowerlike Co₃O₄ nanoparticles were used as a modifier on the glassy carbon electrode to fabricate a quercetin (Qu) sensor. The morphology and crystallinity of the prepared Co₃O₄ material were investigated by scanning electron microscopy and X-ray diffraction. Electrochemical behavior of Qu at the sensor was studied by cyclic voltammetry and semi-derivative voltammetry. Results suggested that the modified electrode exhibited a strong electrocatalytic activity toward the redox of Qu. The electron transfer coefficient (α), the number of electron transfer (n), and the diffusion coefficient (D) of Qu at the sensor were calculated. Under the optimum conditions, the catalytic peak currents of Qu were linearly dependent on the concentrations of Qu in the range from 5.0 × 10⁻⁷ to 3.3 × 10⁻⁴ M, with a detection limit of 1.0 × 10⁻⁷ M. This proposed method was successfully applied to determine the quercetin concentration in Ginkgo leaf tablet and human urine samples.     

Asymmetric polymerization of N-substituted maleimides with organolithium — bisoxazolines complex

Asymmetric anionic polymerizations of achiral N-substituted maleimide (RMI) (N-cyclohexyl (CHMI), N-phenyl (PhMI), N-tert-butyl (TBMI)) by n-butyllithium (n-BuLi) or fluorenyllithium (FlLi) complexes of chiral bisoxazoline derivatives in toluene gave optically active polymers ([α]²⁵ ₄₃₅− 2.9° to − 8.2°). The polymers prerared with initiator of n-BuLi – 2,2′-bis(4,4′-isopropyl-,3-oxazoline) showed negative specific rotations (poly(RMI), [α]²⁵ ₄₃₅− 5.8° to − 8.2°) which were greater than those ([α]²⁵ ₄₃₅− 2.9° to − 5.9°) with other chiral 2,2′-bis(4,4′-alkyl-1,3-oxazoline) (alkyl group = iso-butyl and benzyl). Received: 29 July 1997/Revised: 27 August 1997/Accepted: 1 September 1997     

A New Metal–Organic ZnII Supramolecular Assembled via Hydrogen Bonds and N···N Interactions as a New Precursor for Preparation Zinc(II) Oxide Nanoparticles, Thermal, Spectroscopic and Structural Studies

A new 1D supramolecular involving two different ligands, {[Zn(GB)₂]·(μ-bpe)₃} _n (ClO₄)_2n ·nH₂O (GB = 2-guanidinobenzimidazole and bpe = 1,2-bis(4-pyridyl)ethylene, has been synthesised, characterized by elemental analysis, IR-, ¹H NMR-, ¹³C NMR spectroscopy. The thermal stability of compound {[Zn(GB)₂]·(μ-bpe)₃} _n (ClO₄)_2n ·nH₂O was studied by thermal gravimetric and differential thermal analyses. The single crystal X-ray analysis shows that the complex is a one-dimensional polymer involving macrocycle rings as a result of non-covalent bridging bpe ligands via N–H···N and N···N interactions, N–H···bpe···bpe···H–N, with the basic repeating {[Zn(GB)₂](μ-bpe)₃}(ClO₄)₂·H₂O units and by connecting [Zn(GB)₂]²⁺ nodes. ZnO nanoparticles were obtained by calcination of compound {[Zn(GB)₂]·(μ-bpe)₃} _n (ClO₄)_2n ·nH₂O at 500 °C in air. The nanoparticles were characterized by X-ray diffraction and scanning electron microscopy.     

Diffusivity of bacteria

The effects of motility and aggregation on the diffusion coefficient for bacteria were studied in an aqueous system. The effects of cell concentrations, capillary tube sizes, and dilution rates on the diffusion coefficient were examined. In general, motile cells can diffuse about 1000 times faster than non-motile cells.Pseudomonas aeruginosa, a motile cell, andKlebsiella pneumoniae, a non-motile cell, were used for this research. Diffusion coefficients were measured by the capillary tube assay developed by Adler [1969]. From this procedure the diffusion coefficient ofPseudomonas aeruginosa was 2.1×10⁻⁵ (standard deviation: 1.0× 10⁻⁵) cm²/s and that ofKlebsiella pneumoniae was 0.9×10⁻⁵ (standard deviation : 0.5 × 10⁻⁵) cm²/s. The diffusion coefficient ofPseudomonas aeruginosa was about 2.3 times higher than that ofKlebsiella pneumoniae. The Stokes-Einstein equation could not be used for estimating the diffusion coefficients forKlebsiella pneumoniae andPseudomonas aeruginosa. The experimental value for the diffusion coefficient ofKlebsiella pneumoniae was about 2000 times higher than that (4.5×10⁻⁹ cm₂/s) obtained from the Stokes-Einstein equation. This discrepancy was due to the aggregation ofKlebsiella pneumoniae.     

Sensory Thresholds of Selected Phenolic Constituents from Thyme and their Antioxidant Potential in Sunflower Oil

The odor detection thresholds of carvacrol (5-isopropyl-2-methyl-phenol), thymol (2-isopropyl-5-methyl-phenol) and p-cymene 2,3-diol (2,3-dihydroxy-4-isopropyl-1-methyl-benzene) in sunflower oil, determined by the three-alternative, forced-choice procedure, were 30.97, 124 and 794.33 mg kg⁻¹, respectively. Sunflower oil containing 13, 70, or 335 mg kg⁻¹ of carvacrol, thymol or p-cymene 2,3-diol, respectively, was judged to be similar (P < 0.01) in taste and odor to its antioxidant-free counterpart. The rate constant of sunflower oil oxidation, measured from the increase in peroxide value during storage at 25 °C, was 9.2 × 10⁻⁹ mol kg⁻¹ s⁻¹ while the rate constants were 9.3 × 10⁻⁹, 9.8 × 10⁻⁹, and 4.3 × 10⁻⁹ mol kg⁻¹ s⁻¹ in the presence of 13 mg kg⁻¹ carvacrol, 70 mg kg⁻¹ thymol, and 335 mg kg⁻¹ p-cymene 2,3-diol, respectively. At a level of 335 mg kg⁻¹, p-cymene 2,3-diol did not impart flavor taints and effected a 46.7% reduction in the rate of oxidation of sunflower oil. These findings indicate that the diphenolic p-cymene 2,3-diol could potentially replace synthetic antioxidants and is a valuable addition to the antioxidants used by the food industry in its quest to meet consumer demands for synthetic-additives-free and ‘natural’ foods.     

Effects of quenching mechanisms of carotenoids on the photosensitized oxidation of soybean oil

The effects of 0, 1.0 × 10”⁻⁵, 2.5 × 10⁻⁵, and 5.0 × 10⁻⁵ M β-apo-8'-carotenal, β-carotene, and canthaxanthin on the photooxidation of soybean oil in methylene chloride containing 3.3 × 10⁻⁹ M chlorophyll b were studied by measuring peroxide values and conjugated diene content. β-Apo-8'-carotenal, β-carotene, and canthaxanthin contain 10,11, and 13 conjugated double bonds, respectively. The peroxide values and conjugated diene contents of oils containing the carotenoids were significantly lower (P<0.05) than those of control oil containing no carotenoid. As the number of conjugated double bonds of the carotenoids increased, the peroxide values of soybean oils decreased significantly (P<0.05). The quenching mechanisms and kinetics of the carotenoids in the photosensitized oxidation of soybean oil were studied by measuring peroxide values. The steady-state kinetics study showed that carotenoids quenched singlet oxygen to reduce chlorophyll-sensitized photooxidation of soybean oil. The singlet-oxygen quenching rate constants ofβ- apo-8'-carotenal, β-carotene, and canthaxanthin were 3.06 × 10⁹, 4.60 × 10⁹, and 1.12 × 10¹⁰ M⁻¹sec⁻¹, respectively.