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Physical and Molecular Properties of Lipid Polymorphs - a Review

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Physical and Molecular Properties of Lipid Polymorphs - a Review Food Structure Volume 6 Number 2 Article 7 1987 Physical and Molecular Properties of Lipid Polymorphs - A Review K. Sato Follow this and additional works at: https://digitalcommons.usu.edu/foodmicrostructure Part of the Food Science Commons Recommended Citation Sato, K. (1987) "Physical and Molecular Properties of Lipid Polymorphs - A Review," Food Structure: Vol. 6 : No. 2 , Article 7. Available at: https://digitalcommons.usu.edu/foodmicrostructure/vol6/iss2/7 This Article is brought to you for free and open access by the Western Dairy Center at DigitalCommons@USU. It has been accepted for inclusion in Food Structure by an authorized administrator of DigitalCommons@USU. For more information, please contact [email protected]. FOOD MICROSTRUCTURE, Vol. 6 (1987), pp. 151 - 159 0730-54 19/87$3 . 00+ . 00 Scanning Microscopy International, Chicago (AMF 0' Hare), I L 60666 USA PHYSICAL AND MOLECULAR PROPERTIES OF LIPID POLYMORI'HS - A REVIEW - K. Sa10 Faculty of Applied Biolog ical Sc ience. Hiroshima Un ive rsity Fukuyama 720. Japan Ph one No. 0849- 24- 6211 Abstr:.tct Introduction The phys ical and molecul ar properties of the polymorphism The physical a nd molecul ar properties of lipid polymorphs of stearic acid. oleic acid and SOS (1. 3-distearoyl-2-olcoyl gly­ have drawn the attention of many investigators in the fields of cerol) are comparatively di!<~cu~~cd. Temperature depende nce biological sciences and oil chemical technology. This is due to of Gibbs energy (G·T relation) of three polymorphs of stearic the Fact that the pol ymorphi sm or lip ids is highly releva nt in acid: A. 8 and C. revealed close relationships to each oth er. biologica l sys te ms, and also decisive to the phys ical properties The molecular structures subtly differed in these polymorphs. of foods. cosmetics, etc .. which comprise lipids as the main In comrast. three pol ymorphs of oleic acid . a . Band )'. ex­ co mpound~ of solid fat s hibited remarkably diflerent characteristics. G-T relation showed The polymorphism may be dbcussed in 1c rms of thermody· more diversifi ed ICatures: in pa rti cular. the melling points of namic stability. c rys 1al packing and molecular conformation as a and (3 diffe r by 3°C. An ordcr·disordcr transf( mllation oc· far as the phys ica l aspects arc concerned . The fundamcnlal s of currcd between a ancl -y, as a result of confOrmational dis· the macroscopic ICaturcs of polymorphism, such as morphology. orde ring in the ponion of the oleic acid molecul e from the double solidificati on kinetics and so on. may be explained in terms of bond to the terminal methyl group in a. Finally. five polymorph:-. these phy~ica l a~pccl'i. Each of the above fac to rs is highly dcpen· of SOS we re newly presented, a, "f, pseudo·W . fl1 and 13 t­ dent on the molecular species which co n ~ titut c 1hc li pid. under X·ray spectra and the rmal behaviors proved thai the above li ve a given set of cx1e rnal condi1 ions. This is easil y seen if one com· fo rms arc the independent polymorphs. The author discu:-.scd pares the melting points of stearic acid (69.6°C) wi th oleic acid the multiple polymorphism of SOS. taking in to accoun1 the (16.2°C of !he higiHnclting polymorph). Obviously. this differ· lame ll ar sorting of stearic/oleic acid!> c hain:. accompanied with e ncc is the re:-. ult of a drastic redut·tion in the chain -packing the change in the c hai n length !.tructure. In relatton to the poly· e ne rgy by the inmxluction of one l'is·doublc bond at the ccn· mo rphism of SOS and othe r 1. 3-disaturatcd - l ·tlleoyl glyce· 1ral posi1ion of the polymcthylcnc chain . rides. the author emphasizes 1he possibili1 y thai th.:: convcr:-.ion Very recently, many investigators have tried 10 e lucidate the from Form V 10 VI in cocoa buller might be caused princi pall y physical and molecular propert ies of some principal fatty acids through the polymorphi c trans!Ormalion from (3~ to (3 1 of the and triglyccridcs. Particul<~r effort has been devoted to the lipids highe r· melling fa1 frac tions of cocoa butter. contai ning unsawrated fa tty ac id !:. as the mai n and fun ctiona ll y active constituents. Accord ingly. thi s paper gives a brief review of the polymorphi sm of stearic acid and oleic acid. being repre· scntati ve of the saturated and un:,aturated fatt y acids. rcspcc· ti ve ly. Furthe rmore. new findi ngs are presented on the pol y· morphism of SOS. 1,3-d istcaroy l-2·oleoyltriglyccride. as rcpre· scntative of the symmetric S10S1 (51: saturated acid . 0: oleic Initial paper rec eived March 16, 1987 acid) triglyccrides. FirsL we briefly discu:-.s some conceptual Manuscript received November 5, 1987 Direc t inquiries to K. Sato and methodological background:-. Telephone number: 81 -849-24- 6211x322 Polymor phism : T hcr mod)•namic Stabil ity a nd Crysla llogrdph)' In order to discuss the physical properties of different poly­ morphic forms of certain fatty acids and triglycerides. a preci~e Ke)·n·ords: Lipid. pol ymorphbm. s1earic acid, oleic acid. 1ri· knowledge of thermodynamic stabili!y is pre requisite. For this glyceride, un saturated fatt y acid . thermodynamical stabi lit y. purpose. measurements on the solubili1ics, melting points and phase transformm ion, differential scanning calorime1ry. cocoa transformation paLhways of all the polymorphs arc most charac· butter. tc ri stic. The less slable polymorphs melt at lower temperatures, 151 K. Sato are more soluble in solvent, and transform to more stable ones As for the thermodynamic stability, the so lubilities of A, B either via solid-state (Verma and Krishna. 1966) or via solution­ and C were measured independently (Table I) (Beckmann et mediated (Cardew and Davey, 1985) or via melt-med iated tran­ a\. , 1984) . B has the lowest solubility below 32 oC (Sato ct a\. , si tions (Sato and Kuroda, 1987). The latter two transformations 19 85), whereas Cis the least soluble above that temperature may actually occur if the solid-state transfOrmation is kinetically Form A has a higher solubility than the lowest value at all tem­ hindered. Many long-chain compounds reveal these transfor­ peratures. Accordingly, the thermodynamic stability of the A, mations. Know ing the thermal data, one may draw the relation­ B and C polymorphs of steari c acid may be depicted by the G­ ship between the thermodynamic stability using a crystal Gibbs T diagram shown in Fig. 3. The G values of 8 and C are the energy (G) and temperature (T) diagram same around 32oC. This is apparentl y contradictory to the The crystallographic aspects of the polymorphism of fatty features of the solid-state transformation. Stenhagen and von acids and triglycerides are reflected in the lateral packing and Sydow (1953) reponed that the transformation temperatures on lamella stacking of the hydrocarbon chains, which are most easi­ heating from A to C, and from B to C are 54°C and 46°C, ly measured by X-ray diffractometry or by Infrared (IR) and respectively. Another report (Garti eta\., 1980) says that B trans­ Raman spectroscopy. Indicative of the lateral packing, charac­ forms to Cat 54°C. All these values are higher than the actual terized by the subcell struct ure, are the X-ray short spacings. crossing points of the Gibbs energies of A, Band C. This is These have so far exhibited three specific subcell s; orthorhom­ attri buted to a kinetic hindrance of the transformation in the bic perpendicular (0 1 ) , triclinic parallel (Tp) and pseudo­ solid-state. So, the actual polymorphic transformation in the orthorhombic parallel (0 f) as shown in Fig. I (Abrahamsson crystal may depend on the heating rate, which differs in the above et a!. , IW8). In addition, a hexagonal subcel\ is reported to occur two papers. in highl y metastable states (Abrahamsson et al., 1978) . The satu­ Structural analyses using single crystals of B and C showed rated aliphatic chains are principally packed in 0 1 and T;,1 ac­ that the hydrocarbon chains of Care in the all-trans conforma­ cording to the mode of crystallization and thermodynamic stabili­ tion (Malta et al. , 1971), whereas the C1 - C3 carbons closest to ty, whereas 0 ',; is reported for the low-temperature polymorph the carboxyl group of Bare in gauche conformation (Goto and of oleic acid (Abrahamsson et al. , 1962). Hence this may be Asada , 1978) one of the subcells characterist ic to the cis-un saturated acyl chain . Oleic Acid The lamellar stacking is indicated by the X-ray long spaci ng spectrum which equal s the inter-lamellar distance between the Three polymorphs of oleic acid. a, {3 and -y, were recently terminal CH3 groups of the lipid lamellae. The long spacing confirmed by means of DSC, X-ray diffraction (S uzuki eta\., also can be a measure of the chain length structure, in particular, 1985), IR and Raman spectroscopy (Kobayashi et a\., 1986) . of triglycerides (S mall , 19 86). Normal triglyceridcs, such as The transformation circuit of the three polymorphs is depicted monosaturated acids, reveal a double chain length structure in Fig. 4 (Sato and Suzuki , 1986). a is crystallized by chilling where the long spacing equals the length of two fatty acids and the melt, although it is thermodynamically metastable. The one glycerol group. A change from the double to triple chain preferred crystalli zati on and metastability for a resemble those length structures occurs when the fatty acid moieti es become of a of glycerides.
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