Process for the isolation of oryzanols from rice bran oil...

Details Process for the isolation of oryzanols from rice bran oil... Process for the isolation of oryzanols from rice bran oil...

2001-03-20

2002-06-25

Carr, Deborah (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C554S191000, C554S195000, C554S198000

Reexamination Certificate

active

06410762

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a process for the isolation of oryzanols from rice bran oil soap stock. More particularly, the present invention relates to a process for the isolation of oryzanols from rice bran oil soap stock, obtained during the neutralisation of free fatty acids present in rice bran oil. The normally difficult to handle soap stock is converted into soap nodules which become easier to handle, store and extract. The unsaponifiable matter isolated therefrom by solvent extraction is purified by conventional techniques to isolate oryzanol in 90% purity and 70% yield. The fatty acids are obtained in a purer form than by the conventional method of acid oil splitting of the soap stock.
BACKGROUND OF THE INVENTION
The beneficial physiological effects of oryzanol intake are well documented. The hypocholesterolemic activity of rice bran oil has been shown due to it constituent oryzanols and to other components of unsaponifiable matter [Seetharamaiah G. S., and Chandrashekhar N.,
Artherascierosis
, 78, 219 (1989)]. Lipid peroxidation has been shown to be prevented in the retina by gamma oryzanol due to its anti-oxidant property [Heramitsu T. and Armstrong D.,
Ophthalmic Res
. 23, 196, (1990)]. Oryzanol emulsions are used as antioxidants and preservatives for cosmetics and foods and such emulsions are also effective in preventing colour changes [Japanese Patent 58,45,728 (1983)]. Pharmaceutical preparations containing oryzanols have been shown to reduce wrinkles in aged women [Japanese patent 05,310, 526 (1993)]. Melamin formation accelarating topical preparations containing oryzanol (1% by weight) have been shown to convert gray hair into natural black [Japanese patent 05,255,037 (1993)]. Nail lacquers containing oryzanols prevent discoloration of nails [Japanese patent 02,290,806 (1990)]. Deodorant formulations containing oryzanol are especially effective in controlling odor from perspiration and underarms [Japanese patent 6333322 (1988)]. Oryzanol containing pharmaceutical formulations are used in preventing motion sickness [Japanese patent 82,32,229 (1982)] and in the treatment of nervous system disorders [CN 87,101,519 (1988)]. A plethora of oryzanol containing transdermal pharmaceutical and moisturising cosmetic preparations have been prepared for the treatment of skin disorders [FR 2,688,137 (1993); JP 01, 290,613 (1989; JP 81,161,315 (1981); JP 82, 149, 212 (1982); JP 82,42,621 (1982); JP 59,53,415 (1984); JP 59, 184, 120 (1984)]. Soft capsules containing oryzanols with or without riboflavin butyrate can be used to prevent arteriosclerosis [JP 58,103,315 (1983)]. Batch preparations containing oryzanols (3-20% by weight) are used in the treatment of dermatitis and senile xeroderma [JP 05,279,242 (1993)]. Oryzanols have been shown to be highly effective against lipogenic liver cirrhosis in spontaneously hypertensive rats, an animal having natural abnormalism in lipid metabolism [Ito M., et al., J.
Clin. Biochem. Nutr
., 12, 193 (1992)]. Investigations directed towards the safety assessment of oryzanols clearly indicate that oryzanols possess no genotoxic and carcinogenic initiation activity [Tsushimoto G., et al.,
J Toxicol. Sci
., 16, 191 (1991); Tamagawa M.,
Food Chem. Toxicol
., 30, 49 (1992)].
Rice bran oil is the most readily accessible source for the isolation of oryzanols. The oryzanol content of rice bran oil varies within the range of 1.1 to 2.6 %. The soap stock obtained by the alkali refining of rice bran oil contains 1.3-3.1 % oryzanols. Oryzanols were first isolated from rice bran oil [Kaneko R., and Tsuchiya T.,
J. Chem. Soc. Jpn
. 57, 526, (1954); JP 4895 (1957)] and was presumed to be a single component. Later it was determined to be a mixture containing ferulate (4 -hydroxy-3-methoxy cinnamic acid) esters of triterpene alcohols and plant sterols. Individual components were identified as ferulate ester of cycloartenol, 24 -methylene cycloartenol, compesterol, beta-sitosterol and other sterols.
Attempts have been made to develop methods for the isolation of oryzanols including isolation of cycloartenol ferulate from plant oil suing selective organic solvents for oryzanol extraction followed by chromatographic purification [JP 6314796 (1988); JP 6314797 (1988)], isolation of oryzanols from rice bran dark oil by precipitating the stearins with aluminium sulfate followed by crystallisation of oryzanols from supernatant [JP 8295942 (1982)], highly concentrated separation of oryzanols from rice bran and rice germ oils by two step alkali treatment [JP 76123811 (1976)], recovery of oryzanols from degummed and dewaxed rice bran oil with silica based simulated moving bed chromatography followed by crystallisation from heptane [Michael S. and Gordon J. R.,
J Am. Oil. Chem. Soc
., 75, 1421 (1998)], extraction of rice bran soap stock with diethylether at pH 9.5 followed by its chromatographic purification on a neutral alumina column [Seetharamaiah G. S., and Prabhakar J. V.,
J. Food Sci. Technol
., 23, 270 (1986)], extraction of oryzanols from rice bran oil soap stock with ether after acidification of soap stock with HCI [JP 4895 (1957)], extraction from a soap of rice bran oil by using multiple phase fractional crystallisations [Liu M. and Liu Y.,
Tianyan Chanwu Yanjiu yu Kaifa
, 9, 77 (1997)], isolation of oryzanols by transesterification of rice bran oil with methanol and sulfuric acid followed by column chromatography over pretreated Amberlite IRA-401 using mixed solvents, methanol and ether as the eluent [JP 13649 (1961)], liquid-liquid extraction by using hexane and water saturated furfural as the extractant [JP 6812731 (1968)], isolation by passing carbon dioxide gas through a methanolic solution of soap of rice bran oil [JP 6812731 (1968)] and extraction of oryzanols from the raw oils of rice bran and ferment, maize and barley by the distillation of these oils at comparatively low temperature followed by extracting the residue with hydrosol solvents [German Patent 1301002 (1969)]
U.S. Pat. No. 08785357 (1997) [ corresponding to Indian patent 183660 (2000)] discloses the isolation of oryzanols from crude dark rice bran acid oil comprising (a) distillation of free fatty acids from the acid oil using conventional methods, (b) hydrolysing the resultant residue by conventional methods, (c) dissolving the hydrolysed product in water to form oryzanols containing micellar aggregates and adding drop wise aqueous solution of calcium chloride to form precipitate (d) extracting the oryzanols from dried precipitate with polar organic solvent and (e) purifying the oryzanols from the organic extract by column chromatography. During rice bran oil refining a significant amount of oil gets trapped within the soap stock. This soap stock contains about 1.3-3.1% oryzanols. The soap stock or the acid oil derived for it from the starting material is used for the isolation of oryzanols in most of the prior art methods. However, the prior art methods described above are predominantly laboratory procedures and are not easily translated into commercial activity.
It is therefore important to develop a process for the isolation of oryzanols which is capable of commercial adaptation with high yield and high purity.
OBJECTS OF THE INVENTION
The main object of the present invention is to provide an improved process for the isolation of oryzanols from rice bran oil soap stock which is economical.
It is another object of the present invention to simplify the process of isolation of oryzanols from rice bran oil soap stock.
SUMMARY OF THE INVENTION
Accordingly the present invention provides a process for the isolation of oryzanols from rice bran oil soap stock, said process comprising (a) saponifying the oil present in soap stock with an alkali followed by neutralisation of the excess alkal

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