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(12) United States Patent (10) Patent No.: US 7459.288 B2 Bosley Et Al

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(12) United States Patent (10) Patent No.: US 7459.288 B2 Bosley Et Al US007459288B2 (12) United States Patent (10) Patent No.: US 7459.288 B2 Bosley et al. (45) Date of Patent: Dec. 2, 2008 (54) METHOD OF PRODUCING RETINYL EP O O94771 5, 1983 ESTERS EP O 343 444 5, 1989 GB 2 0263.19 7, 1978 (75) Inventors: John Anthony Bosley, Kettering (GB); JP 56113760 9, 1981 Clive Roderick Harding, Trumbull, CT JP 612125.15 9, 1986 (US); Christopher Rawlins, Shambrook JP 622484.95 10, 1987 (GB); Julia Sarah Rogers, Shambrook JP 6032774 2, 1994 (GB); Ian Richard Scott, Stratford upon WO 99.32105 7, 1999 Avon (GB) WO O 1/78676 10, 2001 (73) Assignee: Unilever Home & Personal Care USA, division of Conopco, Inc., Greenwich, OTHER PUBLICATIONS CT (US) International Search Report, PCT/EP03/12206, mailed Mar. 1, 2004, (*) Notice: Subject to any disclaimer, the term of this 2 pp. patent is extended or adjusted under 35 GB Search Report, GB 0226270.7, dated Apr. 17, 2003, 1 p. U.S.C. 154(b) by 412 days. GB Search Report, GB0226270.7, dated May 21, 2003, 1 p. Maugard, et al., “Enzymatic Synthesis of Derivatives of Vitamin A in (21) Appl. No.: 10/534,520 Organic Media”, Journal of Molecular Catalysis B Enzymatic, vol. 8, No. 4-6, Feb. 18, 2000, pp. 275-280, XP002270 197. (22) PCT Filed: Oct. 27, 2003 O'Connor, et al., “Candida-Cylindracea Lipase-Catalysed Synthesis of Retinyl and Oleyl Palmitates Carbon Chain Length Dependence of (86). PCT No.: PCT/EPO3/12206 Esterase Activity”, Australian Journal of Chemistry, vol. 45, No. 4. 1992, pp. 641-649, XP0008027552. S371 (c)(1), Ajima, et al., “Retinyl Esters Synthesis by Polyethylene Glycol (2), (4) Date: May 11, 2005 Modified Lipase in Benzene'. Biotechnology Letters, vol. 8, No. 8, 1986, pp. 547-552, XP0008027553. (87) PCT Pub. No.: WO2004/044212 Dossat, et al., “Lipase-catalysed Transesterification of High Oleic Sunflower Oil”. Enzyme and Microbial Technology, vol. 30, No. 1, PCT Pub. Date: May 27, 2004 Jan. 8, 2002, pp. 90-94, XP002270.198. Haraldsson, et al., “The Preparation of Concentrates of (65) Prior Publication Data Eicosapentaenoic Acid and Docosahexaenoic Acid by Lipase-cata lyzed Transesterification of Fish Oil with Ethanol”, Journal of the US 2006/O183184 A1 Aug. 17, 2006 American Oil Chemists' Society, American Oil Chemists' Society Campaign, US, vol. 74, No. 11, Nov. 1, 1997, pp. 1419-1424. (30) Foreign Application Priority Data XPOOOT36917. Nov. 11, 2002 (GB) ................................. O2262.70.7 * cited by examiner (51) Int. Cl. Primary Examiner Herbert J Lilling CI2P I3/00 (2006.01) (74) Attorney, Agent, or Firm—Edward A. Squillante, Jr.; CI2P 7/62 (2006.01) Ellen Plotkin CI2P 7/64 (2006.01) (52) U.S. Cl. .......................... 435/67; 435/134: 435/135 (57) ABSTRACT (58) Field of Classification Search ....................... None See application file for complete search history. A method of producing a retinyl ester compound comprising (56) References Cited Subjecting a composition comprising retinyl or a retinyl ester and a fat or oil of animal or vegetable origins to enzyme U.S. PATENT DOCUMENTS catalysed trans-esterification in solvent free conditions to 6.479,618 B1 * 1 1/2002 Vonderhagen .............. 528,274 produce a retinyl ester. FOREIGN PATENT DOCUMENTS DE 10018519 4/2000 7 Claims, 2 Drawing Sheets U.S. Patent Dec. 2, 2008 Sheet 1 of 2 US 7459.288 B2 Fig.1. 105 92 8 100 -0- 22C, CW O C 95 --- 30C, CW s -O- 22C, NS 2 90 O -O-- 30C, NS S. 85 O O 20 30 40 Time (days) 100 90 8O 70 60 50 O O 20 30 40 Time (days) U.S. Patent Dec. 2, 2008 Sheet 2 of 2 US 7459.288 B2 S.s f is .: : CN - ". " ''. $. , try .... .. Z.. 'r L O O O O O 3 CO O V CN (elemeSOW <-unS JeMO) :SXue JO unS US 7,459,288 B2 1. 2 METHOD OF PRODUCING RETNYL to enzyme catalysed trans-esterification in Solvent free con ESTERS ditions to produce a retinyl ester. In a further aspect, there is provided a composition com This invention relates to a method of producing retinyl prising a fat or oil of animal, vegetable or algal origin con esters. In particular, it relates to a beneficial method of pro taining retinyl esters of fatty acids contained in the animal, ducing retinyl esters offatty acids from natural sources. Such vegetable or algal fat or oil. The retinyl esters are preferably as fats and oils of plant and animal origin, using enzyme formed by enzyme catalysed trans-esterification. catalysis. The invention may also provide novel retinyl esters In yet a further aspect, there is provided a retinyl ester of a and oil compositions containing retinyl esters, which may be fatty acid prepared by the method described above. According to yet a further aspect there is provided a topical useful adjuncts to cosmetic compositions. 10 Retinol (vitaminA) and retinyl esters have long been added composition for application to human skin containing a reti to cosmetic compositions to provide topical benefits. Retinol nyl ester or a composition containing a retinyl ester prepared may typically be produced on an industrial scale by a totally as described above. synthetic route using inter alia acetone. The synthesis may According to yet a further aspect there is provided a cos generate retinyl acetate. Retinyl palmitate is another com metic method of treating human skin comprising applying 15 thereto a topical composition as described above. monly used retinyl ester, which may typically be produced by According to yet a further aspect of the invention, there are trans-esterification of retinyl acetate with methyl palmitate, provided novel retinyl fatty acid esters, such as (but not nec with the reaction being chemically catalysed. Retinyl esters essarily limited to) retinyl C18:3 and C18:4 conjugated fatty have traditionally been preferred to retinol in topical products acid esters. since they are easier to formulate, are more stable, and they The method may be used to provide compositions contain are less irritant than the alcohol form, with the ester typically ing a fat or oil of animal, vegetable or algal origin, and which being hydrolysed in use to the alcohol on the skin. contain (or from which may be isolated) retinyl esters with It is also known for retinyl esters to be produced using fatty acid portions which reflect the fatty acid composition of enzymes. For example, JP62248495 describes generally the that animal, vegetable or algal fat or oil. For example, when production of retinyl esters from retinyl acetate and O-meth produced in sunflower oil, the method produces sunflower oxypolyethylene glycol modified lipases to produce long 25 fatty acid retinyl esters from the enzyme catalysed trans chain acid esters. This application also describes the produc esterification of sunflower oil. The resultant retinyl esters are tion of retinyl oleate by similarly modified enzymes in a predominantly the linoleic and oleic forms, reflecting the medium comprising benzene Saturated with water. However, fatty acid composition of the sunflower oil. in this teaching, the reactions between the vitamin A and the The method can be extended to the use of any fat or oil of long chain fatty acids occur in organic solvent systems. Such 30 animal, vegetable or algal origin. as e.g. benzene. Also, as the modified lipase is solubilised in As a result, the method can be used to synthesise retinyl the reaction system, significant further processing is required esters containing fatty acids having C-2 chain lengths, to separate the desired retinyl ester product from the reaction either Saturated or unsaturated. The resulting retinyl esters mixture. and retinyl ester blends have been found to be relatively mild It is also known from the Australian Journal of Chemistry, compared to e.g. retinyl acetate or retinyl palmitate made by 45 (4) 641-649(1992), O'Connor C. J.; Petricevic S. F and conventional routes. The method also provides a route to the Stanley R. A., that C. rugosa can be used in the production of manufacture of retinyl esters and ester blends from a rela retinyl palmitate from free alcohol and fatty acid in aqueous tively cheap starting material, retinyl acetate, which is ethanol or biphasic mixtures of paraffin and water. Again, this cheaper to prepare than materials such as retinyl palmitate. process requires the use of organic solvents. As an enzyme to be used for the trans-esterfication process, In addition, WO 99/32105 (DCV. Inc) describes the pro 40 preferably a lipase enzyme is used. Lipase enzymes are well duction of conjugated linoleic acid esters in the presence of a known for their ability to catalyse (trans) esterification reac lipase, which esters can include retinyl esters. However the tions involving oils and fats. Any suitable source of lipase can application does not statehow the retinyl esters were obtained be utilised, though industrially produced lipases are preferred and the examples shown for other esters require the use of on a cost basis. The lipase should preferably be immobilised Solvent and significant processing to isolate the final prod 45 on a Suitable carrier. uctS. The fat or oil of animal, vegetable or algal origin is in fact It is also suggested in Journal of Molecular Catalysis B: a composition which contains either a free fatty acid, or an Enzymatic, 8, 275-280 (2000) (Maugard T. Legoy M. D) that ester of fatty acids which are of animal, vegetable or algal retinyl esters may be produced by enzymatic routes. The origin. Any such oil or fat, being of natural origin will typi paper describes the production of retinyl adipate. Succinate, 50 cally contain a population of free fatty acids acids oresterified oleate and lactate for incorporation into cosmetic products.
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