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United States Patent (19) 11 Patent Number: 6,066,311 Cheetham Et Al

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United States Patent (19) 11 Patent Number: 6,066,311 Cheetham Et Al US006066311A United States Patent (19) 11 Patent Number: 6,066,311 Cheetham et al. (45) Date of Patent: May 23, 2000 54 PRODUCTION AND USES OF CAFFEIC 63–284117 11/1988 Japan. ACID AND DERVATIVES THEREOF 63–284118 11/1988 Japan. 63–284119 11/1988 Japan. 75 Inventors: Peter S. J. Cheetham; Nigel E. 1013018 1/1989 Japan. Banister, both of Canterbury, United 06199649 7/1994 Japan. Kingdom 06287105 10/1994 Japan. OTHER PUBLICATIONS 73 Assignee: Zylepsis Limited, Ashford, United Kingdom Ellis, B. E., and Amrhein, N., The NIH-Shift During Aromatic OrthoHydroxylation in Higher Plants, Phytochem Appl. No.: 08/750,227 istry, 10, pp. 3069-3072, 1971, Pergamon Press. Freudenberg Karl, Berichte der Deutschen Chemischen PCT Fed: Jun. 7, 1995 Gesellschaft, vol. 53, No. 1, 1920 Weinheim DE, pp. PCT No.: PCT/GB95/01324 232-239. In German-See Ref. AK. Gestentner B., and Conn, Eric E., “The 2-Hydroxylation of S371 Date: Mar. 14, 1997 trans-Cinnamic Acid by Chloroplasts from Melilotus alba S 102(e) Date: Mar. 14, 1997 Desr.” Archives of Biochemistry and Biophysics, 163, pp. 617-624, 1974, Academic Press. 87 PCT Pub. No.: WO95/33706 Sripad, G., Prakash, V., Narasinga Rao, M.S. “Extractability of polyphenols of Sunflower Seed in various Solvents.’, J. PCT Pub. Date: Dec. 14, 1995 BioSci., 4, No. 2, pp. 145-152, 1982. 30 Foreign Application Priority Data Tranchino L., Constantino R., and Sodini G., “Food grade oilseed protein processing, Sunflower and rapeseed.”, Qual Jun. 8, 1994 GB United Kingdom ................... 941 1539 Plant Foods Hum. Nutr., 32, pp. 305-334, 1983. Apr. 10, 1995 GB United Kingdom ................... 9507415 International Search Report for PCT GB95/01324. which 51) Int. Cl." ............................ A01K 7/44; CO7C 229/00 cites References AA, AB, AE, AG and which is in the 52 U.S. Cl. ................................. 424/60; 424/59; 560/38; possession of the USPTO per attached Form PCT/DO/EO/ 560/60; 560/75 903 dated Jun. 18, 1997. 58 Field of Search .......................... 424/60, 59; 560/38, CA 108:19241 (1987). 560/60, 75 Shaku, M. et al. “Efficacy of Sodium Isoferulate as a New Sunscreen Agent”, J. SCCJ, 26 (1), pp 8-17, (1992). 56) References Cited Primary Examiner Paul J. Killos U.S. PATENT DOCUMENTS Attorney, Agent, or Firm-Bromberg & Sunstein LLP 2,213,717 9/1940 Poizat et al. ............................ 260/473 57 ABSTRACT FOREIGN PATENT DOCUMENTS There is disclosed a novel method of producing caffeic acid in large quantities, comprising the esterification of chloro 0272576 6/1988 European Pat. Off.. 272576 6/1988 European Pat. Off.. genic acid with an esterifying enzyme. Caffeic acid and its 0350314 10/1990 European Pat. Off.. derivatives, produced by this method, may be used in 239.0160 5/1978 France. Sunscreen compositions, the caffeic acid and its derivatives 2721394 11/1978 Germany. absorbing both uvA and uvB light. 62-120312 6/1987 Japan. 63–284116 11/1988 Japan. 46 Claims, 8 Drawing Sheets U.S. Patent May 23, 2000 Sheet 1 of 8 6,066,311 FIG. 1 ABS -O O.O O.5 1.O 1.5 1.7 190 3OO n 4OO SOO 6OO -O1 O.O 0.5 1.O 15 1.7 ABS 3 E1% 815 8O3.5 Cm FOR A MOLAR SOLUTION: TOTAL U.V. ABSORBANCE 285 - 450 nm = 84.33OO ABS Inn U.S. Patent May 23, 2000 Sheet 2 of 8 6,066,311 FIG 2 ABS *:-O.3 O.O. O.5 1.O 1.5 2.O 2.5 3.0 3OO nrn 400 5OO 6OO -O3 OO O.5 1.O 1.5 2.O 25 3.0 ABS Figure 2: HEXANOL ESTER OF CAFFEIC ACID 20g ml-1N TLC SOLVENT(HEXANE: ETHANOL, 3:1, & 2% w/v. ACETIC ACID) WAVELENGTH (nm) ABSORBANCE 1747 FOR A MOLAR SOLUTION: TOTAL U.V., ABSORBANCE 285 - 450 nm is 1499520 ABS nrn U.S. Patent May 23, 2000 Sheet 3 of 8 6,066,311 FIG. 3 ABS O.O O.5 1.O 1.5 2.0 190 300 400 500 600 O.O O.5 O 1.5 2.0 ABS Figure 3: SOLTAN SUNCREAM 0.1% w/v IN ETHANOL U.S. Patent May 23, 2000 Sheet 4 of 8 6,066,311 FIG. 4 ABS OO O.5 1.O 1.5 2.0 2.6 190 a 300 n 400 500 600 OO O.5 O 1.5 20 2.6 ABS Figure 4: SOLTAN SUNCREAM 0.1% w/v + CAFFEIC ACID O.002%. VfV N ETHANOL PEAK No. WAVELENGTH (nm) 222 235 ABSORBANCE 2.131 1990 U.S. Patent May 23, 2000 Sheet 5 of 8 6,066,311 FIG. 5 +2.00A O5OO (A/DV) --O.OOA -N 2OO.O 50.0 (NMA DV, ) 5OO.O DMCA O.OO1% Wv N ETHANOL PEAK No. FOR A MOLAR SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 7.3 x 105 ABS nm FOR A 1% w/v SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 3.5 x 104 ABS nm U.S. Patent May 23, 2000 Sheet 6 of 8 6,066,311 F.G. 6 +2.OOA O.5OO (A/DIV) 2OOO 50. O ( NM /DV. ) 500.0 DMCA METHYL ESTER O.001% WW IN ETHANOL PEAK No. 1 WAVELENGTH (nm) 295 ABSORBANCE O.625 O.749 1CT FOR A MOLAR SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 8.4 x 105 ABS nm FOR A 1% Whv SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 3.8 x 104 ABS nm U.S. Patent May 23, 2000 Sheet 7 of 8 6,066,311 FG. 7 +2.00A O.5OO ( A / DV) --O.OO A r/\ NM 2OOO 500 (NMM DV.) 500 - O DMCA PHENY ESTER O.OO1% WW IN E HANOL E1% 563 74.1 FOR A MOAR SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 11.5 x 105 ABS nm FOR A 19. W/V SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 4.1 x 104 ABS nm U.S. Patent May 23, 2000 Sheet 8 of 8 6,066,311 FG. 8 +2.OOA O5OO ( A / DV) --O.OOA NM 2OOO 50.0 (NM / DIV) 5OOO DMCA HEXYL ESTER O.001% W/v IN ETHANOL PEAK No. WAVELENGTH (nm) ABSORBANCE 1ct FOR A MOLAR SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 9.6 x 105 ABS nm FOR A 19, Wi?v SOLUTION: TOTAL U.V. ABSORBANCE 290 - 450 nm = 3.3 x 104 ABS nm 6,066,311 1 2 PRODUCTION AND USES OF CAFFEC to produce and is available only in very Small quantities. At ACID AND DERVATIVES THEREOF present the method of production of caffeic acid is by Solvent extraction from plant tissue and column chromatography. THIS INVENTION relates to the production and uses of This molecule has now been found to absorb both uVA and caffeic acid and derivatives thereof, and more particularly to uVB. The molecule is, further, biodegradable and has excel a method of producing caffeic acids and derivatives from lent antioxidant properties. chlorogenic acid and uses of caffeic acid and derivatives The present invention provides a novel inexpensive thereof as Sunscreen additives. method for producing caffeic acid and derivatives thereof. AS the harmful effects of Strong Sunlight become more widely publicized and concern grows over the depletion of The present invention further allows the use of caffeic acid the OZone layer, the general public is becoming more aware and derivatives thereof as Sunscreen agents. of the harmful effects of atmospheric ultra-violet radiation. According to the present invention there is provided a In particular, the identification of atmospheric radiation as a compound of the formula: major causative agent in Skin cancers has increased the demand for effective and economic protection against atmo RCH -COOR Spheric ultra-violet radiation. Of the three types of ultraviolet radiation, uVA, uvB and 15 CHR uvC, uvC does not penetrate the earth's atmosphere, being absorbed by the ozone layer. Of the two types of ultraviolet radiation that reach the earth's Surface, uVB has been iden tified as the causative agent of skin cancer. Accordingly, the majority of Sunscreens currently available concentrate on the reduction of uvB rays contacting the skin. However, uVA has now been identified as a cause of ageing of skin and Wrinkling. AS Such, it is considered preferable to provide Sunscreen agents which reduce the harmful effects of both or a salt thereof, wherein R is H, OH or NH, R is H, OH uVA and uvB in Sunlight. 25 or NH or R and R form a double bond, R is H, a straight Furthermore, with the increase in environmental aware or branched chain, Substituted or unsubstituted C-C, neSS in the general public, there is an increased requirement alkyl, alkylene, or alkylyne, a Substituted or unsubstituted for “natural products, notably biodegradable products, to homocyclic or heterocyclic aromatic group; or a group avoid environmental damage. There is, therefore, a need for Such biodegradable “natural” products for use in Sunscreens. having a uv absorption extinction coefficient of 2,000 or Finally, there is a desire in the art to produce Sunscreens more, R, R and R are H, or an electron donating group, which not only have the primary function of blocking such as OH, NH, OCH, SH, NHCO, OCOH, or a C to ultraviolet light but also have the secondary function of Cs saturated alkyl group, and R, is OH or OCH. caring for the skin to which they are applied. Thus many Molecules having a uv absorption extinction coefficient of Sunscreens also contain moisturisers and antioxidants as skin 2,000 or more include: care additives.
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