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Perillyl Alcohol As a Bactericide and Yeasticide Perilla-Alkohol Als Bakterien- Und Hefenabtotendes Mittel Alcool Perillique Utilise Comme Bactericide Et Levuricide

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Perillyl Alcohol As a Bactericide and Yeasticide Perilla-Alkohol Als Bakterien- Und Hefenabtotendes Mittel Alcool Perillique Utilise Comme Bactericide Et Levuricide Patentamt Europaisches |||| ||| 1 1|| ||| ||| || || || || ||| || |||| || (19) J European Patent Office Office europeen des brevets (11) EP 0 585 402 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publicationation and mention (51) |nt. CI.6: A01 N 31/00, A61 K 31/045 of the grant of the patent: 09.04.1997 Bulletin 1997/15 (86) International application number: PCT/US92/01008 (21) Application number: 92914522.5 (87) International publication number: (22) Date of filing: 07.02.1992 WO 93/15606 (19.08.1993 Gazette 1993/20) (54) PERILLYL ALCOHOL AS A BACTERICIDE AND YEASTICIDE PERILLA-ALKOHOL ALS BAKTERIEN- UND HEFENABTOTENDES MITTEL ALCOOL PERILLIQUE UTILISE COMME BACTERICIDE ET LEVURICIDE (84) Designated Contracting States: • DATABASE WPI Week 841 3, Derwent AT BE CH DE ES FR GB IT LI NL SE Publications Ltd., London, GB; AN 84-078371 [13] & JP-A-59 029 619 (HASEGAWA) 16 (43) Date of publication of application: February 1984 09.03.1994 Bulletin 1994/10 • DATABASE CHEMABS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US (73) Proprietor: CHASTAIN, Doyle, E. CA90(3):1 7664a Titusville, FL 32780 (US) • PATENT ABSTRACTS OF JAPAN vol. 1 6, no. 1 1 4 (C-921)(5157) & JP-A-03 287 597 (NIPPON Inventors: (72) TERUPEN KAGAKU) 18 December 1991 E. • CHASTAIN, Doyle, • O.-A. NEUMULLER 'Rompps Chemie-Lexikon' Titusville, FL 32780 (US) 1985 FRANCKH'SCHE VERLAGSHANDLUNG • SANDERS, Christine, C. , , STUTTGART, DE Band 4: M-Pk * page 3048, NB 68131 Omaha, (US) 'Perillaaldehydoxim' * • SANDERS, W., Eugene, Jr. • JOURNAL OF THE AMERICAN Omaha, NB 68131 (US) PHARMACEUTICAL ASSOCIATION. SCIENTIFIC EDITION vol. XLV, no. 6 June 1956 (74) Representative: Williams, John Francis et al , , WASHINGTON US 378 - 381 C.M.JASPER WILLIAMS, POWELL & ASSOCIATES pages ET AL. 'The in Vitro Antibacterial of Oils' 34 Tavistock Street Activity • PATENT ABSTRACTS OF JAPAN vol. 1 0, no. 328 London WC2E 7PB (GB) (C-383)(2384) 7 November 1986 & JP-A-61 137 (56) References cited: 802 (MEIJI SEIKA KAISHA) 25 June 1986 • DATABASE CHEMABS CHEMICAL ABSTRACTS • DATABASE WPI Week 9028, Derwent SERVICE, COLUMBUS, OHIO, US Publications Ltd., London, GB; AN 90-213153 CA97(26):222813j X.JI ET AL. 'Studies on the [28] & JP-A-2 142 703 (KURITA WATER IND) 31 volatile oil from Dou Ye Jiu Li Xiang (Murraya May 1990 euchrestifolia Hayata). I' • CHEMICAL ABSTRACTS, Vol. 94, Abst. No. 94: 186 166C, (Chiba City, Japan), KURITA et al., • INDIAN PERFUMER vol. XXI, no. 3 , 1977 pages 129-131 A.K.SINHA ET AL. 'Study of some Agric. Biol. Chem. 1981, 45(4) 945-52 (Eng.), see Aromatic Medicinal Plants' entire article. • AGRICULTURAL AND BIOLOGICAL CHEMISTRY • CHEMICAL ABSTRACTS, Vol. 63, Abst. No. 1819d (Perth, Australia), BLUMANN et al., J. vol. 45, no. 4 , 1981 , TOKYO JP pages 945 - 952 N.KURITA ET AL. 'Antifungal Activity of Chem. Soc. 1965, (April) 2990 (Eng.), see entire CO Components of Essential Oils' article. CM O IO CO Note: Within nine months from the publication of the mention of the grant of the European patent, give 10 any person may notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in o a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. Q_ 99(1) European Patent Convention). LU Printed by Rank Xerox (UK) Business Services 2.14.2/3.4 EP 0 585 402 B1 Description TECHNICAL FIELD 5 This invention relates to the technical field of bactericides and yeasticides. BACKGROUND ART During the study of limonene as a hand cleaner, the applicants found that fully oxygenated limonene is a bacteri- 10 cide. A review of the literature revealed that oxygenated limonene contains several oxidation products including: cis and trans-carveol, trans-p-menth-8-ene-1 ,2-diol, limonene 1 ,2-epoxide, limonene 8,9-epoxide, cis and trans-p-mentha-2, 8- dien-1-ol, and perillyl alcohol, as was outlined by Blumann in Chemical Abstracts, Volume 63, 1965, on page 1819. The applicants found that a principal bactericide generated by the oxidation of limonene is perillyl alcohol which, in bacteri- cidal concentrations, kills bacteria and yeast . 15 Perillyl alcohol is a monocyclic monoterpene similar to limonene. Limonene is not bactericidal. Their chemical for- mulas follow below. C-HoOH C-H3 20 25 h2-9 C-H 30 C-H- 35 C-H 40 HtC-C=CH- H3C-OCH2 Perillyl Alcohol Limonene It should be noted that the formula for perillyl alcohol is identical to the formula for limonene with the exception of a hydroxyl group which replaces a hydrogen atom at carbon 7. Because limonene is not bactericidal, the exchange of a hydroxyl group for a hydrogen atom at carbon 7, was not expected to make the resulting compound (perillyl alcohol) bactericidal. All other monocyclic monoterpenes that have known bactericidal activity are similar to limonene, but have so a hydroxyl group or an oxygen atom replacing a hydrogen atom on the benzene ring at carbons 2, 3, 4 or 8 (as opposed carbon 7, 9, or 10) that is appreciated in the structures of: carveol, carvone, hydrocarveol, hydrocarvone, pulegone, iso- pulegol, menthol, menthone, terpinen-4-ol, and a-terpineol which follow. None of the monocyclic monoterpenes that have bactericidal or yeasticidal activity have a hydroxyl group at the carbon 7, 9, or 10 position. 55 2 EP 0 585 402 B1 C-H- 9"H3 10 H-C-OH 15 -.i2 C-H 20 H3C-C=CH2 25 Carved KtC-C=CH- Dihvdroc 3 EP 0 585 402 B1 4 EP 0 585 402 B1 5 10 <?-H2 15 C-OH 20 H3C-CK-CH3 H-jC-C-OH 25 Tercinen-4-ol a -Terpineol 30 Although it was not expected, the applicants were totally surprised to find that perillyl alcohol is toxic to bacteria and yeast . Perillyl alcohol is an oil with a terpenic aroma. It is insoluble in water, is poorly soluble in propylene glycol, and is 35 almost insoluble in glycerine. Perillyl alcohol is soluble in alcohol and is miscible in oil. It is used as a flavoring agent for cosmetics and perfumes, but heretofore, it has not been used as a bactericide. Perillyl alcohol can be produced by the oxidation of limonene as was demonstrated by Blumann in Chemical Abstracts, Volume 63, 1965 on page 1819, and Bardychev in Chemical Abstracts, Volume 80, 1974, page 359. It can be produced by the acetylation of limonene as described by Ansari, Hifzure R. (German Often 2,513,910 and Canadian Patent No. 1,077,959). Walling made perillyl 40 alcohol (Canadian Patent No. 981 ,695) from betapinene by adding benzyl peroxide to betapinene followed by alkaline hydrolysis to perillyl alcohol. There are several disclosures in the prior art of antimicrobial activity of limonene and other terpenes. Zukerman studies the effect of auto-oxidized d-limonene on bacteria, but found it was weakly bacteriostatic, was unstable, and lost its bacteriostatic effect on keeping as was discussed in Nature 169: 517 (1951). He never studied perillyl alcohol. Kurita 45 investigated the fungicidal activity of several components of essential oils as was reported in Biol. Chem., 45(4), 945- 952, 1981, but he never studied the toxic activity of perillyl alcohol against bacteria nor yeasts. Murdock and Allen showed that the germicidal effect of sodium benzoate against yeast was enhanced by the orange peel oil and d- limonene, as was out-lined in Food Technology, Vol. 14, No. 9, 1960, pages 441-5. They never studied the antimicrobial activity of perillyl alcohol against bacteria nor yeast. Kellner et al demonstrated that several ethereal oils and some of 50 theme constituents have antimicrobial activity as was reported in Arneimittel-Forschung, 5, 224-9, 1955. He confirmed that limonene is not bactericidal. He never studied perillyl alcohol for bactericidal activity. Gauvreau showed a means of producing disinfecting compositions in U.S. Patent No. 3,595,975 by combining cetyl pyridinium hydrochloride with ter- penes to form antiseptics, but he never studied the use of perillyl alcohol alone nor in combination with cetyl pyridinium hydrochloride. The active ingredient in his disinfecting compositions was cetyl pyridinium hydrochloride (and not the ter- 55 penes). A. Morel revealed the sterilizing action of carveol, dihydrocarveol, and their ozonization productions in Comp. Rend. Soc. Biol. Volume 115, pages 536-8 (1934). He never studied the bactericidal effect of perillyl alcohol. It should be pointed out that drugs which are bactericidal are usually not fungicidal, and drugs which are fungicidal are usually not bactericidal. In addition, drugs which are bactericidal frequently promote the growth of yeast. Table A, which follows, exemplifies the bactericidal and fungicidal activity of several commonly used antibacterial, antiyeast, and 5 EP 0 585 402 B1 antifungal antibiotics. TABLE A ANTIBIOTICS ANTIBIOTIC ACTIVITY AGAINST A. Anti -bacterial Gm + Bact Gm - Bact A F Bact Yeast Fungi LAmpicillin Y Y N N N 2. Cephalothin Y Y N N N 3. Chloramphenicol Y Y N N N 4. Erythromycin Y N N N N 5. Ethambutol N N Y N N 6. Gentamicin Y Y N N N 7. Isoniazid N N Y N N 8. Nitrofurantoin N Y N N N 9. Penicillin Y N N N N 10. Rifampin Y N Y N N 1 1 . Streptomycin Y Y Y N N 12. Sulfonamides N Y N N N 13. Tetracycline Y Y N N N 14. Vancomycin Y Y N N N B. Anti-Fungal 1 . Chlotrimazole N N N Y Y 2. Griseofulvin N N N N Y C. Anti-Yeast 1 . Nystatin N N N Y N 2. Gentian Violet N N N Y N Gm + Bact = Gram positive Bacteria, Gm - Bact = Gram Negative Bacteria, A F Bact = Acid Fast Bacteria, Y = Kills Organism, N = No Activity Against Organism It should be noted in the table above that none of the antibacterial antibiotics kill fungi, and none of the antifungal nor anti-yeast antibiotics kill bacteria.
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