Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2006-05-30
2006-05-30
Price, Elvis O. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S017000, C514S587000, C514S580000, C514S547000, C514S585000, C424S401000
Reexamination Certificate
active
07053243
ABSTRACT:
1-(3-methoxybenzyl)-3-substituted thiourea antioxidant compounds and improved lipids compositions which are supplemented with amounts of such antioxidant compounds effective for augmenting oxidative stability of the base lipid are provided. Also provided are methods for enhancing the oxidative stability of a lipid comprising supplementing a base lipid in need of enhanced oxidative stability with at least one 1-(3-methoxybenzyl)-3-substituted thiourea compound of the present invention.
REFERENCES:
patent: 2154341 (1939-04-01), Martin et al.
patent: 2662096 (1953-12-01), Huebner et al.
patent: 3483296 (1969-12-01), Martin et al.
patent: 3743736 (1973-07-01), Porter et al.
patent: 3852348 (1974-12-01), Teach
patent: 3949089 (1976-04-01), Maxwell et al.
patent: 3991008 (1976-11-01), Temin et al.
patent: 4925581 (1990-05-01), Erickson et al.
patent: 5079304 (1992-01-01), DeMarco
patent: 5262072 (1993-11-01), Camenzind et al.
patent: 5434283 (1995-07-01), Wang et al.
patent: 5441984 (1995-08-01), Heath et al.
patent: 5747528 (1998-05-01), Kakidas
patent: 6013818 (2000-01-01), O'Lenick, Jr.
patent: 6136330 (2000-10-01), Soliman et al.
patent: 6180668 (2001-01-01), O'Lenick, Jr. et al.
patent: 6545052 (2003-04-01), Wohlman et al.
patent: 6586628 (2003-07-01), Abbott et al.
patent: 208 298 (1984-05-01), None
patent: 0 466 639 (1991-06-01), None
patent: 0 903 349 (1999-03-01), None
patent: WO 96/28008 (1996-09-01), None
patent: WO 98/05294 (1998-02-01), None
“Proprieta E Applicazioni Cosmetiche Di Un Nuovo Ingrediente Vegetale Dalle Caratteristiche Multifunzionali,” Cosmetic News 117, 406-411 (1997).
Martin G. Ettlinger et al., “The Mustard Oil ofLimnanthes douglasiiSeed, m-Methoxybenzyl Isothiocynate,” Journal of the American Chemical Society, vol. 78, No. 9, pp. 1952-1954 (1956).
T.S. Chao et al., “Some Synergistic Antioxidants for Synthetic Lubricants,” Symposium on Synthetic and Petroleum-Based Lubricants Presented Before the Division of Petroleum Chemistry, Inc., 27(2), 362-379, American Chemical Society, Las Vegas Meeting, Mar. 28-Apr. 2, 1982.
T.P. Abbott, “Oxidative Stability System in Meadowfoam,” Abstract from the 89thAOCS Annual Meeting & Expo, Chicago, Illinois, May 10-13 (1998).
M. Rechcigl, Jr., CRC Handbook of Naturally Occurring Food Toxicants, CRC Press, Inc. (Boca Raton, Florida), pp. 15-30 (1983).
S. Vaughn et al., “Isolation and Identification of (3-Methoxyphenyl) Acetonitrile as a Phytotoxin from Meadowfoam (Limnanthes alba) Seedmeal,” Journal of Chemical Ecology, vol. 22, No. 10, 1939-1949 (1996).
T. Johns et al., “Anti-Reproductive and Other Medicinal Effects ofTropaeolum Tuberosum,” Journal of Ethnopharmacology 5, 149-161 (1982).
T.A. Isbell et al., “Oxidative Stability Index of Vegetable Oils in Binary Mixtures with Meadowfoam Oil,” Industrial Crops and Products 9, 115-123 (1999).
K. Tian et al., “Determination of Oxidative Stability of Oils and Fats,” Anal. Chem. 71, 1692-1698 (1999).
S. El. Migirab et al., “Isothiocyanates, Thioureas et Thiocarbamates Isoles De Pentadip landra Brazzeana,” Phytochemistry 16, 1719-1721 (1977).
W.W. Christie, “Antioxidants,” Bell & Bain Ltd., Glasgow, The Oily Press, Ltd. (Dundee, Scotland, 1988), pp. 133-159.
G. Kajimoto et al., “Changes in Organic Acid Formulation in Volatile Degradation Products During Oxidation of Oils Treated with Antioxidant,” Fac. Nutr., Kobe Gakuin Univ., Kobe, Japan. Nippon Eiyo, Shokuryo Gakkaishi 51(4), 207-212 (1998).
K. Zeigler-Skylakakis, “S-Oxygenation of Thiourea Results in the Formation of Genotoxic Products,” Environ. Mol. Mutagen. 31(4), 362-373 (1998).
S.L. Mali et al., “Phytochemical Oxidation of Phenyl-3-(2-Pyridyl)Thiourea by Singlet Oxygen,” Asian J. Chem. 5(4), 808-812 (1993).
A. Mustafa et al., “Reaction of Thiourea with Hydrogen Peroxide: Carbon-13 NMR Studies of an Oxidative/Reductive Bleaching Process,” Text. Res. J. 62(2), 94-100 (1992).
Internet, “Uses of Meadowfoam Seed Oil™,” Mar. 9, 2000, http://www.meadowfoam.com/uses/htm.
T. Abbott et al., “Antioxidants from Meadowfoam Stabilizes Other Oils,” Abstract, Assoc. for the Adv. or Ind. Crops, Oct. 15-17, 2000, St. Louis, MO.
U.S. Appl. No. 09/840,768, filed Apr. 23, 2001, Thomas P. Abbott et al.
U.S. Appl. No. 10/075,418, filed Feb. 14, 2002, Thomas P. Abbott et al.
U.S. Appl. No. 10/338,313, filed Jan. 8, 2003, Alan Wohlman et al.
U.S. Appl. No. 10/426,122, filed Apr. 29, 2003, Thomas P. Abbott et al.
89thAm. Oil Chem. Soc., May 10-13, 1998, Chicago, Illinois. This Presentation discussed some of the compounds that are present in crude meadowfoam seed oil that do not contribute substantially to the oxidative stability of lipids or oils. It did not discuss any 1-(3-methoxybenzyl)-3-substituted thiourea compounds.
Assoc. for the Adv. of Ind. Crops, Oct. 15-17, 2000, St. Louis, MO. This presentation identified the presence of 1,3-di(3-methoxybenzyl) thiourea in meadowfoam seed oil. No other 1-(3-methoxybenzyl)-3-substituted thiourea compounds were discussed.
Abbott Thomas P.
Wohlman Alan
Feder Scott B.
Hastreiter Roberta L.
Lord, Bissell & Brook LLP
The Fanning Corporation
The United States of America as represented by the Secretary of
LandOfFree
3-Methoxybenzyl thiourea derivatives and improved lipid... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with 3-Methoxybenzyl thiourea derivatives and improved lipid..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 3-Methoxybenzyl thiourea derivatives and improved lipid... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3557719