US2139839A - Alkaloid compound - Google Patents

Alkaloid compound Download PDF

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Publication number
US2139839A
US2139839A US159327A US15932737A US2139839A US 2139839 A US2139839 A US 2139839A US 159327 A US159327 A US 159327A US 15932737 A US15932737 A US 15932737A US 2139839 A US2139839 A US 2139839A
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Prior art keywords
alkaloid
reaction
alkaloid compound
compound
fatty acids
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Expired - Lifetime
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US159327A
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Robert S Mckinney
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine

Definitions

  • This invention relates to new compounds resulting from the reaction of the fatty acids of drying oils with vegetable alkaloids (nicotine, quinine and strychnine).
  • reaction is facilitated by the addition of an appropriate solvent in which the two reactants are soluble.
  • Ethyl alcohol was found to be such a solvent.
  • the solvent may be removed by evaporation as may any excess of the alkaloid if it is volatile.
  • fatty acid-alkaloid substances are nonvolatile, heavy, viscous, sticky fluids, insoluble in Water but soluble in alcohol. Upon treatment of these substances with an alkaline solution, the free alkaloid is liberated and the fatty acid combines with the alkali to give a. soap in solution.
  • the nicotine-fatty acid compound can be used as an insecticide. It has certain advantages in that it is insoluble in water and has adhesive properties.
  • the strychnine-fatty acid compound can be used as the free alkaloid as a poison for predatory animals and in medicine.
  • the quinine compound can be used as the free alkaloid. It appears quite useful as an ingredient in anti-sunburn ointment as it prevents the absorption of most of the ultra-violet rays which cause painful sunburn. (Dr. Th. Ruemele, Salts of Quinine in Cosmetic Compounds Seifeuseider-Ztg., volume 64, page 138, February 24, 1937.)
  • a compound consisting of the water insoluble product of the reaction between fatty acids derived from drying oils and an alkaloid.
  • Acompound consisting of the product of the reaction between the fatty acids of the group of drying oils and an alkaloid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Patented Dec. 13, 1938 UNITED STATES ATENT FFiCE ALKALOID COMPOUND States No Drawing. Application August 16, 1937, Serial No. 159,327
2 Claims.
(Granted under the act of March 3, 1883, as
amended April 30,
This application is made under the act approved March 3, 1883, as amended by the act of April 30, 1928, and the invention herein described, if patented, may be manufactured and used by 5 or for the Government of the United States of America for governmental purposes without the payment to me of any royalty thereon.
I hereby dedicate the invention herein described to the free use of the People of the 10 United States to take eifect on the granting of a patent to me.
This invention relates to new compounds resulting from the reaction of the fatty acids of drying oils with vegetable alkaloids (nicotine, quinine and strychnine).
15 I have found that the fatty acids of drying oils (tung, linseed, fish and soybean) react with vegetable alkaloids (nicotine, quinine and strychnine) to form new and useful compounds. The reaction is preferably carried out in the presence 2 of a common solvent of the two reactants, for example, ethyl alcohol. It was found that the compounds formed are insoluble in water but usually soluble in ethyl alcohol.
In the practice of this invention, commercial 25 crude oil is saponified with the requisite amount of an aqueous alkali solution and the resulting soap solution is broken up by adding a slight excess of mineral acid, and heating. The lower mineral acid layer is then drawn ofi and the 3 remaining fatty acids washed with water until free of the mineral acid. A portion of the alkaloid is weighed into a vessel and an equivalent amount of the fatty acids added. If the alkaloid is a di-acid base, two molecules of fatty acid per molecule of base are used, and if the alkaloid is a mono-acid base, one molecule of fatty acid per molecule of base is used. The
reaction is facilitated by the addition of an appropriate solvent in which the two reactants are soluble. Ethyl alcohol was found to be such a solvent. Upon completion of the reaction, the solvent may be removed by evaporation as may any excess of the alkaloid if it is volatile.
These fatty acid-alkaloid substances are nonvolatile, heavy, viscous, sticky fluids, insoluble in Water but soluble in alcohol. Upon treatment of these substances with an alkaline solution, the free alkaloid is liberated and the fatty acid combines with the alkali to give a. soap in solution.
The nicotine-fatty acid compound can be used as an insecticide. It has certain advantages in that it is insoluble in water and has adhesive properties.
The strychnine-fatty acid compound can be used as the free alkaloid as a poison for predatory animals and in medicine.
The quinine compound can be used as the free alkaloid. It appears quite useful as an ingredient in anti-sunburn ointment as it prevents the absorption of most of the ultra-violet rays which cause painful sunburn. (Dr. Th. Ruemele, Salts of Quinine in Cosmetic Compounds Seifeuseider-Ztg., volume 64, page 138, February 24, 1937.)
Having thus described my invention, what I claim for Letters Patent is:
1. A compound consisting of the water insoluble product of the reaction between fatty acids derived from drying oils and an alkaloid.
2. Acompound consisting of the product of the reaction between the fatty acids of the group of drying oils and an alkaloid.
ROBERT S. MCKINNEY.
US159327A 1937-08-16 1937-08-16 Alkaloid compound Expired - Lifetime US2139839A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2463666A (en) * 1944-10-04 1949-03-08 Charles F Woodward Nicotinium salts and their production
US2644816A (en) * 1947-07-19 1953-07-07 Olin Mathieson Purification of antibiotics with water insoluble carboxylic acids
US4655231A (en) * 1984-01-09 1987-04-07 Advanced Tobacco Products, Inc. Snuff and preparation thereof
US4917120A (en) * 1986-05-21 1990-04-17 Advanced Tobacco Products, Inc. Nicotine impact modification

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2463666A (en) * 1944-10-04 1949-03-08 Charles F Woodward Nicotinium salts and their production
US2644816A (en) * 1947-07-19 1953-07-07 Olin Mathieson Purification of antibiotics with water insoluble carboxylic acids
US4655231A (en) * 1984-01-09 1987-04-07 Advanced Tobacco Products, Inc. Snuff and preparation thereof
US4917120A (en) * 1986-05-21 1990-04-17 Advanced Tobacco Products, Inc. Nicotine impact modification

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