US2070915A - Therapeutical compounds containing metal abietates - Google Patents
Therapeutical compounds containing metal abietates Download PDFInfo
- Publication number
- US2070915A US2070915A US753545A US75354534A US2070915A US 2070915 A US2070915 A US 2070915A US 753545 A US753545 A US 753545A US 75354534 A US75354534 A US 75354534A US 2070915 A US2070915 A US 2070915A
- Authority
- US
- United States
- Prior art keywords
- abietate
- abietates
- abietic acid
- metal
- compounds containing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229910052751 metal Inorganic materials 0.000 title description 17
- 239000002184 metal Substances 0.000 title description 17
- 230000001225 therapeutic effect Effects 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 title description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 17
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 12
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 11
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- 239000004264 Petrolatum Substances 0.000 description 7
- 125000005907 alkyl ester group Chemical group 0.000 description 7
- 229910052797 bismuth Inorganic materials 0.000 description 7
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- 229940066842 petrolatum Drugs 0.000 description 7
- 235000019271 petrolatum Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000341 volatile oil Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 5
- 239000003209 petroleum derivative Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OVXRPXGVKBHGQO-UHFFFAOYSA-N abietic acid methyl ester Natural products C1CC(C(C)C)=CC2=CCC3C(C(=O)OC)(C)CCCC3(C)C21 OVXRPXGVKBHGQO-UHFFFAOYSA-N 0.000 description 3
- 230000002421 anti-septic effect Effects 0.000 description 3
- 229960005233 cineole Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000010642 eucalyptus oil Substances 0.000 description 2
- 229940044949 eucalyptus oil Drugs 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 101100382267 Caenorhabditis elegans cah-1 gene Proteins 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 235000019499 Citrus oil Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- -1 Terpin esters Terpin anhydride Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N cis-p-Menthan-1,8-diol Natural products CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
- 239000010500 citrus oil Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 229930006948 p-menthane-3,8-diol Natural products 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 229950010257 terpin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
Definitions
- This invention relates to a method of producing bland petroleum-hydrocarbon solutions of chemically pure metal abietates, based on the present accepted structural formula oi abietic.
- Citrus oils (lemon, orange, etc.)
- Terpines flesquiterpes I Terpin esters Terpin anhydride They dissolve metal abietates and are also miscible with esters of abietic acid and petroleum hydrocarbons. I
- metal abietate is necessary in the compounded mixture to give theantiseptic efficiency required for therapeutical use.
- To dissolve that amount of metal abietate in the essential oils or related chemical substances will require not less than 30% ct abietic acid esters to 70% petroleum hydrocarbons.
- l-abietic acid was made according to the directions or Steele (J. Am. Chem. Soc, 44, 1333, 1922) from American wood resin. This product is recrystallized several times from methanol and dried in This purified acid is converted into the potassium salt'of the l-abietic acid andthen converted into the silver salt. 0.2 gr. silver abietate. after purification, is triturated with 0.8 cc. eucalyptol U. S. P. until a clear solution is obtained. Then 30 cc. abietic acid methyl ester is added; preferably for better color and stability, vacuum distilled. abietic acid methyl ester or abieticacid methyl ester hydrogenated is used, and now, under constant stirring.
- liquid petrolatum is mixed in. After allowing to stand a few days and filtering, a clear stable, nearly water-white solution is obtained.
- A.bland therapeutic composition containing an abietate-of a metal selected from the group consisting of silver, bismuth, mercury and zinclower alkyl ester of abietic acid, and liquid petrolatum.
- a therapeutic compoaition containing 'a mercury abietate dissolved in eucalyptus oil and dispersed in a lower alkyl ester of abietic acid, and a petroleum hydrocarbon.
- a bland therapeutic composition containing an abietate or a metal selected from the group consisting of silver, bismuth, mercury and zinc dissolved in an essential oil which is a solvent of said abietate and dispersed in a hydrogenated alkyi ester of abietic acid, and liquid petrolatum.
- a bland therapeutic composition containing an aibetate of a metal selected from the group consisting oi silver, bismuth, mercury, and zincdissolved in an essential oil which is a solvent of said abietate and dispersed in a hydrogenated methyl ester of abietic acid, and liquid petrolatum.
- a bland therapeu-' tic composition which consists in dissolving an abietate of a metal selected from the group consisting of silver, mercury, bismuth, and zinc, in an essential oil which is a solvent for said metal abietate, adding a lower albl ester 01' abietic acid, and, under constant stirring, incorporating a petroleum hydrocarbon oil.
- a bland therapeutic composition which consists in dissolving'an abietate of a metal selected from the group consisting of silver, mercury, bismuth, and zinc, in an essential oil which is a solvent for said metal abietate, adding a lower allwl ester of abietic acid and, under constant stirring, incorporating a liquid petrolatum.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Feb. 16, 1937 THERAPEUTICAL COMPOUNDS CONTAIN- 'ING METAL ABIETATES Alien 1.. Omphundro and Emil c; Fanto; Fairiield, Conn, assignors to McKesson 8: Robbins, Inc., a corporation of Maryland No Drawing.
Application November 1'1, 1984, Serial No. 753,545
10 Claims. (CL 167-88) This invention relates to a method of producing bland petroleum-hydrocarbon solutions of chemically pure metal abietates, based on the present accepted structural formula oi abietic.
CaH1
soluble in common solvents like benzene, ether,
' acetone, carbon tetrachloride, chloroiorm, etc.
These solvents are not adaptable for therapeutical 30 or medical use as they are too irritating on exposed body surfaces or mucous membranes.
In accordance with our present invention, we propose these compounds, which we have found to possess eil'ective bacteriological properties, for
5 therapeutical or medicinal uses.
Because of the necessity of using bland oils or bland mixtures for that purpose, we attempted to employ liquid petrolatum U. B. P. X (petroleum hydrocarbons or U. S. P. X standard purity) but 40 iound they could not be used for that purpose be-- cause the metal abietates are not soluble in those oils. 1
We discovered that. by dissolving or dispersing the metal abietate in some 01' the following essen- 45 tial oils or their main constflzuents; intermiscible with petroleum hydrocarbon oils, the antiseptic efllciency was not altered.
A selected list of the most economical or most prominent types of those oils areas follows, and
were found to serve that purpose.
Citrus oils (lemon, orange, etc.)
Turpentine Oil pine Oil conaiba Oil eucalyptus I 5 Eucalyptol -&
Oiinadeput containing as main constituentsz.
Terpines flesquiterpes I Terpin esters Terpin anhydride They dissolve metal abietates and are also miscible with esters of abietic acid and petroleum hydrocarbons. I
We found further that to facilitate this dissolving process, the use of purified alkyl esters 01 natural wood resin or alkyl esters of abietic acid in addition to the petroleum oils, is of 'good advantage to produce clear solutions, without impairing the antiseptic properties of the compounded mixture, The'se alkyl esters are good solvents for all petroleum hydrocarbons. We found that they were intermiscible with the solutions of metalabietates in organic chemicals or essential oils as explainedbeiore.
We found that'20% to 45% of the metal abletates, particularly silver abietate, may be kept in the essential oils or related chemical substances in solution.
For practical purposes, we found that not more than 31% metal abietate is necessary in the compounded mixture to give theantiseptic efficiency required for therapeutical use. To dissolve that amount of metal abietate in the essential oils or related chemical substances will require not less than 30% ct abietic acid esters to 70% petroleum hydrocarbons.
(1) The emciency in regard to antiseptic action 40 can be easily demonstrated by using the petri dish agar medium penetration test, the so-called I-Iimebaugh technique, as described in Bulletin No. 198, December, 1931, of the U. S. Department of Agriculture, using as the organism of ex- 5 perimentation, staphylococcus aureus, the wellknown standard organism for testing bactericidal eiiiciency.
(2) Or the yeast fermentation inhibition, using a technique similar to the Pilcher, Sollman and Leech method by measuring their inhibiting effect on yeast-sugar fermentation.
To illustrate on a sample, our method of preparing and compounding, we proceedsubstantially as follows, l-abietic acid was made according to the directions or Steele (J. Am. Chem. Soc, 44, 1333, 1922) from American wood resin. This product is recrystallized several times from methanol and dried in This purified acid is converted into the potassium salt'of the l-abietic acid andthen converted into the silver salt. 0.2 gr. silver abietate. after purification, is triturated with 0.8 cc. eucalyptol U. S. P. until a clear solution is obtained. Then 30 cc. abietic acid methyl ester is added; preferably for better color and stability, vacuum distilled. abietic acid methyl ester or abieticacid methyl ester hydrogenated is used, and now, under constant stirring.
69 cc. liquid petrolatum is mixed in. After allowing to stand a few days and filtering, a clear stable, nearly water-white solution is obtained.
The scope of this invention is to be determined by-reierence to the following claims, said claims to be interpreted as broadlyas possible,- consistent with the state of the art.
We claim as our invention:
1. A.bland therapeutic composition containing an abietate-of a metal selected from the group consisting of silver, bismuth, mercury and zinclower alkyl ester of abietic acid, and liquid petrolatum.
4. A therapeutic compoaitioncontaining 'a mercury abietate dissolved in eucalyptus oil and dispersed in a lower alkyl ester of abietic acid, and a petroleum hydrocarbon.
5. A therapeutic composition containing 9. bismuth abietate dissolved in eucalyptus oil and dispersed in a lower alkyl ester of abietic acid, and liquid petrolatum.
6. A therapeutic composition containing an abietate of a. metal selected from the group con: sisting of silver, bismuth, mercury and zinc dissolved in eucalyptol and dispersed in a lower alkyl ester of abietic acid, and a petroleum hydrocarbon oil.
I. A bland therapeutic composition containing an abietate or a metal selected from the group consisting of silver, bismuth, mercury and zinc dissolved in an essential oil which is a solvent of said abietate and dispersed in a hydrogenated alkyi ester of abietic acid, and liquid petrolatum.
8. A bland therapeutic composition containing an aibetate of a metal selected from the group consisting oi silver, bismuth, mercury, and zincdissolved in an essential oil which is a solvent of said abietate and dispersed in a hydrogenated methyl ester of abietic acid, and liquid petrolatum.
9. The method of preparing a bland therapeu-' tic composition which consists in dissolving an abietate of a metal selected from the group consisting of silver, mercury, bismuth, and zinc, in an essential oil which is a solvent for said metal abietate, adding a lower albl ester 01' abietic acid, and, under constant stirring, incorporating a petroleum hydrocarbon oil.
10. The method of preparing a bland therapeutic composition which consists in dissolving'an abietate of a metal selected from the group consisting of silver, mercury, bismuth, and zinc, in an essential oil which is a solvent for said metal abietate, adding a lower allwl ester of abietic acid and, under constant stirring, incorporating a liquid petrolatum.
ALLEN L. OMOHUNDRO. EMU; C. FANTO.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US753545A US2070915A (en) | 1934-11-17 | 1934-11-17 | Therapeutical compounds containing metal abietates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US753545A US2070915A (en) | 1934-11-17 | 1934-11-17 | Therapeutical compounds containing metal abietates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2070915A true US2070915A (en) | 1937-02-16 |
Family
ID=25031099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US753545A Expired - Lifetime US2070915A (en) | 1934-11-17 | 1934-11-17 | Therapeutical compounds containing metal abietates |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2070915A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5064642A (en) * | 1989-09-13 | 1991-11-12 | Kao Corporation | Composition for external application |
-
1934
- 1934-11-17 US US753545A patent/US2070915A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5064642A (en) * | 1989-09-13 | 1991-11-12 | Kao Corporation | Composition for external application |
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