US2058403A - Organic bismuth compounds of hydroaromatic endomethylene benzoic acids - Google Patents
Organic bismuth compounds of hydroaromatic endomethylene benzoic acids Download PDFInfo
- Publication number
- US2058403A US2058403A US697078A US69707833A US2058403A US 2058403 A US2058403 A US 2058403A US 697078 A US697078 A US 697078A US 69707833 A US69707833 A US 69707833A US 2058403 A US2058403 A US 2058403A
- Authority
- US
- United States
- Prior art keywords
- endomethylene
- acid
- water
- bismuth
- endo
- 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
- 150000001622 bismuth compounds Chemical class 0.000 title description 5
- 235000010233 benzoic acid Nutrition 0.000 title description 3
- 150000001559 benzoic acids Chemical class 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 11
- 150000001621 bismuth Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- ZURRKVIQUKNLHF-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptane-3-carboxylic acid Chemical compound C1CC2(C)C(C(O)=O)CC1C2(C)C ZURRKVIQUKNLHF-UHFFFAOYSA-N 0.000 description 3
- 229910052797 bismuth Inorganic materials 0.000 description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- -1 methylene-hexahydromethyl-benzoic acid Chemical compound 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 241000193803 Therea Species 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- CJJMLLCUQDSZIZ-UHFFFAOYSA-N oxobismuth Chemical class [Bi]=O CJJMLLCUQDSZIZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/12—Saturated polycyclic compounds
- C07C61/125—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system
- C07C61/13—Saturated polycyclic compounds having a carboxyl group bound to a condensed ring system having two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/94—Bismuth compounds
Definitions
- the present invention relates to organic bismuth compounds of hydroaromatic endomethylene benzoic acids.
- Suitable acids of the said kind are the endomethylene-benzoic acid obtainable by oxidation of camphene and similar compounds, for instance, the camphenilanic acid of the formula CH: 011C003 or the acid of the following formula CH.COOH i or the homologous acid of the formula
- the unsaturated endo-methylene-carboxylic acids obtained as well as the corresponding saturated endo-methylene-carboxylic acids may be transformed into their bismuth salts.
- the saturated endo-methylene-carboxylic acids are obtainable from the unsaturated acids by bydrogenation.
- CILCOOE there may also be used endo-methylene-benzoic acids, wherein the endo-methylene-hydrogen atoms have been exchanged for alkyl groups, for instance, the camphane-carboxylic acids of the formula Beilstein, 4th edition, volume9, page 74) are dis-
- the monoiodo-endomethylene-hexahydromethyl 1" benzoic acid obtainable by addition'of'hydroge'n iodide to the endo-methylene 2.5 'deltas tetra-' hydro-G-methylbenzoic acid, the corresponding diiodo-endtomethylene-hexahydromethyl-benzoic acid obtainable by addition of iodine to the-same parent acid, the mono-iodo-endomethylene-tetrahydromethyl-benzoic acid obtainable 'by-splitei ting off hydrogen iodide from the diiodo-endo methylene-hexahydro
- the new bismuth compounds can be obtained by causing a bismuth salt to act upon a whollylor partially hydrogenated endo-methylene-benzoic acid.
- the new bismuth compounds are amorphous substances which decompose without melting when heated, and are insoluble in water, soluble in ether, chloroform and oils and have a strong bactericidal action especially against spirilli, but only a comparatively small toxicity.
- H P Bi CH: l 011-000- said salt being an amorphous substance, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
- the bismuth salt of isocamphenilanic acid said salt being an amorphous substance, insoluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
- said salt being an amorphous substance, in- 15 soluble in water, soluble in ether, chloroform and oils, decomposing without melting when heated and having a strong bactericidal action, especially against spirilli.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE428147X | 1932-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2058403A true US2058403A (en) | 1936-10-27 |
Family
ID=6477416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US697078A Expired - Lifetime US2058403A (en) | 1932-11-08 | 1933-11-07 | Organic bismuth compounds of hydroaromatic endomethylene benzoic acids |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2058403A (xx) |
| GB (1) | GB428147A (xx) |
| NL (1) | NL37063C (xx) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021598A (en) * | 1989-07-24 | 1991-06-04 | Mooney Chemicals, Inc. | Process for making bismuth carboxylates |
| EP2796531A4 (en) * | 2011-12-22 | 2015-08-12 | G C Dental Ind Corp | AGENT FOR CONFERRING FLUORESCENCE TO CERAMIC |
-
0
- NL NL37063D patent/NL37063C/xx active
-
1933
- 1933-11-07 US US697078A patent/US2058403A/en not_active Expired - Lifetime
- 1933-11-08 GB GB31142/33A patent/GB428147A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021598A (en) * | 1989-07-24 | 1991-06-04 | Mooney Chemicals, Inc. | Process for making bismuth carboxylates |
| EP2796531A4 (en) * | 2011-12-22 | 2015-08-12 | G C Dental Ind Corp | AGENT FOR CONFERRING FLUORESCENCE TO CERAMIC |
Also Published As
| Publication number | Publication date |
|---|---|
| NL37063C (xx) | |
| GB428147A (en) | 1935-05-08 |
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