DE2445384C2 - p-Methoxyzimtsäureester, ihre Herstellung und Verwendung - Google Patents
p-Methoxyzimtsäureester, ihre Herstellung und VerwendungInfo
- Publication number
- DE2445384C2 DE2445384C2 DE19742445384 DE2445384A DE2445384C2 DE 2445384 C2 DE2445384 C2 DE 2445384C2 DE 19742445384 DE19742445384 DE 19742445384 DE 2445384 A DE2445384 A DE 2445384A DE 2445384 C2 DE2445384 C2 DE 2445384C2
- Authority
- DE
- Germany
- Prior art keywords
- methoxycinnamic acid
- preparation
- acid esters
- acid
- salts
- 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
Links
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical class COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000037072 sun protection Effects 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- ZEUMCJIXVFFRFR-UHFFFAOYSA-M COC1=CC=C(C=CC(=O)[O-])C=C1.OC[N+](C)(CO)CO Chemical compound COC1=CC=C(C=CC(=O)[O-])C=C1.OC[N+](C)(CO)CO ZEUMCJIXVFFRFR-UHFFFAOYSA-M 0.000 description 2
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical compound OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- -1 2-hydroxypropyl Chemical group 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- ISGUWSYDOACSAM-UHFFFAOYSA-N azanium;3-(4-methoxyphenyl)prop-2-enoate Chemical compound [NH4+].COC1=CC=C(C=CC([O-])=O)C=C1 ISGUWSYDOACSAM-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1448273A CH580558A5 (enrdf_load_stackoverflow) | 1973-10-11 | 1973-10-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2445384A1 DE2445384A1 (de) | 1975-04-17 |
| DE2445384C2 true DE2445384C2 (de) | 1983-12-22 |
Family
ID=4401208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742445384 Expired DE2445384C2 (de) | 1973-10-11 | 1974-09-23 | p-Methoxyzimtsäureester, ihre Herstellung und Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS5920663B2 (enrdf_load_stackoverflow) |
| AT (1) | AT338435B (enrdf_load_stackoverflow) |
| CH (1) | CH580558A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2445384C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2272069B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1422480A (enrdf_load_stackoverflow) |
| NL (1) | NL7412465A (enrdf_load_stackoverflow) |
| SE (1) | SE412227B (enrdf_load_stackoverflow) |
-
1973
- 1973-10-11 CH CH1448273A patent/CH580558A5/xx not_active IP Right Cessation
-
1974
- 1974-09-20 NL NL7412465A patent/NL7412465A/xx not_active Application Discontinuation
- 1974-09-23 DE DE19742445384 patent/DE2445384C2/de not_active Expired
- 1974-10-09 FR FR7433964A patent/FR2272069B1/fr not_active Expired
- 1974-10-09 JP JP11568574A patent/JPS5920663B2/ja not_active Expired
- 1974-10-10 AT AT816974A patent/AT338435B/de not_active IP Right Cessation
- 1974-10-10 SE SE7412789A patent/SE412227B/xx not_active IP Right Cessation
- 1974-10-10 GB GB4393174A patent/GB1422480A/en not_active Expired
-
1983
- 1983-12-20 JP JP24076783A patent/JPS59130209A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2445384A1 (de) | 1975-04-17 |
| JPS625882B2 (enrdf_load_stackoverflow) | 1987-02-07 |
| ATA816974A (de) | 1976-12-15 |
| JPS5920663B2 (ja) | 1984-05-15 |
| JPS59130209A (ja) | 1984-07-26 |
| AT338435B (de) | 1977-08-25 |
| NL7412465A (nl) | 1975-04-15 |
| SE412227B (sv) | 1980-02-25 |
| CH580558A5 (enrdf_load_stackoverflow) | 1976-10-15 |
| SE7412789L (enrdf_load_stackoverflow) | 1975-04-14 |
| GB1422480A (en) | 1976-01-28 |
| JPS5064242A (enrdf_load_stackoverflow) | 1975-05-31 |
| FR2272069A1 (enrdf_load_stackoverflow) | 1975-12-19 |
| FR2272069B1 (enrdf_load_stackoverflow) | 1978-11-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |