코우마린
쿠마린 · 코우마린 · 2H-Chromen-2-one · COUMARINE · 2H-1-BENZOPYRAN-2-ONE · CUMARIN · 1,2-BENZOPYRONE · CHROMEN-2-ONE
식별자 및 물리적 특성
| CAS No. | 91-64-5 |
|---|---|
| 분자식 | C9H6O2 |
| 평균 분자량 | 146.14 g/mol |
| 단동위원소 질량 | 146.03677943 g/mol |
| SMILES | O=c1ccc2ccccc2o1 |
| InChIKey | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| PubChem CID | 323 |
| ChEMBL | CHEMBL6466 |
| ChEBI | CHEBI:28794 |
| EC No. | 202-086-7 |
| DTXSID | DTXSID7020348 |
| 현지명 | 코우마린 |
화학 및 물리적 성질
| XLogP | 1.4 |
|---|---|
| 극성 표면적 | 26.3 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 196 |
| 녹는점 | 68-73 °C (lit.) |
| 끓는 점 | 298 °C (lit.) |
| 밀도 | 0.935 |
| 증기압 | 0.01 mm Hg ( 47 °C) |
| 굴절률 | 1.5100 (estimate) |
| 인화점 | 162 °C |
| 저장 조건 | Store below +30°C. |
| 용해도 | 1.7g/L |
| 물리적 상태 | 결정 또는 결정성 분말 |
| 색상 | 하얀색 |
| 냄새 | 디프로필렌 글리콜 중 10.00%. 달콤한 건초 통카 새로운 잔디 건초 |
| 향취 유형 | 통카 |
| 생물학적 소스 | synthetic |
| 용해도 | 1.7g/L(20℃) |
| Merck | 14,2562 |
| BRN | 383644 |
| 헨리 상수 | 9.9×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 주요 응용 | 컬러 필터, 유기 발광 다이오드, 액정 디스플레이, 전계 방출 디스플레이, 잉크, 니켈 도금, 세제, 신발 탈취제, 석유 제품, 담배, 개인 위생 용품, 화장품, 자외선 차단 크림, 향수, 핵산 서열 분석, 항염증제, 암 치료, 신경전달 장애, 출혈 장애, 뇌혈관 질환, 혈전증, 치질, 류마티스 질환, 관절염, 간질, 질염, 진통제, 치아 미백제, 피부 미백제, 상처 치유 촉진제 |
| 화장품 원료 기능 | 향수 |
| InChI | 1S/C9H6O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-6H |
| InChIKey | ZYGHJZDHTFUPRJ-UHFFFAOYSA-N |
| SMILES | O=C1Oc2ccccc2C=C1 |
| LogP(분배 계수) | 1.39 at 25℃ |
| NIST | Coumarin(91-64-5) |
| EPA | Coumarin (91-64-5) |
화학적 성질
Coumarin occurs widely in nature and determines, for example, the odor of woodruff. It forms white crystals (mp 70.6°C) with a hay-like, spicy odor. When treated with dilute alkali, coumarin is hydrolyzed to the corresponding coumarinic acid salt [(Z)-2-hydroxycinnamic acid]. Heating with concentrated alkali or with sodium ethanolate in ethanol results in the formation of o-coumaric acid salts [(E)-2-hydroxycinnamic acid]. 3,4-Dihydrocoumarin is obtained by catalytic hydrogenation, for example, with Raney nickel as a catalyst; octahydrocoumarin is obtained if hydrogenation is carried out at high temperature (200–250°C).
안전 및 규제
| 수질 위해 등급(WGK) | 1 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | GN4200000 |
| 운송 번호(UN) | UN 2811 6.1/PG 3 |
| 독성 | LD50 orally in rats, guinea pigs: 680, 202 mg/kg (Jenner) |
| 관세 코드 | 29322010 |
| 위험 문구(R) | 22-40-36/37/38-20/21/22-43 |
| 위험 표시 | Xn |
| 안전 문구(S) | 36-36/37-26 |
| 포장분류 | III |
| 위험 등급 | 6.1Acute Tox. 3 DermalAcute Tox. 3 OralSkin Sens. 1 |
| 기존화학 물질 | KE-02718 |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 유해 물질 데이터 | 91-64-5(Hazardous Substances Data) |
용도
개요
Coumarin is a naturally occurring Benzopyrone compound. It is found in a large number of plants belonging to many different families including tonka beans, woodruff, lavender oil, cassia, melilot (sweet clover), and other plants. It is found in edible plants such as strawberries, cinnamon, peppermint, green tea, carrots, and celery, as well as in partially fermented tea, red wine, beer, and other foodstuffs. Concentrations range from 87 000 ppm in cassia and 40 000 ppm in cinnamon to 20 ppm in peppermint and 5 ppb in tangerines.
출처
Found in many plants and essential oils such as cassia, melilot, orchid, lavender and balsam of Peru (Spth, 1937; Gildemeister & Hoffman, 1966).
용도
coumarin is considered a blood thinner, it can also increase blood flow. Some sources cite anti-oxidant capacities, as well. It is a specific plant constituent and is what creates the fragrance of freshly mowed hay. Coumarin is found in such plants as cherries, lavender, licorice, and sweet clover.
일반 설명
Colorless crystals, flakes or colorless to white powder with a pleasant fragrant vanilla odor and a bitter aromatic burning taste.
제조 및 합성 방법
제조 방법
Coumarin is currently produced by Perkin synthesis from salicylaldehyde. In the presence of sodium acetate, salicylaldehyde reacts with acetic anhydride to produce coumarin and acetic acid. The reaction is carried out in the liquid phase at elevated temperature.A process for the production of coumarin from hexahydrocoumarin by dehydrogenation has also been elaborated.Since the odor of coumarin is relatively weak, strong-smelling by-products (e.g., vinylphenol) must be removed. Many purification methods have been reported and patented.