3,4-디히드록시벤즈알데히드
3,4-다이하이드록시벤즈알데하이드 · 3,4-디히드록시벤즈알데히드 · 프로토카테쿠익알데하이드 · 3,4-DIHYDROXYBENZALDEHYDE · PROTOCATECHUIC ALDEHYDE · Benzaldehyde, 3,4-dihydroxy- · 3,4－Dihydroxybenzyl aldehyde · Catechaldehyde
식별자 및 물리적 특성
| CAS No. | 139-85-5 |
|---|---|
| 분자식 | C7H6O3 |
| 평균 분자량 | 138.12 g/mol |
| 단동위원소 질량 | 138.03169405 g/mol |
| SMILES | O=Cc1ccc(O)c(O)c1 |
| InChIKey | IBGBGRVKPALMCQ-UHFFFAOYSA-N |
| PubChem CID | 8768 |
| ChEMBL | CHEMBL222021 |
| ChEBI | CHEBI:50205 |
| EC No. | 205-377-7 |
| DTXSID | DTXSID4074512 |
| 현지명 | 3,4-디히드록시벤즈알데히드 |
화학 및 물리적 성질
| XLogP | 1.3 |
|---|---|
| 극성 표면적 | 57.5 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 124 |
| 물질 분류 | Other Classes -> Benzaldehydes |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| LogP(분배 계수) | 0.82 |
| 향미제 | EU Flavoring substances |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 증기압 | 0.000116 [mmHg] |
| Physical Description | Solid[Merck Index] Light brown powder[Alfa Aesar MSDS] |
| Collision Cross Section | 126.83 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 녹는점 | 150-157 °C(lit.) |
| 끓는 점 | 213.5°C (rough estimate) |
| 밀도 | 1.2667 (rough estimate) |
| 굴절률 | 1.4600 (estimate) |
| 저장 조건 | Store below +30°C. |
| 용해도 | 6.3g/L |
| 물리적 상태 | 결정성 분말 |
| pKa(산도 계수) | pK (25°) 7.55 |
| 색상 | 약간 갈색 |
| 냄새 | 100.00%에서. 건조 약용 쓴 아몬드 |
| 향취 유형 | 약용 |
| 용해도 | 50g/L(20℃) |
| Merck | 14,7893 |
| BRN | 774381 |
| 안정성 | 안정적인. 강염기, 강산화제와 호환되지 않습니다. |
| 화장품 원료 기능 | 피부의 멜라닌 생성을 줄입니다항산화제피부 컨디셔닝 |
| InChI | 1S/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H |
| InChIKey | IBGBGRVKPALMCQ-UHFFFAOYSA-N |
| SMILES | Oc1ccc(C=O)cc1O |
| LogP(분배 계수) | 1.090 |
| NIST | 3,4-Dihydroxybenzaldehyde(139-85-5) |
| EPA | Benzaldehyde, 3,4-dihydroxy- (139-85-5) |
화학적 성질
Protocatechualdehyde is a phenolic aldehyde crystalline compound with the molecular formula C7H6O3. The compound is released from cork stoppers into wine. protocatechualdehyde can be found in barley, grapevine, green Cavendish, and root of herb S. miltiorrhiza. The compound contains pro-apoptotic and antiproliferative properties against human breast cancer cells as well as colorectal cancer cells by reducing the expression of cyclin D1 and β-catenin.
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 62.7% (89 of 142) of all reports.WarningH315 (34.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 142 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: Benzaldehyde, 3,4-dihydroxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 13-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/343503,4-Dihydroxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard |
| 유해성 요약 | Causes convulsions and respiratory stimulation in intraperitoneal lethal-dose studies of mice (LD50 = 205 mg/kg)[RTECS] A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (34.5%) |
| 유해 작용 | Neurotoxin - Other CNS neurotoxin |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UL0380000 |
| 관세 코드 | 29124900 |
| 위험 문구(R) | 36/37/38-22 |
| 위험 표시 | Xi |
| 안전 문구(S) | 26-36-37/39 |
| 기존화학 물질 | KE-10785 |
| F 고인화성물질 | 9 |
| 위험 참고 사항 | Irritant/Air Sensitive |
| 위험 등급 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Protocatechualdehyde is extracted from roots of the common traditional Chinese medicine Salvia miltiorrhiza Bge, which was harvested in autumn for better quality. Take root and remove stems, leaves and fibrous roots, then dry it. Most of them are wide, and they are mainly cultivated in recent years. South Salvia and Gansu Salvia are also widely used. Besides, there are a variety of sibling plant roots used as Salvia miltiorrhiza in Yunnan. Now, the existence of protocatechualdehyde has been found in variety of herbs, for example, in the leaf of Stenoloma Chusanum (L.) Ching and Ilex chinensis Sims.
역사
In the 1940s, the research was conducted overseas to obtain protocatechualdehyde form herbs. In 1972, the chemical group of Chinese herbal medicine in Nanjing College of Pharmacy systematically studied chemical composition in purple flower holly leaf and separated six monomers including protocatechualdehyde. Then they compared the effect of protocatechualdehyde, Salvia miltiorrhiza injection and hairy holly root injection, in which protocatechualdehyde is the most effective in increasing coronary sinus flow. Further experiments examined that protocatechualdehyde can increase coronary flow and improve coronary circulation, so it was called after perhexiline. Further clinical observation indicated that protocatechualdehyde has effect on coronary heart disease. The graduates of Nanjing College of Pharmacy in 1975 extracted, separated, isolated, and identified protocatechualdehyde in Salviamiltiorrhiza during the internship in Nanjing Municipal Hospital and studied its distribution, excretion, and toxicity in animals for clinical rational drug usage
용도
3,4-Dihydroxybenzaldehyde is used in as an apoptosis inducer of human leukemia cells.
일반 설명
3,4-Dihydroxybenzaldehyde has been recognized as one of the antifungal compound extracted from the outer skin of green Cavendish bananas. It can be synthesized from catechol via Fries rearrangement.