노르디하이드로구아야레트산
노르디하이드로구아야레트산 · 노르다이하이드로구아이아레틱애씨드 · NDGA · ACTINEX · NORDIHYDROGUAIRETIC ACID · NSC 4291 · TIMTEC-BB SBB005930 · LABOTEST-BB LT00233087
식별자 및 물리적 특성
| CAS No. | 500-38-9 |
|---|---|
| 분자식 | C18H22O4 |
| 평균 분자량 | 302.4 g/mol |
| 단동위원소 질량 | 302.15180918 g/mol |
| SMILES | CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1 |
| InChIKey | HCZKYJDFEPMADG-UHFFFAOYSA-N |
| PubChem CID | 4534 |
| ChEMBL | CHEMBL52 |
| ChEBI | CHEBI:7625 |
| EC No. | 207-903-0 |
| DTXSID | DTXSID5022437 |
| 현지명 | 노르디하이드로구아야레트산 |
화학 및 물리적 성질
| XLogP | 4.3 |
|---|---|
| 극성 표면적 | 80.9 |
| 수소 결합 공여자 수 | 4 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 22 |
| 형식 전하 | 0 |
| 복잡도 | 303 |
| 물질 분류 | Biological Agents -> Plant Toxins |
| 화장품 | Antioxidant |
| 식품 첨가물 | ANTIOXIDANT -> FDA Substance added to food |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Food Contact Substances | FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR |
| Physical Description | Solid[Merck Index] White odorless powder[Alfa Aesar MSDS] |
| Collision Cross Section | 167.5 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID5022437] |
| 녹는점 | 184-186 °C (lit.) |
| 끓는 점 | 363.4°C (rough estimate) |
| 밀도 | 1.0772 (rough estimate) |
| 굴절률 | 1.4230 (estimate) |
| 저장 조건 | Inert atmosphere,Room Temperature |
| 용해도 | DMSO(약간 용해됨), 메탄올(약간 용해됨) |
| 물리적 상태 | 가루 |
| pKa(산도 계수) | 9.56±0.10(Predicted) |
| 색상 | 흰색에서 황백색까지 |
| 생물학적 소스 | Larrea divaricata (creosote bush) |
| 용해도 | 약간 용해됨 |
| Merck | 14,6693 |
| BRN | 2056825 |
| 안정성 | 안정적인. 산화제와 호환되지 않습니다. |
| 화장품 원료 기능 | 항산화제 |
| InChI | 1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3 |
| InChIKey | HCZKYJDFEPMADG-UHFFFAOYSA-N |
| SMILES | CC(Cc1ccc(O)c(O)c1)C(C)Cc2ccc(O)c(O)c2 |
| LogP(분배 계수) | 4.640 (est) |
| NIST | Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-(500-38-9) |
| EPA | Nordihydroguaiaretic acid (500-38-9) |
화학적 성질
Nordihydroguaiaretic acid is a white to light yellow crystalline powder. Melting range 183～185℃. Insoluble in water. Slightly soluble in hot water. Soluble in alcohol, ether, glycerol, propylene glycol. About 0.5% is dissolved in oil. It has good antioxidant effect and is also effective against mildew. It has a synergistic effect when used in combination with citric acid and ascorbic acid.
안전 및 규제
| GHS 분류 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 188 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis- |
| 유해성 요약 | This CAS# refers to the unspecified stereoisomer formThe meso- form is CAS# 27686-84-6[Merck Index] A skin and strong eye irritantHarmful by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UX1750000 |
| 관세 코드 | 29072990 |
| 위험 문구(R) | 22-36/37/38 |
| 위험 표시 | Xn |
| 안전 문구(S) | 26-36/37-37/39-24/25-22 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Nordihydroguaiaretic acid (NDGA) is a grayish-white crystalline compound that was widely used as an antioxidant in animal fats in the 1950s and 1960s. It possesses phenolic properties similar to gallates, including their advantages and disadvantages. Besides the isolation of natural material (resinous exudate of creosote bush), NDGA has also been chemically synthesized. As the result of unfavorable toxicological findings, NDGA is prohibited from use in the US. More specifically, NDGA is a potent lipoxygenase inhibitor which interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carbox- ylesterase,and,to a lesser extent, cyclooxygenase.
일반 설명
Nordihydroguaiaretic acid (NDGA) is used as an powerful antioxidant and potent scavenger of reactive oxygen species (ROS). NDGA is a phenolic lignan obtained from Larrea tridentata, that has been used in traditional medicine for the treatment of numerous diseases such as cancer, renal, cardiovascular, immunological, and neurological disorders, and even aging.
제조 및 합성 방법
제조 방법
Nordihydroguaiaretic acid is obtained by hydrodemethylation of dimethyl ether of guaiacolinic acid, a component of guaiac resin. It is also produced from desert plant, creosote bush (Larrea divaricata Cav. Or Corillea tridentate), which can be widely found in the border zone of southern of USA and northern of Mexico.