기본 정보
- 표준 SMILES
CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1- InChIKey
HCZKYJDFEPMADG-UHFFFAOYSA-N- 분자식
- C18H22O4
- 평균 분자량
- 302.4 g/mol
- 단동위원소 질량
- 302.15180918
개요
Nordihydroguaiaretic acid is a tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. It has a role as a ferroptosis inhibitor, a geroprotector, an antioxidant and a plant metabolite. It is a lignan, a member of catechols and a tetrol.
이름 및 식별자
- 우선 이름
- Nordihydroguaretic acid
- IUPAC
- 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
- 현지명
- 노르디하이드로구아야레트산
- 영어명
- Nordihydroguaiaretic acid
- 분자식
- C18H22O4
- 분자량
- 302.36
이름 및 동의어
nordihydroguaretic acid2,3-bis(3,4-dihydroxybenzyl)butaneRefChem:854717NORDIHYDROGUAIARETIC ACID500-38-9NDGA4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diolNorhydroguaiaretic acidNorguaiaretic acid, dihydro-1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-NSC 42914,4'-(2,3-Dimethyltetramethylene)dipyrocatechol
이름 더 보기
노르디하이드로구아야레트산노르다이하이드로구아이아레틱애씨드ACTINEXNORDIHYDROGUAIRETIC ACIDTIMTEC-BB SBB005930LABOTEST-BB LT00233087NDGA, LARREA DIVARICATAnordihydroguaiareticacidihydronorguaiareticaciddihydro-norguaiareticaci
MFCD000022062,3-Bis(3,4-dihydroxyphenylmethyl)butaneDTXSID5022437Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-4,4'-(2,3-Dimethyl-1,4-butanediyl)bis(pyrocatechol)nordihydroguaiaretateCHEMBL52Butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
데이터베이스 식별자
- CAS
500-38-9- PubChem CID
- 4534
- DTXSID
DTXSID5022437- ChEMBL
CHEMBL52- ChEBI
CHEBI:7625- EC Number
- 207-903-0
- Nikkaji
- J9.195B
물성
구조 계산 물성
- XLogP
- 4.3
- 극성 표면적
- 80.9 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 22
- 형식 전하
- 0
- 복잡도
- 303
실험 및 물리화학적 성질
Chemical ClassesBiological Agents -> Plant Toxins
CosmeticsAntioxidant
Food AdditivesANTIOXIDANT -> FDA Substance added to food
Endocrine DisruptorsPotential endocrine disrupting compound
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical DescriptionSolid; [Merck Index] White odorless powder; [Alfa Aesar MSDS]
Collision Cross Section167.5 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID5022437]
물리화학적 성질
- 녹는점
- 184 · 184-186 °C (lit.)
- 끓는 점
- 363.4 °C · 363.4°C (rough estimate)
- 밀도
- 1.0772 · 1.0772 (rough estimate)
- 굴절률
- 1.423 · 1.4230 (estimate)
- 저장 조건
- Inert atmosphere,Room Temperature
- 용해도
- DMSO(약간 용해됨), 메탄올(약간 용해됨)
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 9.56 · 9.56±0.10(Predicted)
- 색상
- 흰색에서 황백색까지
- 생물학적 소스
- Larrea divaricata (creosote bush)
- 수용성
- 약간 용해됨
- Merck
- 14 · 14,6693
- BRN
- 2056825 · 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
- 4.64 · 4.640 (est)
- NIST
- 4 · 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
GHS Classification
Warning
H302 (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.
유해성 정보
Regulatory InformationChemical: 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
Hazards SummaryThis CAS# refers to the unspecified stereoisomer form; The meso- form is CAS# 27686-84-6; [Merck Index] A skin and strong eye irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (100%)
안전 데이터
- wgk
- 3
- rtecs
- UX1750000
- HS 번호
- 29072990
- risk_code
- 22-36/37/38
- hazard_code
- Xn
- safety_code
- 26-36/37-37/39-24/25-22
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
용도 및 제조
Uses
Occurs in the creosote bush; Used as an antioxidant in foods and as an antineoplastic; [Merck Index]
Banned for use as an antioxidant in food; [EPA]
Use Classification
Food Additives -> ANTIOXIDANT -> JECFA Functional Classes
Food Additives -> ANTIOXIDANT -> JECFA Functional Classes
Cosmetics -> Antioxidant
응용 분야
개요Nordihydroguaiaretic 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 설명Nordihydroguaiaretic 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 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.
상·하류 제품 정보
상류 원료
하류 제품
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추가 설명
정의ChEBI: Nordihydroguaiaretic acid is a tetrol that is butane which is substituted at positions 2 and 3 by 3,4-dihydroxybenzyl groups. Masoprocol, the meso-form found in the leaves of the creosote bush (Larrea divaricata), is a potent lipoxygenase inhibitor. It has a role as an antioxidant, a plant metabolite, a ferroptosis inhibitor and a geroprotector. It is a member of catechols, a tetrol and a lignan.
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