4,4'-(2,3-ジメチルテトラメチレン)ジピロカテコール

Nordihydroguaretic acid

HCID 4534CAS 500-38-9
部分構造検索類似構造を探す

基本情報

標準SMILES
CC(Cc1ccc(O)c(O)c1)C(C)Cc1ccc(O)c(O)c1
InChIKey
HCZKYJDFEPMADG-UHFFFAOYSA-N
分子式
C18H22O4
平均分子量
302.4 g/mol
単同位体質量
302.15180918

概要

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.

名称と識別子

優先名称
Nordihydroguaretic acid
IUPAC
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
現地名
4,4'-(2,3-ジメチルテトラメチレン)ジピロカテコール
英語名
Nordihydroguaiaretic acid
分子式
C18H22O4
分子量
302.36

名称と別名

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
名称をさらに表示
4,4'-(2,3-ジメチルテトラメチレン)ジピロカテコール4,4'-(2,3-ジメチルブタン-1,4-ジイル)ビス(ベンゼン-1,2-ジオール)4,4'-(2,3-ジメチル-1,4-ブチレン)ジピロカテコール4,4'-(2,3-ジメチル-1,4-ブタンジイル)ビスカテコールノルジヒドログアヤレチック酸ノルジヒドログアイアレト酸ジヒドロノルグアイアレト酸ノルジヒドログアイアレチン酸ノルジヒドログアイヤレチン酸ノルジヒドログアヤレチン酸4,4'-(2,3-ジメチル-1,4-ブタンジイル)ビス(1,2-ベンゼンジオール)4,4'-(2,3-ジメチルテトラメチレン)ビスカテコール4，4’-（2，3-ジメチルブタン-1，4-ジイル）ジベンゼン-1，2-ジオールノルジヒドログアイレチン酸ノルジヒドログアヤレチック酸標準品ノルジヒドログアイレチン酸, 97%ノルジヒドログアヤレト酸4,4′-(2,3-ジメチル-1,4-ブタンジイル)ビス(1,2-ベンゼンジオール)4,4′-(2,3-ジメチル-1,4-ブタンジイル)ビスカテコール4,4′-(2,3-ジメチルブタン-1,4-ジイル)ビス(ベンゼン-1,2-ジオール)ACTINEXNORDIHYDROGUAIRETIC 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-

データベース識別子

CAS
500-38-9
PubChem CID
4534
DTXSID
DTXSID5022437
ChEMBL
CHEMBL52
ChEBI
CHEBI:7625
EC Number
207-903-0
Nikkaji
J9.195B

物性

構造計算による物性

XLogP
4.3
極性表面積
80.9 Ų
水素結合供与体数
4
水素結合受容体数
4
回転可能結合数
5
重原子数
22

実験および物理化学的性質

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]

物理化学的性質

融点
184 · 184-186 °C (lit.)
沸点
363.4 °C · 363.4°C (rough estimate)
比重(密度)
1.0772 · 1.0772 (rough estimate)
屈折率
1.423 · 1.4230 (estimate)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
DMSO（微量）、メタノール（微量）
化学的性質 · 1 件

化学的特性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.

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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%)

安全データ

wgk
3
rtecs
UX1750000
hs_code
29072990
risk_code
22-36/37/38
hazard_code
Xn
safety_code
26-36/37-37/39-24/25-22

化学と産業

用途と製造

Uses · 2 件

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 · 3 件

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Food Additives -> ANTIOXIDANT -> JECFA Functional Classes

Cosmetics -> Antioxidant

応用分野 · 2 件

説明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.

一般的な説明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.

調製方法 · 2 件

製造方法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.

純化方法Crystallise the acid from dilute acetic acid. [Beilstein 6 IV 7771.]

上流・下流製品情報

サプライヤー50 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
成都健腾生物技术有限公司028-85159085 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
補足説明 · 2 件

定義本品は、次の化学式で表されるリグナン誘導体である。

定義ChEBI: 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.

関連反応

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