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
識別子と物理属性
| CAS No. | 500-38-9 |
|---|---|
| 分子式 | C18H22O4 |
| 平均分子量 | 302.4 g/mol |
| 単同位体質量 | 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 |
| 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 |
化学・物理的性質
| XLogP | 4.3 |
|---|---|
| 極性表面積 | 80.9 |
| 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 |
| 形式電荷 | 0 |
| 複雑度 | 303 |
| 物質分類 | Biological Agents -> Plant Toxins |
| 化粧品 | Antioxidant |
| 食品添加物 | 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] |
| 融点 | 184-186 °C (lit.) |
| 沸点 | 363.4°C (rough estimate) |
| 密度 | 1.0772 (rough estimate) |
| 屈折率 | 1.4230 (estimate) |
| 貯蔵条件 | Inert atmosphere,Room Temperature |
| 溶解度 | DMSO（微量）、メタノール（微量）わずかに溶ける |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 9.56±0.10(Predicted) |
| 色 | ホワイトからオフホワイト |
| 由来生物 | Larrea divaricata (creosote bush) |
| Merck | 14,6693 |
| BRN | 2056825 |
| 安定性 | 安定。酸化剤と相容れない。 |
| 化粧品成分の機能 | 抗酸化物質 |
| 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（分配係数） | 4.640 (est) |
| CAS データベース | 500-38-9(CAS DataBase Reference) |
| NISTの化学物質情報 | Pyrocatechol, 4,4'-(2,3-dimethyltetramethylene)di-(500-38-9) |
| EPAの化学物質情報 | Nordihydroguaiaretic acid (500-38-9) |
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.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | Chemical: 1,2-Benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis- |
| 有害性の概要 | 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%) |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | UX1750000 |
| 税関コード | 29072990 |
| 危険文句（R） | 22-36/37/38 |
| 危険表示 | Xn |
| 安全措置（S） | 26-36/37-37/39-24/25-22 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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.
製法・合成法
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.]