チモキノン is a compound extracted from black grass seeds, with the chemical formula C10H12O2. At room temperature, it is a light yellow oily liquid with a unique irritating odor. Difficult to dissolve in water, easy soluble in organic solvents such as ethanol and ether. Has a unique irritating odor. Difficult to dissolve in water, but can dissolve in organic solvents such as ethanol, ether, and chloroform. It has inhibitory effects on various bacteria, including Gram positive and Gram negative bacteria. This compound exerts antibacterial effects by interfering with bacterial metabolic processes or damageaging bacterial cell walls. It has also been studied for use in oral care products, such as mouthwash, toothpaste, etc. It can inhibit the growth of bacteria in the the oral cavity and reduce the occurrence of oral diseases such as oral ulcers and 歯齦炎。
(製品 リンク: https://www.bloomtechz.com/合成化学/添加剤/チモキノン粉末-cas-490-91-5.html)
この 方法 involves a process of synthesizing Thimoquinone through multi-step reactions starting from 6-oxo isophorone. This method has the advantages of simple operation, easy availability of raw materials, and high product purity.
合成 ステップ:
1. 脱水 中 アルドール 凝縮
使用 アセトン および ホルムアルデヒド as raw materials, a aldol 縮合 反作用 起こる under weak alkaline conditions (such as NH4OH, NaOH, etc.), generating - 不飽和 ブテノン. The main chemical equation for this step is as follows:
R-CHO+CH3-CO-R '→ R-CH=CH-R'+H2O
2. 1,2-求核 付加 反応
適用 結果 得られた から 前 ステップ - 不飽和 ブテン ケトン 受ける a 1,2-求核 付加 反応 with アセチレン under acidic conditions (such as HCl, H2SO4, etc.) to produce hexacarbyne tertiary alcohol. The corresponding chemical equation is as follows:
R-CH=CH-R '+HC ≡ CH → R-CH (OH) - CH2-C ≡ CH
3. 並べ替え 反応
下 作用 の 硫酸 酸, ヘキサアセチレン 第三級 アルコール 受ける 転位 反応 に 生成する ターゲット 化合物 化学 方程式 のために この ステップ である として 次の:
R-CH (OH) - CH2-C ≡ CH+H2SO4 → R-C (OH)=C (OH) - C ≡ CH
4. 保護 ヒドロキシル 基
R-C (OH)=C (OH) - C ≡ CH+R'OH → R-C (OR ')=C (OR') - C ≡ CH+H2O
5. Reaction with 6-oxo isophorone
反応 製品 得られた で 前 ステップ で 6-oxo isophorone under weak acid or weak base conditions to form the intermediate of Thimoquinone. The corresponding chemical equation is as follows:
R-C (OR ')=C (OR') - C ≡ CH+6-O-C (R ")=O → R-C (OR ')=C (OR') - C (R")=O+R'COOH/R "COOH
6. 二国間 Wittig 反作用
アンダー the action of strong bases (such as NaOH, KOH, etc.), a 両側性 Wittig reaction is carried out on the intermediate to ultimately synthesize thymoquinone. The chemical equation for this step is as follows:
R-C (OR')=C (OR') - C (R")=O+Ph3P=CHCOOEt → Ph3P=CR'- CH (OR')=CR'COOH+Ph3P=O+EtOH
7. Post treatment and purification
によって means of extraction, distillation, and recrystallization, the product is purified to obtain high-purity Thymoquinone. The specific post-processing methods can be selected according to actual needs.
BASF has adopted a unique synthesis method to prepare Thimoquinone, which involves protecting hydroxyl groups, conversion with 6-oxo isophorone, and rearrangement during the conversion process.
合成 ステップ:
1. ヒドロキシル プロテクション
まず, protect the hydroxyl group of the intermediate hexaacetylene tert alcohol, commonly used protectants include esterification or etherification reagents. For example, formic acid, methanol, or ethyl acetate can be used for protection. The corresponding chemical equation is as follows:
R-CH (OH) - CH2-C ≡ CH+R'OH → R-CH (OR ') - CH2-C ≡ CH+H2O
2. 反応 with 6-oxo isophorone
反応 保護 ヒドロキシル グループ with 6-oxo isophorone under specific conditions. The purpose of this step is to connect 6-oxo isophorone to hexaacetylene tert alcohol while maintaining the protective state of the hydroxyl group. The corresponding chemical equation is as follows:
R-CH (OR ') - CH2-C ≡ CH+6-O-C (R ")=O → R-CH (OR')=C (OR") - C (R ")=O+R'COOH/R" COOH
3. 再注文 中 変換 プロセス
中 反応 プロセス, 中間体 may undergo rearrangement reactions, which are mainly achieved through intramolecular reactions or interactions with other functional groups. The specific rearrangement method depends on the reaction conditions and the structure of the intermediate. The reranged chemical equations may be more complex and need to be written according to actual situation.
4. Remove protection and product separation
最後に, the previously protected hydroxyl group is deprotected under specific conditions to obtain the target product, Thimoquinone. This step can be deprotected through methods such as hydrolysis, reduction, or acid/base catalysis, and the specific method needs to be selected based on the actual protective group. After deprotection, Thimoquinone can be separated and purified to obtain high-purity products.
main route for synthesizing astaxanthin in China is to - Using violet ketone as the raw material, astaxanthin is finally synthesized through a series of chemical reactions. This method has the advantages of easy availability of raw materials, mild reaction conditions, and high product purity.
合成 ステップ:
1. Treatment with m-クロロペロキシ安息香酸 酸
まず, integrate - Violet ketone reacts with m-chloroperoxybenzoic acid and undergoes oxidation to - A hydroxyl group is introduced on the side chain of violet ketone to form an intermediate. The purpose of this step is to provide the necessary functional groups for subsequent chemical reactions. The chemical equation is as follows:
(CH3) 2C=CHCH2CH2CHO+(COCl) 2 (CCl4) → (CH3) 2C=CHCH2CH2COOH+(COCl) 2 (COOH)
2. Intermediate conversion
3. Acid rearrangement
下 作用 の 臭化水素酸, 中間体 受ける 酸性化 再配列 反応. 目的 の これ ステップ である さらに 調整する 分子 構造 通す 再配列 反応, in preparation for subsequent reactions. 特異的 化学的 equations need to be written according to the actual situation.
4. 相互作用 with トリフェニルホスフィン
中間体 反応 と トリフェニルホスフィン に 農産物 ペンタデカン トリフェニル 第四級 ホスホニウム 塩. 目的 の これ ステップ である に 導入する 特異的 機能 グループ スルー 反応 トリフェニルホスフィン, in preparation for subsequent reactions. 特異的 化学的 方程式 必要性 に に 書かれている 一致する に 実際の 状況。
5. 双方向 Wittig 反応
最後に, the quaternary phosphonium salt was converted to astaxanthin through a bidirectional Wittig reaction. The key to this step is to ensure the smooth progress of the the Wittig reaction and achieve a high yield. The specific chemical equations need to be written according to the actual situation.