基本情報
- CAS
51-49-0- 標準SMILES
[NH3+][C@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(=O)[O-]- InChIKey
XUIIKFGFIJCVMT-GFCCVEGCSA-N- 分子式
- C15H11I4NO4
- 平均分子量
- 776.87 g/mol
- 単同位体質量
- 776.6867
概要
The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (monoiodotyrosine) and the coupling of iodotyrosines (diiodotyrosine) in the thyroglobulin. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine which exerts a broad spectrum of stimulatory effects on cell metabolism.
名称と識別子
- 優先名称
- (2R)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
- IUPAC
- (2R)-2-azaniumyl-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate
- 現地名
- (R)-2-アミノ-3-[3,5-ジヨード-4-(3,5-ジヨード-4-ヒドロキシフェノキシ)フェニル]プロピオン酸
- 英語名
- D-Thyroxine
- 分子式
- C15H11I4NO4
- 分子量
- 776.87
名称と別名
D-チロキシンO-(4-ヒドロキシ-3,5-ジヨードフェニル)-3,5-ジヨード-D-チロシン(R)-2-アミノ-3-[3,5-ジヨード-4-(3,5-ジヨード-4-ヒドロキシフェノキシ)フェニル]プロピオン酸(+)-D-チロキシン(+)-チロキシンデベトロール(+)-O-(4-ヒドロキシ-3,5-ジヨードフェニル)-3,5-ジヨード-D-チロシンデキストロチロキシン(2R)-2-アミノ-3-[4-(4-ヒドロキシ-3,5-ジヨードフェノキシ)-3,5-ジヨードフェニル]プロパン酸D-T4DEBETROLD-THYROXINE
名称をさらに表示
of D-ThyroxinedextrothyroxineD-Thyroxine,97%Thyroxine, D- (8CI)D-thyroxine free acidD-Thyroxine USP/EP/BPLevothyroxine D-Isomer
データベース識別子
- CAS
51-49-0- PubChem CID
- 90657408
物性
構造計算による物性
- XLogP
- 3
- 極性表面積
- 97.2 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 4
- 回転可能結合数
- 4
- 重原子数
- 24
- 形式電荷
- 0
- 複雑度
- 414
実験および物理化学的性質
LogP4
Solubility8.98e-03 g/L
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point
235-236 °C
235 - 236 °C
Physical DescriptionSolid
物理化学的性質
- 融点
- 235 °C · ~235 °C (dec.)
- 比旋光度
- 21546 · 21546 +2.97° (0.74 g in 6 g of 0.5N NaOH and 14 g of alcohol)
- 沸点
- 576.3 · 576.3±50.0 °C(Predicted)
- 比重(密度)
- 2.444 · 2.4440 (estimate)
- 貯蔵温度
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- 酸性アルコール（わずかに）、水性酸（わずかに、超音波処理）、水性塩基（Sli
- 外見
- 個体
- 酸解離定数(Pka)
- 2.12 · 2.12±0.30(Predicted)
- 色
- オフホワイトからベージュ
- 安定性
- 吸湿性
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
安全データ
- F
- 8-10
- wgk
- 3
- risk_code
- 20/21/22-40
- hazard_code
- Xn
- safety_code
- 36/37-36-22
化学と産業
薬理情報
PharmacodynamicsDextrothyroxine, the dextrorotary isomer of the synthetic thyroxine, is a antihyperlipidemic.
Mechanism of Action
Dextrothyroxine is a antihyperlipidemic. The mechanism of action is not completely understood, but dextrothyroxine apparently acts in the liver to stimulate formation of low-density lipoprotein (LDL) and, to a much greater extent, to increase catabolism of LDL. This leads to increased excretion of cholesterol and bile acids via the biliary route into the feces, with a resulting reduction in serum cholesterol and LDL. Dextrothyroxine has no significant effect on high-density lipoproteins (HDL). Inherently, it will also bind to thyroid receptors and as it is a prohormone, it will bind as a substrate to iodide peroxidase.
Cellular LocationsCytoplasm
応用分野
使用One of the thyroid hormones involved in the maintenance of metabolic homeostasis. Synthesized and stored as amino acid residues of thyroglobulin, the major protein component of the thyroid follicular colloid. Synthesis and secretion are regulated by the pituitary hormone (TSH). Deiodinated in peripheral tissues to the active metabolite, liothyronine. The D-form has very little activity as a thyroid hormone, but has been used to treat hyperlipidemia.
調製方法
純化方法Recrystallise D-thyroxine from H2O (needles) or from an ammonical solution by dilution with H2O, MeOH or Me2CO. It has also been purified by dissolving ~6.5 g in a mixture of MeOH (200mL) and 2N HCl (20mL), adding charcoal, filtering then adding NaOAc solution to pH 6. On standing the thyroxine separates, it is filtered off, washed with MeOH then Me2CO and dried in vacuo. N-Formyl-D-thyroxine has m 210o and [] 21 -26.9o (c 5, EtOH). (±)-Thyroxine has m 256o and is purified in the same way. [Nahm & Siedel Chem Ber 96 1 1963, Salter Biochem J 24 471 1930, Beilstein 14 I 671, 14 II 384, 14 III 1566, 14 IV 2374.]
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