プレグネノロン
プレグネノロン · 3β-ヒドロキシプレグン-5-エン-20-オン · プレノロン · 3β-ヒドロキシ-5-プレグネン-20-オン · 3β-ヒドロキシプレグナ-5-エン-20-オン · 20-オキソプレグナ5-エン-3β-オール · 20-オキソプレグナ-5-エン-3β-オール · Δ5-プレグネン-3β-オール-20-オン
識別子と物理属性
| CAS No. | 145-13-1 |
|---|---|
| 分子式 | C21H32O2 |
| 平均分子量 | 316.5 g/mol |
| 単同位体質量 | 316.24023026 g/mol |
| SMILES | CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | ORNBQBCIOKFOEO-QGVNFLHTSA-N |
| PubChem CID | 8955 |
| ChEMBL | CHEMBL253363 |
| ChEBI | CHEBI:16581 |
| EC No. | 205-647-4 |
| DTXSID | DTXSID1036541 |
| 現地名 | プレグネノロン |
化学・物理的性質
| XLogP | 4.2 |
|---|---|
| 極性表面積 | 37.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 23 |
| 形式電荷 | 0 |
| 複雑度 | 550 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 脂質 | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203] |
| SpringerMaterials Properties | Chemical shift |
| LogP（分配係数） | 4.22 |
| 溶解度 | 0.00706 mg/mL at 37 °Cエタノール：可溶 10mg/mL 無色透明～微黄色41mg/L(室温) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 融点 | 192 °C188-190 °C |
| Physical Description | Solid |
| Collision Cross Section | 172.95 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]177.25 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]174 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]214.8 Ų [M+Na]+ |
| 比旋光度 | 28.5 º (c=1, EtOH) |
| 沸点 | 395.89°C (rough estimate) |
| 密度 | 1.0382 (rough estimate) |
| 蒸気圧 | 0-0Pa at 20-25℃ |
| 屈折率 | 1.5344 (estimate) |
| 引火点 | 9℃ |
| 貯蔵条件 | Refrigerator |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 15.00±0.70(Predicted) |
| 色 | ホワイトからオフホワイト |
| Merck | 7733 |
| BRN | 2059026 |
| 主な用途 | 臨床検査臨床検査 |
| InChI | 1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1 |
| InChIKey | ORNBQBCIOKFOEO-QGVNFLHTSA-N |
| SMILES | O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)C)(CC3)C)CC=C2C1)C |
| LogP（分配係数） | 4.4 at 20℃ |
| CAS データベース | 145-13-1(CAS DataBase Reference) |
| NISTの化学物質情報 | Pregnenolone(145-13-1) |
化学的特性
white to off-white powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 13% (3 of 23) of reports.WarningH302 (87%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 23 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Status: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26422 |
| Hazard Classes and Categories | Acute Tox. 4 (87%) |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | TU5560700 |
| 輸送番号（UN） | UN 1648 3 / PGII |
| 税関コード | 29372900 |
| 安全措置（S） | 22-24/25 |
| 危険等級 | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2 |
| 貯蔵分類 | 3 - Flammable liquids |
用途
解説
(3β)-3-hydroxypregn-5-en-20-one．C21H32O2(316.48)．プレグネノロンは，コレステロール，ジオスゲニン，スチグマステロールなどから合成される．無色の針状結晶．融点190 ℃．[α]D＋28°(エタノール)．クロロホルムに可溶，エタノールに微溶，ベンゼン，石油エーテルに難溶．副じん皮質ホルモン，プロゲステロンなどの合成で重要な中間体である．森北出版「化学辞典（第2版）
用途
プレグネノロン (pregnenolone) は、プロゲステロン、コルチコイド、アンドロゲン、およびエストロゲンのステロイド生成にかかわるプロホルモンである。
用途
プレグネノロンは体内であらゆるホルモンに変換されるプロホルモンである。
説明
Pregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a number of physiologically active C21 steroids, including the female sex hormone progesterone and the adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19 steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18 female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens.
使用
Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA an tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A
一般的な説明
Pregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards.