Pregnenolone
3β-Hydroxypregn-5-en-20-one · Pregnelone · prenenolone · 5-pregnen-3B-ol-20-one · 5-pregnen-3β-ol-20-one · DELTA5-PREGNEN-3BETA-OL-20-ONE · 5-Preg · ZK-5553
식별자 및 물리적 특성
| CAS No. | 145-13-1 |
|---|---|
| 분자식 | C21H32O2 |
| 평균 분자량 | 316.5 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 4.2 |
|---|---|
| 극성 표면적 | 37.3 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 23 |
| 형식 전하 | 0 |
| 복잡도 | 550 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 지질 | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203] |
| SpringerMaterials Properties | Chemical shift |
| LogP(분배 계수) | 4.22 |
| 용해도 | 0.00706 mg/mL at 37 °C에탄올: 용해성10mg/mL, 투명, 무색 내지 희미한 노란색 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 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]+ |
| 끓는 점 | 395.89°C (rough estimate) |
| 밀도 | 1.0382 (rough estimate) |
| 증기압 | 0-0Pa at 20-25℃ |
| 굴절률 | 1.5344 (estimate) |
| 인화점 | 9℃ |
| 저장 조건 | Refrigerator |
| 물리적 상태 | 가루 |
| pKa(산도 계수) | 15.00±0.70(Predicted) |
| 색상 | 흰색에서 황백색까지 |
| 용해도 | 41mg/L(상온) |
| Merck | 7733 |
| BRN | 2059026 |
| 주요 응용 | 임상 시험임상 시험 |
| 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(분배 계수) | 4.4 at 20℃ |
| NIST | Pregnenolone(145-13-1) |
화학적 성질
white to off-white powder
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | Status: Active Update: 29-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26422 |
| Hazard Classes and Categories | Acute Tox. 4 (87%) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | TU5560700 |
| 운송 번호(UN) | UN 1648 3 / PGII |
| 관세 코드 | 29372900 |
| 안전 문구(S) | 22-24/25 |
| 위험 등급 | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2 |
| 저장 분류 | 3 - Flammable liquids |
용도
개요
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.
용도
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
일반 설명
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.