캠페스테롤
캠페스테롤 · Campesterin · Ergost-5-en-3-ol · 24α-methyl Cholesterol · (24R)-Ergost-5-en-3β-ol · C01789 · CAMPESTROL · Campasterol
식별자 및 물리적 특성
| CAS No. | 474-62-4 |
|---|---|
| 분자식 | C28H48O |
| 평균 분자량 | 400.7 g/mol |
| 단동위원소 질량 | 400.37051615 g/mol |
| SMILES | CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | SGNBVLSWZMBQTH-PODYLUTMSA-N |
| PubChem CID | 173183 |
| ChEMBL | CHEMBL520535 |
| ChEBI | CHEBI:28623 |
| EC No. | 207-484-4 |
| DTXSID | DTXSID801009891 |
| 현지명 | 캠페스테롤 |
화학 및 물리적 성질
| XLogP | 8.8 |
|---|---|
| 극성 표면적 | 20.2 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 29 |
| 형식 전하 | 0 |
| 복잡도 | 620 |
| 물질 분류 | Biological Agents -> Plant Oils and Extracts |
| 지질 | Lipids -> Sterol Lipids [ST] -> Sterols [ST01] -> Ergosterols and C24-methyl derivatives [ST0103] |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 157.5 °C156-160 °C |
| Physical Description | Solid[Merck Index] White crystalline solid[Sigma-Aldrich MSDS] |
| 끓는 점 | 463.29°C (rough estimate) |
| 밀도 | 0.98±0.1 g/cm3 (20 ºC 760 Torr) |
| 굴절률 | 1.5100 (estimate) |
| 저장 조건 | -20°C |
| 용해도 | 클로로포름(소량으로 용해), 메탄올(약간 용해됨, 초음파 처리) |
| pKa(산도 계수) | 15.03±0.70(Predicted) |
| 물리적 상태 | 수정 같은 |
| 색상 | 하얀색 |
| 생물학적 소스 | Glycine max (soybean) |
| Merck | 13,1736 |
| BRN | 3216975 |
| InChIKey | SGNBVLSWZMBQTH-ZRUUVFCLSA-N |
| SMILES | [H][C@@]12CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])[C@H](C)CC[C@H](C)C(C)C |
| LogP(분배 계수) | 9.972 (est) |
화학적 성질
White Solid
안전 및 규제
| GHS 분류 | 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, P317, 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 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: Ergost-5-en-3-ol, (3.beta.,24R)- |
| 유해성 요약 | Phytosterol esters containing 26-29% campesterol demonstrate no significant adverse effects in a 90-day oral study of ratsPhytosterol esters containing 27.9% campesterol produced decreased body weights, increased frequency of cardiomyopathy (males), and changes in hematology parameters in a 13-week oral study of rats at the highest tested dose (9,000 mg/kg/day)Phytosterol esters show no evidence of reproductive or developmental toxicity in rats[JECFA] A moderate irritantHarmful by ingestion, inhalation, and skin absorptionTargets the eyes, kidney, liver, and heart[Sigma-Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 수질 위해 등급(WGK) | 3 |
| 운송 번호(UN) | UN 1888 6.1/PG 3 |
| 관세 코드 | 29061990 |
| 위험 문구(R) | 20/21/22-36/37/38-48/20/22-40-38-22 |
| 위험 표시 | Xn,T |
| 안전 문구(S) | 26-36-45-36/37/39-23 |
| 위험 등급 | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
24α-methyl Cholesterol is a phytosterol found in vegetables, fruits, nuts, and seeds that competitively inhibits the absorption of intestinal cholesterol and decreases the transcription of genes important for cholesterol metabolism. The cholesterol lowering effects of phytosterols, such as 24α-methyl cholesterol, have been reported to be beneficial for lowering the incidence of atherosclerotic plaques. 24α-methyl Cholesterol can also act as an agonist at liver X receptors (LXR) and, through activation of LXR signaling, has been shown to suppress the proliferation of prostate and breast cancer cells.
용도
Campesterol may be used as a plant sterol to test its effect on the transcriptional activation of liver X receptor α (LXRA) in breast cancer cells. It may also be used as a sterol standard for calibration curve generation in liquid chromatography multiple reaction monitoring (LC-MRM) analysis.
일반 설명
Campesterol is a plant sterol, which is an analog of cholesterol and a brassinosteroid (BR) precursor. The enzyme diminute/dwarf1 mediates the synthesis of campesterol from 24-methylenecholesterol. Campesterol possesses methyl group at C-24 position of the side chain in the cholesterol structure.