4-콜레스텐-3-원
4-콜레스텐-3-원 · cholest-4-en-3-one · CHOLESTENONE · (+)-4-Cholesten-3-one · 4-Cholestenone · 4-CHOLESTEN-3-ONE · 3-Oxocholest-4-ene · 3-OXO-4-CHOLESTENE
식별자 및 물리적 특성
| CAS No. | 601-57-0 |
|---|---|
| 분자식 | C27H44O |
| 평균 분자량 | 384.6 g/mol |
| 단동위원소 질량 | 384.33921603 g/mol |
| SMILES | CC(C)CCCC(C)C1CCC2C3CCC4=CC(=O)CCC4(C)C3CCC12C |
| InChIKey | NYOXRYYXRWJDKP-UHFFFAOYSA-N |
| PubChem CID | 440 |
| ChEBI | CHEBI:180953 |
| DTXSID | DTXSID50862271 |
| 현지명 | 4-콜레스텐-3-원 |
화학 및 물리적 성질
| XLogP | 8.4 |
|---|---|
| 극성 표면적 | 17.1 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 28 |
| 형식 전하 | 0 |
| 복잡도 | 630 |
| 녹는점 | 79-82 °C |
| 끓는 점 | 451.27°C (rough estimate) |
| 밀도 | 0.9717 (rough estimate) |
| 굴절률 | 1.5100 (estimate) |
| 저장 조건 | -20°C |
| 용해도 | 클로로포름 (소량), 메탄올 (소량, 가열)에 용해 |
| 물리적 상태 | 고체 |
| 색상 | 흰색에서 황백색까지 |
| 용해도 | <0.5g/L |
| BRN | 4707774 |
| 안정성 | 안정적인. 강한 산화제와 호환되지 않습니다. |
| InChI | 1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1 |
| InChIKey | NYOXRYYXRWJDKP-GYKMGIIDSA-N |
| SMILES | [H][C@@]12[C@]([C@](CC3)(C)C(CC2)=CC3=O)([H])CC[C@@]4(C)[C@@]1([H])CC[C@]4([H])[C@]([H])(C)CCCC(C)C |
| NIST | Cholest-4-en-3-one(601-57-0) |
| EPA | Cholest-4-en-3-one (601-57-0) |
화학적 성질
white to light yellow crystals or powder
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | FZ7700000 |
| 관세 코드 | 29142900 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 22-24/25-36-26 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol. It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 μg/ml. Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.
용도
4-Cholesten-3-one is used as a chiral building block for proteomics research. It is an intestinal metabolite of cholesterol and exhibits an anti-obesity effect on animals.
일반 설명
Cholestenone is a cholesterol metabolite and analog, which substitutes membrane cholesterol and elevates membrane fluidity.