7,8-디테하이드로콜레스테롤
7,8-디테하이드로콜레스테롤 · 7-데하이드로콜레스테롤 · 7-DHC · PROVITAMIN D3 · Dehydrocholesterol · cholesta-5,7-dien-3β-ol · Provitamine · Cholesta-5,7-dien-3-ol
식별자 및 물리적 특성
| CAS No. | 434-16-2 |
|---|---|
| 분자식 | C27H44O |
| 평균 분자량 | 384.6 g/mol |
| 단동위원소 질량 | 384.33921602 g/mol |
| SMILES | CC(C)CCCC(C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC21C |
| InChIKey | UCTLRSWJYQTBFZ-UHFFFAOYSA-N |
| PubChem CID | 172 |
| 현지명 | 7,8-디테하이드로콜레스테롤 |
화학 및 물리적 성질
| XLogP | 8 |
|---|---|
| 극성 표면적 | 20.2 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 1 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 28 |
| 형식 전하 | 0 |
| 복잡도 | 643 |
| 녹는점 | 148-152 °C(lit.) |
| 끓는 점 | 451.27°C (rough estimate) |
| 밀도 | 0.9717 (rough estimate) |
| 굴절률 | 1.5100 (estimate) |
| 저장 조건 | -20°C |
| 용해도 | 클로로포름(소량으로 용해), DMSO(약간 용해됨, 가열, 초음파 처리), 에틸아세테이트(약간 용해됨) |
| pKa(산도 계수) | 14.91±0.70(Predicted) |
| 물리적 상태 | 고체 |
| 색상 | 흰색에서 노란색으로 |
| 생물학적 소스 | synthetic |
| 용해도 | 불용성 |
| Merck | 13,2887 |
| BRN | 2224615 |
| 안정성 | 감광성 |
| 화장품 원료 기능 | 점도 조절피부 컨디셔닝유화 안정화 |
| InChIKey | UCTLRSWJYQTBFZ-DDPQNLDTSA-N |
| SMILES | [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C |
| LogP(분배 계수) | 9.460 (est) |
| NIST | Cholesta-5,7-dien-3-ol, (3«beta»)-(434-16-2) |
| EPA | Cholesta-5,7-dien-3-ol, (3.beta.)- (434-16-2) |
화학적 성질
white to off-white fine crystalline powder. It is easy to oxidize when exposed to air.
안전 및 규제
| 수질 위해 등급(WGK) | 3 |
|---|---|
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | FZ5650000 |
| 관세 코드 | 29061990 |
| 안전 문구(S) | 24/25 |
| F 고인화성물질 | 8-10-23 |
| 저장 분류 | 11 - Combustible Solids |
용도
용도
7-Dehydrocholesterol is a vitamin D3 precursor, which is a sterol found in animals. Vitamin D3 is produced by the action of sunlight or ultraviolet irradiation from the precursor, 7-dehydrocholesterol (7-DC), that is synthesized in the skin of animals and humans.In most tissues of the body, 7-dehydrocholesterol is the immediate precursor of cholesterol. It is reduced to cholesterol by the enzyme 3β-hydroxysterol-Δ7-reductase (DHCR7) in the last step of cholesterol biosynthesis. 7-DHC accumulates in Smith-Lemli-Opitz syndrome (SLOS), a disorder characterized by a mutation in the DHCR7 gene and decreased cholesterol levels in bodily tissues and fluids, as well as microcephaly, intellectual disability, and distinctive dysmorphic features. It is highly susceptible to free radical oxidation, giving rise to several oxysterols that may be involved in the pathogenesis of SLOS. 7-DHC levels are increased in brain, liver, and serum in a rat model of SLOS induced by the DHCR7 inhibitor AY 9944. 7-DHC is a provitamin that is converted to vitamin D3 by ultraviolet-B (UVB) light in a human skin equivalent system and in isolated human skin samples.
일반 설명
7-Dehydrocholesterol, a 5,7-conjugated diene sterol is a biosynthetic precursor of cholesterol. It helps in the production of vitamin D3 when exposed to ultraviolet B (UVB) radiation. It has been used as an internal standard to determine sterols. 7-dehydrocholesterol is also used in the diagnosis of Smith-Lemli-Opitz syndrome. Blood and tissue of infants with Smith- Lemli-Opitz (SLO) syndrome contain reduced amounts of cholesterol and greatly increased concentrations of 7-dehydrocholesterol and of its isomer 8-dehydrocholesterol.