卡泊三醇
卡泊三醇用途
卡泊三醇名称
[ CAS 号 ]:
112965-21-6
[ 中文名 ]:
卡泊三醇搽剂
[ 英文名 ]:
Calcipotriene
[中文别名 ]:
[英文别名 ]:
- Didrogyl
- Calcipotriol hydrate
- 25-HYDROXYCHOLECALCIFEROL
- Calcifediol
- 25-HYDROXYVITAMIN D3
- Calcipotriene
- CALCIPOTRIENE,EP5.3
- VITAMIN D3,25-HYDROXY
- 25-OH vitamin D3
- MFCD00866630
卡泊三醇生物活性
[ 描述 ]:
[ 相关类别 ]:
[ 靶点 ]
Vitamin D receptor[1]
[体外研究]
[体内研究]
[细胞实验]
[动物实验]
[参考文献]
[相关活性小分子]
卡泊三醇物理化学性质
[ 密度 ]:
1.1±0.1 g/cm3
[ 沸点 ]:
582.0±50.0 °C at 760 mmHg
[ 熔点 ]:
166-168ºC
[ 分子式 ]:
C27H40O3
[ 分子量 ]:
412.605
[ 闪点 ]:
250.6±24.7 °C
[ 精确质量 ]:
412.297760
[ PSA ]:
60.69000
[ LogP ]:
5.43
[ 外观性状 ]:
白色结晶固体
[ 蒸汽压 ]:
0.0±3.7 mmHg at 25°C
[ 折射率 ]:
1.580
[ 储存条件 ]:
Desiccate at -20°C
卡泊三醇毒性和生态
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- VS2830000
- CHEMICAL NAME :
- 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1-alpha,3-beta,5Z,7E,22E,24S)-
- CAS REGISTRY NUMBER :
- 112965-21-6
- LAST UPDATED :
- 199703
- DATA ITEMS CITED :
- 11
- MOLECULAR FORMULA :
- C27-H40-O3
- MOLECULAR WEIGHT :
- 412.67
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Human - woman
- DOSE/DURATION :
- 10 gm/kg/6W-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - changes in calcium
- REFERENCE :
- BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 306,896,1993
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 11 gm/kg/11W-I
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - changes in calcium
- REFERENCE :
- BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 306,896,1993
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >15 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - ataxia Nutritional and Gross Metabolic - weight loss or decreased weight gain
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(Suppl 2),277,1996
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 2190 ug/kg
- TOXIC EFFECTS :
- Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(Suppl 2),277,1996
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- >1500 ug/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Gastrointestinal - nausea or vomiting Musculoskeletal - other changes
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(Suppl 2),277,1996 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 560 ug/kg/4W-I
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - corneal damage Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - changes in calcium
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(Suppl 2),287,1996
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 364 ug/kg/26W-I
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - changes in calcium
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(Suppl 2),325,1996
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Administration onto the skin
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 728 ug/kg/26W-I
- TOXIC EFFECTS :
- Kidney, Ureter, Bladder - other changes in urine composition Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - changes in calcium
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(Suppl 2),365,1996 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 275 ug/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - other effects Reproductive - Specific Developmental Abnormalities - musculoskeletal system
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(suppl 2),403,1996
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 650 ug/kg
- SEX/DURATION :
- female 17-21 day(s) after conception lactating female 21 day(s) post-birth
- TOXIC EFFECTS :
- Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(suppl 2),439,1996
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 13 ug/kg
- SEX/DURATION :
- female 6-18 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - other effects Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
- REFERENCE :
- JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 21(suppl 2),425,1996
卡泊三醇安全信息
[ 危害码 (欧洲) ]:
Xi
[ 风险声明 (欧洲) ]:
36/37/38
[ 安全声明 (欧洲) ]:
26
[ 危险品运输编码 ]:
UN 2811 6.1 / PGIII
卡泊三醇合成路线
卡泊三醇上下游产品
卡泊三醇上游产品
卡泊三醇下游产品
卡泊三醇制备
以维生素D2(Ⅰ)为原料。
维生素D2(12.5g,31.5mmo1)溶于50ml液体二氧化硫,搅拌回流30min,蒸出二氧化硫,残液真空干燥。然后溶于100ml二甲基甲酰胺,再加入咪唑(4.5g,66mmo1)和叔丁基二甲基氯化硅(5.0g,33mmo1),在20℃搅拌90min。将反应液在500ml乙酸乙酯和200ml水之间进行分配。分取有机层,用水和盐水洗,干燥,浓缩。残液层析分离(用30%乙醚的石油醚溶液洗脱),得9.4g化合物(Ⅱa),收率52%,熔点117~118℃(分解);和7.7g化合物(Ⅱb),收率42%,熔点121~122℃(分解)。
化合物(Ⅱa)或(Ⅱb)或它们的混合物(16.4g,28.5mmo1)悬浮于250ml 96%乙醇中,加入20g碳酸氢钠,回流90min。冷却,减压部分浓缩,剩余液在乙酸乙酯和水之间进行分配。分取有机层,用水和盐水洗,干燥,浓缩。残液溶于含N-甲基吗啉N-氧化物单水合物(16g,119mmo1)的160ml二氯甲烷溶液。过滤,在回流下往滤液中快速加人二氧化硒(3.0g,27mmo1)在160ml甲醇的溶液。加毕再回流50min。冷却,用二氯甲烷稀释后,用水和盐水洗,干燥,浓缩。残液溶于80ml二甲基甲酰胺,加入咪唑(4.3g,63mmo1)和叔丁基二甲基氯化硅(5.1g,34mmo1),在20℃搅拌90min,,将反应液在450ml乙酸乙酯和200ml水之间进行分配。分取乙酸乙酯层,用水和盐水洗,干燥,浓缩,得结晶性固体。将该固体经硅胶分离(1%乙醚的石油醚溶液洗脱),然后用乙醚-乙醇重结晶,得5.7g化合物(Ⅲ),熔点113~114℃。
化合物(Ⅲ)(4.0g,6.2mmol)溶于10ml乙醚和50ml液体二氧化硫,搅拌30min。蒸出二氧化硫和乙醚,残液减压干燥,再经层析分离(20%乙醚的石油醚溶液洗脱),得化合物(Ⅳa),熔点107~109℃(分解);和化合物(Ⅳb)。
化合物(Ⅳ a) (4.4g,6.2mmo1)溶于120ml二氯甲烷和40ml甲醇,在-65℃通入O3至原料完全反应,约需40min。通入氮气鼓泡,再加入三苯膦(2.5g,9.5mmo1)。缓慢升温至0℃,加二氯甲烷稀释,依次用5%碳酸氢钠溶液、水和盐水洗,干燥,浓缩。残液层析分离(30%乙醚的石油醚溶液洗脱),得3.2g化合物(Va),收率81%,熔点122~124℃(分解);并同时得化合物(Vb)。
化合物(V)(14.3g,22mmo1)悬浮于300ml乙醇中,加入14g碳酸氢钠,回流90min。冷却,减压部分浓缩。剩余液在350ml乙酸乙酯和200ml水之间进行分配。分取有机层,用水和盐水洗,干燥,浓缩。得12.6g结晶性产物,其中含90%化合物(Ⅵa)和5%化合物(Ⅳb),直接用于下步反应。
上述化合物(Ⅵa)和(Ⅵb)的混合物(10.5g)和锛化物(X)(15g,44mmo1)溶于60ml二甲亚砜,在105℃反应4h。冷却,在250ml乙酸乙酯和200ml水之间进行分配。分取乙酸乙酯层,用水和盐水洗,干燥,减压浓缩。残液层析提纯(10%乙醚的石油醚溶液洗脱),再用乙醚-甲醇重结晶得7.51g化合物(Ⅶ),收率63%[以化合物(V)计],熔点123~124℃。
化合物(Ⅶ)(4.31g,6.74mmo1)溶于8ml四氢呋喃,在冰浴冷却和搅拌下,加入18ml 0.4mol/L CeCl3?6H2O的甲醇溶液,再加入9ml甲醇。在5min中,分批加入0.50g硼氢化钠。加毕,再搅拌10min。在250ml乙酸乙酯和200ml水之间进行分配。分取有机层,用100ml水洗,干燥,减压浓缩。残液层析分离,得1.42g化合物(Ⅷ),收率33%,熔点122~123℃。
化合物(Ⅷ)(1.13g,1.76mmo1)、170mg蒽和1滴三乙胺溶于75ml甲苯,用高压紫外灯在20℃照射60min。过滤,减压浓缩。残液层析提纯(15%乙酸乙酯的石油醚溶液洗脱),得1.04g化合物(Ⅸ),收率92%。
化合物(Ⅸ)(1.03g,1.61mmo1)和四丁基氟化铵(2.1g,6.7mmo1)溶于40ml四氢呋喃,在60℃反应50min。冷却,在150ml乙酸乙酯和100ml 2%碳酸氢钠溶液之间进行分配。分取有机层,用水和盐水洗,干燥,浓缩。残物经硅胶柱层析提纯(乙酸乙酯洗脱),得483mg卡泊三醇,收率73%,熔点166~168℃。
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标题:卡泊三醇_用途_密度_熔点_卡泊三醇CAS号【112965-21-6】_化源网 地址:https://www.chemsrc.com/amp/cas/112965-21-6_453209.html