4-Pregnene-17a,21-diol-3,11,20-trione 21-acetate 21-乙酰氧基-17α-羟基孕甾-4-烯-3,11,20-三酮

CAS 50-04-4 MFCD00003609

化学结构图

50-04-4
SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@@]21C

化学属性

Mol. FormulaC23H30O6
Mol. Weight402.48
Melting Point237-240
Appearance D 20 白色针状结晶或结晶性粉末(丙酮),无气味。在空气中稳定。Mp239- 241℃,比旋光度[α] 25 +208°-+217°(二氧六环),本品的乙醇溶液在240nm波长处有最大吸收。易溶于氯仿(1:4),溶于丙酮(1:75),微溶于乙醇和乙醚,难溶于水。本品溶于硫酸呈黄色而无荧光(与醋酸氢化可的松相区别)。 +169°(氯仿)、[α] +164°(0.5%,丙酮)、[α] 23
Refractive index212 ° (C=1, MeOH)
SolubilityDMSO 7 mg/mL Water <1 mg/mL Ethanol <1 mg/mL
Density
Boiling Point

别名和识别编码

Chemical Name4-Pregnene-17a,21-diol-3,11,20-trione 21-acetate
CAS Number50-04-4
Synonym Cortisone acetate {LY} Cortisone acetate {} {LY} Cortisone acetate {} {} {LY} Cortisone acetate {} {} {} {LY} Cortisone acetate {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cortisone acetate {} {} {} {} {} {} {} {} {}
MDL NumberMFCD00003609
PubChem Substance ID5745
Beilstein Registry Number2067543
EC Number200-006-5
Reaxys-RN2067543
Merck Number2539
Chemical Name Translation21-乙酰氧基-17α-羟基孕甾-4-烯-3,11,20-三酮
Wiswesser Line NotationL E5 B666 CV OV MUTJ A1 E1 FV1OV1 FQ
LabNetwork Molecule IDLN00238619
InChIInChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21-,22-,23-/m0/s1
Canonical SMILESC[C@@]1(C2)[C@](C(COC(C)=O)=O)(O)CC[C@@]1([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])C2=O)=O
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分类

  • {Chemicalbook} 生物化学品: 生化试剂: 激素
  • {SNA} Bioactive Small Molecules, CI-CY, Cell Signaling and Neuroscience, Corticosteroid, Cytokines, Growth Factors and Hormones, Hormones, Steroid Hormones, 细胞生物学
  • {SNA} Bioactive Small Molecules, CI-CY, Cell Biology, Cell Signaling and Neuroscience, Corticosteroid, Cytokines, Growth Factors and Hormones, Hormones, Steroid Hormones
  • Bioactive Small Molecules, CI-CY, Cell Biology, Cell Signaling and Neuroscience, Corticosteroid, Cytokines, Growth Factors and Hormones, Hormones, Steroid Hormones
  • {SNA} Analytical Standards, Analytic

产品应用

  • Cortisone Acetate is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone (H71461

相关文献及参考

  • [2]. McCue RE, et, al. The effect of cortisone on the accumulation, activation, and necrosis of macrophages in tuberculous lesions. Inflammation. 1978 Jun;3(2):159-76.
  • [3]. Seleem D, et, al. In Vivo Antifungal Activity of Monolaurin against Candida albicans Biofilms. Biol Pharm Bull. 2018;41(8):1299-1302.
  • [4]. Rusu VM, et, al. In vivo effects of cortisone on the B cell line in chickens. J Immunol. 1975 Nov;115(5):1370-4.
  • Beil. 8 ,IV,3481
  • Colburn, W. et al.: J. Clin. Pharmacol., 20, 428 (1980); Bailey, J.M. et al.: Atherosclerosis, 17, 515 (1973);
  • FT-IR 2 (3), 4251:B / FT-NMR 1 (3), 602:B / RegBook 1 (2), 2873:F / Sigma FT-IR 1 (1), 1224:B / Structure Index 1 , 460:C:5
  • Merck 14 ,2539
  • [1]. Hirano T, et, al. Cortisone counteracts
  • [1]. Hirano T, et, al. Cortisone counteracts apoptosis-inducing effect of cortisol in human peripheral-blood mononuclear cells. Int Immunopharmacol. 2001 Nov;1(12):2109-15.

安全信息

WGK Germany3
RTECSGM9140000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
GHS Symbol
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 35 mg/kg
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Vascular - tumors
   Musculoskeletal - tumors
REFERENCE :
   EXPEAM Experientia.  (Birkhaeuser Verlag, POB 133, CH-4010 Basel,
   Switzerland)  V.1-    1945-  Volume(issue)/page/year: 33,1640,1977

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Bacillus subtilis
DOSE/DURATION           : 5 gm/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 42,19,1977

TYPE OF TEST            : DNA repair
TEST SYSTEM             : Bacteria - Bacillus subtilis
DOSE/DURATION           : 5 gm/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 42,19,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 30 mg/kg
SEX/DURATION            : female 14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - other effects to embryo
REFERENCE :
   DEVPED Development (Cambridge, UK). (Biochemical society Book Depot, POB 32,
   Commerce Way, Colchester, Essex CO2 8HP, UK) V.99-   1987-
   Volume(issue)/page/year: 100,611,1987

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 400 mg/kg
SEX/DURATION            : female 1-8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - pre-implantation mortality (e.g. reduction in
   number of implants per female; total number of implants per corpora lutea)
REFERENCE :
   FESTAS Fertility and Sterility.  (American Fertility Soc., 608 13th Ave. S,
   Birmingham, AL 35282) V.1-    1950-  Volume(issue)/page/year: 28,464,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 56 mg/kg
SEX/DURATION            : male 14 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
   Reproductive - Paternal Effects - testes, epididymis, sperm duct
   Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland,
   accessory glands
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 113,27,1955

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Ocul

UN Number
Hazard Codes
Signal word
Risk Statements
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P302+P352
  • P304+P312
  • P304+P340
  • P308+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P322 Specific measures (see …on this label). 具体治疗(见本标签上的)。
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Packing Group
Hazard statements
  • H312 Harmful in contact with skin 皮肤接触有害
  • H332 Harmful if inhaled 吸入有害
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官

其他信息

  • 用途二:泼尼松醋酸酯的中间体。本身为抗炎剂。用于治疗肾上腺皮质低功能症、类风湿性关节炎、风湿病、红斑狼疮等病。
  • 醋酸可的松价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C0389 醋酸可的松 Cortisone Acetate 1G 421元 2014/06/02 C0389 醋酸可的松 Cortisone Acetate 5G 1240元 2010/06/16 C0389 乙酸可的松 Cortisone Acetate 25G 3410元
  • TCI Shanghai:乙酸可的松 Cortisone Acetate,>;99.0%(LC)(50-04-4)
  • 醋酸可的松价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 C0389 醋酸可的松 Cortisone Acetate 1G 332元 2011/04/16 C0389 醋酸可的松 Cortisone Acetate 5G 971元 2010/06/16 C0389 乙酸可的松 Cortisone Acetate 25G 3410元
  • 用途一:生化研究,肾上腺皮质激素类药物,具有抗炎、抗过敏等作用。
  • 方法一:以醋酸孕甾双烯醇酮为原料,依次经过氧化氢氧化、沃氏氧化、黑根菌生物氧化、铬酐氧化得11-酮基-16,17α环氧黄体酮,经氢溴酸开环,氢化脱溴得可的松,后者与碘反应,再与熔融醋酸钾作用得粗品,最后重结晶而得。
  • Sigma Aldrich:50-04-4(sigmaaldrich)
  • 上游原料:过氧化氢 --> 镍 --> 三氧化铬 --> 醋酸妊娠双烯醇酮酯 --> 乙酸钾 --> 16,17-环氧黄体酮 --> 铬酸 --> 皂素 --> 可的松 --> 16-妊娠双烯醇酮
  • 方法二:用妊娠双烯醇酮经环氧化、沃氏氧化、霉菌氧化、铬酸氧化、溴化氢开环,雷尼镍催化脱溴、碘化并乙酰氧基置换制得。
  • MOL 文件:50-04-4.mol
  • 下游产品:氢化可的松 --> 泼尼松 --> 醋酸泼尼松
  • 图谱信息:醋酸可的松(50-04-4)红外图谱(IR2) 醋酸可的松(50-04-4)质谱(MS) 醋酸可的松(50-04-4)红外图谱(IR1) 醋酸可的松(50-04-4)核磁图( 13 CNMR)
  • 参考质量标准:含量达97.0%-103.0%,mp≥238C,比旋光度[α] 20 D +208°- +217°,检测干燥失重及灼烧残渣等杂质含量。

系列性分类


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