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罗他霉素 | 74014-51-0

罗他霉素结构式图片|74014-51-0结构式图片
罗他霉素
ROKITAMYCIN
74014-51-0
C42H69NO15
827.99496
如需查看该化合物的详细结构式,mol文件,smile,InChi 请点击:罗他霉素结构式
5282211
罗他霉素价格
简介
罗他霉素又称为“罗吉他霉素”“丙酰吉他霉素”或“丙酰白霉素”,是一种大环内酯类抗生素。 是由北里链霉菌(Streptomyces kitasatoensis)的菌株中发现的。罗他霉素不溶于水,极易溶于乙醇,常温下为白色至微黄色粉末,无臭、味苦。该抗生素对革兰阳性菌、厌氧菌和支原体属等均有较强的抗菌活性。
名称和标识符
MDL MFCD00941397
InChIKey VYWWNRMSAPEJLS-RVPGWPFOSA-N
Inchi InChI=1S/C42H69NO15/c1-11-16-32(48)55-40-27(6)53-34(23-42(40,7)58-31(47)12-2)56-37-26(5)54-41(36(50)35(37)43(8)9)57-38-28(19-20-44)21-24(3)29(45)18-15-13-14-17-25(4)52-33(49)22-30(46)39(38)51-10/h13-15,18,20,24-30,34-41,45-46,50H,11-12,16-17,19,21-23H2,1-10H3/t24-,25-,26-,27+,28+,29+,30-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
SMILES O[C@H]([C@H]([C@H](O[C@@]1([H])C[C@](C)([C@@H](OC(CCC)=O)[C@H](C)O1)OC(CC)=O)[C@@H](C)O2)N(C)C)[C@]2([H])O[C@H]3[C@H](C[C@H]([C@H](/C=C/C=C/C[C@@H](C)OC(C[C@@H](O)[C@@H]3OC)=O)O)C)CC=O
别名信息
- 中文别名 -
  • 罗他霉素
  • 洛其他黴素
  • 柱晶白霉素A4
  • 柱晶白霉素V 4B-丁酸酯3B-丙酸酯
- 英文别名 -
  • ROKITAMYCIN
  • 3''-Propionylleucomycin A5
  • Leucomycin V, 4B-butanoate 3B-propanoate (9CI)
  • Ricamycin
  • TMS 19Q
  • Leummycin V 4B-bu-tanoate 3 B-propanoate
  • M-19-Q
  • Rikamycin
  • Leucomycin V,4B-butanoate 3B-propanoate
  • 3''-O-propionyl leucomycin A5
  • Rokital
  • T'urimyein H4
  • ZPT03UEM0E
  • ZPT03UEM0E
  • ZPT03UEM0E
  • ROKITAMYCIN [MART.]
  • ROKITAMYCIN [MART.]
  • ROKITAMYCIN [MART.]
  • Rokitamycinum [Latin]
  • Rokitamycinum [Latin]
  • Rokitamycinum [Latin]
  • BRN 5220127
  • BRN 5220127
  • BRN 5220127
  • rokitamycin
  • rokitamycin
  • rokitamycin
  • Rokitamicina [Spanish]
  • Rokitamicina [Spanish]
  • Rokitamicina [Spanish]
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
  • NS00011664
  • NS00011664
  • NS00011664
  • UNII-ZPT03UEM0E
  • UNII-ZPT03UEM0E
  • UNII-ZPT03UEM0E
  • Rokitamycin [INN:JAN]
  • Rokitamycin [INN:JAN]
  • Rokitamycin [INN:JAN]
  • CHEMBL1908350
  • CHEMBL1908350
  • CHEMBL1908350
  • GTPL12879
  • GTPL12879
  • GTPL12879
  • 3''-propionylleucomycin a5
  • 3''-propionylleucomycin a5
  • 3''-propionylleucomycin a5
  • Rokitamycinum
  • Rokitamycinum
  • Rokitamycinum
  • 3''-O-propionylleucomycin A5
  • 3''-O-propionylleucomycin A5
  • 3''-O-propionylleucomycin A5
  • CHEBI:32103
  • CHEBI:32103
  • CHEBI:32103
  • ROKITAMYCIN [WHO-DD]
  • ROKITAMYCIN [WHO-DD]
  • ROKITAMYCIN [WHO-DD]
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-dimethylamino-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-dimethylamino-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
  • [(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-dimethylamino-5-hydroxy-2-methyloxan-3-yl]oxy-2,4-dimethyl-4-propanoyloxyoxan-3-yl] butanoate
  • Rokitamycine [French]
  • Rokitamycine [French]
  • Rokitamycine [French]
  • Rokitamycin, Antibiotic for Culture Media Use Only
  • Rokitamycin, Antibiotic for Culture Media Use Only
  • Rokitamycin, Antibiotic for Culture Media Use Only
  • Rokicid
  • Rokicid
  • ROKITAMYCIN [INN]
  • Rokicid
  • ROKITAMYCIN [INN]
  • DB13409
  • DB13409
  • ROKITAMYCIN [INN]
  • DTXSID6023521
  • DB13409
  • DTXSID6023521
  • Ricamycin (TN)
  • DTXSID6023521
  • ROKITAMYCIN [JAN]
  • Ricamycin (TN)
  • Ricamycin (TN)
  • Leucomycin V, 4(sup B)-butanoate 3(Sup B)-propanoate
  • ROKITAMYCIN [JAN]
  • ROKITAMYCIN [JAN]
  • AKOS016010142
  • Leucomycin V, 4(sup B)-butanoate 3(Sup B)-propanoate
  • Leucomycin V, 4(sup B)-butanoate 3(Sup B)-propanoate
  • Propionylleucomycin
  • AKOS016010142
  • AKOS016010142
  • CCRIS 5267
  • Propionylleucomycin
  • Propionylleucomycin
  • Rokitamycine
  • CCRIS 5267
  • CCRIS 5267
  • Rokitamycin (JAN/INN)
  • Rokitamycine
  • Rokitamycine
  • ((4R,5S,6S,7R,9R,10R,11E,13E,16R)-7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl)-3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-butyrate 3'-propionate
  • Rokitamycin (JAN/INN)
  • Rokitamycin (JAN/INN)
  • D01897
  • ((4R,5S,6S,7R,9R,10R,11E,13E,16R)-7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl)-3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-butyrate 3'-propionate
  • ((4R,5S,6S,7R,9R,10R,11E,13E,16R)-7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl)-3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4'-butyrate 3'-propionate
  • Q3940221
  • D01897
  • D01897
  • TMS-19Q
  • Q3940221
  • Q3940221
  • 74014-51-0
  • TMS-19Q
  • TMS-19Q
  • ((4R,5S,6S,7R,9R,10R,11E,13E,16R)-7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl)-3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4''-butyrate 3''-propionate
  • 74014-51-0
  • 74014-51-0
  • Rokitamicina
  • ((4R,5S,6S,7R,9R,10R,11E,13E,16R)-7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl)-3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4''-butyrate 3''-propionate
  • ((4R,5S,6S,7R,9R,10R,11E,13E,16R)-7-(Formylmethyl)-4,10-dihydroxy-5-methoxy-9,16-dimethyl-2-oxooxacyclohexadeca-11,13-dien-6-yl)-3,6-dideoxy-4-O-(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-3-(dimethylamino)-beta-D-glucopyranoside 4''-butyrate 3''-propionate
  • TMS-19-Q
  • Rokitamicina
  • Rokitamicina
  • TMS-19-Q DS 200
  • TMS-19-Q
  • TMS-19-Q
  • R-6900
  • TMS-19-Q DS 200
  • TMS-19-Q DS 200
  • ROKITAMYCIN [MI]
  • R-6900
  • R-6900
  • SCHEMBL136367
  • ROKITAMYCIN [MI]
  • ROKITAMYCIN [MI]
  • Leucomycin V, 4B-butanoate 3B-propanoate
  • SCHEMBL136367
  • SCHEMBL136367
  • Leucomycin V, 4B-butanoate 3B-propanoate
  • Leucomycin V, 4B-butanoate 3B-propanoate
物化性质
实验特性
LogP 3.15750
PSA 206.05000
折射率 1.535
沸点 879.3 °C at 760 mmHg
熔点 116°
闪点 485.6 °C
颜色与性状 白色至微黄色粉末,无臭,味苦。
比旋光度 D20 -71° (c = 1.0 in chloroform)
密度 1.21
计算特性
精确分子量 827.46700
氢键供体数量 3
氢键受体数量 16
可旋转化学键数量 15
同位素质量 827.467
重原子数量 58
复杂度 1380
同位素原子数量 0
确定原子立构中心数量 16
不确定原子立构中心数量 0
确定化学键立构中心数量 2
不确定化学键立构中心数量 0
共价键单元数量 1
疏水参数计算参考值(XlogP) 3
互变异构体数量 4
表面电荷 0
拓扑分子极性表面积 206A^2
生产方法和用途
用途 大环内酯类抗菌素,对革兰阳性菌、厌氧菌和支原体属等均有较强的抗崔活性。用于敏感菌所引起的各种感染,如肺炎、支原体性肺炎、外耳炎、中马炎、牙周炎、副鼻窦炎、皮下脓肿、汗腺炎、喉炎、急性支气管炎、扁桃体炎疖子、丹毒等。
生产方法 以吉他霉素氏为原料。10g吉他霉素A5溶于50ml干燥1,2-二氯乙烷和4.2ml乙酸酐,在室温下搅拌0.5h。将反应液加到200ml冰水中,用7%氨水调至Ph=10,再用50ml 1,2-二氯乙烷提取。提取液用无水硫酸钠干燥,减压浓缩得.10g 2’-O-乙酰吉他霉素A5(I)粗品,收率94.8%。10g2’-O-乙酰吉他霉素A5(I)溶于50ml干燥的二氯乙烷中,加入10g三苄基胺和6.6ml三甲基氯硅烷,在5~10℃下搅拌15h。然后把反应液倾入200rnl水中,用7%氨水调至Ph=9.5后,用1,2-二氯乙烷提取。提取液水洗后,用无水硫酸镁干燥。减压蒸去溶剂,得12.7g 2’-O-乙酰-3,9-二-O-三甲基硅吉他霉素A5(Ⅱ)粗品,收率96.1%。将上述(Ⅱ)的粗品溶于50ml干燥1,2-二氯乙烷,加入31g三苄胺,然后在冰浴冷却和搅拌下,滴加11.25ml丙酰氯,在75℃下搅拌20h。反应液倾入200ml水中,用氨水调至Ph值为9.5后,用100ml 1,2-二氯乙烷提取。提取液经无水硫酸镁干燥后,减压蒸去溶剂,得2’-O-乙酰-17,18-烯醇-18,3’’-二-O-丙酰-3,9-二-O-三甲基硅吉他霉素A5(Ⅲ)和小量的2’-O-乙酰-3”-O-丙酰-3,9-二-O-三甲基硅吉他霉素A5(Ⅳ)及大量三苄胺的混合物。无需分离,加入495ml甲醇和55ml 8%碳酸钾水溶液,在室温下搅拌1h,得含2’-O-乙酰-3”-O-丙酰-吉他霉素A5(V)的溶液。用乙酸调至Ph=7.5,回流20h,然后减压浓缩。剩余物溶于1,2-二氯乙烷,用3%氨水洗1次,再水洗2次,然后减压浓缩。剩余物溶于冷甲醇,过滤除去不溶的三苄胺。滤液减压浓缩,得10.4g罗他霉素粗品,收率94.7%。将粗品溶于少量苯中,用硅胶进行柱层析(1.5crn×60cm),洗脱液为苯-乙酸乙酯-甲醇(36:4:1,体积比),收集Rf=0.57附近的各部分洗脱液,合并减压蒸干,即得7.5g纯罗他霉素精品,熔点约116℃。总收率70%。
专业数据库参考
PubChemId 5282211
化合物详情(旧版)

SMILES

CCCC(=O)O[C@@H]1[C@@](OC(=O)CC)(C)C[C@@H](O[C@H]1C)O[C@H]2[C@H](N(C)C)[C@@H](O)[C@@H](O[C@@H]2C)O[C@@H]3[C@@H](OC)[C@H](O)CC(=O)O[C@H](C)C/C=C/C=C/[C@H](O)[C@H](C)C[C@@H]3CC=O

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