化学品概述
可燃, 火场排出辛辣刺激烟雾
基本信息
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中文名称:
莽草酸
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中文别名:
3,4,5-三羟基-1-环己烯-1-甲酸;莽草酸;(-)-莽草酸;3A,4A,5Β-三羟基环已烯羧酸;蟒草酸;3,4,5-三羥-1-環己烯甲酸;卡瓦根提取物;莽草酸,98%
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英文名称:
Shikimic acid
- 英文别名:
-
分子式:
C7H10O5
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分子量:
174.1513 [g/mol]
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CAS:
138-59-0
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EINECS编号:
205-334-2
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MDL编号:
MFCD00066278
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精确质量:
174.052823
- InChI:
- InChI Key:
-
MOL文件:
138-59-0.mol
- PSA:
- LogP:
- FEMA编码:
- COE编码:
理化性质
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外观性质:
Powder;White to light beige or light gray
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熔点:
185-187 °C(lit.)
- 沸点:
-
密度:
1.52 g/cm3 (27.2℃)
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折射率:
-180 ° (C=1, H2O)
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比旋光度:
-180 º (c=4, H2O 25 ºC)
- 闪点:
- 溶解性:
-
酸度系数(pKa):
18 g/100 mL (20 ºC)
- 相对极性:
- PH值:
- 爆炸极限值(explosive limit):
-
敏感性:
Hygroscopic
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储存条件:
-20°C Freezer
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检测方法:
HPLC
- 蒸气压:
-
Merck:
14,8480
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BRN:
4782717
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NIST化学物质信息:
http://webbook.nist.gov/cgi/cbook.cgi?ID=138-59-0&Units=SI
- EPA化学物质信息:
安全信息
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危化品标志:
Xi
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危化代码:
36/37/38
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安全代码:
22-24/25-36-26
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海关编码/HS编码:
29181980
- 危化品运输编码:
-
WGK Germany:
3
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RTECS:
GW4600000
- TSCA:
- 危化等级:
- 包装类别:
-
毒理资料:
中毒
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灭火剂:
水, 二氧化碳, 干粉, 砂土
应用领域
莽草酸是许多生物碱,芳胺酸,吲哚衍生物和手性药物合成的关键前体。最近,莽草酸被用于奥塞米韦(达菲的活性成分) 的起始原料,奥塞米韦是 神经氨酸酶 抑制剂 ,可用于治疗和预防流感A和流感B。是一种抗肿瘤药物,同时也是二恶霉素、乙二醛酶抑制剂等抗肿瘤药物的合成原料
制备方法/合成路线
参考资料
- Naturally occurring (-)-form is a major biosynthetic precursor of phenylalanine, tyrosine, and tryptophan and hence of the majority of plant alkaloids. It is also involved in the biosynthesis of lignin, q.v., flavonoids and other important aromatic compounds. Isoln from the fruit of the oriental plant Illicium religiosum Sieb. et Zucc., Magnoliaceae (called in Japanese shikimi-no-ki): J. F. Eykman, Rec. Trav. Chim. 4, 32 (1885); idem, Ber. 24, 1278 (1891). Structural study: H. O. L. Fischer, G. Dangshat, Helv. Chim. Acta 17, 1200 (1934). Configuration: eidem, ibid. 18, 1206 (1935); 20, 705 (1937). Conformation in soln: L. D. Hall, J. Org. Chem. 29, 297 (1964). Enzymatic synthesis: P. R. Srinivasan et al., J. Am. Chem. Soc. 77, 4943 (1955). Stereospecific synthesis: R. McCrindle et al., J. Chem. Soc. 1960, 1560; E. E. Smissman et al., J. Am. Chem. Soc. 84, 1040 (1962). Improved synthesis: J. L. Pawlak, G. A. Berchtold, J. Org. Chem. 52, 1765 (1987). Synthesis of the (±)-form: R. Grewe, I. Hinrichs, Ber. 97, 443 (1964); R. Grewe, S. Kersten, Angew. Chem. 77, 859 (1965). Carcinogenicity study: I. A. Evans, M. A. Osman, Nature 250, 348 (1974). Reviews: B. A. Bohm, Chem. Rev. 65, 435-466 (1965); B. Ganem, Tetrahedron 34, 3353-3383 (1978); J. B. Harborne, Biosynthesis 6, 40-75 (1980). Books: E. Haslam, The Shikimate Pathway (Halsted Press, New York, 1974) 316 pp; idem, "Shikimic Acid Metabolites" in Comprehensive Organic Chemistry vol. 5 (Pergamon Press, Oxford, 1979) pp 1167-1205; U. Weiss, J. M. Edwards, The Biosynthesis of Organic Compounds (Wiley, New York, 1980) 728 pp.
- MSDS
图谱
计算化学数据
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疏水参数计算参考值(XlogP):
-1.7
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氢键供体数量 :
4
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氢键受体数量:
5
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可旋转化学键数量:
1
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拓扑分子机型表面积(TPSA) :
98
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重原子数量:
12
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形式电荷:
0
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复杂度:
222
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同位素原子数量:
0
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确定原子立构中心数量:
3
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不确定原子立构中心数量:
0
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确定化学键立构中心数量:
0
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不确定化学键立构中心数量:
0
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共价键单元数量:
1