(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

• ChemBase编号: 119443
• 分子式: C7H10O5
• 平均质量: 174.1513
• 单一同位素质量: 174.05282342
• SMILES: C1(=C[C@H]([C@H]([C@@H](C1)O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O
• InChI: InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
• InChIKey: JXOHGGNKMLTUBP-HSUXUTPPSA-N

名称和登记号

名称

• IUPAC标准名: (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
• IUPAC传统名: (-)-shikimate
• 别名: (-)-莽草酸; Shikimic acid; (3R,4S,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid; (3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid; Shikimic acid; L-Shikimic acid; NSC 59257; (3R,4S,5R)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid; 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid; (-)-Shikimic acid

登记号

• CAS号: 138-59-0
• EC号: 205-334-2
• MDL号: MFCD00066278
• Beilstein号: 2210055; 4782717
• 默克索引号: 148480
• PubChem SID: 24899647; 162102624
• PubChem CID: 8742
• CHEBI ID: 16119
• CHEMBL: 290345
• Chemspider ID: 8412
• KEGG ID: C00493
• 维基百科标题: Shikimic_acid

理论计算性质

• Acid pKa: 4.103319
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): -3.0506496
• LogD (pH = 7.4): -4.7369246
• Log P: -1.6400741
• 摩尔折射率: 38.9603 cm^3
• 极化性: 15.229941 Å^3
• 极化表面积: 97.99 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Methanol; Water
• 外观: Powder; White to Off-White Solid
• 熔点: ~185 °C (dec.); 183-185°C (dec.); 184-188°C; 185–187 °C; 185-187 °C(lit.)
• 比旋光度: [α]20/D -175±10°, c = 2% in H2O; -175 (c=2 in water)

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: Hygroscopic
• RTECS编号: GW4600000
• 德国WGK号: 3
• TSCA收录: 否
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥97.0% (T); ≥99%; 98%
• 燃烧残渣: ≤1%
• Empirical Formula (Hill Notation): C7H10O5
• 分类: Rare Genuine Natural Compounds

详细说明

Sigma Aldrich - S5375

Biochem/physiol Actions
Biosynthetic precursor of aromatic amino acids, as well as many alkaloids and other aromatic metabolites.
包装
10 mg in autosmp vl

Sigma Aldrich - 85091

Other Notes
Intermediate in the biosynthesis of aromatic amino acids 1; Preparation of derivatives 2,3

Toronto Research Chemicals - S357100

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, flavonpids and other important aromatic compounds.

参考文献

• Evans, I.A., et al.: Nature, 250, 348 (1974)
• Harborne, J.B., et al.: Biosynthesis, 6, 40 (1974)
• Key intermediate in the biosynthesis of aromatic amino acids.
• Monograph: E. Haslam, Shikimic Acid, Wiley, Chichester (1993). Reviews: Chem. Rev., 65, 435 (1965); Tetrahedron, 34, 3353 (1978); Biosynthesis, 6, 40 (1980); Natural Prod. Rep., 10, 233 (1993); Synthesis, 179 (1993).