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

• ChemBase编号: 125373
• 分子式: C7H8O5
• 平均质量: 172.13542
• 单一同位素质量: 172.03717336
• SMILES: O=C1C=C(C(=O)O)C[C@@H](O)[C@@H]1O
• Canonical SMILES: O[C@@H]1CC(=CC(=O)[C@H]1O)C(=O)O
• InChI: InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/t5-,6-/m1/s1
• InChIKey: SLWWJZMPHJJOPH-PHDIDXHHSA-N

名称和登记号

名称

• IUPAC标准名: (4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid
• IUPAC传统名: 3-dehydroshikimic acid
• 别名: 3-Dehydroshikimate; 3-DHS; (-)-3-DHS; 3-Dehydroshikimic acid; (4S,5R)-(-)-4,5-Dihydroxy-3-oxo-1-cyclohexene-1-carboxylic acid; 5-Dehydroshikimic acid; 3-Dehydroshikimic acid; DHS, 5-Dehydroshikimic Acid, 1-Cyclohexene-1-carboxylic Acid, 4,5-Dihydroxy-3-oxo trans; (-)-3-Dehydro Shikimic Acid

登记号

• CAS号: 2922-42-1
• MDL号: MFCD00216518
• PubChem SID: 162219723
• PubChem CID: 439774
• 维基百科标题: 3-Dehydroshikimic_acid

理论计算性质

• Acid pKa: 3.214242
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -3.288802
• LogD (pH = 7.4): -4.467806
• Log P: -1.0248979
• 摩尔折射率: 38.1936 cm^3
• 极化性: 14.702371 Å^3
• 极化表面积: 94.83 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: Chloroform; DMSO
• 外观: Off-White Powder
• 比旋光度: [α]/D -59.0±3.0°, c = 1 in ethanol

安全信息

• 保存条件: -20°C Freezer
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C7H8O5

详细说明

Sigma Aldrich - 05616

Biochem/physiol Actions
Metabolite of the shikimate pathway with a chromophore suitable for continuous spectrophotometric assay. Precursor of aromatic metabolites in microorganisms.
Application
3-Dehydroshikimic acid is a biochemical intermediate from D-glucose in the synthesis of pro-catechuic acid. 3-Dehydroshikimic acid has been used in a study to describe the synthesis of catechuic acid (1) and ethyl 2,4,5-trihydroxybenzoate (2) from D-glucose-derived β-ketoester. 3-Dehydroshikimic acid has also been used in studies to evaluate the shikimate biosynthetic pathway, in order to develop nontoxic antimicrobial agents, herbicides, and antiparasite drugs.

Toronto Research Chemicals - D230475

A metabolite of Shikimic Acid.

参考文献

• Lauhon, C.T. and Bartlett, P.A.: Biochemistry, 33, 14100 (1994)
• Balasubramanian, S., et al.: Biochemistry, 34, 341 (1994)