(1R,3R,4S,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

• ChemBase编号: 128564
• 分子式: C16H18O9
• 平均质量: 354.30872
• 单一同位素质量: 354.09508216
• SMILES: O=C(O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](OC(=O)/C=C/c2ccc(O)c(O)c2)C1
• Canonical SMILES: O=C(O[C@@H]1C[C@](O)(C[C@H]([C@@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
• InChI: InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1
• InChIKey: CWVRJTMFETXNAD-NXLLHMKUSA-N

名称和登记号

名称

• IUPAC标准名: (1R,3R,4S,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid; (1R,3R,4S,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• IUPAC传统名: (1R,3R,4S,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid; neochlorogenic acid
• 别名: 新绿原酸; 5-O-(trans-3,4-Dihydroxycinnamoyl)-D-quinic acid; trans-5-O-Caffeoylquinic acid; Neochlorogenic acid; 5-O-Caffeoylquinic acid; Neochlorogenic acid

登记号

• CAS号: 906-33-2
• EC号: 212-997-1
• MDL号: MFCD10566639
• PubChem SID: 162222871
• PubChem CID: 5280633
• CHEBI ID: 16384
• CHEMBL: 249450
• Chemspider ID: 4444237
• 维基百科标题: Neochlorogenic_acid

理论计算性质

• Acid pKa: 3.3338532
• 质子受体: 8
• 质子供体: 6
• LogD (pH = 5.5): -2.4192955
• LogD (pH = 7.4): -3.6938899
• Log P: -0.26852977
• 摩尔折射率: 83.2347 cm^3
• 极化性: 32.441044 Å^3
• 极化表面积: 164.75 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

理化性质

• 外观: Powder
• 比旋光度: [α]/D +11.5±1.5°, c = 0.1 in methanol

安全信息

• 德国WGK号: 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95.0% (HPLC); ≥98.0% (HPLC)
• 级别: analytical standard
• 杂质: ≤5.0% water
• 有效期: (limited shelf life, expiry date on the label)
• 干燥失重: ≤3.0% loss on drying
• Empirical Formula (Hill Notation): C16H18O9

详细说明

Sigma Aldrich - 94419

Biochem/physiol Actions
Neochlorogenic acid is an isomer of chlorogenic acid. Chlorogenic and neochlorogenic acid may function as chemopreventive compounds due to growth inhibition seen in breast cancer cell line MDA-MB-435.1