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

• ChemBase编号: 72930
• 分子式: C16H18O9
• 平均质量: 354.30872
• 单一同位素质量: 354.09508216
• SMILES: C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/c1cc(c(cc1)O)O)O)O
• 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-JUHZACGLSA-N

名称和登记号

名称

• IUPAC标准名: (1S,3R,4R,5R)-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid; (1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• IUPAC传统名: chlorogenic acid
• 别名: 1,3,4,5-四羟基环己烷羧酸 3-(3,4-二羟基肉桂酸酯); 3-(3,4-二羟基肉桂酰基)奎宁酸; 绿原酸; (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic acid; 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid 3-(3,4-dihydroxycinnamate); Chlorogenic acid; Chlorogenic acid; 3-(3,4-Dihydroxycinnamoyl)quinate; 3-(3,4-Dihydroxycinnamoyl)quinic acid; 3-Caffeoylquinate; 3-Caffeoylquinic acid; 3-CQA; 3-O-Caffeoylquinic acid; Chlorogenate; Chlorogenic acid; Heriguard; 3-trans-Caffeoylquinic acid

登记号

• CAS号: 327-97-9
• EC号: 206-325-6
• MDL号: MFCD00003862
• PubChem SID: 24892649; 162037850
• PubChem CID: 1794427
• CHEBI ID: 16112
• CHEMBL: 284616
• Chemspider ID: 1405788
• 维基百科标题: Chlorogenic_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

• 溶解度: ethanol: soluble, clear to hazy
• 外观: crystalline; Powder
• 熔点: 207 - 209°C; 208-210°C; 210 °C (dec.)(lit.)
• 密度: 1.28 g/cm^3
• 比旋光度: [α]25/D -35°, c = 2.8 in H2O

安全信息

• 保存条件: -20°C
• RTECS编号: GU8480000
• 德国WGK号: 3
• 危险公开号: -
• 安全公开号: S24 S25 S28 S37 S45
• NFPA704:
  

  0

  1
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: rat ... G6pc(25634)

产品相关信息

• 纯度: ≥95% (titration); 95+%
• 级别: primary reference standard
• 成盐信息: Free Base
• 适用性: plant cell culture tested
• Empirical Formula (Hill Notation): C16H18O9

详细说明

MP Biomedicals - 05202172

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2280

Research Area: Cardiovascular Disease , Immunology
Biological Activity:
Chlorogenic acid is a hydroxycinnamic acid and a member of a family of naturally occurring organic compounds. [1] These are esters of polyphenolic caffeic acid and cyclitol (-)-quinic acid. It is an important biosynthetic intermediate. It also is one of the phenols found in coffee, bamboo Phyllostachys edulis, as well as many other plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. [2]

Sigma Aldrich - C3878

Caution
在乙醇中可生成浑浊溶液
包装
1, 5 g in poly bottle
250 mg in poly bottle

Sigma Aldrich - 00500590

Application
草药产品分析的参考标准
General description
由 HWI Analytik 生产和检验 证书上注明了由定量 NMR 确定的准确含量

参考文献

• ohnston KL et al. Am J Clin Nutr. 2003 Oct;78(4):728-33.