(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

• ChemBase编号: 107335
• 分子式: C15H14O6
• 平均质量: 290.26806
• 单一同位素质量: 290.07903817
• SMILES: O[C@@H]1Cc2c(O[C@@H]1c1ccc(O)c(O)c1)cc(O)cc2O
• Canonical SMILES: Oc1cc2O[C@H](c3ccc(c(c3)O)O)[C@@H](Cc2c(c1)O)O
• InChI: InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
• InChIKey: PFTAWBLQPZVEMU-UKRRQHHQSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• IUPAC传统名: ent-epicatechin; (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
• 别名: (-)-顺式-3,3′,4′,5,7-五羟基黄烷; (2R,3R)-2-(3,4-二羟基苯基)-3,4-二氢-1(2H)-苯并吡喃-3,5,7-三醇; (-)-表儿茶素; L-EPICATECHIN; (-)-cis-3,3′,4′,5,7-Pentahydroxyflavane; (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol; (-)-Epicatechin; (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol; epi-Catechin; epi-Catechol; l-Acacatechin; l-Epicatechin; l-Epicatechol; (-)-Epicatechin; Epicatechol; Teacatechin I; Acacatechin; Kakaol; Colatein; Epicatechin

登记号

• CAS号: 490-46-0
• EC号: 207-710-1
• MDL号: MFCD00075648
• Beilstein号: 92760
• PubChem SID: 162093204; 24894538; 24894431; 24874522; 24864472
• PubChem CID: 72276

理论计算性质

• Acid pKa: 9.004574
• 质子受体: 6
• 质子供体: 5
• LogD (pH = 5.5): 1.7949721
• LogD (pH = 7.4): 1.784451
• Log P: 1.795107
• 摩尔折射率: 73.9997 cm^3
• 极化性: 28.420568 Å^3
• 极化表面积: 110.38 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: DMSO; Methanol
• 外观: Powder; White to Off-White Solid
• 熔点: 234-237°C (dec.); 240 °C (dec.)(lit.); 240-245 °C (dec.)
• 比旋光度: [α]20/D -54°, c = 1 in acetone: water (1:1); [α]20/D -56±3°, c = 1% in acetone: water (1:1)

安全信息

• 保存条件: Hygroscopic, Refrigerator, Under Inert Atmosphere
• RTECS编号: KB3745000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26; 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... BACE1(23621), CYP1A2(1544)
• 生物活性机理: Converts proinsulin to insulin; Modulator of erythrocyte membrane bound

产品相关信息

• 纯度: ≥90% (HPLC); ≥90% (sum of enantiomers, HPLC); ≥95.0% (HPLC); ≥97.0% (HPLC); ≥98% (HPLC); 90%; 97%
• 级别: analytical standard; purum
• 生物来源: from green tea; Widespread in plants. First isol. in 1832 from Gambir-catechu (from Nauclea gambir) (most early isolates a mixt. of (+)-catechin and (?-epicatechin)
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Antidiabetic; Antiinflammatory agent; Shows hepatotropic activity
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C15H14O6

详细说明

MP Biomedicals - 05203364

MP Biomedicals Rare Chemical collection

Sigma Aldrich - E4018

Biochem/physiol Actions
Antioxidant found in chocolate.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - E1753

Biochem/physiol Actions
Antioxidant
包装
1, 5 g in glass bottle

Sigma Aldrich - 525952

包装
1 g in glass bottle

Sigma Aldrich - 39263

Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Toronto Research Chemicals - E582260

Potent antioxidant and antineoplastic agent.

参考文献

• Wu, Z., et al.: J. Agric. Food Chem., 59, 10737 (2011)
• Zheng, R., et al.: Int. J. Mol. Sci., 12, 5200 (2011)
• Rossouw, W. et al., Tetrahedron, 1990, 50, 12477, (pmr, abs config)
• Urano, M. et al., J. Het. Chem., 1991, 28, 1845, (synth)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1353
• Shen, C.-C. et al., Phytochemistry, 1993, 34, 843, (pmr, cmr)
• Davis, A.L. et al., Magn. Reson. Chem., 1996, 34, 887-890, (pmr, cmr, gallates)
• Seto, R. et al., Biosci., Biotechnol., Biochem., 1997, 61, 1434-1439, (isol, pmr, cmr)
• van Rensberg, H. et al., Tet. Lett., 1997, 38, 3089, (synth)
• Miketova, P. et al., J. Nat. Prod., 1998, 61, 461-467, (ms)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CCP875
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 1120D, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 326A, (nmr)
• Bokaida, M.M. et al., Proc. Chem. Soc., London, 1960, 280, (stereochem)
• Batterham, T.J. et al., Aust. J. Chem., 1964, 17, 428, (pmr)
• Clark-Lewis, J.W. et al., Aust. J. Chem., 1968, 21, 3025, (ms)
• Haslam, E., J.C.S.(C), 1969, 1824, (isol)
• Weinges, K. et al., Annalen, 1970, 234, 46, (deriv)
• Karrer, W. et al., Konstitution und Vorkommen der Organischen Pflanzenstoffe, 2nd edn., Birkhuser Verlag, Basel, 1972, nos. 1762-1764, (occur)
• Markham, K.R. et al., Tetrahedron, 1976, 32, 2607, (cmr)
• Alhadeff, M., Drugs of Today (Barcelona), 1977, 13, 60, (rev)
• Jacques, D. et al., J.C.S. Perkin 1, 1977, 1637, (biosynth)
• Foo, L.Y. et al., J.C.S. Perkin 1, 1983, 1535, (synth, cmr)
• Singh, J. et al., J. Indian Chem. Soc., 1984, 61, 1044, (props)
• Delgado, G. et al., Phytochemistry, 1984, 23, 675; 1986, 34, 633; 643, (derivs)
• Morimoto, S. et al., Chem. Pharm. Bull., 1985, 33, 2281, (deriv)
• Elliger, C.A., Synth. Commun., 1985, 15, 1315, (synth)
• Miyata, T. et al., Yakugaku Zasshi, 1985, 105, 59, (cryst struct)
• Porter, L.J. et al., J. Chem. Res., Synop., 1986, 86, (pmr, conformn)
• Perrissoud, D., Prog. Clin. Biol. Res., 1986, 213, 559, (rev, pharmacol)
• Kiehlmann, E. et al., Magn. Reson. Chem., 1988, 26, 204, (cmr)