(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one

• ChemBase编号: 72949
• 分子式: C28H34O15
• 平均质量: 610.56056
• 单一同位素质量: 610.18977039
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)O[C@@H](CC2=O)c1ccc(c(c1)O)OC)O)O)O)O)CO[C@H]1[C@H](O)[C@@H]([C@H]([C@@H](O1)C)O)O
• Canonical SMILES: COc1ccc(cc1O)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O[C@@H]1O[C@H](CO[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
• InChIKey: QUQPHWDTPGMPEX-QJBIFVCTSA-N

名称和登记号

名称

• IUPAC标准名: (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one
• IUPAC传统名: hesperidin
• 别名: Hesperidin; Hesperetin 7-rhamnoglucoside; Hesperitin-7-rutinoside; Hesperidin; (2S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-1-benzopyran-4-one; (2S)-Hesperidin; Atripliside B; Cirantin; Hesperetin 7-Rutinoside; NSC 44184; Hesperidine

登记号

• CAS号: 520-26-3
• EC号: 208-288-1
• MDL号: MFCD00075663
• Beilstein号: 75140
• PubChem SID: 162037869; 24895680
• PubChem CID: 10621
• CHEBI ID: 28775
• CHEMBL: 449317
• Chemspider ID: 10176
• 美国药典/FDA物质标识码: E750O06Y6O
• 维基百科标题: Hesperidin

理论计算性质

• Acid pKa: 8.609446
• 质子受体: 15
• 质子供体: 8
• LogD (pH = 5.5): -0.31489173
• LogD (pH = 7.4): -0.34045622
• Log P: -0.314557
• 摩尔折射率: 140.767 cm^3
• 极化性: 56.677265 Å^3
• 极化表面积: 234.29 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; Pyridine
• 外观: light brown; Powder; Yellow Solid
• 熔点: 233-236°C; 250-255 °C (dec.)(lit.)
• 比旋光度: [α]20/D -75±5°, c = 1% in pyridine (dry matter)

安全信息

• 保存条件: -20°C; -20°C Freezer
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ~90% (HPLC); ≥80%; ≥97.0% (HPLC)
• 级别: analytical standard
• 成盐信息: Free Base
• 简要说明: Stereoisomers
• 有效期: (limited shelf life, expiry date on the label)
• 干燥失重: ≤5% loss on drying, 110 °C
• Empirical Formula (Hill Notation): C28H34O15
• 分类: Genuine Natural Compounds

详细说明

Selleck Chemicals - S2309

Research Area: Cardiovascular Disease , Inflammation
Biological Activity:
Hesperidin is a flavanone glycoside found abundantly in citrus fruits. It is believed to play a role in plant defense. It acts as an antioxidant according to in vitro studies. [1] In human nutrition, it contributes to the integrity of the blood vessels. Various preliminary studies reveal novel pharmaceutical properties. It reduced cholesterol and blood pressure in rats. In a mouse study, large doses of the glucoside hesperidin decreased bone density loss. Another animal study showed protective effects against sepsis. Hesperidin has anti-inflammatory effects. It is also a potential sedative, possibly acting through opioid or adenosine receptors. [2][3]

Sigma Aldrich - H5254

Biochem/physiol Actions
Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2
Application
Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Sigma Aldrich - 50162

Biochem/physiol Actions
Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2
Application
Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Sigma Aldrich - 52040

Biochem/physiol Actions
Flavonoid phytochemical extracted from citrus species. It is the rhamnoglucoside (rutinoside) of hesperetin.2
Application
Studies of the behavior of hesperidin and hesperetin (the aglycone) with DMPC liposomes find the aglycone penetrates more deeply and binds more strongly to the "membrane." This may explain the better bioavailability of bioflavonoid aglycones in general.1

Toronto Research Chemicals - H281185

A flavanone found in citrus fruits, also regarded as Vitamin P.

参考文献

• Guzmán-Gutiérrez SL et al. Planta Med. 2009 Mar;75(4):295-301.
• Ananth, V., et al.: J. Pharm. Res., 2, 1739 (2009)
• Cejudo B., et al.: J. Agric. Food Chem., 58, 11814 (2009)