3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one

• ChemBase编号: 5444
• 分子式: C15H14O5
• 平均质量: 274.26866
• 单一同位素质量: 274.08412355
• SMILES: c1c(cc(c(c1O)C(=O)CCc1ccc(cc1)O)O)O
• Canonical SMILES: Oc1ccc(cc1)CCC(=O)c1c(O)cc(cc1O)O
• InChI: InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
• InChIKey: VGEREEWJJVICBM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
• IUPAC传统名: dihydronaringenin; phloretin; 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
• 别名: 根皮素; Floretin; NSC 407292; Naringenin Dihydrochalcone; RJC 02792; β-(p-Hydroxyphenyl)phloropropiophenone; Dihydronaringenin; Phloretol; Phloretin; β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone; 2′,4′,6′-Trihydroxy-3-(4-hydroxyphenyl)propiophenone; Phloretin; 3-(4-HYDROXYPHENYL)-1-(2,4,6-TRIHYDROXYPHENYL)PROPAN-1-ONE; 2',4',6'-Trihydroxy-3-(4-hydroxyphenyl)-propiophenone; Naringenin chalcone; β-(4-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone; 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone; 2',4',6'-Trihydroxy-3-(4-hydroxyphenyl)propiophenone; Asebogenol; Dihydronarigenin

登记号

• CAS号: 60-82-2
• EC号: 200-488-7
• MDL号: MFCD00002288
• Beilstein号: 1887240
• 默克索引号: 147326
• PubChem SID: 24278652; 24887442; 99444281; 160968872
• PubChem CID: 4788
• Chemspider ID: 4624
• 美国药典/FDA物质标识码: S5J5OE47MK
• 维基百科标题: Phloretin

理论计算性质

JChem

• Acid pKa: 7.958485
• 质子受体: 5
• 质子供体: 4
• LogD (pH = 5.5): 3.8940427
• LogD (pH = 7.4): 3.7892191
• Log P: 3.8955405
• 摩尔折射率: 73.7073 cm^3
• 极化性: 27.944435 Å^3
• 极化表面积: 97.99 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.23
• LOG S: -3.32
• 溶解度: 1.32e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Ethanol; Methanol
• 外观: Light Tan Solid; Powder
• 熔点: ~260 °C; >262°C (dec.); 260-262°C (decomposes); 260-262°C(dec); ca 263°C dec.

安全信息

• 保存条件: -20°C; 2-8°C; Refrigerator
• 保存注意事项: IRRITANT
• 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; 26-37
• TSCA收录: false; 否
• 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; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

药理学性质

• 生物活性机理: Antioxidant; Inhibits the stimulation of cAMP accumulation by prostaglandins; Prostanoid receptor antagonist

产品相关信息

• 纯度: ≥98.0% (TLC); ≥99%; 98%
• 成盐信息: Free Base
• 生物来源: Found in free state in Helichrysum splendidum
• 应用领域: Antibacterial; Antioxidant
• Empirical Formula (Hill Notation): C15H14O5

详细说明

MP Biomedicals - 02191511

Crystalline

DrugBank - DB07810

Drug information: experimental

Selleck Chemicals - S2342

Research Area: Inflammation
Biological Activity:
Phloretin(Dihydronaringenin) is a dihydrochalcone, a type of polyphenol. It is the phloroglucin ester of paraoxyhydratropic acid. It can be found in apple tree leaves. Phloretin hydrolase uses phloretin and water to produce phloretate and phloroglucinol. [1]

Toronto Research Chemicals - P339000

The aglucon of Phlorizin. A glucose transport inhibitor. Also inhibits protein kinase C and has been shown to inhibit the entry of five enveloped viruses into human fibroblasts.

Sigma Aldrich - 79310

General description
Major polyphenol found in apple; aglycone of phloridzin.
Biochem/physiol Actions
Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.1

Sigma Aldrich - P7912

Biochem/physiol Actions
Blocks L-type Ca2+ channels; activates Ca2+-activated K+ channels in amphibian myelinated nerve fibers. Monocarboxylate transporter inhibitor.
Reacts with vic-dicarbonyl compounds such as glyoxal and methylglyoxal, preventing cytotoxic conjugation with biological macromolecules.1
General description
Major polyphenol found in apple; aglycone of phloridzin.

参考文献

• Inflammation
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• Wang, X., et al.: Biochem. J., 290, 249
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 866B, (nmr)
• Eykman, J.F., Ber., 1883, 16, 2769, (isol)
• Zempln, R. et al., Ber., 1942, 75, 645; 1298, (synth)
• Murakami, S., Yakugaku Zasshi, 1955, 75, 573; 603, (isol)
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• Farkas, L. et al., Chem. Ber., 1965, 98, 2926, (synth)
• King, B. et al., Phytochemistry, 1975, 14, 1448, (deriv)
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• Bohlmann, F. et al., Phytochemistry, 1979, 18, 885, (isol)
• Braz Filho, R. et al., Phytochemistry, 1980, 19, 1195, (derivs)
• Hufford, C.D. et al., Phytochemistry, 1980, 19, 2036, (cmr)
• Hutz, C. et al., Z. Naturforsch., C, 1982, 37, 337, (isol)
• Bohm, A., The Flavonoids: Advances in Research since 1980, (Ed. Harborne, J.B.), Chapman and Hall, London, 1988, 346, (rev)
• Barrero, A.F., J. Nat. Prod., 1997, 60, 65, (cmr)