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1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one | 111316-17-7

中文名称
——
中文别名
——
英文名称
1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
英文别名
4,2′,4′-trihydroxy-6′-methoxydihydrochalcone;2',4,4'-trihydroxy-6'-methoxydihydrochalcone;4,2',4'-trihydroxy-6'-methoxydihydrochalcone;2'-O-methyl-phloretin;uvangoletin;1-(2,4-dihydroxy-6-methoxy-phenyl)-3-(4-hydroxy-phenyl)-propan-1-one
1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one化学式
CAS
111316-17-7
化学式
C16H16O5
mdl
——
分子量
288.3
InChiKey
PDZBWDAJMIPJSK-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    531.7±29.0 °C(Predicted)
  • 密度:
    1.325±0.06 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    3
  • 重原子数:
    21
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.19
  • 拓扑面积:
    87
  • 氢给体数:
    3
  • 氢受体数:
    5

制备方法与用途

2′-O-甲基化 Fireplace 黄酮可以从 Melodorum siamensis 的叶子中提取,这种化合物能够抑制肿瘤细胞的增殖。

上下游信息

反应信息

  • 作为产物:
    描述:
    naringin 在 palladium on activated charcoal 盐酸氢氧化钾氢气二异丙胺 作用下, 以 1,4-二氧六环甲醇 为溶剂, 20.0~100.0 ℃ 、303.98 kPa 条件下, 反应 2.0h, 生成 1-(2,4-dihydroxy-6-methoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
    参考文献:
    名称:
    Dihydrochalcones:  Evaluation as Novel Radical Scavenging Antioxidants
    摘要:
    Dihydrochalcones are a family of bicyclic flavonoids, defined by the presence of two benzene rings joined by a saturated three carbon bridge. In the present study, we systematically examined the antioxidant activities of dihydrochalcones against the stable free radical (1,1-diphenyl-2-picrylhydrazyl) and lipid peroxidation in the erythrocyte membrane. All dihydrochalcones exhibited higher antioxidant activities than the corresponding flavanones. The H-1 NMR analysis indicated that the active dihydrochalcone has a time-averaged conformation in which the aromatic A ring is orthogonal to the carbonyl group, while the inactive dihydrochalcone such as 2'-O-methyl-phloretin has a strongly hydrogen-bonded phenolic hydroxyl group, suggestive of a coplanar conformation. A hydroxyl group at the 2'-position of the dihydrochalcone A ring, newly formed by reduction of the flavanone C ring, is an essential pharmacophore for its radical scavenging potential.
    DOI:
    10.1021/jf0341060
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文献信息

  • Arylfluorophosphate Inhibitors of Intestinal Apical Membrane Sodium/Phosphate Co-Transport
    申请人:Peerce Brian
    公开号:US20130059822A1
    公开(公告)日:2013-03-07
    The present invention is directed to fluorophosphates, and pharmaceutical compositions thereof, which are inhibitors of intestinal apical sodium/phosphate co-transport and are useful in the treatment of hyperphosphatemia, in reducing blood phosphate levels, and in treating hypertension.
    本发明涉及氟磷酸盐及其制药组合物,它们是肠道顶端钠/磷共转运抑制剂,可用于治疗高磷血症,降低血磷水平,并用于治疗高血压。
  • Phenolic constituents from seeds of Coptis japonica var. dissecta
    作者:Min Zhi-da、Hiroko Murata、Mizuo Mizuno、Hiroyuki Kojima、Toshiyuki Tanaka、Munekazu Iinuma、Rie Kimura
    DOI:10.1016/s0031-9422(00)81760-4
    日期:——
    Abstract In addition to coumarinolignans (cleomiscosin A aquillochin) and 7,4′-dihydroxy-5-methoxyflavanone, a new dihydrochalcone, 2′,4,4′-trihydroxy-6′-methoxydihydrochalcone, was isolated from the seeds of Coptis japonica var. dissecta. The structure of the dihydrochalcone was confirmed by comparison with relevant synthetic samples.
    摘要 除了香豆素木脂素(cleomiscosin A aquillochin)和7,4'-二羟基-5-甲氧基黄烷酮外,从黄连变种的种子中分离出一种新的二氢查耳酮,2',4,4'-三羟基-6'-甲氧基二氢查耳酮。 . 解剖。通过与相关合成样品的比较,证实了二氢查尔酮的结构。
  • Synthesis, Crystal Structure, and Biological Evaluation of a Series of Phloretin Derivatives
    作者:Li Wang、Zheng-Wei Li、Wei Zhang、Rui Xu、Fei Gao、Yang-Feng Liu、Ya-Jun Li
    DOI:10.3390/molecules191016447
    日期:——
    A one-step synthesis of phloretin derivatives 2–11 from phloretin in good to excellent yields is reported. Their structures were characterized by 1H-NMR, 13C-NMR and MS, and the structures of 8 and 11 were determined by X-ray diffraction analysis. A mechanism for the formation of 9–11 is proposed. Compared with the anticancer drug docetaxel, phloretin, phloretin derivatives and phlorizin exhibited
    报道了从根皮素一步合成根皮素衍生物 2-11 的方法,收率很好。它们的结构通过1H-NMR、13C-NMR和MS表征,8和11的结构通过X射线衍射分析确定。提出了形成 9-11 的机制。与抗癌药物多西紫杉醇相比,根皮素、根皮素衍生物和根皮苷对 MDA-MB-231、SPC-A1、A549、MCF-7 和 EC109 细胞系表现出中等的细胞毒性。在所有测试的化合物中,7 种对五种细胞系表现出最强的细胞毒性,并且在 MDA-MB-231 细胞中比多西他赛更有活性。我们的研究结果表明,这些衍生物作为抗癌剂的进一步开发具有广阔的前景。
  • Composition Comprising the Extract of Anemarrhena Asphodeloides Bunge or the Compounds Isolated from the Same for Preventing and Treating Lipid Metabolism Disorder
    申请人:Seo Eun Kyoung
    公开号:US20120070515A1
    公开(公告)日:2012-03-22
    The present invention relates to a composition comprising an extract of Anemarrhena asphodeloides Bunge or the compounds isolated from the same, as an active ingredient. In particular, the extract and compounds have the excellent inhibitory effects on adipocyte differentiation, and thus can be used in a pharmaceutical composition and functional food for the prevention and treatment of lipid metabolism disorders.
    本发明涉及一种包含知母提取物或从中分离出的化合物的组合物,作为活性成分。具体来说,该提取物和化合物具有出色的抑制脂肪细胞分化作用,因此可用于制备用于预防和治疗脂质代谢紊乱的药物组合物和功能性食品。
  • Multifunction "Crown Complexes" from Amino Acids and Peptides for Skin and Hair Restoration
    申请人:Gupta K Shyam
    公开号:US20070099886A1
    公开(公告)日:2007-05-03
    This invention relates to Schiff's bases derived from amino acids and hydroxyaryl alkyl ketones, or a plant extract containing the same, having general chemical structure in FIG. 1 for topical application. This invention also relates to certain metal complex of said Schiff's bases, which have a crown-like appearance in their three-dimensional chemical structure, as in FIG. 2 . The Schiff's bases and their metal complexes of the present invention are useful for the modulation of metal-activated enzymes and metalloenzymes, such as Phenylalanine Hydroxylase, Tyrosine Transaminase, Phenylalanine Transaminase, Tyrosinase, various MMP (Matrix metalloproteases), Superoxide dismutase, 5-Alpha Reductase, and citrate lyase. These are further suitable for multifunctional topical methods for skin whitening, skin wrinkles reduction, skin antiaging, collagen synthesis, acne control, hair loss prevention, hair graying control, and facial oil control.
    本发明涉及从氨基酸和羟基芳基烷基酮衍生的席夫碱,或含有该类化合物的植物提取物,其具有图1中的一般化学结构,用于局部应用。本发明还涉及所述席夫碱的某些金属配合物,其在三维化学结构中呈冠状外观,如图2所示。本发明的席夫碱及其金属配合物对于调节金属活化酶和金属酶,例如苯丙氨酸羟化酶、酪氨酸转氨酶、苯丙氨酸转氨酶、酪氨酸酶、各种基质金属蛋白酶、超氧化物歧化酶、5α-还原酶和柠檬酸裂解酶具有用途。此外,它们还适用于多功能局部方法,如美白肌肤、减少皮肤皱纹、抗衰老、胶原蛋白合成、控制痤疮、预防脱发、控制白发和面部油脂控制。
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