维生素K3-D8 | 478171-80-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 维生素K3-D8
• 中文别名: 维生素K3-d8；维生素 K3-D8 标准品
• 英文名称: d₈-2-methyl-1,4-naphthoquinone
• 英文别名: d₈-vitamin K₃；K₃-d₈；menadion-d8；2-Methyl-1,4-naphthoquinone-d8；2,5,6,7,8-pentadeuterio-3-(trideuteriomethyl)naphthalene-1,4-dione
• CAS: 478171-80-1
• 化学式: C₁₁H₈O₂
• 分子量: 180.12
• InChiKey: MJVAVZPDRWSRRC-JGUCLWPXSA-N

物化性质

• 熔点：
  105-107 °C(lit.)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  维生素K3-D8 在 sodium dithionite 、 水 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2-Methyl-1,4-naphthalenediol-d8
  参考文献：
  名称：

  Structure–activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines

  摘要：

  To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.035

文献信息

• Structure–Activity Relationship of Novel Menaquinone-4 Analogues: Modification of the Side Chain Affects their Biological Activities
  作者：Yoshitomo Suhara、Norika Hanada、Takashi Okitsu、Miho Sakai、Masato Watanabe、Kimie Nakagawa、Akimori Wada、Kazuyoshi Takeda、Kazuhiko Takahashi、Hiroaki Tokiwa、Toshio Okano

  DOI：10.1021/jm2013166

  日期：2012.2.23

  We synthesized new vitamin K analogues with demethylation or reduction of the double bonds of the side chain of menaquinone-4 (MK-4) and evaluated their SXR-mediated transcriptional activity as well as the extent of their conversion to MK-4. The results indicated that the analogue with the methyl group deleted at the 7' site of the side chain part affected conversion activity to MK-4. In contrast, a decrease in the number of the double bonds in the side chain moiety appeared to decrease the SXR-mediated transcriptional activity.
• Elucidation of the mechanism producing menaquinone-4 in osteoblastic cells
  作者：Yoshitomo Suhara、Akimori Wada、Toshio Okano

  DOI：10.1016/j.bmcl.2009.01.021

  日期：2009.2

  Vitamin K is an essential nutrient and a cofactor for the carboxylation of specific glutamyl residues of proteins to gamma-glutamyl residues, which activates osteocalcin related to bone formation. Among vitamin K homologues, menaquinone-4 (MK-4) is the most active biologically, up-regulating the gene expression of bone markers, and thus has been clinically used in the treatment of osteoporosis in Japan. Recently, we confirmed that MK-4 was converted from dietary phylloquinone (PK), and then accumulated in various tissues at high concentrations. This system should play an important role in biological functions including bone formation, however, the pathway by which MK- 4 is converted remains unclear. In this study, we studied the mechanism of MK-4's conversion with chemical techniques using deuterated analogues. (C) 2009 Elsevier Ltd. All rights reserved.
• Structure–activity relationships in the conversion of vitamin K analogues into menaquinone-4. Substrates essential to the synthesis of menaquinone-4 in cultured human cell lines
  作者：Yoshitomo Suhara、Akimori Wada、Yoji Tachibana、Masato Watanabe、Kanae Nakamura、Kimie Nakagawa、Toshio Okano

  DOI：10.1016/j.bmc.2010.03.035

  日期：2010.5

  To reveal an essential biological role of menaquinone-4, we have clarified that dietary PK was converted to menaquinone-4 (MK-4) in animal tissues using deuterated vitamin K analogues. However, the kinds of analogue converted into MK-4 have not been elucidated. In this study, we examined structure-activity relationships in the conversion of several vitamin K analogues, with a substituted side chain, into MK-4 using cultured human cell lines. The results differed with the side chain of the analogues, that is, (1) the length of the isoprene unit and (2) the number of double bonds in the side chain. These findings would be useful for clarifying the mechanism of conversion of other vitamin K homologs into MK-4 as well as related enzymes. (c) 2010 Elsevier Ltd. All rights reserved.