辅酶Q6 | 1065-31-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 辅酶Q6
• 中文别名: 泛醌-6；泛醌-30；2,3-二甲氧基-5-甲基-6-(法呢基法呢基)-1,4-苯并醌
• 英文名称: ubiquinone-6
• 英文别名: CoQ₆；coenzyme Q₆；Ubichinon-6；Coenzyme Q6；2-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaenyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
• CAS: 1065-31-2
• 化学式: C₃₉H₅₈O₄
• 分子量: 590.887
• InChiKey: GXNFPEOUKFOTKY-LPHQIWJTSA-N

物化性质

• 沸点：
  688.7±55.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  43
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  辅酶Q6 在 sodium hydroxide 、 维生素 C 作用下， 以 乙醇 为溶剂， 生成 ubiquinol-6
  参考文献：
  名称：

  The Surprisingly High Reactivity of Phenoxyl Radicals

  摘要：

  Rate constants have been measured in nonaqueous media for hydrogen atom abstraction by the phenoxyl radical from some biologically important phenols and related compounds. Although the thermochemistry for these reactions must be very similar to the thermochemistry for H atom abstraction from the same substrate by a peroxyl radical, the phenoxyl rate constants, k(5), are ca. 100-300 times greater than the (already well-known) peroxyl rate constants, k(1). For example, with alpha-tocopherol in benzene/di-tert-butyl peroxide (1:3, v/v) k(5)(293K) = 1.1 X 10(9) M(-1) s(-1) vs k(1)(303K) = 3.2 X 10(6) M(-1) s(-1) in a similar nonpolar medium, and with ubiquinol-10 in the same solvent mixture k(5)(293K) = 8.4 X 10(7) M(-1) s(-1), while the corresponding value for k(1) is 3.5 X 10(5) M(-1) s(-1). The greater reactivity of the phenoxyl radical has been traced to the fact that the Arrhenius preexponential factors are much larger than for the corresponding peroxyl radical reactions, i.e., A(5) similar to 10(2)A(1). For example, with alpha-naphthol log(A(5)/M(-1) s(-1)) = 8.9 and E(5) = 2.2 kcal/mol vs log(A(1)/M(-1) s(-1)) = 6.4 and E(1) = 1.7 kcal/mol. The preexponential factors for II-atom donors more reactive than alpha-naphthol are even greater; for example, with alpha-tocopherol in CH3CN/di-tert-butyl peroxide (1:2, v/v) log(A(5)/M(-1) s(-1)) = 10.0 and E(5) 2.0 kcal/mol, and with ubiquinol-0 in benzene/di-tert-butyl peroxide (1:3, v/v) log(A(5)/M(-1) s(-1)) = 10.5 and E(5) = 3.5 kcal/mol. The role that intermediate hydrogen-bonded complexes between the reacting radical and the phenolic hydrogen donor may play in these reactions is discussed, and it is pointed out that our results are likely to be relevant to in vivo radical chemistry.

  DOI：

  10.1021/ja00100a005
• 作为产物：
  描述：

  2,3,4,5-四甲氧基甲苯 在 盐酸 、 ammonium cerium(IV) nitrate 、 四(三苯基膦)镍 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 辅酶Q6
  参考文献：
  名称：

  A Convergent Approach to Coenzyme Q

  摘要：

  Syntheses of coenzyme Q(3-8) are described, as well as related systems such as plastoquinone-5. Preparation of thr higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.

  DOI：

  10.1021/ja992164p
• 作为试剂：
  描述：

  L-氢化乳清酸 在 dihydroorotate dehydrogenase 、 二氯异丙醚 、 辅酶Q6 、 Triton X-100 作用下， 以 水 为溶剂， 生成 乳清酸
  参考文献：
  名称：

  Stereoselectivity in the enzymic oxidation and nonenzymic hydrogen-exchange reactions of dihydroorotate

  摘要：

  DOI：

  10.1021/ja00288a036

文献信息

• Die Struktur des Ubichinons aus Hefe
  作者：U. Gloor、O. Isler、R. A. Morton、R. Rüegg、O. Wiss

  DOI：10.1002/hlca.19580410746

  日期：——

  An ubiquinone compound isolated from baker's yeast has been identified as 2,3-dimethoxy-5-methyl-6-all-trans-farnesylfarnesyl-1,4-benzoquinone by its total synthesis starting from 2,3-dimethoxy-5-methyl-hydroquinone and all-trans-farnesylnerolidol. The name ubiquinone(30) is proposed for this compound.

  从面包酵母中分离出来的泛醌化合物已被确定为2,3-二甲氧基-5-甲基-6-全反式-法呢基法呢基-1,4-苯醌，其合成起始于2,3-二甲氧基-5-甲基-。对苯二酚和全反式法呢基神经甾醇。该化合物的名称为泛醌（30）。
• Regio- and stereoselective synthesis of coenzymes Qn (n = 2-10), vitamin K, and related polyprenylquinones
  作者：Yoshinori Naruta

  DOI：10.1021/jo01309a006

  日期：1980.10
• A Convergent Approach to Coenzyme Q
  作者：Bruce H. Lipshutz、Gerd Bulow、Fernando Fernandez-Lazaro、Sung-Kyu Kim、Richard Lowe、Paul Mollard、Kirk L. Stevens

  DOI：10.1021/ja992164p

  日期：1999.12.1

  Syntheses of coenzyme Q(3-8) are described, as well as related systems such as plastoquinone-5. Preparation of thr higher homologues of the ubiquinones relies on two new conjunctive reagents, or "linchpins", each of which ultimately corresponds to two or three prenyl units. These allow for attachment of a polyprenyl halide at one end, followed by a Ni(0)-catalyzed cross-coupling at the other terminus with a chloromethylated p-quinone.
• The Surprisingly High Reactivity of Phenoxyl Radicals
  作者：M. Foti、K. U. Ingold、J. Lusztyk

  DOI：10.1021/ja00100a005

  日期：1994.10

  Rate constants have been measured in nonaqueous media for hydrogen atom abstraction by the phenoxyl radical from some biologically important phenols and related compounds. Although the thermochemistry for these reactions must be very similar to the thermochemistry for H atom abstraction from the same substrate by a peroxyl radical, the phenoxyl rate constants, k(5), are ca. 100-300 times greater than the (already well-known) peroxyl rate constants, k(1). For example, with alpha-tocopherol in benzene/di-tert-butyl peroxide (1:3, v/v) k(5)(293K) = 1.1 X 10(9) M(-1) s(-1) vs k(1)(303K) = 3.2 X 10(6) M(-1) s(-1) in a similar nonpolar medium, and with ubiquinol-10 in the same solvent mixture k(5)(293K) = 8.4 X 10(7) M(-1) s(-1), while the corresponding value for k(1) is 3.5 X 10(5) M(-1) s(-1). The greater reactivity of the phenoxyl radical has been traced to the fact that the Arrhenius preexponential factors are much larger than for the corresponding peroxyl radical reactions, i.e., A(5) similar to 10(2)A(1). For example, with alpha-naphthol log(A(5)/M(-1) s(-1)) = 8.9 and E(5) = 2.2 kcal/mol vs log(A(1)/M(-1) s(-1)) = 6.4 and E(1) = 1.7 kcal/mol. The preexponential factors for II-atom donors more reactive than alpha-naphthol are even greater; for example, with alpha-tocopherol in CH3CN/di-tert-butyl peroxide (1:2, v/v) log(A(5)/M(-1) s(-1)) = 10.0 and E(5) 2.0 kcal/mol, and with ubiquinol-0 in benzene/di-tert-butyl peroxide (1:3, v/v) log(A(5)/M(-1) s(-1)) = 10.5 and E(5) = 3.5 kcal/mol. The role that intermediate hydrogen-bonded complexes between the reacting radical and the phenolic hydrogen donor may play in these reactions is discussed, and it is pointed out that our results are likely to be relevant to in vivo radical chemistry.