food yellow 3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: food yellow 3
• 英文别名: Sunset Yellow FCF；FD and C Yellow No. 6；6-hydroxy-5-[(E)-(4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate；6-hydroxy-5-[(4-sulfonatophenyl)diazenyl]naphthalene-2-sulfonate
• 化学式: C₁₆H₁₀N₂O₇S₂
• 分子量: 406.397
• InChiKey: KEYWXKLGZZGHMT-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  food yellow 3 在 Pd-BaSO₄ 氢气 作用下， 以 水 为溶剂， 生成 1-amino-2-hydroxynaphthalene-6-sulfonate
  参考文献：
  名称：

  Autoxidation Reactions of Different Aromatic o-Aminohydroxynaphthalenes That Are Formed during the Anaerobic Reduction of Sulfonated Azo Dyes

  摘要：

  Mono- and disulfonated naphthalene derivatives with a hydroxy group in ortho-position to an amino group are commonly occurring products of the anaerobic reduction of azo dyes by microorganisms. These substituted o-aminohydroxybenzenes and o-aminohydoxynaphthalenes are oxygen-sensitive and decompose under aerobic conditions. To evaluate their behavior under aerobic conditions, 1-amino-2-hydroxynaphthalene-6-sulfonate [AHNS; a reduction product of Sunset Yellow FCF (FD&C Yellow No.6, C.I. No. 15985)], 1-amino-2-hydroxynaphthalene-3,6-disulfonate [AHNDS; a reduction product of Amaranth (Acid Red 27, C.I. No. 16185)], and 1,2,7-triamino-8-hydroxynaphthalene-3,6-disulfonate [TAHNDS; a reduction product of Naphthol Blue Black B (Acid Black 1, C.I. No. 20470)] were chemically prepared and exposed to sir at neutral pH. The reactions were analyzed, and the autoxidation products were characterized mainly by LC-MS and UV/VIS spectroscopy. Autoxidation of AHNS led to the formation of a dimer. With AHNDS, 1,2-naphrhoquinone-3,6-disulfonate was found as intermediate, which subsequently reacted to a disulfonated cinnamic acid derivative. From TAHNDS a stable autoxidation product with a deep blueish color was formed that was identified as a naphthoquinone imine derivative of the parent compound. The spontaneous autoxidation reactions were compared to the behavior of the o-aminohydroxynaphthalenes and their products In the presence of activated sludge under aerobic conditions over the period of 1 month. In the presence of activated sludge, a biological conversion of the stable autoxidation product of TAHNDS was observed.

  DOI：

  10.1021/es9808346

文献信息

• Nanohybrids of edible dyes intercalated in ZnAl layered double hydroxides
  作者：Jin-Ho Choy、Yun-Kyung Kim、You-Hwan Son、Young Bin Choy、Jae-Min Oh、Hyun Jung、Seong-Ju Hwang

  DOI：10.1016/j.jpcs.2007.11.009

  日期：2008.5

  successfully intercalated into the gallery spaces of ZnAl layered double hydroxides (LDHs). Those organic–inorganic nanohybrids were synthesized by co-precipitating the aqueous solution of zinc nitrate and aluminum nitrate simultaneously in the presence of anionic dyes. From the X-ray diffraction and infrared spectroscopic analyses, we found that the dye molecules could be intercalated into hydroxide layers

  摘要 食用染料，如 Allura ® Red AC (C 18 H 14 N 2 O 8 S 2 2− )、日落黄 FCF (C 16 H 10 N 2 O 7 S 2 2− ) 和亮蓝 FCF (C 37 H 34 N 2 O 9 S 3 2- ) 成功地嵌入到 ZnAl 层状双氢氧化物 (LDH) 的通道空间中。这些有机-无机纳米杂化物是通过在阴离子染料的存在下同时共沉淀硝酸锌和硝酸铝的水溶液来合成的。从 X 射线衍射和红外光谱分析中，我们发现染料分子可以插入到氢氧化物层中，而其化学和结构性质没有任何变化。Allura ® Red AC、Sunset Yellow FCF 和 Brilliant Blue FCF 插入的 LDH 的基础间距分别确定为 24.0、20.3 和 24.7 A。
• Autoxidation Reactions of Different Aromatic <i>o</i>-Aminohydroxynaphthalenes That Are Formed during the Anaerobic Reduction of Sulfonated Azo Dyes
  作者：Michael Kudlich、Malcolm J. Hetheridge、Hans-Joachim Knackmuss、Andreas Stolz

  DOI：10.1021/es9808346

  日期：1999.3.1

  Mono- and disulfonated naphthalene derivatives with a hydroxy group in ortho-position to an amino group are commonly occurring products of the anaerobic reduction of azo dyes by microorganisms. These substituted o-aminohydroxybenzenes and o-aminohydoxynaphthalenes are oxygen-sensitive and decompose under aerobic conditions. To evaluate their behavior under aerobic conditions, 1-amino-2-hydroxynaphthalene-6-sulfonate [AHNS; a reduction product of Sunset Yellow FCF (FD&C Yellow No.6, C.I. No. 15985)], 1-amino-2-hydroxynaphthalene-3,6-disulfonate [AHNDS; a reduction product of Amaranth (Acid Red 27, C.I. No. 16185)], and 1,2,7-triamino-8-hydroxynaphthalene-3,6-disulfonate [TAHNDS; a reduction product of Naphthol Blue Black B (Acid Black 1, C.I. No. 20470)] were chemically prepared and exposed to sir at neutral pH. The reactions were analyzed, and the autoxidation products were characterized mainly by LC-MS and UV/VIS spectroscopy. Autoxidation of AHNS led to the formation of a dimer. With AHNDS, 1,2-naphrhoquinone-3,6-disulfonate was found as intermediate, which subsequently reacted to a disulfonated cinnamic acid derivative. From TAHNDS a stable autoxidation product with a deep blueish color was formed that was identified as a naphthoquinone imine derivative of the parent compound. The spontaneous autoxidation reactions were compared to the behavior of the o-aminohydroxynaphthalenes and their products In the presence of activated sludge under aerobic conditions over the period of 1 month. In the presence of activated sludge, a biological conversion of the stable autoxidation product of TAHNDS was observed.