2,3-dihydroxy-5-oxohexane-1,6-dioic acid | 17480-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2,3-dihydroxy-5-oxohexane-1,6-dioic acid
• 英文别名: DOHA；2-dehydro-3-deoxy-D-glucaric acid；(2S,3S)-2,3-dihydroxy-5-oxohexanedioic acid
• CAS: 17480-06-7
• 化学式: C₆H₈O₇
• 分子量: 192.125
• InChiKey: QUURPCHWPQNNGL-OKKQSCSOSA-N

物化性质

• 沸点：
  555.7±50.0 °C(Predicted)
• 密度：
  1.751±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-dihydroxy-5-oxohexane-1,6-dioic acid 在 sodium tetraborate decahydrate 、 硫酸 、 platinum on carbon 、 sodium hydroxide 作用下， 反应 0.17h， 生成 2,5-呋喃二甲酸
  参考文献：
  名称：

  [EN] METHODS FOR PREPARING 2,5-FURANDICARBOXYLIC ACID
  [FR] PROCÉDÉS POUR PRÉPARER L'ACIDE 2,5-FURANEDICARBOXYLIQUE

  摘要：

  提供的方法可以从可再生资源如海藻、藻酸盐、寡聚藻酸盐、果胶、寡聚果胶、多聚半乳糖酸、半乳糖酸和/或寡聚半乳糖酸中生产2,5-呋喃二甲酸（FDCA）。可再生资源中的糖可以转化为一个或多个中间体，如4-脱氧-L-红鼻子-5-己糖醛酸（DEHU）、4-脱氧-L-反-5-己糖醛酸（DTHU）、5-羟甲基糠醛（HMF）、2,5-二羟甲基呋喃（DHMF）和5-甲酰基-2-呋喃羧酸（FFA），通过脱水和环化转化为5-甲酰基-2-呋喃羧酸（FFA），然后氧化产生FDCA。DEHU或DTHU也可以通过氧化转化为2,3-二羟基-5-氧代己二酸（DOHA），然后进行脱水和环化产生FDCA。

  公开号：

  WO2013049711A1
• 作为产物：
  描述：

  4-deoxy-L-erythro-5-hexoseulose uronic acid 在 platinum on carbon 作用下， 以 aq. phosphate buffer 、 水 为溶剂， 反应 48.0h， 生成 2,3-dihydroxy-5-oxohexane-1,6-dioic acid
  参考文献：
  名称：

  [EN] METHODS FOR PREPARING 2,5-FURANDICARBOXYLIC ACID
  [FR] PROCÉDÉS POUR PRÉPARER L'ACIDE 2,5-FURANEDICARBOXYLIQUE

  摘要：

  提供的方法可以从可再生资源如海藻、藻酸盐、寡聚藻酸盐、果胶、寡聚果胶、多聚半乳糖酸、半乳糖酸和/或寡聚半乳糖酸中生产2,5-呋喃二甲酸（FDCA）。可再生资源中的糖可以转化为一个或多个中间体，如4-脱氧-L-红鼻子-5-己糖醛酸（DEHU）、4-脱氧-L-反-5-己糖醛酸（DTHU）、5-羟甲基糠醛（HMF）、2,5-二羟甲基呋喃（DHMF）和5-甲酰基-2-呋喃羧酸（FFA），通过脱水和环化转化为5-甲酰基-2-呋喃羧酸（FFA），然后氧化产生FDCA。DEHU或DTHU也可以通过氧化转化为2,3-二羟基-5-氧代己二酸（DOHA），然后进行脱水和环化产生FDCA。

  公开号：

  WO2013049711A1

文献信息

• Process for making esters of 2,5-furandicarboxylic acid
  申请人：Archer Daniels Midland Company

  公开号：US11078174B2

  公开（公告）日：2021-08-03

  A process is provided for making esters of FDCA, in which an aqueous feed comprising glucaric acid is first reacted with a high boiling first alcohol in the presence of an acid catalyst and with removing water during the reaction, to form a first product mixture comprising a first ester of FDCA and the high boiling first alcohol, then unreacted high boiling first alcohol is removed from the first product mixture. The first ester of FDCA and the high boiling first alcohol is then transesterified with a lower boiling second alcohol selected from the group consisting of methanol, ethanol, isopropanol and n-propanol, to form a second product mixture comprising a second ester of FDCA with the lower boiling second alcohol, and the second ester of FDCA with the lower boiling second alcohol is recovered.

  本发明提供了一种制造 FDCA 酯的工艺，在该工艺中，首先在酸催化剂存在下，将包含葡 萄酸的水性进料与高沸点第一醇反应，并在反应过程中除去水，以形成包含 FDCA 第一酯和高 沸点第一醇的第一产品混合物，然后从第一产品混合物中除去未反应的高沸点第一醇。然后将 FDCA 第一酯和高沸点第一醇与选自甲醇、乙醇、异丙醇和正丙醇的低沸点第二醇进行酯交换反应，形成由 FDCA 第二酯和低沸点第二醇组成的第二产物混合物，并回收 FDCA 第二酯和低沸点第二醇。
• COMPOSITIONS AND METHODS FOR PRODUCING CHEMICALS AND DERIVATIVES THEREOF
  申请人：Synthetic Genomics, Inc.

  公开号：US20140206047A1

  公开（公告）日：2014-07-24

  The present invention provides methods for producing a product of one or more enzymatic pathways. The pathways used in the methods of the invention involve one or more conversion steps such as, for example, an enzymatic conversion of guluronic acid into D-glucarate (Step 7); an enzymatic conversion of 5-ketogluconate (5-KGA) into L-Iduronic acid (Step 15); an enzymatic conversion of L-Iduronic acid into Idaric acid Step 7b); and an enzymatic conversion of 5-ketocluconate into 4,6-dihydroxy 2,5-diketo hexanoate (2,5-DDH) (Step 16). In some embodiments the methods of the invention produce 2,5-furandicarboxylic acid (FDCA) as a product. The methods include both enzymatic and chemical conversions as steps. Various pathways are also provided for converting glucose into 5-dehdyro-4-deoxy-glucarate (DDG), and for converting glucose into 2,5-furandicarboxylic acid (FDCA). The methods also involve the use of engineered enzymes that perform reactions with high specificity and efficiency. Additional products that can be produce include metabolic products such as, but not limited to, guluronic acid, L-iduronic acid, idaric acid, glucaric acid. Any of the products can be produced using glucose as a substrate or using any intermediate in any of the methods or pathways of the invention.
• USE OF CARBOXYLIC ACIDS AND FURANIC MOLECULES FOR ESTERIFICATION
  申请人：Archer Daniels Midland Company

  公开号：US20170015643A1

  公开（公告）日：2017-01-19

  A process for recovering and using an organic/carboxylic acid or furanic molecule by means of making an ester of a free carboxylic acid or furanic molecule with an alcohol in carbon dioxide (CO 2 ) without the presence of any other acid catalyst at a reaction temperature and pressure that corresponds to supercritical, critical or near critical conditions for the alcohol and/or CO 2 is described. The process can constitute part of a general process of refining carboxylic acids derived from a fermentation broth or use in the production of a variety of chemical compounds, such as C 4 platform compounds or polymers.
• PROCESS FOR MAKING ESTERS OF 2,5-FURANDICARBOXYLIC ACID
  申请人：Archer Daniels Midland Company

  公开号：US20200102280A1

  公开（公告）日：2020-04-02

  A process is provided for making esters of FDCA, in which an aqueous feed comprising glucaric acid is first reacted with a high boiling first alcohol in the presence of an acid catalyst and with removing water during the reaction, to form a first product mixture comprising a first ester of FDCA and the high boiling first alcohol, then unreacted high boiling first alcohol is removed from the first product mixture. The first ester of FDCA and the high boiling first alcohol is then transesterified with a lower boiling second alcohol selected from the group consisting of methanol, ethanol, isopropanol and n-propanol, to form a second product mixture comprising a second ester of FDCA with the lower boiling second alcohol, and the second ester of FDCA with the lower boiling second alcohol is recovered.
• US9528133B2
  申请人：——

  公开号：US9528133B2

  公开（公告）日：2016-12-27