(5-甲酰基呋喃-2-基)甲基硫酸氢酯 | 159091-35-7

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (5-甲酰基呋喃-2-基)甲基硫酸氢酯
• 中文别名: 5-硫代氧代甲基糖醛
• 英文名称: 5-Sulfooxymethylfurfural
• 英文别名: 5-sulfoxymethylfurfural；(5-formylfuran-2-yl)methyl hydrogen sulfate
• CAS: 159091-35-7
• 化学式: C₆H₆O₆S
• 分子量: 206.176
• InChiKey: WVMJEBICTINBRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

ADMET

代谢

5-磺酸甲氧基甲基呋喃醛是5-羟基甲基呋喃醛的人类已知代谢物。

5-Sulfooxymethylfurfural is a known human metabolite of 5-hydroxymethylfurfural.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  (5-甲酰基呋喃-2-基)甲基硫酸氢酯 、 2'-脱氧腺苷 反应 24.0h， 生成 N6-((2-formylfuran-5-yl)methyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Mutagenicity of 5-Hydroxymethylfurfural in V79 Cells Expressing Human SULT1A1: Identification and Mass Spectrometric Quantification of DNA Adducts Formed

  摘要：

  5-Hydroxymethylfurfural (HMF), a heterocyclic product of the Mallard reaction, is a ubiquitous food contaminant. It has demonstrated hepatocarcinogenic activity in female mice. This effect may originate from sulfo conjugation of the benzylic alcohol yielding 5-sulfooxymethylfurfural (SMF), which is prone to react with DNA via nucleophilic substitution. Indeed, we showed that HMF induces gene mutations in Chinese hamster V79 cells engineered for the expression of human (h) sulfotransferase (SULT)1A1 but not in parental V79 cells. In order to identify potential DNA adducts, we incubated DNA samples with SMF or HMF in aqueous solution. Modified DNA was digested and surveyed by liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) for adducts that may be formed by nucleosides either via nucleophilic substitution at the electrophilic carbon atom of SMF or via imine formation with the aldehyde group present in HMF and SMF. The most abundant adducts formed from SMF, N-6-((2-formylfuran-5-yl)methyl)-2'-deoxyadenosine (N-6-FFM-dAdo) and N-2((2-formylfuran-5-yl)methyl)-2'-deoxyguanosine (N-2-FFM-dGuo), were synthesized, purified, and characterized by H-1 NMR Imine adducts were only detected when DNA was incubated with very high levels of HMF following reduction of the imines to corresponding secondary amines by NaBH3CN. Sensitive techniques based on LC-MS/MS multiple reaction monitoring for the quantification of the adducts in DNA samples were devised using isotope-labeled [N-15(5)]N-6-FFM-dAdo and [C-13(10),N-15(15)]N-2-FFM-dGuo as internal standards. Both 5-methylfurfuryl adducts were detected in DNA from V79-hSULT1A1 treated with HMF but not in DNA from V79 control cells. Considering the lack of other known mutagenic metabolites, we hypothesize that the hepatocarcinogenic potential of HMF originates from the formation of mutagenic SMF.

  DOI：

  10.1021/tx300150n

文献信息

• USE OF ULTRASOUND IN WINE-MAKING PROCESSES
  申请人：Productos Agrovin S.A.

  公开号：EP3117899A1

  公开（公告）日：2017-01-18

  The present invention refers to a method and an equipment for the extraction of compounds from grapes by means of ultrasound in vinification processes generated through a sonoplate coupled to the walls of the pipe/duct through which the crushed grapes flow. During this extraction the transfer of phenols responsible for color from the solid portion (skin) to the liquid portion after crushing the grapes takes place as a consequence of the phenomenon known as cavitation, which allows the breaking of the skin cells and makes the phenolic compounds responsible for the color available to the liquid medium to be integrated in said liquid medium enhancing wine color.

  本发明涉及一种方法和设备，用于在酿造过程中通过超声波从葡萄中提取化合物，超声波是通过与管道壁相连的声波板产生的，粉碎的葡萄流经管道。在萃取过程中，由于所谓的空化现象，使葡萄果皮细胞破损，导致葡萄固态部分（果皮）的酚类物质转移到液态部分，从而使液体介质中的酚类化合物增加葡萄酒的颜色。
• Application of ultrasound in vinification processes
  申请人：PRODUCTOS AGROVIN, S.A.

  公开号：US11045782B2

  公开（公告）日：2021-06-29

  The present invention refers to a method and an equipment for the extraction of compounds from grapes by means of ultrasound in vinification processes generated through a sonoplate coupled to the walls of the pipe/duct through which the crushed grapes flow. During this extraction the transfer of phenols responsible for color from the solid portion (skin) to the liquid portion after crushing the grapes takes place as a consequence of the phenomenon known as cavitation, which allows the breaking of the skin cells and makes the phenolic compounds responsible for the color available to the liquid medium to be integrated in said liquid medium enhancing wine color.

  本发明涉及一种方法和设备，用于在酿造过程中通过超声波从葡萄中提取化合物，超声波是通过与管道壁相连的声波板产生的，粉碎的葡萄流经管道。在萃取过程中，由于所谓的空化现象，使葡萄果皮细胞破损，导致葡萄固态部分（果皮）的酚类物质转移到液态部分，从而使液体介质中的酚类化合物增加葡萄酒的颜色。
• METHOD FOR EXTRACTING COMPOUNDS FROM GRAPES BY ULTRASOUNDS
  申请人：Productos Agrovin S.A.

  公开号：EP3117899B1

  公开（公告）日：2019-02-20
• ULTRASOUND EQUIPMENT AND USE THEREOF FOR EXTRACTION OF COMPOUNDS FROM GRAPES IN VINIFICATION PROCESSES
  申请人：Productos Agrovin S.A.

  公开号：EP3485970B1

  公开（公告）日：2021-02-17
• APPLICATION OF ULTRASOUND IN VINIFICATION PROCESSES
  申请人：PRODUCTOS AGROVIN, S.A.

  公开号：US20170065960A1

  公开（公告）日：2017-03-09

  The present invention refers to a method and an equipment for the extraction of compounds from grapes by means of ultrasound in vinification processes generated through a sonoplate coupled to the walls of the pipe/duct through which the crushed grapes flow. During this extraction the transfer of phenols responsible for color from the solid portion (skin) to the liquid portion after crushing the grapes takes place as a consequence of the phenomenon known as cavitation, which allows the breaking of the skin cells and makes the phenolic compounds responsible for the color available to the liquid medium to be integrated in said liquid medium enhancing wine color.