(E)-2-heptadecenal | 120681-49-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-heptadecenal
• 英文别名: 8Z-Heptadecenal；2-Heptadecenal；(E)-heptadec-2-enal
• CAS: 120681-49-4
• 化学式: C₁₇H₃₂O
• 分子量: 252.44
• InChiKey: UQLOJDJIDRLJJE-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-heptadecenal 、 2-二苯基乙酰-1,3-茚酮-1-腙 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Activation of the Kelch-like ECH-Associated Protein 1 (Keap1)/NF-E2-Related Factor 2 (Nrf2) Pathway through Covalent Modification of the 2-Alkenal Group of Aliphatic Electrophiles in Coriandrum sativum L.

  摘要：

  Phytochemicals able to activate the transcription factor NF-E2-related factor 2 (Nrf2) were isolated from an extract of Coriandrum sativum L. (C. sativum) leaves by preparative octadecyl silica column chromatography. Ultraperformance liquid chromatography and liquid chromatography-tandem mass spectrometry analysis of the isolated components after derivatization with 2-diphenylacetyl-1,3-inandione-1-hydrazone and experiments with HepG2 cells revealed that (E)-2-alkenals with different carbon numbers play a role in Nrf2 activation in these cells. Such Nrf2 activation appears to be attributable to S-alkylation of Kelch-like ECH-associated protein 1 (Keap1), the negative regulator for Nrf2, as determined by a biotin-PEAC(5)-maleimide assay. Interestingly, (E)-2-butenal caused Keap1 modification and Nrf2 activation, whereas butanal did not. These results suggest that (E)-2-alkenals with an alpha,beta-unsaturated aldehyde moiety, which is a common substituent in phytochemicals isolated from C. sativum leaves, activate the Keap1/Nrf2 pathway associated with cellular protection.

  DOI：

  10.1021/jf5030592
• 作为产物：
  描述：

  1-Methoxyheptadec-1-ene 在 十八硫醇 、 copper diacetate 、 palladium dichloride 作用下， 以 水 、 乙腈 为溶剂， 反应 22.0h， 以72%的产率得到(E)-2-heptadecenal
  参考文献：
  名称：

  无配体和水性条件下，极低的Pd催化剂负载下烯醇醚的Saegusa氧化：对Pd（II）/ Cu（II）-催化剂体系的了解

  摘要：

  Saegusa氧化的高效实用的Pd（II）/ Cu（OAc）2-催化剂体系，可在无配体的情况下以极低的催化剂负载量（500 mol ppm）将烯醇醚转化为具有多种底物的相应烯醛和水性条件，描述。催化剂体系在重要的自然分子上的大规模应用证明了其合成用途。这项工作使Saegusa氧化成为制备enals的一种高度实用的方法，并且还为对Pd（II）/ Cu（II）-用于羰基化合物脱氢和降低Pd-催化剂负载量的催化剂体系提出了新的见解。

  DOI：

  10.1021/acs.joc.0c02987

文献信息

• [DE] (Z)-8-CYCLOHEPTADECEN-1-ON ALS RIECHSTOFF<br/>[EN] (Z)-8-CYCLOHEPTADECENE-1-ONE USED AS A PERFUME<br/>[FR] (Z)-8-CYCLOHEPTADECENE-1-ONE UTILISEE COMME PARFUM
  申请人：SYMRISE GMBH & CO KG

  公开号：WO2006032665A1

  公开（公告）日：2006-03-30

  Beschrieben wird (Z)-8-Cycloheptadecen-1-on als Riechstoff sowie eine Riech- oder Aromastoffmischung umfassend (Z)-8-Cycloheptadecen-1-on und einen oder mehrere weitere Riech- oder Aromastoffe.

  (Z)-8-Cycloheptadecen-1-on被描述为一种香味物质，以及一种包含(Z)-8-Cycloheptadecen-1-on和一个或多个其他香气物质的香气或香味混合物。
• Ailanthone derivatives
  申请人：SUNTORY LIMITED

  公开号：EP0080570A2

  公开（公告）日：1983-06-08

  Novel antineoplastic ailanthone derivatives (IIb) represented by the following formula wherein R2 is C5-C18 α, β-unsaturated acyl group and its related compounds are disclosed. Particularly, some of the above compounds are far more effective than mitomycin C against mouse lymphocytic leucemia p388. These compound can be synthesized from known ailanthone via important intermediates, triacyloxy ailanthone, represented by the formula: wherein R, is acyl group.

  本研究公开了由下式（其中 R2 为 C5-C18 α、β-不饱和酰基）代表的新型抗肿瘤紫罗兰酮衍生物（IIb）及其相关化合物。 特别是，上述某些化合物对小鼠淋巴细胞白血病 p388 的疗效远高于丝裂霉素 C。 这些化合物可以从已知的艾兰通通过重要的中间体合成，三乙氧基艾兰通，由式表示： 其中 R 是酰基。
• (Z)-8-CYCLOHEPTADECEN-1-ON ALS RIECHSTOFF
  申请人：Symrise GmbH & Co. KG

  公开号：EP1797026A1

  公开（公告）日：2007-06-20
• NEUE RIECHSTOFFE MIT ROSENGERUCH
  申请人：Symrise AG

  公开号：EP3826986A1

  公开（公告）日：2021-06-02
• COOLING SENSATION AGENT COMPOSITION AND SENSORY STIMULATION AGENT COMPOSITION
  申请人：Ishida Kenya

  公开号：US20110117147A1

  公开（公告）日：2011-05-19

  The invention relates to a cooling sensation agent composition with a prolonged cool sensation effect comprising at least one compound selected from Formula (1) wherein each of A and B is a hydrogen atom or a hydrocarbon group which may have one or more substituents, in which A and B are not hydrogen atoms simultaneously, and the total number of carbon atoms in A and B is in the range of 6 to 18; and Formulae (2) to (4) wherein R1, R2, and R3 each represent a residue of an alcohol selected from 1-menthol, 1-isopulegol, 3-(1-menthoxy)propan-1,2-diol, 2-(1-menthoxy)ethan-1-ol, 3-(1-menthoxy)propan-1-ol, 2-methyl-3-(1-menthoxy)propan-1,2-diol and para-menthan-3,8-diol), and R4 represents a residue of a branched or straight-chain, cyclic or linear, or saturated or unsaturated alcohol having 6 to 18 carbon atoms that may have one or more aromatic rings that may have a condensed ring and substituent groups such as hydroxyl and ether groups; and R6 represents a hydrocarbon group having 11 to 19 carbon atoms that may be branched and contain one or more unsaturated bonds. The invention also relates to a sensory stimulation agent composition comprising the cooling sensation agent composition; a flavor or fragrance composition, a beverage or food product, a perfume or cosmetic product, a toiletry product, a daily utensil product or grocery, a fiber, a fiber product, a cloth or a medicine comprising the cooling sensation agent composition or the sensory stimulation agent composition; a production method thereof; a cooling processing method of a fiber, fiber product or a cloth, comprising compounding the cooling sensation agent composition or the sensory stimulation agent composition; and new compounds.