二甲基甲氧基苯并二氢吡喃醇 | 83923-51-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 二甲基甲氧基苯并二氢吡喃醇
• 英文名称: 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran
• 英文别名: dimethyl methoxy chromanol；7-methoxy-2,2-dimethylchroman-6-ol；CR-6；Lipochroman 6；Dimethylmethoxy chromanol；7-methoxy-2,2-dimethyl-3,4-dihydrochromen-6-ol
• CAS: 83923-51-7
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: JXPHIHWXMBYJAU-UHFFFAOYSA-N

物化性质

• 沸点：
  329.0±42.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

制备方法与用途

二甲基甲氧基苯并二氢吡喃醇具有双重抗氧化作用，能捕捉对氧自由基（ROS）和氮自由基（RNS）。它还能抑制过氧亚硝基阴离子引发的脂质过氧化反应，并防止由此导致的皮肤细胞损害。此外，通过抑制紫外线A产生的氧自由基，这种成分能够有效抗污染，净化肌肤。

反应信息

• 作为反应物：
  描述：

  二甲基甲氧基苯并二氢吡喃醇 在 溶剂黄146 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 0.03h， 以50%的产率得到3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-5-nitro-1(2H)-benzopyran
  参考文献：
  名称：

  Prevention of glutamate neurotoxicity in cultured neurons by 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran (CR-6), a scavenger of nitric oxide

  摘要：

  Glutamate neurotoxicity in cerebellar neurons in culture is mediated by excessive production of nitric oxide (NO). We anticipated that 3,4-dihydro 6-hydroxy-7-methoxy-2,2-dimethyl-1(2H) -benzopyran (CR-6) could act as a scavenger of NO since it contains a position (C-5) highly activated towards nitration reaction. The aim of this work was to assess whether CR-6 acts as an NO scavenger and prevents glutamate neurotoxicity in cultures of cerebellar neurons. It was shown that CR-6 reduced, in a dose-dependent manner, glutamate-induced formation of cGMP (EC50 approximate to 15 mu M) and prevented glutamate neurotoxicity. The protection was approximate to 50% at 3-10 mu M and nearly complete at 100 mu M. CR-6 did not prevent glutamate-induced activation of NO synthase, but interfered with the glutamate-NO-cGMP pathway at a later step. CR-6 reduced the formation of cGMP induced by S-nitroso-N-acetylpenicillamine (SNAP), an NO-generating agent, indicating that CR-6 acts as a scavenger of NO in cultured neurons. This was further supported by experiments showing that in neurons treated with CR-6 and glutamate, the 5-nitro derivative of CR-6 was formed, as determined by GC-MS analyses. Moreover, in vitro incubation of CR-6 with SNAP also produced the 5-nitroderivative, thus confirming that CR-6 directly reacts with NO. The results reported indicate that CR-6 acts as an NO scavenger in neurons and prevents glutamate neurotoxicity. (C) 1999 EIsevier Science Inc.

  DOI：

  10.1016/s0006-2952(99)00104-5
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 lithium aluminium tetrahydride 、 PPA 作用下， 以 乙醚 为溶剂， 反应 5.5h， 生成 二甲基甲氧基苯并二氢吡喃醇
  参考文献：
  名称：

  Anastasis, Panayiotis; Brown, Philip E., Journal of the Chemical Society. Perkin transactions I, 1982, # 9, p. 2013 - 2018

  摘要：

  DOI：

文献信息

• Cosmetic compositions
  申请人：Symrise AG

  公开号：EP2745878A1

  公开（公告）日：2014-06-25

  Suggested is a cosmetic compositions comprising (a) a crosspolymer obtained from copolymerisation of at least two different polyols and at least one dicarboxylic acid and (b) at least one fragrance.

  建议的是一种化妆品组合物，包括 (a) 由至少两种不同的多元醇和至少一种二羧酸共聚得到的交联聚合物，以及 (b) 至少一种香料。
• NOVEL USE OF SUBSTITUTED CHROMAN-6-OLS
  申请人：DSM IP ASSETS B.V.

  公开号：US20210030022A1

  公开（公告）日：2021-02-04

  The present invention is directed towards the use of substituted chroman-6-ols of formula (I) wherein R 1 and R 2 are independently from each other H or C 1-11 -alkyl or (CH 2 ) n —OH with n being an integer from 1 to 4, or R 1 and R 2 represent together a keto group, 10 A is CHR 3 or C(═O), and wherein R 3 , R 4 and R 6 are independently from each other H or C 1-4 -alkyl, and wherein R 5 is H or OH or C 1-4 -alkyl or C 1-4 -alkoxy, as antioxidants, especially in feed such as pet food and feed ingredients such as fish meal, insect meal and poultry meal, as well as PUFA-containing oil such as marine oil, microbial oil, fungal oil, algal oil and PUFA-containing plant oil. The present invention is further directed towards feed ingredients and feed for insects, aquatic and terrestrial animals comprising such substituted chroman-6-ols of formula (I).

  本发明涉及使用式(I)的取代基氧杂环己烯-6-醇，其中R1和R2分别独立地为H或C1-11-烷基或(CH2)n—OH，其中n为1至4的整数，或者R1和R2共同表示酮基，A为CHR3或C(═O)，其中R3、R4和R6分别独立地为H或C1-4-烷基，R5为H或OH或C1-4-烷基或C1-4-烷氧基，作为抗氧化剂，特别是在饲料中，如宠物食品和饲料成分，如鱼粉、昆虫粉和禽畜粉，以及富含PUFA的油，如海洋油、微生物油、真菌油、藻类油和富含PUFA的植物油。本发明还涉及含有式(I)的这种取代基氧杂环己烯-6-醇的饲料成分和用于昆虫、水生和陆生动物的饲料。
• A study of the reaction of different phenol substrates with nitric oxide and peroxynitrite
  作者：Susana Yenes、Angel Messeguer

  DOI：10.1016/s0040-4020(99)00877-7

  日期：1999.12

  investigated. In general, nitration is the major reaction with peroxynitrite, while reactions with aqueous solutions of nitric oxide led to mixtures of nitro and nitroso derivatives depending upon the phenol. Nitrosation occurs on phenol substrates bearing a free para- position with respect to the OH group with the exception of 1-naphthol, which afforded a 1:1 mixture of the 2- and the 4-nitroso derivatives

  研究了不同酚类底物与一氧化氮和过氧亚硝酸盐的反应性。通常，硝化作用是与过氧亚硝酸盐的主要反应，而与一氧化氮水溶液的反应则导致硝基和亚硝基衍生物的混合物（取决于苯酚）。亚硝化作用发生在相对于OH基具有自由对位的苯酚底物上，1-萘酚除外，后者提供了2-和4-亚硝基衍生物的1：1混合物。Chromans 7和8与过氧亚硝酸盐具有最高的反应活性，这表明它们可以作为这种有毒中间体的有效清除剂。在两种情况下，相应的5-硝基衍生物都是唯一检测到的反应产物。最后，苯并二氢吡喃8与一氧化氮反应以90％的收率得到对苯醌衍生物22a这一事实表明，这种抗氧化剂也有可能作为生物组织中特定的一氧化氮示踪剂使用。
• COMPOUNDS FOR PREVENTING, REDUCING AND/OR ALLEVIATING ITCHY SKIN CONDITION(S)
  申请人：SCHMAUS Gerhard

  公开号：US20160008297A1

  公开（公告）日：2016-01-14

  The present invention primarily relates to the use of one or more specific compounds and/or one or more respective salt(s) thereof for preventing, reducing or alleviating itchy skin condition(s), and/or as PAR-2 antagonist. Furthermore, the present invention relates to compositions (products or, respectively, formulations), in particular for topical administration, preferably cosmetic or pharmaceutical compositions, in particular for preventing, reducing or alleviating one or more itchy skin conditions and/or for providing a PAR-2 antagonistic effect, comprising or consisting of an effect amount of such compound(s) and/or salt(s) and one or more cosmetically and/or pharmaceutically acceptable carriers.

  本发明主要涉及使用一种或多种特定化合物和/或其一个或多个相应盐来预防、减少或缓解瘙痒皮肤状况，和/或作为PAR-2拮抗剂。此外，本发明涉及组合物（产品或相应的配方），特别是用于局部给药，优选为化妆品或药用组合物，特别是用于预防、减少或缓解一种或多种瘙痒皮肤状况和/或产生PAR-2拮抗作用的组合物，包括或由效果量的这种化合物和/或盐以及一个或多个化妆品和/或药用可接受载体组成。
• USE OF DIHYDRODEHYDRODIISOEUGENOL AND PREPARATIONS COMPRISING DIHYDRODEHYDRODIISOEUGENOL
  申请人：Meyer Imke

  公开号：US20130101650A1

  公开（公告）日：2013-04-25

  This invention relates to cosmetic and pharmaceutical preparations comprising (i) a diastereomer or a mixture of two or more diastereomers of the compound of formula (I) or (ii) a salt of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I) or (iii) a mixture of two or more salts of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I), a diastereomer, salt or a mixture as defined above as a drug for topical application and/or for the treatment of lipoatrophy; the non-therapeutic use of a diastereomer, salt or a mixture as defined above for the prevention, treatment or reduction of skin aging, especially skin wrinkles; the use of a diastereomer, salt or a mixture as defined above for the production of an orally administered non-pharmaceutical preparation.

  本发明涉及包含(i)化合物的对映异构体或两个或两个以上对映异构体的混合物或(ii)化合物的对映异构体或两个或两个以上对映异构体的混合物的盐或(iii)化合物的对映异构体或两个或两个以上对映异构体的混合物的两个或两个以上盐的混合物的化妆品和药用制剂，上述对映异构体、盐或混合物被定义为用于局部应用的药物和/或治疗脂肪萎缩；上述对映异构体、盐或混合物的非治疗用途被定义为用于预防、治疗或减少皮肤老化，特别是皱纹；上述对映异构体、盐或混合物被定义为用于制造口服非药用制剂。