5-甲基-2-呋喃甲硫醇 | 59303-05-8

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 5-甲基-2-呋喃甲硫醇
• 英文名称: 5-methyl-2-furanmethanethiol
• 英文别名: 5-methyl-2-furfurylthiol；5-methylfurfurylthiol；2-Mercaptomethyl-5-methyl-furan；(5-Methyl-[2]furyl)-methanthiol；(5-Methylfuran-2-yl)methyl mercaptan；5-methyl-2-furanylmethylmercaptan；(5-methylfuran-2-yl)methanethiol
• CAS: 59303-05-8
• 化学式: C₆H₈OS
• 分子量: 128.195
• InChiKey: MGLMZOFGBDYNMH-UHFFFAOYSA-N

物化性质

• 沸点：
  180℃
• 密度：
  1.078
• 闪点：
  63℃
• LogP：
  2.36
• 物理描述：
  Colourless to yellow clear liquid; Sulfurous roasted coffee aroma
• 溶解度：
  Slightly soluble in water
• 折光率：
  1.523-1.529
• 保留指数：
  993

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  14.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险类别：
  9
• 危险性防范说明：
  P210,P261,P264,P270,P271,P280,P302+P352,P304+P340,P305+P351+P338,P310,P330,P332+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501,P273
• 危险品运输编号：
  3334
• 危险性描述：
  H302,H315,H318,H335,H227,H410
• 包装等级：
  III

反应信息

• 作为反应物：
  描述：

  5-甲基-2-呋喃甲硫醇 在 二叔丁基过氧化物 、 potassium ethoxide 作用下， 以 乙醇 为溶剂， 生成 5-Methylfuran-2-thioaldehyde anion radical
  参考文献：
  名称：

  Rotational conformers of furan- and thiophenethioaldehyde anion radicals

  摘要：

  The radical anions of the four isomeric furan and thiophene thioaldehydes have been obtained by photolysis, in an alkaline medium, of the corresponding thiols in the presence of di-tert-butyl peroxide. The same reaction also yields the four corresponding aldehyde radical anions, starting from the appropriate alcohols. The ESR spectra show that in most cases the two rotational conformers (E and Z) are present at the equilibrium. By means of appropriate methyl-substituted derivatives it has been possible to assign the structure of the two conformers. In the case of the 2-furan and 2-thiophene aldehyde anion radicals it has been also found that the conformational preference is the same as that exhibited by the corresponding molecules.

  DOI：

  10.1021/jo00022a023
• 作为产物：
  描述：

  5-甲基呋喃醛 在 baker's yeast 、 phosphate buffer 作用下， 以 水 为溶剂， 反应 1.0h， 生成 5-甲基-2-呋喃甲硫醇
  参考文献：
  名称：

  Generation of Thiols by Biotransformation of Cysteine−Aldehyde Conjugates with Baker's Yeast

  摘要：

  Baker's yeast was shown to catalyze the transformation of cysteine-furfural conjugate into 2-furfurylthiol. The biotransformation's yield and kinetics were influenced by the reaction parameters such as pH, incubation mode (aerobic and anaerobic), and substrate concentration. 2-Furfurylthiol wets obtained in an optimal 37% yield when cysteine-furfural conjugate at a 20 mM concentration wets anaerobically incubated with whole cell baker's yeast at pH 8.0 and 30 degreesC. Similarly to 2-furfurylthiol, 5-methyl-2-furfurylthiol (11%), benzylthiol (8%), 2-thiophenemethanethiol (22%), 3-methyl-2-thiophenemethanethiol (3%), and 2-pyrrolemethanethiol (6%) were obtained from the corresponding cysteine-aldehyde conjugates by incubation with baker's yeast. This work indicates the versatile bioconversion capacity of baker's yeast for the generation of thiols from cysteine-alclehyde conjugates. Thanks to its food-grade character, baker's yeast provides a biochemical tool to produce thiols, which can be used as flavorings in foods and beverages.

  DOI：

  10.1021/jf026198j

文献信息

• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• Pteridine compounds for the treatment of psoriasis
  申请人：——

  公开号：US20030055250A1

  公开（公告）日：2003-03-20

  The invention provides pteridine compounds of formula (I), processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in therapy. Formula (I) in which A is a group of formula (a) or (b).

  本发明提供了式(I)的蝶啶化合物，制备这些化合物的方法和中间体，含有这些化合物的药物组合物，以及它们在治疗中的用途。式(I)中，A为式(a)或式(b)的基团。
• 7-amino-2-alkylthiopteridin-4-yl-amines for the treatment of chemokine-related diseases
  申请人：——

  公开号：US20040102447A1

  公开（公告）日：2004-05-27

  Pteridine compounds of formula (I) in which R 1 , R 2 , R 3 and R 4 are as specified in the claims, processes and intermediates used in their preparation, pharmaceutical compositions containing them and their use in the treatment of inflammatory diseases such as psoriasis, rheumatoid arthritis, diseases in which angiogenesis is assocated with raised CXCR2 chemokine levels (diabetic retinopathy) and COPD. The compounds are ligands for chemokine receptors and medical indications mentioned in the description include: diseases of the respiratory tract (COPDD, asthma, bronchitis, rhinitis, fibroid lung, pneumonia, etc.), diseases of the bones and joints (arthritis, etc.), skin-diseases (psoriasis, etc), diseases of the gastrointestinal tract, diseases in other tissues and systemic disease (multipe sclerosis, atherosclerosis, AIDS, type 1 diabetes, leprosy, sepsis, etc.), allograft rejection, cancers, cystic fibrosis, stroke, burn wounds, skin ulcers, reproductive disease and more.

  式(I)的蝶啶化合物，其中R1、R2、R3和R4如权利要求中所定义，用于其制备的方法和中间体，含有它们的药物组合物，以及它们在治疗如牛皮癣、类风湿性关节炎、与升高的CXCR2趋化因子水平相关的血管生成疾病（糖尿病性视网膜病变）和慢性阻塞性肺病（COPD）等炎症性疾病中的用途。这些化合物是趋化因子受体的配体，描述中提到的医疗适应症包括：呼吸道疾病（COPD、哮喘、支气管炎、鼻炎、纤维化肺、肺炎等）、骨关节疾病（关节炎等）、皮肤病（牛皮癣等）、胃肠道疾病、其他组织疾病和全身性疾病（多发性硬化症、动脉粥样硬化、艾滋病、1型糖尿病、麻风病、败血症等）、异体移植排斥、癌症、囊性纤维化、中风、烧伤伤口、皮肤溃疡、生殖疾病等。
• Highly enantioselective sulfa-Michael addition reactions using N-heterocyclic carbene as a non-covalent organocatalyst
  作者：Jiean Chen、Sixuan Meng、Leming Wang、Hongmei Tang、Yong Huang

  DOI：10.1039/c5sc00878f

  日期：——

  We report the first asymmetric sulfa-Michael addition (SMA) reactions using chiral N-heterocyclic carbene (NHC) as a non-covalent organocatalyst. We demonstrate that a triazolium salt derived NHC functions as an excellent...

  我们报告使用手性N-杂环卡宾（NHC）作为非共价有机催化剂的第一个不对称磺胺-迈克尔加成（SMA）反应。我们证明了三唑盐衍生的NHC具有出色的...
• Structure–Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol
  作者：Sebastian Schoenauer、Peter Schieberle

  DOI：10.1021/acs.jafc.8b00857

  日期：2018.4.25

  seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure–odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers

  呋喃-2-基甲硫醇（2-糠硫醇； 2-FFT，1）是众所周知的烘烤和磨碎咖啡中的主要气味剂，先前还被广泛用于肉类，面包和烘焙等热处理食品中芝麻籽。其独特的咖啡香气质量非常低浓度引起，而事实上，呈现出类似的结构，只有极少数的化合物先前已在食品中描述使1结构-气味活性研究的合适人选。为了深入了解在低浓度下会发出类似咖啡的气味的结构特征，合成了46种杂环硫醇和硫醚，其中32种首次合成，并确定了它们的气味质量和气味阈值。巯基向3位的移动保持了咖啡样的香气，但是导致了气味阈值的增加。由于碳侧链的延长，硫醇基团与呋喃环的分离导致咖啡味气味的损失，并且还导致气味阈值的增加，尤其是对于ω-（呋喃-2-基）烷烃-在侧链中具有六个或七个碳原子的1-硫醇。呋喃环被噻吩环取代对大多数所研究化合物的气味特性没有显着影响，但是新合成的长链1-（呋喃-2-基）-和1-（噻吩-2-基）烷烃-1-硫醇引发了令人兴奋的百香果

表征谱图