CAS: 498-00-0; 4-(Hydroxymethyl)-2-Methoxyphenol

该化合物是一种含有分子式C8H10O3的酚类衍生物,它是白白的,白白的晶状固体,在极地有机溶剂中可溶,在水中可略溶. 作为多种用途的中间体,香醇广泛用于制药合成,香味生产,并用作香林和其他调味化合物的前体.其主要优势包括高纯度,标准条件下的稳定性,以及与各种化学反应的兼容性,如氧化和醚化. 化合物的双功能氢氧和甲氧基混合物对精细的化学应用很有价值,为定制合成提供了精确的再活动性. 建议妥善处理和储存以保持其完整性.

结构式图片

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

CAS号121-33-5 香草醛 | CAS号121-34-6 香草酸 | CAS号93-51-6 2-甲氧基-4-甲基苯酚 | CAS号1058649-10-7 4-((ethoxymetho... | CAS号1058649-06-1 2-methoxy-4-((m... | CAS号86534-11-4 (3-methoxy-4-pr... | CAS号93-07-2 藜芦酸 | CAS号33693-48-0 4-苄氧基-3-甲氧基苯甲醇 | CAS号495-76-1 胡椒醇 | CAS号109685-13-4 2-methoxy-4-(me... | CAS号1078-26-8 1,2,3,4-四氢-6-甲氧... | CAS号33693-48-0 4-苄氧基-3-甲氧基苯甲醇 | CAS号3897-89-0 3,4-二羟基苄醇 | CAS号3251-56-7 2-甲氧基-4-硝基苯酚 | CAS号6635-20-7 5-硝基香草醛 | CAS号56024-44-3 3-(4-羟基-3-甲氧基苯基)丙酸甲酯 | CAS号4468-59-1 3-甲氧基-4-羟基苯乙腈 | CAS号2207-57-0 2-甲氧基-3-甲基-[1,4... | CAS号18102-32-4 4-hydroxy-3-met...

合成工艺路线路线简述

    香草醛置于二(三苯基膦)环戊二烯基氯化钌(II),苯硅烷,四丁基氟化铵体系中,用 甲苯 作为反应溶剂,化学反应 24.5H,以63%的收率获得产物4-羟基-3-甲氧基苄醇
    参考文献:环戊二烯基钌(II)配合物可作为还原羰基化合物的有效催化剂
    标题:环戊二烯基钌(II)配合物可作为还原羰基化合物的有效催化剂
    摘要:这项工作报告说,使用phsih 3 / [cpru(pph 3)2 Cl]系统可以很好地还原产率很高的化合物,并且具有很高的化学选择性,可以还原多种醛和酮.催化剂[cpru(pph 3)2 Cl]可用于至少12个催化循环,具有出色的催化活性,并且在无溶剂条件下还原了几种底物.
    DOI:10.1016/j.Tet.2017.01.067

    海关参考信息

    专利信息


    专利号:US-10308588-B2
    优先权日:2014-12-15
    标 题 :Synthesis of amides and amines from aldehydes or ketones by heterogeneous metal catalysis
    发明人:CÓRDOVA ARMANDO; PALO-NIETO CARLOS; AFEWERKI SAMSON
    权利人:ORGANOFUEL SWEDEN AB
    摘要:A mild and efficient synthesis of primary amines and amides from aldehydes or ketones using a heterogeneous metal catalyst and amine donor is disclosed. The initial heterogeneous metal-catalyzed reaction between the carbonyl and the amine donor components is followed by the addition of a suitable acylating agent component in one-pot, thus providing a catalytic one-pot three-component synthesis of amides. Integration of enzyme catalysis allows for eco-friendly one-pot co-catalytic synthesis of amides from aldehyde and ketone substrates, respectively. The process can be applied to asymmetric synthesis or to the co-catalytic one-pot three-component synthesis of capsaicin and its analogues from vanillin or vanillyl alcohol. A co-catalytic reductive amination/dynamic kinetic resolution (dkr) relay sequence for the asymmetric synthesis of optically active amides from ketones is disclosed. Implementation of a catalytic reductive amination/kinetic resolution (kr) relay sequence produces the corresponding optically active amide product and optical active primary amine product with the opposite stereochemistry from the starting ketones.

    专利号:US-11168050-B2
    优先权日:2014-03-27
    标 题 :Efficient synthesis of amines and amides from alcohols and aldehydes by using cascade catalysis
    发明人:CÓRDOVA ARMANDO; BERGLUND PER; ANDERSON MATTIAS; AFEWERKI SAMSON
    权利人:XP CHEMISTRIES AB
    摘要:The present invention relates generally to an eco-friendly methodology for the conversion of alcohols and aldehydes to amines and amides using an integrated enzyme cascade system with metal- and organocatalysis. More specifically, the present invention relates to synthesis of capsaicinoids starting from vanillin alcohol and using a combination of an enzyme cascade system and catalysts. Furthermore, the method also relates to synthesis of capsaicinoids derivatives starting from vanillin alcohol derivatives and using a combination of an enzyme cascade system and catalysts.

    专利号:US-6372461-B1
    优先权日:1998-09-18
    标题 :Synthesis of vanillin from a carbon source
    发明人:FROST JOHN W
    权利人:DIRECTORS OPERATING MICHIGAN S
    摘要:A bioengineered synthesis scheme for the production of vanillin from a carbon source is provided. The bioconversion methods of the present invention comprise the steps of microbe-catalyzed conversion of a carbon source to vanillic acid followed by enzyme-catalyzed reduction of the vanillic acid to produce vanillin. As shown in the synthesis scheme of FIG. 2, the microbe-catalyzed conversion step of the present invention requires five enzymes which are provided by a recombinant microbe. In a preferred embodiment, the recombinant microbe is Escherichia coli designed to cause dehydration of 3-dehydroshikimic acid and regioselective methylation of the resulting protocatechuic acid. The enzyme-catalyzed reduction step of the present invention comprises the reduction of vanillic acid to vanillin by aryl-aldehyde dehydrogenase.

    专利号:EP-1548006-B1
    优先权日:2003-12-12
    标题 :Synthesis of tetraazapentamethine derivatives, keratin fibers dyeing process which uses such synthesis
    发明人:PEREIRA RUI; BURGAUD HERVE
    权利人:OREAL
    摘要:Producing tetraazapentamethine compounds (I) comprising reacting an azine compound with an oxidizing agent, is new. Producing tetraazapentamethine compounds of formula (I) comprises reacting an azine compound of formula (VI) or (VII) with an oxidizing agent; [Image] [Image] W1a cationic heteroaromatic group of formula (II) or (III); W2a heteroaromatic group of formula (IV) or (V); Z14Z7 or Z1; Z15Z8 or Z2; Z16Z13 or Z0; R25R5 or R1; Z17Z9 or Z3; Z18Z10 or Z4; Z19Z11 or Z5; Z20Z12 or Z6; R26R8 or R3; R27R7 or R4; R28, R29H, 1-6C alkyl or 1-6C alkoxy, but not both H; Z0CR2, N or NR21; Z1O, S or NR9; Z2N or CR10; Z3N or CR11; Z4N or CR12; Z5N or CR13; Z5N or CR13; Z6N or CR14; Z7O, S or NR15; Z8N or CR16; Z9N or CR17; Z10N or CR18; Z11N or CR19; Z12N or CR20; Z13CR6, N or NR22; R2, R6, R10, R16H; 1-4C alkyl substituted with 0-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH or SO3H; phenyl substituted with 0-2 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino; COOH; sulfonylamino; R1, R4, R5, R7, R9, R15, R21, R221-6C alkyl substituted with 0-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH or SO3H; R0, R3, R8, R11-R14, R17-R20H; 1-6C linear or branched hydrocarbyl with 0-3 unsaturations, optionally substituted with 1-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH, SO3H, sulfonylamino, 2-4C (poly)hydroxyalkylamino or halo and optionally interrupted by O, N, S or SO2; phenyl optionally substituted with 1-3 of OH, 1-2C alkoxy, 2-4C (poly)hydroxyalkoxy, NH2, 1-2C (di)alkylamino, COOH, SO3H, sulfonylamino, 2-4C (poly)hydroxyalkylamino or halo; pyrazolyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, triazolyl, pyridyl, pyrimidinyl, triazinyl, pyrazinyl or pyridazinyl; X : an anion; R2+R10, R11+R12, R6+R16, R17+R18 can form a 5-6C aromatic ring substituted with 0-2 of OH, NH2, 1-2C (di)alkylamino, 1-2C alkoxy, 2-4C (poly)hydroxyalkylamino. An independent claim is also included for dyeing keratinic fibers by applying (VI) or (VII) onto the wet or dry fibers in the presence of an oxidizing agent. [Image].

    专利号:US-7288120-B2
    优先权日:2003-12-12
    标题 :Synthesis of tetraazapentamethine compounds, and processes for dyeing keratin fibers using this synthesis
    发明人:PEREIRA RUI; BURGAUD HERVE
    权利人:OREAL
    摘要:The present disclosure relates to processes for synthesizing tetraazapentamethine compounds that comprise reacting at least one compound of azine type with at least one oxidizing agent. The disclosure also relates to processes for dyeing keratin fibers, for example human keratin fibers, that comprise using such synthetic processes.

    专利号:US-7462470-B2
    优先权日:2005-06-17
    标 题 :Method for the producing vanillic acid and vanillin from waste residue of rice bran oil by fermentation and biotransformation
    发明人:SUN ZHIHAO; ZHENG PU; GUO XINFU; LIN GUANYU; YIN HANGHUA; WANG JUN; BAI YANBING
    权利人:ZHEJIANG HANGZHOU XINFU PHARMA
    摘要:A method for the production of vanillic acid and vanillin from waste residue (niger) of rice bran oil by microbial fermentation and biotransformation is provided. The method of the present invention comprises the steps of hydrolization of ferulic acid esters in waste residue of rice bran oil to ferulic acid and further conversion into vanillic acid using microbial strain Aspergillus niger CGMCC 0774 screened and preserved by the present inventor, followed by conversion of vanillic acid to produce vanillin using another microbial strain Pycnoporus cinnabarinus CGMCC 1115. The method for the production of vanillin according to the present invention utilizes renewable source from rice processing and alleviates the environmental pollution caused by the chemical synthesis of vanillin.
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    主要参考文献

    [参考文献]: Chen Z, Et Al. Establishing An Artificial Pathway For De Novo Biosynthesis Of Vanillyl Alcohol In Escherichia Coli. Acs Synth Biol. 2017 Sep 15;6(9):1784-1792.
    [参考文献]: Aditya M Kunjapur, Et Al. Synthesis And Accumulation Of Aromatic Aldehydes In An Engineered Strain Of Escherichia Coli. J Am Chem Soc. 2014 Aug 20;136(33):11644-54.
    [参考文献]: Farid Khallouki, Et Al. Ethnobotanical Survey, Chemical Composition, And Antioxidant Capacity Of Methanolic Extract Of The Root Bark Of Annona Cuneata Oliv. J Med Food. 2011 Nov;14(11):1397-402.
    [参考文献]: Hanqi Gu, Et Al. High Tolerance And Physiological Mechanism Of Zymomonas Mobilis To Phenolic Inhibitors In Ethanol Fermentation Of Corncob Residue. Biotechnol Bioeng. 2015 Sep;112(9):1770-82.
    [参考文献]: Kambiz Morabbi Heravi, Et Al. Transcriptional Regulation Of The Vanillate Utilization Genes (Vanabk Operon) Of Corynebacterium Glutamicum By Vanr, A Padr-Like Repressor. J Bacteriol. 2015 Mar;197(5):959-72.

    合成参考文献


    摘要:Lamm, A. S.; Venkitasubramanian, P.; Rosazza, J. P. N., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 470.
    摘要:Lamm, A. S.; Venkitasubramanian, P.; Rosazza, J. P. N., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 2, 473.
    摘要:Ewing, T. A.; Fraaije, M. W.; van Berkel, W. J. H., Science of Synthesis: Biocatalysis in Organic Synthesis, (2015) 3, 165.
    参考文献:10.1007/s00253-001-0926-z
    摘要:Ichinose H, Nakamizo M, Wariishi H, Tanaka H. Metabolic response against sulfur-containing heterocyclic compounds by the lignin-degrading basidiomycete Coriolus versicolor. Applied Microbiology and Biotechnology. 2002 Feb 01;58(4):517–26. doi: 10.1007/s00253-001-0926-z.
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