CAS: 58749-22-7; (E)-3-(4-Hydroxy-2-Methoxy-5-(2-Methylbut-3-En-2-yl)Phenyl)-1-(4-Hydroxyphenyl)Prop-2-En-1-One

该化合物是天然产生的铬衍生物,主要与液晶根(Glycyrriza 物种)分离,它显示出显著的生物活动,包括抗炎,抗氧化剂和抗微生物特性,使它成为药物和化妆品研究的复合物.从结构上看,它具有一种带有氢氧基和甲基氧替代成分的铬骨干,有助于其再活动以及与生物目标的相互作用.Lecochacone A 已经证明有可能抑制诸如乙酰胆碱酶和环氧酶等酶,这表明在皮肤护理和治疗配方中应用了这种酶,已经研究了其稳定性和生物利用率,以优化运载系统.该化合物因其多功能特征和自然来源而具有价值.

结构式图片

欧盟法规

C&L通报

上下游产品

4-Hydroxy-2-methoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone 2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde 2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]benzaldehyde1-(4-hydroxyphenyl)-3-(5-(1,1-dimethylpropenyl)-4-hydroxy-2-methoxyphenyl)propan-1-one 23H24O5C23H24O5 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone

合成工艺路线路线简述

    4-Hydroxy-2-Methoxy-4'-(Methoxymethoxy)-5-(α,α-Dimethylallyl)Chalcone置于盐酸体系中,用 甲醇 作为反应溶剂,化学反应 0.17H,以300 Mg的收率获得产物甘草查耳酮a
    参考文献:Khan,Saeed Ahmad; Krishnamurti,M.,Indian Journal Of Chemistry-Section B Organic And Medicinal Chemistry,1983,Vol. 22,# 3,P. 276-277
    标题:Khan,Saeed Ahmad; Krishnamurti,M.,Indian Journal Of Chemistry-Section B Organic And Medicinal Chemistry,1983,Vol. 22,# 3,P. 276-277

    海关参考信息

    专利信息


    专利号:US-2007243147-A1
    优先权日:2004-07-24
    标 题:Skin and/or Hair Composition Containing Compounds for Increasing The Tanning of Skin
    发明人:WOLBER RAINER; TOM DIECK KAREN; SCHERNER CATHRIN; SCHLENZ KATHRIN; KRUSE INGE
    权利人:BEIERSDORF AG
    摘要:The invention relates to agents that are to be applied to the skin or hair and contain compounds for intensifying tanning of the skin and increasing melanin synthesis in skin or hair. The invention particularly relates to cosmetic or dermatological preparations. Using said preparations results in inducing and intensifying the tanning mechanisms of the skin, intensifying the hair color, and thus also increasing intrinsic protection of the skin or hair.

    专利号:US-2007189984-A1
    优先权日:2003-09-08
    标题:Agents for use on skin and/or hair containing quadruply substituted cyclohexene compounds
    发明人:WOLBER RAINER; SCHERNER CATHRIN; TOM DIECK KAREN; SCHLENZ KATHRIN; VIETZKE JENS-PETER
    权利人:BEIERSDORF AF
    摘要:The invention relates to agents for use on skin or hair, particularly for increasing skin tanning and the synthesis of melanin in skin or hair. The invention contains, in particular, cosmetic or dermatological preparations containing quadruply substituted cyclohexene compounds. The use of the preparations leads to the induction and intensification of the tanning mechanisms of skin, the intensification of hair color and thus also to an intensification of the skin's and hair's intrinsic protection.

    专利号:WO-2024083930-A1
    优先权日:2022-10-18
    标 题:Topically applied preparation for improving skin condition
    发明人:HEUER ANDREA; HÜPEDEN JENNIFER
    权利人:BEIERSDORF AG
    摘要:The invention relates to a topically applied preparation comprising a combination of substances including antimicrobial peptides (AMP), in particular cyclic peptide compounds based on the synthesis of thiazolidine and oxazolidine components, and skin-soothing substances such as menthoxypropanediol, substances to strengthen the skin barrier such as omega-6 fatty acids, and/or flavonoids such as licochalcone, which act synergetically and selectively against pathogenic bacteria, such as S. aureus and C. acnes , however not against skin-commensal bacteria, such as S. epidermidis . The preparations can be used advantageously for the treatment of acne or atopic dermatitis and to care for skin that has been damaged by acne or atopic dermatitis.

    专利号:WO-2024083413-A1
    优先权日:2022-10-18
    标题:Topically applied preparation with antimicrobial peptides
    发明人:HEUER ANDREA; HÜPEDEN JENNIFER
    权利人:BEIERDSORF AG
    摘要:The invention relates to a topically applied preparation comprising a combination of substances including antimicrobial peptides (AMP), in particular cyclic peptide compounds based on the synthesis of thiazolidine and oxazolidine components, and skin-soothing substances such as menthoxypropanediol, substances to strengthen the skin barrier such as omega-6 fatty acids, and/or flavonoids such as licochalcone, which act synergetically and selectively against pathogenic bacteria, such as S. aureus and C. acnes, however not against skin-commensal bacteria, such as S. epidermidis. The preparations can be used advantageously for the treatment of acne or atopic dermatitis and to care for skin that has been damaged by acne or atopic dermatitis.

    专利号:US-8367680-B2
    优先权日:2008-03-28
    标题:Antibacterial small molecules and methods for their synthesis
    发明人:BLACKWELL HELEN E; BOWMAN MATTHEW D; STRINGER JOSEPH R
    权利人:WISCONSIN ALUMNI RES FOUND; BLACKWELL HELEN E; BOWMAN MATTHEW D; STRINGER JOSEPH R
    摘要:The present invention relates generally to compounds providing antibacterial therapeutic agents and preparations, and related methods of using and making antibacterial compounds. Antibacterial compounds of the present invention include chalcone, alkylpyrimidine, aminopyrimidine and cyanopyridine compounds and derivatives thereof exhibiting minimum inhibitory concentrations (MIC) similar to or less than conventional antibacterial compounds in wide use.

    专利号:CN-107311936-A
    优先权日:2017-02-24
    标题 :A cyclization derivative of licochalcone A and phenformin with antitumor activity and its synthesis method
    南京沛微生物科技有限公司
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    主要参考文献


    1: Park MR, Kim SG, Cho IA, Oh D, Kang KR, Lee SY, Moon SM, Cho SS, Yoon G, Kim CS, Oh JS, You JS, Kim DK, Seo YS, Im HJ, Kim JS. Licochalcone-A induces intrinsic and extrinsic apoptosis via ERK1/2 and p38 phosphorylation-mediated TRAIL expression in head and neck squamous carcinoma FaDu cells. Food Chem Toxicol. 2015 Mar;77:34-43. doi: 10.1016/j.fct.2014.12.013.
    2: Kim SH, Yang M, Xu JG, Yu X, Qian XJ. Role of licochalcone A on thymic stromal lymphopoietin expression: implications for asthma. Exp Biol Med (Maywood). 2015 Jan;240(1):26-33. doi: 10.1177/1535370214545020.
    3: Choi JS, Choi JS, Choi DH. Effects of licochalcone A on the bioavailability and pharmacokinetics of nifedipine in rats: possible role of intestinal CYP3A4 and P-gp inhibition by licochalcone A. Biopharm Drug Dispos. 2014 Oct;35(7):382-90. doi: 10.1002/bdd.1905. doi: 10.1007/s13277-014-1985-y. doi: 10.1007/s13277-014-1877-1. doi: 10.1158/1940-6207.CAPR-13-0117. doi: 10.1111/jdv.13529. doi: 10.1371/journal.pone.0067728. Erratum in: PLoS One. 2013;8(7). doi:10.1371/annotation/59a7568c-915d-4d9c-b912-f93af72acdcb.

    合成参考文献


    参考文献:10.1128/aac.46.5.1226-1230.2002
    摘要:Tsukiyama R, Katsura H, Tokuriki N, Kobayashi M. Antibacterial Activity of Licochalcone A against Spore-Forming Bacteria. Antimicrob Agents Chemother. 2002 May;46(5):1226–30. doi: 10.1128/aac.46.5.1226-1230.2002.
    参考文献:10.1016/s1567-5769(01)00202-8
    摘要:Barfod L, Kemp K, Hansen M, Kharazmi A. Chalcones from Chinese liquorice inhibit proliferation of T cells and production of cytokines. Int Immunopharmacol. 2002 Mar;2(4):545–55. doi: 10.1016/s1567-5769(01)00202-8.
    参考文献:10.1111/j.1439-0507.2011.02028.x
    摘要:Messier C, Grenier D. Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. Mycoses. 2011 Nov;54(6):e801–6. doi: 10.1111/j.1439-0507.2011.02028.x.
    参考文献:10.3892/ijo.2014.2461
    摘要:Cho JJ, Chae JI, Yoon G, Kim KH, Cho JH, Cho SS, Cho YS, Shim JH. Licochalcone A, a natural chalconoid isolated from Glycyrrhiza inflata root, induces apoptosis via Sp1 and Sp1 regulatory proteins in oral squamous cell carcinoma. Int J Oncol. 2014 Aug;45(2):667–74. doi: 10.3892/ijo.2014.2461.
    参考文献:10.1021/acs.jnatprod.6b00783
    摘要:Li K, Ji S, Song W, Kuang Y, Lin Y, Tang S, Cui Z, Qiao X, Yu S, Ye M. Glycybridins A-K, Bioactive Phenolic Compounds from Glycyrrhiza glabra. J Nat Prod. 2017 Feb 24;80(2):334–46. doi: 10.1021/acs.jnatprod.6b00783.
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