CAS: 517-88-4; (S)-5,8-Dihydroxy-2-(1-Hydroxy-4-Methylpent-3-En-1-yl)Naphthalene-1,4-Dione

该化合物是天然形成的环烷磺酮化合物,主要来自Alkana锡工厂(俗称alkanet)的根部,其特点是深红至紫色,在化妆品和食品等各种应用中,它是一种有价值的染色物. (-) Alkanin的分子配方是C16H16O5, 其结构复杂,有多种功能组,包括氢氧和碳基,有助于其再活性和生物活动.该化合物具有抗氧化特性,并研究其潜在的治疗效果,包括防炎和抗微生物活动.(-)-Alkanin因其独特的特性和生物意义,还因其稳定乳胶和增强所用配方稳定性的能力而闻名.溶剂的溶解性因溶剂在有机溶剂中比在水中更溶.

结构式图片

上下游产品

2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthoquinone 5,8-diacetoxy-2-(1-acetoxy-4-methyl-3-pentenyl)-1,4-naphthoquinone (R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester 4-methyl-pent-3-enoic acid shikonin-β,β-dimethylacrylate propionylshikonin 2-butenoic acid Shikonin Crotonate

合成工艺路线路线简述

    4-甲基-3-戊烯酸置于吡啶,4-二甲氨基吡啶,Sodium Tetrahydroborate,正丁基锂,Ammonium Cerium(Iv) Nitrate,四溴化碳,三乙胺,三苯基膦,叔丁醇体系中,用 四氢呋喃,甲醇,正己烷,二氯甲烷,乙腈 作为反应溶剂,化学反应 10.24H,反应生成 紫草素
    参考文献:A New Efficient Route For Multigram Asymmetric Synthesis Of Alkannin And Shikonin
    标题:A New Efficient Route For Multigram Asymmetric Synthesis Of Alkannin And Shikonin
    摘要:A Short And Convergent Approach For The Synthesis Of Alkannin,Shikonin And Shikalkin Is Presented. A Hauser-Type Annulation Of Cyanophthalide 26 With Enone 7 Affords The Complete Aromatic System In Just One Step With Concomitant Attachment Of The Entire Side Chain. Subsequent Corey'S Oxazaborolidine Mediated Asymmetric Reduction Of The Above Advanced Intermediate,Leads To The Required Isomer In High Enantiomeric Excess. Finally,A Selective And High Yielding Deprotection Protocol Furnishes The Title Compounds As Pure Crystalline Precipitates. Thus,A Multigram Synthesis Of Shikonin,Alkannin And Shikalkin Is Achieved In High Yield And Enantioselectivity.
    DOI:10.1002/1521-3765(20020415)8:8<1795::Aid-Chem1795>3.0.Co;2-V

    海关参考信息

    专利信息


    专利号:WO-2013087821-A1
    优先权日:2011-12-15
    标题:Overproduction of jasmonates in transgenic plants
    发明人:CHAMPION ANTONY
    权利人:INST RECH DEVELOPPEMENT IRD
    摘要:La present invention relates to the use of a nucleic sequence allowing the synthesis of Gh ERF-IIa, Gh ERF-IIb or Gh ERF-IIc in a plant in order to induce, in the plant, an overproduction or accumulation of jasmonic acid and/or OPDA. The accumulation of jasmonic acid and/or OPDA confers, in particular, to the transformed plant an improved resistance to bioagressors. The nucleic sequences, transformation methods and transformed plants according to the invention may also been used for the production of pharmaceutically important secondary metabolites whose synthesis is induced by jasmonates.

    专利号:US-9987208-B2
    优先权日:2013-04-04
    标题 :Elastin synthesis/regeneration promoting agent
    发明人:NISHIZAKI TOMOYUKI; TANAKA AKITO
    权利人:NISHIZAKI BIOINFORMATION RES INSTITUTE
    摘要:8-[2-(2-Pentyl-cyclopropylmethyl)-cyclopropyl]-octanoic acid (DCP-LA) has an action to promote synthesis and regeneration of elastin, and is useful as an agent for the prophylaxis or improvement of wrinkles, and an anti-aging drug.

    专利号:US-6103956-A
    优先权日:1998-03-31
    标题:Polyhydroxyalkanoate synthesis in plants
    发明人:SRIENC FRIEDRICH; SOMERS DAVID A; HAHN J J; ESCHENLAUER ARTHUR C
    权利人:UNIV MINNESOTA
    摘要:Novel transgenic plants and plant cells are capable of biosynthesis of polyhydroxyalkanoate (PHA). Heterologous enzymes involved in PHA biosynthesis, particularly PHA polymerase, are targeted to the peroxisome of a transgenic plant. Transgenic plant materials that biosynthesize short chain length monomer PHAs in the absence of heterologous beta -ketothiolase and acetoacetyl-CoA reductase are also disclosed.

    专利号:KR-102686376-B1
    优先权日:2022-09-01
    标 题 :Carbon quantum dots based on by-products of gromwell root and a method for synthesis of carbon quantum dots based on by-products of gromwell root

    专利号:CN-101407783-A
    优先权日:2008-11-26
    标 题 :A method of using rare earth elements to promote the synthesis of shikonin in yunnanensis yunnanensis cells

    专利号:US-2025082601-A1
    优先权日:2023-09-08
    标题:Significantly non-toxic novel Cobalt(III) Schiff base complex induces apoptosis via G2-M cell cycle arrest in human breast cancer cell line MCF-7 and cell cycle arrest of colon cancer cell lines HCT-116 and SW- 480 via G0-G1
    发明人:DASGUPTA SANCHARI; KAR KANISHA PAL; BARUA ATISH; GHOSH DIYA; KABI BIKASH; DEWAN KOUSHIK; CHANDRA ARPITA; BHAR SUNANDITA; DAS TANIMA
    权利人:CHITTARANJAN NAT CANCER INSTITUTE
    摘要:A significantly non-toxic novel mononuclear cobalt(III)-Schiff base complex (1) capable to induce apoptosis via G2-M cell cycle arrest in human breast cancer cell line MCF-7 and cell cycle arrest of colon cancer cell lines HCT-116 and SW-480 via G0-G1. The Schiff base complex (1) having >99% purity has been synthesized by a facile “One potâ€? synthesis method and has been characterized with standard spectroscopic techniques. Complex 1 exhibits cytotoxicity (IC50=16.81±1.33 μM) at much lower concentration in comparison to oxaliplatin (IC50=31.4±0.69 μM) against MCF-7 cells and causes apoptosis in colon cancer cell lines HCT-116 and SW-480 by arresting the cell cycle at the G0-G1 phase having IC50 values of 15.27±1.18 μM and 10.04±1.98 μM respectively comparable with the IC50 values of oxaliplatin which are 16.73±1.78 μM and 7.87±1.54 μM respectively after 24 h of treatment without being overly toxic to human PBMCs (IC50=>60 μM). In vivo subacute toxicity (28 days) and systemic chronic toxicity (40 days) studies were carried out in normal Swiss albino mice showed 1 is sinificantly nontoxic to the host.
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    ✅ COA系统入驻 | 共享模式

    主要参考文献


    1: Kumar N, Singh JV, Bhagat K, Gulati HK, Sharma A, Rani A, Duggal A, Gulati P, Singh H, Bedi PMS, Kaur S. Discovery of potent inhibitors for Mpro enzyme of SARS-COV2 by multi-stage in-silico screening of Alkannin/shikonin. Nat Prod Res. 2021 Dec
    15:1-5. doi: 10.1080/14786419.2021.2013212. Epub ahead of print.
    2021:5083302. doi: 10.1155/2021/5083302.

    合成参考文献


    摘要:S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118
    参考文献:10.1021/jf9902853
    摘要:Cho MH, Paik YS, Hahn TR. Physical stability of shikonin derivatives from the roots of Lithospermum erythrorhizon cultivated in Korea. J Agric Food Chem. 1999 Oct;47(10):4117–20. doi: 10.1021/jf9902853.
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