1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s
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inquiryGromwell Root Extract Powder Latin name: Lithospermum erythrorhizon Part used: Root Active ingredient: Shikonin Specification: 10%~98% tested by HPLC Cas No.: 517-89-5 Mol
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inquiryAs a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch
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inquirySpecifications Type: Gromwell Root Extract Form: Powder Part: Root Extraction Type: Solvent Extraction Packaging: Bottle, Can, Drum,
With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufactu
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inquiryHenan Tianfu Chemical Co., Ltd. is located in Zhengzhou High-tech Development Zone with import and export license. We passed ISO 9001:2008 in 2009, and won "High-tech Enterprise" by provincial government in 2013.The objective of the com
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inquiryWITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et
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inquiryName: Shikonin / ALKANNIN Cas No:517-89-5 Molecular Formula:C16H16O5 Purity:95%min(HPLC) 1% glycerol acetate solution 0.5% aqueous solution Molecular Weight:288.3 Appearance: Dark purple fine Powder Storage:Store in cool and dry place, away from
1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized
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inquiryWe are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery
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inquiryOur company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At pres
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inquiry5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS:517-89-5 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical inte
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inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
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inquiry5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione CAS: 517-89-5 Specification product name: gromwell root extract powder appearance: brown yellow fine powder
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inquiryWe product this chemical more than 10 years . We are very experience to export it to many countries, Our superior & stable quality , competitive price gain warm reception from our customers. Specification : Tokyo Violet;(R)-5,8-Dihydroxy-2-
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inquiryHangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det
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inquiryJ&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia
A substitute for perfluorooctanoic acid, mainly used as a surfactant, dispersant, additive, etc Appearance:White solid or Colorless liquid Purity:99.3 % We will ship the goods in a timely manner as required We can provide relevant documents acc
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inquiryMassive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and
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inquiryWe are leading fine chemicals supplier in China with ISO certificate, Our main business covers the fields below: 1.Noble Metal Catalysts (Pt.Pd...) 2.Organic Phosphine Ligands (Tert-butyl-phosphine.Cyclohexyl-phosphine...) 3.OLED
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inquiryOur Advantages A. International Top level TechnologyOur company owned biomedicine experts are famous at home and abroad with rich experience in research and development in the field of efficient chiral functional molecules research and development an
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inquiryGMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,
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inquiry(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol
shikonin
Conditions | Yield |
---|---|
Stage #1: (1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol With pyridine; dmap; acetic anhydride In dichloromethane at 0 - 20℃; for 0.333333h; Stage #2: With ammonium cerium (IV) nitrate In dichloromethane; water at 20℃; for 0.25h; Further stages; | 85% |
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 0.33 h / 20 °C 1.2: 0.25 h / 20 °C 2.1: dmap; triethylamine; zinc / 2 h / 20 °C 3.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C 3.2: 6 h View Scheme | |
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 0.33 h / 20 °C 1.2: 0.25 h / 20 °C 2.1: dmap; triethylamine; zinc / 2 h / 20 °C 3.1: ammonium cerium (IV) nitrate / acetonitrile / 0.17 h / 20 °C 3.2: 6 h View Scheme |
(R)-2-(<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dihydroxynaphtho-1,4-quinone
shikonin
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 40h; Ambient temperature; | 51% |
(R)-4-Methyl-1-(1,3,6,8-tetraoxa-pyren-4-yl)-pent-3-en-1-ol
shikonin
Conditions | Yield |
---|---|
With lithium perchlorate In water; acetonitrile at 25℃; anodic oxidation, graphite electrodes, 3V; Yield given; |
(R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester
A
shikonin
B
(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
Conditions | Yield |
---|---|
Stage #1: (R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester With ammonium cerium(IV) nitrate In acetonitrile at 25℃; for 0.25h; Stage #2: With sodium hydroxide at 25℃; for 1h; Title compound not separated from byproducts; |
acetylshikonin
shikonin
Conditions | Yield |
---|---|
With sodium hydroxide In methanol |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 2.1: tetrahydrofuran / 0.33 h / -20 °C 3.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 3.2: 8 percent / tetrahydrofuran; hexane / 3 h 4.1: NaBH4 / methanol / 0.33 h / 0 °C 5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 6.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 2.1: tetrahydrofuran / 0.33 h / -20 °C 3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 3.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 4.1: NaBH4 / methanol / 0.33 h / 0 °C 5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 6.2: aq. NaOH / 1 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 90 percent / aq. NaOH / methanol / 8 h / Heating 2.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 3.1: tetrahydrofuran / 0.33 h / -20 °C 4.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 4.2: 8 percent / tetrahydrofuran; hexane / 3 h 5.1: NaBH4 / methanol / 0.33 h / 0 °C 6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 7.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: 90 percent / aq. NaOH / methanol / 8 h / Heating 2.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 3.1: tetrahydrofuran / 0.33 h / -20 °C 4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 4.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 5.1: NaBH4 / methanol / 0.33 h / 0 °C 6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 7.2: aq. NaOH / 1 h / 25 °C View Scheme |
6-methyl-hepta-1,5-dien-3-one
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 8 percent / tetrahydrofuran; hexane / 3 h 2.1: NaBH4 / methanol / 0.33 h / 0 °C 3.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 4.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 4.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 1.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 2.1: NaBH4 / methanol / 0.33 h / 0 °C 3.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 4.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 4.2: aq. NaOH / 1 h / 25 °C View Scheme |
2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: aq. Na2S2O4 / diethyl ether / 0.33 h 2.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 3.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 3.2: aq. NaOH / 1 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 86 percent / dimethylformamide / 48 h / 25 °C 2.1: 90 percent / aq. NaOH / methanol / 8 h / Heating 3.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 4.1: tetrahydrofuran / 0.33 h / -20 °C 5.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 5.2: 8 percent / tetrahydrofuran; hexane / 3 h 6.1: NaBH4 / methanol / 0.33 h / 0 °C 7.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 8.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 8.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: 86 percent / dimethylformamide / 48 h / 25 °C 2.1: 90 percent / aq. NaOH / methanol / 8 h / Heating 3.1: 85 percent / CBr4; PPh3; pyridine / CH2Cl2 4.1: tetrahydrofuran / 0.33 h / -20 °C 5.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 5.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 6.1: NaBH4 / methanol / 0.33 h / 0 °C 7.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 8.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 8.2: aq. NaOH / 1 h / 25 °C View Scheme |
N-methoxy-N,4-dimethylpent-3-enamide
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 0.33 h / -20 °C 2.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.2: 8 percent / tetrahydrofuran; hexane / 3 h 3.1: NaBH4 / methanol / 0.33 h / 0 °C 4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 5.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: tetrahydrofuran / 0.33 h / -20 °C 2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 2.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 3.1: NaBH4 / methanol / 0.33 h / 0 °C 4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 5.2: aq. NaOH / 1 h / 25 °C View Scheme |
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C 1.2: 764 mg / tetrahydrofuran / 2 h / 25 °C 2.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C 3.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 3.2: 8 percent / tetrahydrofuran; hexane / 3 h 4.1: NaBH4 / methanol / 0.33 h / 0 °C 5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 6.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C 1.2: 764 mg / tetrahydrofuran / 2 h / 25 °C 2.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C 3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 3.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 4.1: NaBH4 / methanol / 0.33 h / 0 °C 5.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 6.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 6.2: aq. NaOH / 1 h / 25 °C View Scheme |
3-(3-methyl-buten-2-yl)-2-vinyl-[1,3]-dioxolane
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C 2.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.2: 8 percent / tetrahydrofuran; hexane / 3 h 3.1: NaBH4 / methanol / 0.33 h / 0 °C 4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 5.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C 2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 2.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 3.1: NaBH4 / methanol / 0.33 h / 0 °C 4.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 5.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 5.2: aq. NaOH / 1 h / 25 °C View Scheme |
[2-(3-methyl-buten-2-yl)-[1,3]-dioxolan-2-yl]-methanol
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 1.5 h / -78 - 25 °C 2.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C 2.2: 764 mg / tetrahydrofuran / 2 h / 25 °C 3.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C 4.1: n-BuLi; t-BuOH / tetrahydrofuran; hexane / 0.33 h / -78 °C 4.2: 8 percent / tetrahydrofuran; hexane / 3 h 5.1: NaBH4 / methanol / 0.33 h / 0 °C 6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 7.2: aq. NaOH / 1 h / 25 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 1.5 h / -78 - 25 °C 2.1: (Me3Si)2NNa / tetrahydrofuran / 2 h / -10 °C 2.2: 764 mg / tetrahydrofuran / 2 h / 25 °C 3.1: Amberlyst 15; H2O / tetrahydrofuran / 6 h / 25 °C 4.1: LDA / tetrahydrofuran / 0.5 h / -78 °C 4.2: 60 percent / tetrahydrofuran / 0.08 h / -78 °C 5.1: NaBH4 / methanol / 0.33 h / 0 °C 6.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 7.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 7.2: aq. NaOH / 1 h / 25 °C View Scheme |
1-(1,4-dihydroxy-5,8-dimethoxy-naphthalen-2-yl)-4-methyl-pent-3-en-1-one
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: NaBH4 / methanol / 0.33 h / 0 °C 2.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 3.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 3.2: aq. NaOH / 1 h / 25 °C View Scheme |
2-(1-hydroxy-4-methyl-pent-3-enyl)-5,8-dimethoxy-naphthalene-1,4-diol
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 254.8 mg / Et3N; DMAP / CH2Cl2 / 5 h / 25 °C 2.1: aq. CAN / acetonitrile / 0.25 h / 25 °C 2.2: aq. NaOH / 1 h / 25 °C View Scheme |
2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h 2: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h 3: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V View Scheme |
naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine)
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 70 percent / NBS / CHCl3 / 12 h / 25 °C 2: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h 3: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h 4: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V View Scheme |
2-(4-methyl-3-pentene-1-one)-1,8:4,5-bis(methylenedioxy)naphthalene
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) (-)-DIP-Cl, 2.) CH3CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h 2: LiClO4 / acetonitrile; H2O / 25 °C / anodic oxidation, graphite electrodes, 3V View Scheme |
(R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoic Acid
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: p-toluenesulfonic acid / 48 h / Ambient temperature 2: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature 3: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C 4: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h 5: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C 6: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 7: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme |
Ethyl (R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature 2: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C 3: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h 4: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C 5: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 6: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme |
(R)-2-(1-<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dimethoxynaphtho-1,4-quinone
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 2: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme |
(R)-3-(tert-butyldimethylsilyloxy)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanal
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h 2: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C 3: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 4: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 3.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 3.2: 0.25 h / 20 °C View Scheme |
(R)-tert-butyldimethyl-(4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyloxy)silane
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C 2: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 3: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 2.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 2.2: 0.25 h / 20 °C View Scheme |
Ethyl (R)-3-<(1,1-Dimethylethyl)dimethylsilyloxy>-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C 2: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h 3: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C 4: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 5: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme |
(1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90 percent / KOH / methanol; H2O / 2.5 h / Heating 2: p-toluenesulfonic acid / 48 h / Ambient temperature 3: 4-(dimethylamino)pyridine, imdazole / dimethylformamide / 72 h / Ambient temperature 4: diisobutylaluminum hydride / CH2Cl2 / 29 h / -78 °C 5: 1) 1.6M n-BuLi / 1) Et2O, 0 deg C, 1.5 h, 2) Et2O, r.t., 24 h 6: 54 percent / 4)2(NO3)6> / acetonitrile; CHCl3; H2O / 1 h / 0 °C 7: 29 percent / AgO, 6 N HNO3 / dioxane / 0.75 h / Ambient temperature 8: 51 percent / (n-C4H9)4NF*3H2O / tetrahydrofuran / 40 h / Ambient temperature View Scheme |
A
shikonin
B
(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
Conditions | Yield |
---|---|
With methanol; sodium hydroxide at 20℃; for 12h; |
ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: sodium hydroxide / methanol; water / 2 h / 20 °C 2.1: dmap; bis(2-oxo-3-oxazolidinyl)phosphane; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 3.1: 1H-imidazole; dmap / dichloromethane / 24 h / 0 - 20 °C 4.1: pyridine; phosphorus pentachloride / dichloromethane / 8 h / 0 °C 5.1: dichloromethane / 1 h / -30 - -20 °C 6.1: water / dichloromethane / 12 h / 20 °C 7.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 8.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 8.2: 2 h / 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 10.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 10.2: 0.25 h / 20 °C View Scheme |
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dichloromethane / 1 h / -30 - -20 °C 2.1: water / dichloromethane / 12 h / 20 °C 3.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 4.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 4.2: 2 h / 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 6.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 6.2: 0.25 h / 20 °C View Scheme |
shikonin
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: water / dichloromethane / 12 h / 20 °C 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 12 h / -78 °C 3.1: n-butyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere 3.2: 2 h / 20 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 5.1: pyridine; dmap; acetic anhydride / dichloromethane / 0.33 h / 0 - 20 °C 5.2: 0.25 h / 20 °C View Scheme |
shikonin
(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid
Conditions | Yield |
---|---|
Stage #1: (R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 98% |
Conditions | Yield |
---|---|
Stage #1: N-phthaloylphenylalanine With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 98% |
Conditions | Yield |
---|---|
Stage #1: Nα-phthaloyl-L-phenylalanine With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 97% |
shikonin
Conditions | Yield |
---|---|
Stage #1: 2-(1,3-dioxooctahydroisoindol-2-yl)propionic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 93% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; | 92.3% |
Stage #1: shikonin With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 60℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide for 5h; | 76.6% |
shikonin
dimethyl sulfate
(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol
Conditions | Yield |
---|---|
With sodium dithionite; tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere; | 90% |
shikonin
Conditions | Yield |
---|---|
Stage #1: C11H15NO4 With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 90% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere; | 87.5% |
shikonin
Conditions | Yield |
---|---|
Stage #1: C11H15NO4 With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 87% |
(R)-2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylic acid
shikonin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice; | 87% |
Conditions | Yield |
---|---|
Stage #1: 4-Chlorophenoxyacetic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.25h; Stage #2: shikonin In dichloromethane at 0 - 20℃; for 6h; | 85.2% |
shikonin
chloromethyl methyl ether
2-(1-hydroxy-4-methylpent-3-enyl)-5,8-bis-(methoxymethoxy)-naphthalene-1,4-dione
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 3h; | 84.5% |
Stage #1: shikonin With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h; Inert atmosphere; Stage #2: chloromethyl methyl ether In N,N-dimethyl-formamide at 40℃; for 1h; Inert atmosphere; | 77.1% |
shikonin
acetic acid
acetylshikonin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere; | 83% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h; | |
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 3h; ice cooling; |
shikonin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice; | 83% |
shikonin
propionic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere; | 81% |
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane | 67% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h; |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere; | 81% |
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane | 59% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h; |
shikonin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice; | 80% |
Conditions | Yield |
---|---|
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #3: (E)-3-phenylacrylic acid In dichloromethane for 12h; Cooling with ice; Inert atmosphere; | 79% |
shikonin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice; | 79% |
Conditions | Yield |
---|---|
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #3: (E)-3-phenylacrylic acid In dichloromethane for 12h; Cooling with ice; Inert atmosphere; | 76% |
shikonin
Conditions | Yield |
---|---|
Stage #1: C17H17NO5 With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: shikonin With dmap In dichloromethane for 12h; Cooling with ice; | 76% |
shikonin
(4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice; | 75% |
4,4,4-trifluorobutyric acid
shikonin
2-[1-(4,4,4-trifluorobutyryloxy)-4-methyl-3-pentenyl]naphthazarin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere; | 74% |
2-thiophenebutyric acid
shikonin
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(thiophen-2-yl)butanoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere; | 74% |
ibuprofen
shikonin
Conditions | Yield |
---|---|
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.333333h; Inert atmosphere; Cooling with ice; Stage #2: With dmap In dichloromethane for 0.25h; Cooling with ice; Inert atmosphere; Stage #3: ibuprofen In dichloromethane for 14h; Cooling with ice; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
Stage #1: shikonin With dicyclohexyl-carbodiimide In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #2: With dmap In dichloromethane for 0.25h; Inert atmosphere; Cooling with ice; Stage #3: (E)-3-phenylacrylic acid In dichloromethane for 12h; Cooling with ice; Inert atmosphere; | 73% |
Difluoroacetic acid
shikonin
2-[1-(2,2-difluoroacetoxy)-4-methyl-3-pentenyl]naphthazarin
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere; | 73% |
2-thiophenylcarboxylic acid
shikonin
(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl thiophene-2-carboxylate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere; | 73% |
shikonin
(E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid
Conditions | Yield |
---|---|
Stage #1: (E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.333333h; Stage #2: shikonin In dichloromethane | 73% |
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