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517-89-5

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517-89-5 Usage

Description

Different sources of media describe the Description of 517-89-5 differently. You can refer to the following data:
1. Shikonin could be found in the plant of Lithospermum erythrorhizon Sieb. et. Zucc and Arnebia euchroma (Royle) Johnst. It could also be produced using plant cell culture techniques. Shikonin is recorded in British Pharmacopoeia as a reference compound. Zicao, a traditional Chinese medicine firstly recorded in Shen Nong’s Herbal Classic, has long been used medically in history . Chinese Pharmacopoeia (Edition 2015) recorded the root of Arnebia euchroma (Royle) Johnst and Arnebia guttata Bge as Zicao, which is mainly used for inflammatory diseases such as macular eruptions, measles, sore throat, carbuncles, and burns.
2. Shikonin is a naturally occurring naphthoquinine isolated from the dried root of L. erythrorhizon, an herb used in traditional Chinese medicine. It increases glucose uptake by adipocytes and myocytes and inhibits the activity of phosphatase and tensin homolog (PTEN; IC50 = 2.7 μM). It inhibits glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (IC50 = 0.3 μM). Shikonin induces cell death consistent with necroptosis in MCF-7 and HEK293 cancer cell lines. It inhibits leukocyte migration, downregulates chemokine receptor expression, and inhibits HIV-1 replication at nanomolar concentrations. Shikonin exhibits anti-inflammatory activity, reducing joint swelling and cartilage destruction in a mouse model of collagen-induced arthritis.

Physical properties

Appearance: purple lamellae or crystalline powder. Melting point: 147 °C. Specific optical rotation: +138°(benzene). Solubility: soluble in ethanol, vegetable oils, and other organic solvents.

History

Kuroda and Majima firstly identified acetyl shikonin from L. erythrorhizon in 1922 , followed by the discovery of other shikonin derivatives, including shikonin. The chemical structure of shikonin was not precisely identified till 1936 for its high physicochemical similarity with naphthazarin . There have been about 500 publications on shikonin up to now. Great attention has also been paid on the biosynthesis of shikonin and its derivatives, and an increasing number of shikonin derivatives have been designed and synthesized for exploring their antitumor effect. There are two types of derivatives: one is modifications of 1′-OH with parent nucleus naphthazarin remained and the other is modifications of both 1′-OH and parent nucleus naphthazarin, as shown in Fig. 3c, d .

Uses

Different sources of media describe the Uses of 517-89-5 differently. You can refer to the following data:
1. A naphthoquinone derivative with angiogenesis inhibitor properties.
2. Shikonin (CI 75535) occurs as an acetyl derivative in the Japanese shikone, Lithospermum erythrorhizon, another member of the Boraginaceae family. It is the (R)-optical isomer of alkannin. Tissue cultures of L. erythrorhizon are used in Japan to manufacture shikonin mainly for cosmetic use. Both alkannin and shikonin are mordant dyes producing violet to gray colors on fabrics. In Japan, shikonin was used to dye fabrics a color known as Tokyo Violet. Shikalkin the racemate, has been synthesized.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Pharmacology

Shikonin possesses anti-inflammatory, antioxidant, antiviral, cardiovascular protective,and antitumor activities. Shikonin reduces inflammation by inhibiting the biosynthesis of leukotrienes and 5-hydroxyeicosatetraenoic acid and thus reduces synthesis of inflammation-related active molecules, which selectively block chemokine binding to CC chemokine receptor 1 . Shikonin shows free radical scavenging and antioxidant (especially toward superoxide anion and DPPH) activities. It significantly inhibits autoxidation caused by β-carotene and linoleic acid . Its anti-HCV effects have been reported recently with an EC50 at 25 ng/mL, which is lower than that of ribavirin (2.6 μg/mL) . Recent studies also reveal shikonin possesses cardiovascular protective effects. Shikonin inhibits the activity of TNF-α promoter, revealing its transcriptional antagonism to pro-inflammatory cytokine . Shikonin also shows antitumor potentials by inducing apoptosis and/or necrosis, inhibiting DNA topoisomerase activity and angiogenesis, and regulating proliferative signaling pathways (including MAPK, VEGF, and PTKs ). In addition, shikonin circumvents cancer drug resistance by induction of necroptotic cell death .

Clinical Use

Shikonin and its derivatives have not been approved for clinical use yet. Studies are confined to cellular and animal experiments. Its original plant Zicao has a long history of medical use both orally and externally in China. Various dosage forms of Zicao, including tablets, injections, oils, creams, tinctures, plastics, and pastes, have been developed for different clinical applications especially in dermatology, gynecology, pediatrics, ophthalmology, and otorhinolaryngology. Among them, puccoon oil and lithospermum cream are the most widely used forms.

Check Digit Verification of cas no

The CAS Registry Mumber 517-89-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 517-89:
(5*5)+(4*1)+(3*7)+(2*8)+(1*9)=75
75 % 10 = 5
So 517-89-5 is a valid CAS Registry Number.
InChI:InChI=1/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1

517-89-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione

1.2 Other means of identification

Product number -
Other names 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:517-89-5 SDS

517-89-5Synthetic route

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol
197573-96-9

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-96-0

(R)-2-(<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dihydroxynaphtho-1,4-quinone

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
206996-08-9

(R)-4-Methyl-1-(1,3,6,8-tetraoxa-pyren-4-yl)-pent-3-en-1-ol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
443686-76-8

(R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester

A

shikonin
517-89-5

shikonin

B

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
517-88-4, 517-89-5, 11031-58-6, 54952-43-1, 85921-41-1

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione

Conditions
ConditionsYield
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;
Conditions
ConditionsYield
With sodium hydroxide In methanol
4-methyl-pent-3-enoic acid
504-85-8

4-methyl-pent-3-enoic acid

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
4-methyl-3-pentenenitrile
4786-23-6

4-methyl-3-pentenenitrile

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
33698-69-0

6-methyl-hepta-1,5-dien-3-one

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
145668-25-3

2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
prenyl bromide
870-63-3

prenyl bromide

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
206996-05-6

N-methoxy-N,4-dimethylpent-3-enamide

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
2-(3-methyl-buten-2-yl)-[1,3]-dioxolane-2-carbaldehyde

2-(3-methyl-buten-2-yl)-[1,3]-dioxolane-2-carbaldehyde

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
443686-72-4

3-(3-methyl-buten-2-yl)-2-vinyl-[1,3]-dioxolane

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
443686-71-3

[2-(3-methyl-buten-2-yl)-[1,3]-dioxolan-2-yl]-methanol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
443686-50-8

1-(1,4-dihydroxy-5,8-dimethoxy-naphthalen-2-yl)-4-methyl-pent-3-en-1-one

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
443686-67-7

2-(1-hydroxy-4-methyl-pent-3-enyl)-5,8-dimethoxy-naphthalene-1,4-diol

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
88051-30-3

2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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)
88051-28-9

naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine)

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
206996-06-7

2-(4-methyl-3-pentene-1-one)-1,8:4,5-bis(methylenedioxy)naphthalene

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-90-4

(R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoic Acid

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135523-23-8

Ethyl (R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-95-9

(R)-2-(1-<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dimethoxynaphtho-1,4-quinone

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-92-6

(R)-3-(tert-butyldimethylsilyloxy)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanal

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-93-7

(R)-tert-butyldimethyl-(4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyloxy)silane

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-91-5

Ethyl (R)-3-<(1,1-Dimethylethyl)dimethylsilyloxy>-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
135504-88-0, 135504-89-1

(1'R)-3-Hydroxy-3-(1,4,5,8-tetramethoxynaphthyl)propanoic Acid 2'-Hydroxy-1',2',2'-triphenylethyl Ester

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
1'-tigloylshikonin

1'-tigloylshikonin

A

shikonin
517-89-5

shikonin

B

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione
517-88-4, 517-89-5, 11031-58-6, 54952-43-1, 85921-41-1

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione

Conditions
ConditionsYield
With methanol; sodium hydroxide at 20℃; for 12h;
ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate
438036-54-5

ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
C31H42ClNO5Si

C31H42ClNO5Si

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
C32H45NO6Si

C32H45NO6Si

shikonin
517-89-5

shikonin

Conditions
ConditionsYield
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
517-89-5

shikonin

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid
3588-64-5, 5123-55-7, 32150-90-6, 38229-08-2

(R)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions
ConditionsYield
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%
shikonin
517-89-5

shikonin

N-phthaloylphenylalanine
3588-64-5

N-phthaloylphenylalanine

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions
ConditionsYield
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%
shikonin
517-89-5

shikonin

Nα-phthaloyl-L-phenylalanine
5123-55-7

Nα-phthaloyl-L-phenylalanine

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

Conditions
ConditionsYield
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%
2-(1,3-dioxooctahydroisoindol-2-yl)propionic acid

2-(1,3-dioxooctahydroisoindol-2-yl)propionic acid

shikonin
517-89-5

shikonin

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

Conditions
ConditionsYield
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%
shikonin
517-89-5

shikonin

methyl iodide
74-88-4

methyl iodide

(R)-2-(1-hydroxy-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-dione

(R)-2-(1-hydroxy-4-methylpent-3-enyl)-5,8-dimethoxynaphthalene-1,4-dione

Conditions
ConditionsYield
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
517-89-5

shikonin

dimethyl sulfate
77-78-1

dimethyl sulfate

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol
197573-96-9

(1R)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-ol

Conditions
ConditionsYield
With sodium dithionite; tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere;90%
shikonin
517-89-5

shikonin

C11H15NO4

C11H15NO4

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)propanoate

Conditions
ConditionsYield
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%
shikonin
517-89-5

shikonin

3-trimethylsilyloxypropionic acid
860407-29-0

3-trimethylsilyloxypropionic acid

C22H28O7Si
1253934-33-6

C22H28O7Si

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere;87.5%
shikonin
517-89-5

shikonin

C11H15NO4

C11H15NO4

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1Hisoindol-2(3H)-yl)propanoate

(2S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-(1,3-dioxohexahydro-1Hisoindol-2(3H)-yl)propanoate

Conditions
ConditionsYield
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
1196463-67-8

(R)-2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylic acid

shikonin
517-89-5

shikonin

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;87%
4-Chlorophenoxyacetic acid
122-88-3

4-Chlorophenoxyacetic acid

shikonin
517-89-5

shikonin

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-chlorophenoxy)acetate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-chlorophenoxy)acetate

Conditions
ConditionsYield
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
517-89-5

shikonin

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

2-(1-hydroxy-4-methylpent-3-enyl)-5,8-bis-(methoxymethoxy)-naphthalene-1,4-dione
1253934-34-7

2-(1-hydroxy-4-methylpent-3-enyl)-5,8-bis-(methoxymethoxy)-naphthalene-1,4-dione

Conditions
ConditionsYield
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%
Conditions
ConditionsYield
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
517-89-5

shikonin

C11H10FNO3S

C11H10FNO3S

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(2-fluoro-6-methoxyphenyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(2-fluoro-6-methoxyphenyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;83%
shikonin
517-89-5

shikonin

propionic acid
802294-64-0

propionic acid

[(1R)-1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methylpent-3-enyl] propanoate

[(1R)-1-(5,8-dihydroxy-1,4-dioxo-2-naphthyl)-4-methylpent-3-enyl] propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;81%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane67%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;
shikonin
517-89-5

shikonin

butyric acid
107-92-6

butyric acid

2-[1-(butyryloxy)-4-methyl-3-pentenyl]naphthazarin

2-[1-(butyryloxy)-4-methyl-3-pentenyl]naphthazarin

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;81%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane59%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 4h;
shikonin
517-89-5

shikonin

(R)-2-(3'-methylphenyl)-4-carboxy-4,5-dihydrothiazole

(R)-2-(3'-methylphenyl)-4-carboxy-4,5-dihydrothiazole

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(m-tolyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(m-tolyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;80%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

shikonin
517-89-5

shikonin

C26H24O7
1384955-82-1

C26H24O7

Conditions
ConditionsYield
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
517-89-5

shikonin

C10H8INO2S

C10H8INO2S

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-iodophenyl)-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-iodophenyl)-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;79%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

shikonin
517-89-5

shikonin

C25H21ClO6
1384955-73-0

C25H21ClO6

Conditions
ConditionsYield
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%
C17H17NO5

C17H17NO5

shikonin
517-89-5

shikonin

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-((4R,7S)-1,3-dioxohexahydro-1H-4,7-epoxyisoindol-2(3H)-yl)-3-phenylpropanoate

(2R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-3-yl)-4-methylpent-3-en-1-yl-2-((4R,7S)-1,3-dioxohexahydro-1H-4,7-epoxyisoindol-2(3H)-yl)-3-phenylpropanoate

Conditions
ConditionsYield
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
517-89-5

shikonin

(4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid
19983-15-4, 116179-34-1, 62096-93-9

(4R)-2-phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-phenyl-4,5-dihydrothiazole-4-carboxylate

(4R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-phenyl-4,5-dihydrothiazole-4-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;75%
4,4,4-trifluorobutyric acid
406-93-9

4,4,4-trifluorobutyric acid

shikonin
517-89-5

shikonin

2-[1-(4,4,4-trifluorobutyryloxy)-4-methyl-3-pentenyl]naphthazarin
1380298-17-8

2-[1-(4,4,4-trifluorobutyryloxy)-4-methyl-3-pentenyl]naphthazarin

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;74%
2-thiophenebutyric acid
4653-11-6

2-thiophenebutyric acid

shikonin
517-89-5

shikonin

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(thiophen-2-yl)butanoate
1397292-84-0

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 4-(thiophen-2-yl)butanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;74%
ibuprofen
15687-27-1

ibuprofen

shikonin
517-89-5

shikonin

(1R)-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-isobutylphenyl)propanoate

(1R)-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 2-(4-isobutylphenyl)propanoate

Conditions
ConditionsYield
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%
(E)-3-phenylacrylic acid
140-10-3

(E)-3-phenylacrylic acid

shikonin
517-89-5

shikonin

C26H24O6
1384955-72-9

C26H24O6

Conditions
ConditionsYield
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
381-73-7

Difluoroacetic acid

shikonin
517-89-5

shikonin

2-[1-(2,2-difluoroacetoxy)-4-methyl-3-pentenyl]naphthazarin
1380298-10-1

2-[1-(2,2-difluoroacetoxy)-4-methyl-3-pentenyl]naphthazarin

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;73%
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

shikonin
517-89-5

shikonin

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl thiophene-2-carboxylate
1397292-79-3

(R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl thiophene-2-carboxylate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;73%
shikonin
517-89-5

shikonin

(E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid
15254-22-5

(E)-4-(2,5-dimethylphenyl)-4-oxo-2-butenoic acid

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (E)-4-(2,5-dimethylphenyl)-4-oxobut-2-enoate

1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl (E)-4-(2,5-dimethylphenyl)-4-oxobut-2-enoate

Conditions
ConditionsYield
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%

517-89-5Relevant articles and documents

A novel and efficient total synthesis of shikonin

Wang, Rubing,Guo, Hui,Cui, Jiahua,Li, Shaoshun

, p. 3977 - 3980 (2012)

A novel and efficient synthesis of shikonin was accomplished with excellent enantiomeric excess (99.3% ee) and high overall yield (47%) in only six steps. The synthetic strategy involved an efficient Ru(II)-catalyzed asymmetric hydrogenation employing C2-symmetric planar chiral ruthenocene phosphinooxazoline ligand (L-3), followed by the subsequent removal of the methyl protecting groups. Meanwhile, it could be preliminarily confirmed that the chiral side chain of shikonin was difficult to be constructed in one step with both stereoselectivity and α-regioselectivity.

An improved and practical synthesis route to antiproliferative (±)-shikonin and its O-acyl derivatives

Ono, Mana,Abe, Shouki,Higai, Koji,Higashi, Shoko,Saito, Setsuo,Saito, Ryota

, p. 738 - 746 (2020/12/09)

Shikonin and its O-acyl derivatives are attracting increasing levels of attention among medicinal chemists due to their potencies as highly selective cytotoxic agents against cancer cells. However, providing a large number of shikonin-related samples by organic synthesis remains challenging. In the present study, we developed an improved and practical synthesis route to shikonin derivatives by olefin metathesis that has enabled the gram-scale preparation of a prenylated tetramethylnaphthazaline, a key intermediate in the synthesis of shikonin. In addition, a method for the selective cleavage of the acyl protecting groups at the phenolic positions of tri-O-acylated shikonins has been developed that provides concise routes to diverse O-acylshikonin derivatives.

Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of Lithospermum erythrorhizon

Ito, Yusai,Onobori, Kenichi,Yamazaki, Takeshi,Kawamura, Yoko

experimental part, p. 117 - 119 (2011/02/28)

Tigloylshikonin, a new shikonin derivative esterified with tiglic acid ((E)-2-methylbut-2-enoic acid), was isolated as a minor pigment from a food colorant "Shikon color," a commercial root extract from Lithospermum erythrorhizon SIEBOLD et ZUCCARINI. The structure of tigloylshikonin was elucidated using 1H, 13C, the difference nuclear Overhauser effect (NOE), and 2D NMR techniques. Its stereochemistry was determined by chiral-phase HPLC analysis. Tigloylshikonin was also found in the roots of L. erythrorhizon, which indicated that this new shikonin derivative is a typical component of naphthoquinone pigments in the roots of L. erythrorhizon.

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