Shikonin supplier | CasNO.517-89-5

Name
5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione
EINECS
CAS No. 517-89-5
Article Data21
CAS DataBase
Density 1.373 g/cm³
Solubility insoluble in water
Melting Point 147 °C
Formula C₁₆H₁₆O₅
Boiling Point 567.4 °C at 760 mmHg
Molecular Weight 288.3
Flash Point 311 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols
Synonyms 1,4-Naphthalenedione,5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-;1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-pentenyl]- (9CI);1,4-Naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-(8CI);Shikonin (6CI);(+)-Shikonin;C.I. 75535;Isoarnebin 4;NSC 252844;Shikonin S;Shikonine;Tokyo Violet;
PSA 94.83000
LogP 2.12040

Synthetic route

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

: 517-89-5
shikonin

Conditions

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

: 135504-96-0
(R)-2-(<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dihydroxynaphtho-1,4-quinone

: 517-89-5
shikonin

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 40h; Ambient temperature;	51%

: 206996-08-9
(R)-4-Methyl-1-(1,3,6,8-tetraoxa-pyren-4-yl)-pent-3-en-1-ol

: 517-89-5
shikonin

Conditions

Conditions	Yield
With lithium perchlorate In water; acetonitrile at 25℃; anodic oxidation, graphite electrodes, 3V; Yield given;

: 443686-76-8
(R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester

A: 517-89-5
shikonin

B: 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

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;

: 24502-78-1, 34232-27-4, 38222-13-8, 54984-93-9, 106295-33-4
acetylshikonin

: 517-89-5
shikonin

Conditions

Conditions	Yield
With sodium hydroxide In methanol

: 504-85-8
4-methyl-pent-3-enoic acid

: 517-89-5
shikonin

Conditions

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

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

: 4786-23-6
4-methyl-3-pentenenitrile

: 517-89-5
shikonin

Conditions

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

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

: 33698-69-0
6-methyl-hepta-1,5-dien-3-one

: 517-89-5
shikonin

Conditions

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

: 145668-25-3
2-(1'-hydroxy-4'-methylpent-3'-en-1'-yl)-5,8-dimethoxy-1,4-naphthaquinone

: 517-89-5
shikonin

Conditions

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

: 870-63-3
prenyl bromide

: 517-89-5
shikonin

Conditions

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

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

: 206996-05-6
N-methoxy-N,4-dimethylpent-3-enamide

: 517-89-5
shikonin

Conditions

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

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

: 517-89-5
shikonin

Conditions

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

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

: 443686-72-4
3-(3-methyl-buten-2-yl)-2-vinyl-[1,3]-dioxolane

: 517-89-5
shikonin

Conditions

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

: 443686-71-3
[2-(3-methyl-buten-2-yl)-[1,3]-dioxolan-2-yl]-methanol

: 517-89-5
shikonin

Conditions

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

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

: 443686-50-8
1-(1,4-dihydroxy-5,8-dimethoxy-naphthalen-2-yl)-4-methyl-pent-3-en-1-one

: 517-89-5
shikonin

Conditions

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

: 443686-67-7
2-(1-hydroxy-4-methyl-pent-3-enyl)-5,8-dimethoxy-naphthalene-1,4-diol

: 517-89-5
shikonin

Conditions

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

: 88051-30-3
2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene

: 517-89-5
shikonin

Conditions

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

: 88051-28-9
naphtho[1,8-de:4,5-d'e']bis([1,3]dioxine)

: 517-89-5
shikonin

Conditions

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

: 206996-06-7
2-(4-methyl-3-pentene-1-one)-1,8:4,5-bis(methylenedioxy)naphthalene

: 517-89-5
shikonin

Conditions

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

: 135504-90-4
(R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoic Acid

: 517-89-5
shikonin

Conditions

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

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

: 135523-23-8
Ethyl (R)-3-Hydroxy-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate

: 517-89-5
shikonin

Conditions

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

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

: 135504-95-9
(R)-2-(1-<(1,1-Dimethylethyl)dimethylsilyloxy>-4-methyl-3-pentenyl)-5,8-dimethoxynaphtho-1,4-quinone

: 517-89-5
shikonin

Conditions

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

: 135504-92-6
(R)-3-(tert-butyldimethylsilyloxy)-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanal

: 517-89-5
shikonin

Conditions

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

: 135504-93-7
(R)-tert-butyldimethyl-(4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-enyloxy)silane

: 517-89-5
shikonin

Conditions

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

: 135504-91-5
Ethyl (R)-3-<(1,1-Dimethylethyl)dimethylsilyloxy>-3-(1,4,5,8-tetramethoxy-2-naphthyl)propanoate

: 517-89-5
shikonin

Conditions

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

: 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

: 517-89-5
shikonin

Conditions

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

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

: 1'-tigloylshikonin

A: 517-89-5
shikonin

B: 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

Conditions	Yield
With methanol; sodium hydroxide at 20℃; for 12h;

: 438036-54-5
ethyl 3-hydroxy-3-(1,4,5,8-tetramethoxynaphthalen-2-yl)propanoate

: 517-89-5
shikonin

Conditions

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

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

: C31H42ClNO5Si

: 517-89-5
shikonin

Conditions

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

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

: C32H45NO6Si

: 517-89-5
shikonin

Conditions

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

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

: 517-89-5
shikonin

: 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

Conditions

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%

: 517-89-5
shikonin

: 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

Conditions

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%

: 517-89-5
shikonin

: 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

Conditions

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%

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

: 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

Conditions

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%

: 517-89-5
shikonin

: 74-88-4
methyl iodide

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

Conditions

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%

: 517-89-5
shikonin

: 77-78-1
dimethyl sulfate

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

Conditions

Conditions	Yield
With sodium dithionite; tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 20℃; for 3h; Inert atmosphere;	90%

: 517-89-5
shikonin

: 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

Conditions

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%

: 517-89-5
shikonin

: 860407-29-0
3-trimethylsilyloxypropionic acid

: 1253934-33-6
C22H28O7Si

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1h; Inert atmosphere;	87.5%

: 517-89-5
shikonin

: 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

Conditions

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%

: 1196463-67-8
(R)-2-(4-bromophenyl)-4,5-dihydrothiazole-4-carboxylic acid

: 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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;	87%

: 122-88-3
4-Chlorophenoxyacetic acid

: 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

Conditions

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%

: 517-89-5
shikonin

: 107-30-2
chloromethyl methyl ether

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

Conditions

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%

: 517-89-5
shikonin

: 64-19-7
acetic acid

: 24502-78-1, 34232-27-4, 38222-13-8, 54984-93-9, 106295-33-4
acetylshikonin

Conditions

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;

: 517-89-5
shikonin

: 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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;	83%

: 517-89-5
shikonin

: 802294-64-0
propionic acid

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

Conditions

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;

: 517-89-5
shikonin

: 107-92-6
butyric acid

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

Conditions

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;

: 517-89-5
shikonin

: (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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;	80%

: 140-10-3
(E)-3-phenylacrylic acid

: 517-89-5
shikonin

: 1384955-82-1
C26H24O7

Conditions

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%

: 517-89-5
shikonin

: 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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;	79%

: 140-10-3
(E)-3-phenylacrylic acid

: 517-89-5
shikonin

: 1384955-73-0
C25H21ClO6

Conditions

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%

: C17H17NO5

: 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

Conditions

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%

: 517-89-5
shikonin

: 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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h; Cooling with ice;	75%

: 406-93-9
4,4,4-trifluorobutyric acid

: 517-89-5
shikonin

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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;	74%

: 4653-11-6
2-thiophenebutyric acid

: 517-89-5
shikonin

: 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

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;	74%

: 15687-27-1
ibuprofen

: 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

Conditions

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%

: 140-10-3
(E)-3-phenylacrylic acid

: 517-89-5
shikonin

: 1384955-72-9
C26H24O6

Conditions

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%

: 381-73-7
Difluoroacetic acid

: 517-89-5
shikonin

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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; Inert atmosphere;	73%

: 527-72-0
2-thiophenylcarboxylic acid

: 517-89-5
shikonin

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

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;	73%

: 517-89-5
shikonin

: 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

Conditions

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%

Shikonin Specification

The IUPAC name of Shikonin is 5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methylpent-3-enyl]naphthalene-1,4-dione. With the CAS registry number 517-89-5, it is also named as Tokyo Violet. The product's categories are Anthraquinones, Hydroquinones and Quinones. Besides, it is purple-brown crystals, which should be stored in a cool, dry, well ventilated warehouse to prevent direct sunlight. In addition, its molecular formula is C₁₆H₁₆O₅ and molecular weight is 288.3.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.34; (4)ACD/LogD (pH 7.4): 3.85; (5)ACD/BCF (pH 5.5): 1162.77; (6)ACD/BCF (pH 7.4): 378.24; (7)ACD/KOC (pH 5.5): 5404.5; (8)ACD/KOC (pH 7.4): 1758.03; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.642; (13)Molar Refractivity: 75.86 cm³; (14)Molar Volume: 209.9 cm³; (15)Surface Tension: 65.1 dyne/cm; (16)Density: 1.373 g/cm³; (17)Flash Point: 311 °C; (18)Melting Point: 147 °C; (19)Enthalpy of Vaporization: 89.61 kJ/mol; (20)Boiling Point: 567.4 °C at 760 mmHg; (21)Vapour Pressure: 1.04E-13 mmHg at 25 °C.

Preparation and Uses of Shikonin: you can extract alkanet by the use of Ethanol, Propylene glycol, Edible oil and water. Then you will obtain this chemical. Furthermore, this product can be used as food colorants, It also can be used for coloring of cosmetic.

When you are using this chemical, please be cautious about it as the following: it is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
(1)SMILES: O=C\2c1c(O)ccc(O)c1C(=O)/C(=C/2)C(O)C\C=C(/C)C
(2)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
(3)InChIKey: NEZONWMXZKDMKF-UHFFFAOYAK
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: NEZONWMXZKDMKF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	20mg/kg (20mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: ATAXIA	Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 73, Pg. 193, 1977.
mouse	LD50	oral	> 1gm/kg (1000mg/kg)		Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 73, Pg. 193, 1977.
rabbit	LD50	intravenous	16mg/kg (16mg/kg)		Pakistan Journal of Pharmacology. Vol. 3(1-2), Pg. 43, 1986.

Product Name

5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione

Synthetic route

Shikonin Specification

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