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Basic Information
CAS No.: 517-89-5
Name: 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione
Article Data: 21
Molecular Structure:
Molecular Structure of 517-89-5 (5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione)
Formula: C16H16O5
Molecular Weight: 288.3
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;
Density: 1.373 g/cm3
Melting Point: 147 °C
Boiling Point: 567.4 °C at 760 mmHg
Flash Point: 311 °C
Solubility: insoluble in water
Risk Codes: 20/21/22
Safety: 26-36/37/39
PSA: 94.83000
LogP: 2.12040
Related products
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
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
135504-96-0

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

517-89-5

shikonin

Conditions
ConditionsYield
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
ConditionsYield
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
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;
24502-78-1, 34232-27-4, 38222-13-8, 54984-93-9, 106295-33-4

acetylshikonin

517-89-5

shikonin

Conditions
ConditionsYield
With sodium hydroxide In methanol
504-85-8

4-methyl-pent-3-enoic acid

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
4786-23-6

4-methyl-3-pentenenitrile

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
33698-69-0

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

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
145668-25-3

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

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
870-63-3

prenyl bromide

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
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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.