CAS No.517-89-5,5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione Suppliers

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Basic Information

Molecular Structure:
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

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

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

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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.