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Shikonin

Product Name
Shikonin
CAS No.
517-89-5
Chemical Name
Shikonin
Synonyms
Isoarnebin 4;SHIKONIN;Shikonine;c.i.75535;NSC 252844;Shikonin-RM;SHIKONIN(AS);Tokyo Violet;(-)-SHIKONIN;gromwell red
CBNumber
CB2251044
Molecular Formula
C16H16O5
Formula Weight
288.3
MOL File
517-89-5.mol
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Shikonin Property

Melting point:
148℃
Boiling point:
567.4±50.0 °C(Predicted)
Density 
1.373±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO : ≥ 31 mg/mL (107.53 mM);
pka
7.34±0.20(Predicted)
form 
Red crystalline solid.
color 
Brown
LogP
4.350 (est)
CAS DataBase Reference
517-89-5(CAS DataBase Reference)
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Safety

Risk Statements 
20/21/22-50/53-20
Safety Statements 
26-36/37/39-61
RIDADR 
3077
HS Code 
29146990
Hazardous Substances Data
517-89-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
565850
Product name
Shikonin - CAS 517-89-5 - Calbiochem
Purity
A naphthoquinone found in the Chinese herb Shiunko.
Packaging
10MG
Price
$130
Updated
2024/03/01
Sigma-Aldrich
Product number
PHL89791
Product name
Shikonin
Purity
phyproof? Reference Substance
Packaging
10MG
Price
$284
Updated
2023/06/20
Cayman Chemical
Product number
14751
Product name
Shikonin
Purity
≥98%
Packaging
5mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
14751
Product name
Shikonin
Purity
≥98%
Packaging
10mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
14751
Product name
Shikonin
Purity
≥98%
Packaging
50mg
Price
$184
Updated
2024/03/01
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Shikonin Chemical Properties,Usage,Production

Description

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.

Chemical Properties

Purple-brown crystals with a needle-like shape, melting at 147 ° C, with a rotativity of αD20 = +135 ° (in benzene). It dissolves readily in phenethyl ether, acetone, chloroform, methanol, ethanol, glycerol, animal and vegetable oils, and alkaline aqueous solutions, but is insoluble in water. Its color changes depending on the pH value: at pH 4-6, it turns red; at pH 8, it becomes purple; and at pH 10-12, it appears blue. It exhibits excellent resistance to light, heat, and oxidation, but is reactive to reducing agents, causing the formation of dark purple when exposed to iron ions. Additionally, Shikonin has certain antibacterial effect.

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

Shikonin has been used as a red dye for centuries and is reported to possess medicinal properties such as antibacterial, anti-inflammatory and antitumor activities. It 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.

Definition

ChEBI: Shikonin is a hydroxy-1,4-naphthoquinone. It is a naphthoquinone derivative with angiogenesis inhibitor properties.

General Description

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.

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.

storage

Store at -20°C

Shikonin Preparation Products And Raw materials

Raw materials

Preparation Products

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Shikonin Suppliers

Xi’an Originherb Tech Co., Ltd(YSD)
Tel
029-88396399 13892891777
Email
xianyuansheng@vip.sina.com
Country
CHINA
ProdList
1
Advantage
58
Nanjing Dasf Biotechnology Co., Ltd.
Tel
025-+86-02585846866 +86-18094231287
Fax
025-83144123
Email
eric@dasfbio.com
Country
China
ProdList
1988
Advantage
58
Shaanxi xintianyu Biotechnology Co., Ltd.
Tel
17749282610
Fax
029-32562222
Email
3002817800@qq.com
Country
China
ProdList
981
Advantage
58
Hubei wei shi reagent group ltd., company
Tel
027-59105166 13125137732
Email
2853863890@qq.com
Country
China
ProdList
2981
Advantage
58
Wuhan Wsem Biological Co., Ltd.
Tel
027-83778876 13667159345
Fax
027-83778876
Email
13667159345@163.com
Country
China
ProdList
1990
Advantage
55
Shaanxi xinyanghe Biotechnology Co., Ltd
Tel
18391023245
Email
1138024985@qq.com
Country
China
ProdList
793
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
Advantage
60
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View Lastest Price from Shikonin manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
Shikonin 517-89-5
Price
US $79.00-38.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-11-21
Changsha Staherb Natural Ingredients Co., Ltd.
Product
Shikonin 517-89-5
Price
US $0.00/KG
Min. Order
1KG
Purity
95%; 98% HPLC
Supply Ability
1000KG
Release date
2022-09-23
Wuhan Haorong Biotechnology Co.,Ltd
Product
Shikonine 517-89-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5000
Release date
2023-08-07

517-89-5, ShikoninRelated Search:


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