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Shikonin

CAS No.
517-89-5
Chemical Name:
Shikonin
Synonyms
Isoarnebin 4;SHIKONIN;Shikonine;c.i.75535;NSC 252844;SHIKONIN(AS);Tokyo Violet;(-)-SHIKONIN;gromwell red;SHIKONIN 98+%
CBNumber:
CB2251044
Molecular Formula:
C16H16O5
Molecular Weight:
288.3
MDL Number:
MFCD00075680
MOL File:
517-89-5.mol
MSDS File:
SDS
Last updated:2023-10-23 17:06:52

Shikonin Properties

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)
FDA UNII 3IK6592UBW

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319
Precautionary statements  P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Risk Statements  20/21/22-50/53-20
Safety Statements  26-36/37/39-61
RIDADR  3077
HS Code  29146990

Shikonin price More Price(49)

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

Shikonin Chemical Properties,Uses,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

Global( 307)Suppliers
Supplier Tel Email Country ProdList Advantage
Wuhan Haorong Biotechnology Co.,ltd
+8618565342920 sales@chembj.net China 268 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9354 55
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
Chengdu Greenpure Biopharma CO.,Ltd
18283602253 jancyzheng@gcgreenpure.com China 952 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29914 58
Chengdu GLP biotechnology Co Ltd
028-87075086 13350802083 scglp@glp-china.com CHINA 1824 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3424 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Shandong chuangyingchemical Co., Ltd.
18853181302 sale@chuangyingchem.com CHINA 5909 58

View Lastest Price from Shikonin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Shikonin pictures 2024-03-28 Shikonin
517-89-5
US $0.00 / KG 1KG 95%; 98% HPLC 1000KG Changsha Staherb Natural Ingredients Co., Ltd.
Shikonine pictures 2024-03-26 Shikonine
517-89-5
US $0.00-0.00 / KG 1KG 99% 5000 Wuhan Haorong Biotechnology Co.,Ltd
Shikonin pictures 2023-11-30 Shikonin
517-89-5
US $300.00 / KG 1KG 30%-99%HPLC,USP Standard 800KGs ZhenYiBio Technology Inc
  • Shikonin pictures
  • Shikonin
    517-89-5
  • US $0.00 / KG
  • 95%; 98% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Shikonine pictures
  • Shikonine
    517-89-5
  • US $0.00-0.00 / KG
  • 99%
  • Wuhan Haorong Biotechnology Co.,Ltd
  • Shikonin pictures
  • Shikonin
    517-89-5
  • US $300.00 / KG
  • 30%-99%HPLC,USP Standard
  • ZhenYiBio Technology Inc
5,8-Dihydroxy-2-[(R)-1-hydroxy-4-methyl-3-pentenyl]-1,4-naphthalenedione Tokyo Violet (R)-5,8-Dihydroxy-2-(1-hydroxy-4-Methylpent-3-en-1-yl)naphthalene-1,4-dione SHIKONIN(AS) Shikonin, froM Arnebia sp. (-)-ShikoninChina Shikonine Shikonin 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione Shikonin(Shikonin/Alkannin≒6:1) 1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]- Caprylic/Capric Triglyceride (and) Lithospermum Erythrorhizon Root Extract (+)-5,8-DIHYDROXY-2-(1-HYDROXY-4-METHYL-3-PENTENYL)-1,4-NAPHTHOQUINONE 8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-4-naphthalenedion(r)-5 8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-4-naphthoquinon(+)-5 c.i.75535 (-)-SHIKONIN SHIKONIN 98+% Shikonin (C.I. 75535) 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione (+)-5,8-Dihydroxy-2-[(R)-1-hydroxy-4-methyl-3-pentenyl]-1,4-naphthalenedione (1-hydroxy-4-methyl-3-pentenyl)-, (R)- 1,4-Naphthalenedione, 5,8-dihydroxy-2- gromwell pigment GromweIl pigment Shikonin (Anchusin) Shikonin, 99%, from Lithospermum erythrorhizon Sieb. & Zucc. Shikonin, 99%, from Arnebia sp. 5,8-dihydroxy-2-methylnaphthalene-1,4-dione Soluble SHIKONIN, Liposomal SHIKONIN, SHIKONIN NanoEmulsion, NanoActive SHIKONIN gromwell red Lithospermum erythrocyte Shikonin Standard Shikonin (mixture of optical isomers, about 6:1) NSC 252844 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione USP/EP/BP (+)-Shikonin,Alkannin TIANFU-CHEM - 5,8-Dihydroxy-2-[(1R)-1-hydroxy-4-methyl-pent-3-enyl]naphthalene-1,4-dione Isoarnebin 4 Shikonin (6CI) SHIKONIN 517-89-5 C16H16O5 Inhibitors chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract Anthraquinones, Hydroquinones and Quinones