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

Edible oil Soybean oil Propylene glycol

Preparation Products

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Shikonin Suppliers

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View Lastest Price from Shikonin manufacturers

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

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

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:

Alkannin Taxifolin griffonin Paclitaxel ELEUTHEROSIDE B DIHYDRO CUMINYL ALCOHOL Murexide CASTICIN Pterostilbene VIOLAXANTHIN Purpureaside C Corydaline CORYNOLINE lithospermic acid Dihydroechinofuran VIOLURIC ACID VIOLURIC ACID MONOHYDRATE DECURSINOL ANGELATE

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

Shikonin (Anchusin)

Shikonin, 99%, from Lithospermum erythrorhizon Sieb. & Zucc.

(1-hydroxy-4-methyl-3-pentenyl)-, (R)-

1,4-Naphthalenedione, 5,8-dihydroxy-2-

gromwell pigment

GromweIl pigment

Shikonin, 99%, from Arnebia sp.

5,8-dihydroxy-2-methylnaphthalene-1,4-dione

Soluble SHIKONIN, Liposomal SHIKONIN, SHIKONIN NanoEmulsion, NanoActive SHIKONIN

gromwell red

Isoarnebin 4

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

Shikonin (6CI)

SHIKONIN

NSC 252844|||Isoarnebin 4|||(+)-Shikonin|||Alkanna Red|||C.I. 75535|||Anchusa acid

Shikonin-RM

517-89-5

C16H16O5

Inhibitors

chemical reagent

pharmaceutical intermediate

phytochemical

reference standards from Chinese medicinal herbs (TCM).

standardized herbal extract

Anthraquinones, Hydroquinones and Quinones