Shikonin

Base Information

• Chemical Name: Shikonin
• CAS No.: 517-89-5
• Deprecated CAS: 874325-10-7,876010-87-6
• Molecular Formula: C16H16O5
• Molecular Weight: 288.3
• Hs Code.: 29146990
• DSSTox Substance ID: DTXSID30199653
• Nikkaji Number: J13.981E
• Wikidata: Q27155024
• Pharos Ligand ID: 7GFJBL4VNMYG
• Metabolomics Workbench ID: 143562
• ChEMBL ID: CHEMBL9470
• Mol file: 517-89-5.mol

Synonyms:(+)-shikonin;(+-)-shikonin;(R)-(+)-shikonin;1,4-naphthalenedione, 5,8-dihydroxy-2-((1R)-1-hydroxy-4-methyl-3-penten-1-yl)-;1,4-naphthalenedione, 5,8-dihydroxy-2-((1r)-1-hydroxy-4-methyl-3-pentenyl)-;1,4-naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (R)-;1,4-naphthoquinone, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-, (+)-;2-((1R)-1-hydroxy-4-methyl-3-pentenyl)-5,8-dihydroxy-1,4-naphthoquinone;5,8-dihydroxy-2-((1R)-1-hydroxy-4-methyl-3-penten-1-yl)-1,4-naphthalenedione;5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthalenedione;isoarnebin 4;shikonin;shikonin, (+)-isomer

Chemical Property of Shikonin

Chemical Property:

• Vapor Pressure: 1.04E-13mmHg at 25°C
• Melting Point: 147 °C
• Refractive Index: 1.642
• Boiling Point: 567.4 °C at 760 mmHg
• PKA: 7.34±0.20(Predicted)
• Flash Point: 311 °C
• PSA: 94.83000
• Density: 1.373 g/cm³
• LogP: 2.12040
• Storage Temp.: -20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 288.09977361
• Heavy Atom Count: 21
• Complexity: 501

Purity/Quality:

99.90% ^*data from raw suppliers

Shikonin ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22-50/53-20
• Safety Statements: 26-36/37/39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC(C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• Isomeric SMILES: CC(=CC[C@H](C1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)O)C
• 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. 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.
• Physical properties: Appearance: purple lamellae or crystalline powder. Melting point: 147 °C. Specific optical rotation: +138°(benzene). Solubility: soluble in ethanol, vegetable oils, and other organic solvents.
• Uses: A naphthoquinone derivative with angiogenesis inhibitor properties. Shikonin (CI 75535) 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.
• 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.

Technology Process of Shikonin

There total 115 articles about Shikonin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

(S)-4-Methyl-1-(1,3,6,8-tetraoxa-pyren-4-yl)-pent-3-en-1-ol (206996-07-8) → (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione (517-88-4,517-89-5,11031-58-6,54952-43-1,85921-41-1)

Guidance literature:

With lithium perchlorate; copper(II) acetate monohydrate; In water; acetonitrile; for 3h; Electrochemical reaction;

DOI:10.3184/030823410X12709960181221

Reference yield:

shikonin (517-88-4,517-89-5,11031-58-6,54952-43-1,85921-41-1) → shikonin (517-89-5) + (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione (517-88-4,517-89-5,11031-58-6,54952-43-1,85921-41-1)

Guidance literature:

With Sino-Chiral OD column; In ethanol; Further stages; Resolution of racemate;

Reference yield:

shikonin (517-88-4,517-89-5,11031-58-6,54952-43-1,85921-41-1) → shikonin (517-89-5) + (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione (517-88-4,517-89-5,11031-58-6,54952-43-1,85921-41-1)

Guidance literature:

With Sino-Chiral OD column; In ethanol; Further stages; Resolution of racemate;

upstream raw materials:

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

5,8-diacetoxy-2-(1-acetoxy-4-methyl-3-pentenyl)-1,4-naphthoquinone

(R,S)-acetic acid 4-acetoxy-3-(1-acetoxy-4-methyl-pent-3-enyl)-5,8-dimethoxynaphthalen-1-yl ester

4-methyl-pent-3-enoic acid

Downstream raw materials:

shikonin-β,β-dimethylacrylate

arnebin-7

propionylshikonin

acetylshikonin

Refernces

• 1、 -. "High performance liquid chromatography resolution method of alkannin raceme and naphthazarin parent nucleus hydroxyl methylated carbonyl oxime derivative of alkannin raceme". Paragraph 0036-0045. . Retrieved 2021/04/17.
• 2、 Wang, Rubing,Zhou, Shanshan,Jiang, Hudagula,Zheng, Xiaogang,Zhou, Wen,Li, Shaoshun. "An efficient multigram synthesis of alkannin and shikonin". supporting information; experimental part. p. 1373 - 1379. Retrieved 2012/04/04.