C.I. Natural Red 20

Base Information

• Chemical Name: C.I. Natural Red 20
• CAS No.: 54952-43-1
• Deprecated CAS: 11019-15-1,11031-58-6,14265-21-5
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.3
• European Community (EC) Number: 684-467-1
• NSC Number: 407295,94524,291845,252844
• DSSTox Substance ID: DTXSID00862100
• Nikkaji Number: J20.957K
• Wikidata: Q105178326
• Metabolomics Workbench ID: 130057
• ChEMBL ID: CHEMBL29285
• Mol file: 54952-43-1.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 C.I. Natural Red 20

Chemical Property:

• Melting Point: 144-145 °C
• 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.: 2-8°C
• Solubility.: methanol: soluble1mg/mL
• 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:

98%,99%, ^*data from raw suppliers

(±)-Shikonin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 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
• Uses: Shikonin has been used:to enhance the anti-tumor activity of gefitinib on tyrosine kinase receptor epidermal growth factor receptor (EGFR) in wild-type lung cancer cellsas an inhibitor of renal aerobic glycosis and a potentialas an anti-inflammatory agent to test its role to improve lipopolysaccharide (LPS)-induced cardiac dysfunctionto stimulate bone marrow-derived macrophages (BMDMs) to test the effect of Interferon regulatory factor 1 on cell death

Technology Process of C.I. Natural Red 20

There total 72 articles about C.I. Natural Red 20 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:

2-bromo-1,8:4,5-bis(methylenedioxy)naphthalene (88051-30-3) → (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:

Multi-step reaction with 3 steps

1: 63 percent / t-BuLi / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 1.5 h

2: 1.) (+)-DIP-Cl, 2.) CH₃CHO / 1.) THF, -40 to -25 deg C, 3 h, 2.) THF, 0 deg C, 12 h

3: LiClO₄ / acetonitrile; H₂O / 25 °C / anodic oxidation, graphite electrodes, 3V

With tert.-butyl lithium; lithium perchlorate; acetaldehyde; B-chlorodiisopinocampheylborane; In tetrahydrofuran; water; acetonitrile;

DOI:10.1002/(SICI)1521-3773(19980403)37:6<839::AID-ANIE839>3.0.CO;2-J

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

propionylshikonin

isovalerylshikonin

alkannin isovalerate

Refernces

• 1、 Ono, Mana,Abe, Shouki,Higai, Koji,Higashi, Shoko,Saito, Setsuo,Saito, Ryota. "An improved and practical synthesis route to antiproliferative (±)-shikonin and its O-acyl derivatives". . p. 738 - 746. Retrieved 2020/12/09.
• 2、 Ito, Yusai,Onobori, Kenichi,Yamazaki, Takeshi,Kawamura, Yoko. "Tigloylshikonin, a new minor shikonin derivative, from the roots and the commercial root extract of Lithospermum erythrorhizon". experimental part. p. 117 - 119. Retrieved 2011/02/28.