Alkannin

Base Information

• Chemical Name: Alkannin
• CAS No.: 517-88-4
• Deprecated CAS: 8001-98-7
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.3
• European Community (EC) Number: 208-245-7
• UNII: 075CRZ9995
• DSSTox Substance ID: DTXSID201029621
• Nikkaji Number: J3.024.325K,J9.234G
• Wikipedia: Alkannin
• Wikidata: Q418237
• Metabolomics Workbench ID: 67888
• ChEMBL ID: CHEMBL28457,CHEMBL4127840
• Mol file: 517-88-4.mol

Synonyms:alkannin

Chemical Property of Alkannin

Chemical Property:

• Vapor Pressure: 1.04E-13mmHg at 25°C
• Melting Point: 149°
• 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: 1.373g/cm³
• LogP: 2.12040
• 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:

95%, ^*data from raw suppliers

Alkannin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Uses: Alkannin is a enantiomeric dye from Alkanna tinctoria and Lithospermum erythrorhizon, which has known as dyestuff, wound healing, anti-inflammatory, anti-bacterial and anti-tumor substances. Alkannin (cas# 23444-65-7) inhibits proliferation, migration and invasion of human Huh7 and Hep3B2.1-7 hepatocellular carcinoma cells via regulation of miR92a. It is also useful in the application of macromolecular crowding to investigate naphthoquinones shikonin, naphthazarin and related analogs for treatment of dermal scars in human.

Technology Process of Alkannin

There total 72 articles about Alkannin 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

(S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione

2-(5',5'-dimethyl-2'-tetrahydrofuranyl)-1,4,5,8-tetraacetoxynapthalene

isobutyrylalkannin

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.