1'-Acetoxychavicol acetate

Base Information

• Chemical Name: 1'-Acetoxychavicol acetate
• CAS No.: 52946-22-2
• Molecular Formula: C13H14O4
• Molecular Weight: 234.252
• Hs Code.: 2915390090
• European Community (EC) Number: 861-631-2
• UNII: SQV3080A20
• DSSTox Substance ID: DTXSID80967420
• Nikkaji Number: J553.238H
• Wikidata: Q27070798
• Pharos Ligand ID: 3HSWZ1AHTKDB
• Metabolomics Workbench ID: 49226
• ChEMBL ID: CHEMBL323727
• Mol file: 52946-22-2.mol

Synonyms:1'-acetoxychavicol acetate

Chemical Property of 1'-Acetoxychavicol acetate

Chemical Property:

• Boiling Point: 325.4 °C at 760 mmHg
• Flash Point: 157.8 °C
• PSA: 52.60000
• Density: 1.122 g/cm³
• LogP: 2.40210
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 234.08920892
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

99%, ^*data from raw suppliers

D,L-1′-Acetoxychavicol Acetate ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1=CC=C(C=C1)C(C=C)OC(=O)C
• Isomeric SMILES: CC(=O)OC1=CC=C(C=C1)[C@H](C=C)OC(=O)C
• Description: D,L-1′-Acetoxychavicol acetate is a natural compound first isolated from the rhizomes of ginger-like plants. It has a wide array of cellular effects that may be largely explained by its ability to inhibit exportin 1 and prevent the export of proteins from the nucleus. In this way, D,L-1′-acetoxychavicol acetate reduces several intracellular signaling pathways, including NF-κB, impacting inflammation, cancer, viral replication, and other processes.

Technology Process of 1'-Acetoxychavicol acetate

There total 10 articles about 1'-Acetoxychavicol acetate 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: 100.0%

4-((S)-1-Hydroxy-allyl)-phenol (169436-30-0) + acetic anhydride (108-24-7) → <1'S>-1'-acetoxychavicol acetate (52946-22-2)

Guidance literature:

With pyridine;

DOI:10.1016/j.bmcl.2009.03.047

Reference yield: 98.0%

acetic anhydride (108-24-7) + 4-(1-hydroxy-2-propenyl)phenol (53580-61-3) → 1-acetoxychavicol acetate (52946-22-2,108147-21-3,53890-21-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.bmc.2016.10.001

Reference yield:

→ 1-acetoxychavicol acetate (52946-22-2,108147-21-3,53890-21-4)

Guidance literature:

Aus p-Hydroxybenzaldehyd: 1:)BrMgCH=CH2, 2.)Essigsaeureanhydrid/Pyridin;

upstream raw materials:

acetic anhydride

4-(1-hydroxy-2-propenyl)phenol

4-((S)-1-Hydroxy-allyl)-phenol

1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol

Downstream raw materials:

(E)-3-(4-acetoxyphenyl)-2-propenyl acetate

acetic acid (E)-4-(3-hydroxypropenyl)phenyl ester

C₁₅H₁₉NO₄S

(+/-)-2',3'-dihydroacetoxychavicol acetate

Refernces

• 1、 Tamura, Satoru,Shiomi, Atsushi,Kaneko, Masafumi,Ye, Ying,Yoshida, Minoru,Yoshikawa, Masayuki,Kimura, Tominori,Kobayashi, Motomasa,Murakami, Nobutoshi. "New Rev-export inhibitor from Alpinia galanga and structure-activity relationship". scheme or table. p. 2555 - 2557. Retrieved 2010/03/03.
• 2、 Azuma, Hideki,Miyasaka, Keita,Yokotani, Tsuyoshi,Tachibana, Taro,Kojima-Yuasa, Akiko,Matsui-Yuasa, Isao,Ogino, Kenji. "Lipase-catalyzed preparation of optically active 1′-acetoxychavicol acetates and their structure-activity relationships in apoptotic activity against human leukemia HL-60 cells". . p. 1811 - 1818. Retrieved 2007/10/03.