52946-22-2

Basic information

• Product Name: ACETOXYCHAVICOL ACETATE, D/L-1''-
• Synonyms: D/L-1''-ACETOXCHAVICOL ACETATE;D,L-1'-ACETOXYCHAVICOL ACETATE;ACETOXYCHAVICOL ACETATE, D/L-1''-;1'-Acetoxychavicol acetate;DL-1''-ACETOXYCAVICOL ACETATE;(S)-4-(Acetyloxy)-alpha-ethenylbenzenemethanol acetate;Galangal acetate;AcetoXychvicol acetate, D/L-1''-
• CAS NO: 52946-22-2
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.25
• Product Categories: fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis
• Mol File: 52946-22-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 325.4 °C at 760 mmHg
• Flash Point: 157.8 °C
• Appearance: /
• Density: 1.122 g/cm³
• CAS DataBase Reference: ACETOXYCHAVICOL ACETATE, D/L-1''-(CAS DataBase Reference)
• NIST Chemistry Reference: ACETOXYCHAVICOL ACETATE, D/L-1''-(52946-22-2)
• EPA Substance Registry System: ACETOXYCHAVICOL ACETATE, D/L-1''-(52946-22-2)

Safety Data

• Hazardous Substances Data: 52946-22-2(Hazardous Substances Data)

Usage

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.

Definition

ChEBI: An acetate ester that is chavicol acetate substituted by an acetoxy group at position 1'.

Upstream product

• 108-24-7 acetic anhydride 
• 53580-61-3 4-(1-hydroxy-2-propenyl)phenol 
• 52946-22-2 1-acetoxychavicol acetate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 387351-55-5 (S)-4-O-tert-butyldimethylsilyl-1'-hydroxychavicol 
• 194156-04-2 1-(4-((tert-butyldimethylsilyl)oxy)phenyl)prop-2-en-1-ol 
• 169436-30-0 4-((S)-1-Hydroxy-allyl)-phenol 

Downstream Products

• 113944-48-2 (E)-3-(4-acetoxyphenyl)-2-propenyl acetate 
• 94723-93-0 acetic acid (E)-4-(3-hydroxypropenyl)phenyl ester 
• 1160172-97-3 C₁₅H₁₉NO₄S 
• 129319-15-9 (+/-)-2',3'-dihydroacetoxychavicol acetate 

Relevant articles and documents

Melanogenesis inhibitory activity of a 7-O-9'-linked neolignan from Alpinia galanga fruit

An aqueous acetone extract from the fruit of Alpinia galanga (Zingiberaceae) demonstrated inhibitory effects on melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells (IC50= 7.3 μg/mL). Through bioassay-guided separation of the extract, a new 7-O-9'-linked neolignan, named galanganol D diacetate (1), was isolated along with 16 known compounds including 14 phenylpropanoids (2–15). The structure of 1, including its absolute stereochemistry in the C-7 position, was elucidated by means of extensive NMR analysis and total synthesis. Among the isolates, 1 (IC50= 2.5 μM), 1'S-1'-acetoxychavicol acetate (2, 5.0 μM), and 1'S-1'-acetoxyeugenol acetate (3, 5.6 μM) exhibited a relatively potent inhibitory effect without notable cytotoxicity at effective concentrations. The following structural requirements were suggested to enhance the inhibitory activity of phenylpropanoids on melanogenesis: (i) compounds with 4-acetoxy group exhibit higher activity than those with 4-hydroxy group; (ii) 3-methoxy group dose not affect the activity; (iii) acetylation of the 1'-hydroxy moiety enhances the activity; and (iv) phenylpropanoid dimers with the 7-O-9'-linked neolignan skeleton exhibited higher activity than those with the corresponding monomer. Their respective enantiomers [1' (IC50= 1.9 μM) and 2' (4.5 μM)] and racemic mixtures [(±)-1 (2.2 μM) and (±)-2 (4.4 μM)] were found to exhibit melanogenesis inhibitory activities equivalent to those of the naturally occurring optical active compounds (1 and 2). Furthermore, the active compounds 1–3 inhibited tyrosinase, tyrosine-related protein (TRP)-1, and TRP-2 mRNA expressions, which could be the mechanism of melanogenesis inhibitory activity.

New Rev-export inhibitor from Alpinia galanga and structure-activity relationship

Bioassay-guided separation by use of the fission yeast expressing NES of Rev, an HIV-1 viral regulatory protein, disclosed 1′-acetoxychavicol acetate (ACA, 1) as a new inhibitor for nuclear export of Rev from the roots of Alpinia galanga. Both analysis for mechanism of action with biotinylated probe (2) and several synthesized analogs established crucial portions in 1 for Rev-export inhibitory activity.

Structure-activity relationships of 1′S-1′-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages

1′S-1′-Acetoxychavicol acetate from the rhizomes of Alpinia galanga inhibited nitric oxide (NO) production in lipopolysaccharide-activated mouse peritoneal macrophages with an IC50 value of 2.3 μM. To clarify the structure-activity relationship of 1′S-1′- acetoxychavicol acetate, various natural and synthetic phenylpropanoids and synthetic phenylbutanoids were examined, and the following structural requirements were clarified. (1) The para or ortho substitution of the acetoxyl and 1-acetoxypropenyl groups at the benzene ring was essential. (2) The S configuration of the 1′-acetoxyl group was preferable. (3) The presence of the 3-methoxyl group and disappearance of the 2′-3′ double bond by hydrogenation reduced the activity. (4) The substitution of acetyl groups with propionyl or methyl groups reduced the activity. (5) Lengthening of the carbon chain between the 1′- and 2′-positions reduced the activity.